IUPAC-NIST Solubility Data Series. 105. Solubility of Solid Alkanoic Acids, Alkenoic Acids, Alkanedioic Acids, and Alkenedioic Acids Dissolved in Neat Organic Solvents, Organic Solvent Mixtures, and Aqueous–Organic Solvent Mixtures. III. Alkanedioic Acids and Alkenedioic Acids

Acree, William E.; Waghorne, W. Earle

doi:10.1063/5.0158382

Solubility data are compiled and reviewed for 19 alkanedioc and alkenedioic acids dissolved in neat organic solvents and well-defined binary organic and aqueous–organic solvent mixtures. The compiled solubility data were retrieved from the published chemical, engineering, and pharmaceutical literature covering the period between 1910 and the beginning of 2021.

1. Preface

1.1. Scope of this volume

This volume in the IUPAC–NIST Solubility Data Series is devoted to the solubility of solid alkanoic acids, alkenoic acids, alkanedioic acids, and alkenedioic acids dissolved in neat organic solvents, organic solvent mixtures, and aqueous–organic solvent mixtures. This volume will be published in three separate parts, with each part representing a compilation and evaluation of published solubility data for different classes of organic carboxylic acids. Nearly 110 years of the published chemical and engineering literature were searched during the preparation of this volume.

Parts 1 and 2 of this volume compiled and critically evaluated solubility data for akanoic acids and alkenoic acids dissolved in a wide range of organic mono-solvents and binary solvent mixtures.^1,2 This volume concludes with part 3, which provides a discussion of the published solubility data for the following alkanedioic acids and alkenedioic acids: hexanedioic acid (also called adipic acid), nonanedioic acid (azelaic acid), tridecanedioic acid (brassylic acid), (E) 2-butenedioic acid (also fumaric acid), pentanedioic acid (glutaric acid), methylenebutanedioic acid (itaconic acid), (±) hydroxybutanedioic acid (malic acid), (S) hydroxybutanedioic acid (L-malic acid), propanedioic acid (malonic acid), 2-sulfanylbutanedioic acid (2-sulfanylbutanedioic acid, mercaptosuccinic acid), ethanedioic acid (oxalic acid), heptanedioic acid (pimelic acid), decanedioic acid (sebacic acid), octanedioic acid (suberic acid), butanedioic acid (succinic acid), (2S,3S)-(−)-2,3-dihydroxybutanedioc acid (D-tartaric acid), (R*,R*)-(±)-2,3-dihydroxybutanedioc acid (DL-tartaric acid), and (2R,3R)-2,3-dihydroxybutanedioic acid (L-tartaric acid). In total, solubility data for more than 45 different carboxylic acids are contained in this volume.

This volume will provide both the chemical manufacturing sector and the scientific community with an easily accessible compilation of experimental solubility data for alkanoic acids, alkenoic acids, alkanedioic acids, and alkenedioic acids dissolved in neat organic mono-solvents and in binary solvent mixtures. Many of the carboxylic acids contained in this volume are used in the preparation of consumer products. Moreover, researchers who perform experimental solubility studies will also benefit from this volume in that the Guide to Authors of several chemical engineering and thermodynamics journals requires that the authors compare the measured data against published literature values if available. Volumes in the IUPAC–NIST Solubility Data Series provide a convenient source of published experimental data for such comparisons.

1.2. Concentration units used to report solubility data

Composition of a liquid nonelectrolyte solution can be expressed in a variety of ways as follows:

The ratio of the number of moles of one component to the number of moles of a second component, n₁/ n₂, etc.,
molar concentration:
$c_{i} = [i] = \frac{n_{i}}{V}, {SI base units: mol dm}^{- 3},$
(1)
mole fraction:
$x_{i} = \frac{n_{i}}{n_{1} + n_{2} + \dots + n_{i} + \dots},$
(2)
mass fraction:
$w_{i} = \frac{mass of component i}{total mass of solution},$
(3)
or
volume fraction:
$φ_{i} = \frac{n_{i} V_{i}}{n_{1} V_{1} + n_{2} V_{2} + \dots + n_{i} V_{i} + \dots} .$
(4)
Strictly speaking, the true volume of a real solution is not equal to the sum of the volumes of the individual components but is the fraction sum of partial volumes, which for a ternary solution is V = x₁V₁ + x₂V₂ + x₃V₃. For purposes of this study, volume fractions are defined in terms of the molar volumes of the pure unmixed components, V_m,i (molar mass of component i divided by density of component i),
$φ_{i} = \frac{n_{i} V_{m, i}}{n_{1} V_{m, 1} + n_{2} V_{m, 2} + \dots + n_{i} V_{m, i} + \dots},$
(5)
as this quantity serves as an input parameter in expressions for estimating solubilities in mixed solvents since it requires no a priori knowledge concerning volumetric behavior. Solute solubilities can be found in the chemical literature in terms of any of the aforementioned concentration variables, or as molality, m_i, which is the number of molecules of solute i divided by the mass of the solvent,
$m_{i} = \frac{n_{i}}{n_{solvent} M_{solvent}}, {SI base units: mol kg}^{- 1},$
(6)
where M_solvent is the molar mass of the solvent.

2. Critical Evaluation of Solubility Data

The solubilities of alkanedioic acids are commonly expressed as amount fractions, x₁, and reported as functions of the thermodynamic temperature. Where the solubilities were reported in terms of masses, they were converted to amount fractions. In a few cases, solubilities were reported in mol l⁻¹ of solution; since conversion of these data to mole fractions requires the solution densities, these were not converted nor evaluated.

A number of techniques have been used to determine the solubilities. The experimental details are summarized in the relevant compilations, but, briefly, the following four methods have been used:

Gravimetry: By determination of the masses of the solute and solvent in the saturated solution by evaporation, to constant mass, of a known mass of solution, where the solvent is much more volatile than the solute.
Turbidometry: To determine the temperature at which the solute just dissolves/precipitates (temperature increasing/decreasing) in a system of known composition. The technique used for systems considered here used a laser detection system to monitor the turbidity.
Analysis of a sample of the saturated solution by acid/base titration, liquid chromatography, spectroscopy, and, in one case, heat flow calorimetry.
The use of differential scanning calorimetry to determine the precipitation temperature.

Each of these techniques is relatively direct and, with proper calibration and application, should be free of systematic error.

Solid phase identification. One issue that complicates the evaluation of these data, and solubilities of solids in general, is the lack of detailed information about the solid phase in equilibrium with the solution. Early measurements generally make no reference to the solid phase. More recent work commonly reports x-ray diffraction (XRD) results showing that the equilibrium solids and starting material are similar.

These results indicate that there has been no change in the crystal structure, but authors generally do not provide information as to which crystal structure is present. Moreover, these almost always refer to the solid recovered from the equilibrated solution at a single temperature.

The lack of detailed knowledge of the solid phases presents an obvious difficulty, since solubilities may be dependent on the crystal structure of the solid phase.

A review of the crystal structures of alkanedioic acids is outside of the scope of this volume.

2.1. Methodology used in the critical evaluations

The method adopted was to determine consensus values of the solubilities. This requires data at common temperatures, but the data are commonly reported at a variety of temperatures. The solution chosen was to fit each data set to a function of temperature and then calculate values at common temperatures within the temperature range where data sets overlapped.

Initially, the solubilities x₁(T) were fitted to the Van’t Hoff equation as

\ln (x_{1} / (m o l / m o l)) = A + \frac{B}{T},

(7)

but in virtually all cases, the plots showed curvature, often outside of reasonable experimental uncertainties. Thus, all datasets were fitted to the modified Apelblat equation,

\ln x_{1} = A + \frac{B}{T} + C \ln T,

(8)

using the linear least-squares method as implemented in the Microsoft Excel^® LINEST function. This gave a working equation for ln x₁ for each data set. Generally, the reported data show relatively good agreement with Eq. . The uncertainty of a value of ln x obtained at a temperature T from fitted coefficients in Eqs. or may be calculated using the propagation of uncertainty (Gauss’s formula).³ This requires the covariance matrix of the coefficients, which may also be calculated in Excel.

However, analysis of the data shows that there are systematic errors among different data sets for the same systems. Additionally, these uncertainties commonly increase with x₁. Throughout the evaluations, the uncertainties are expressed in terms of the uncertainty in ln x₁ [u(ln x₁)], which implies a constant relative uncertainty in x_1.^4,5

In view of the clear presence of systematic errors, the data were analyzed using the DerSimonian–Laird method.⁵ In this method, the heterogeneity among the values from different studies, τ², which has become known as “dark uncertainty,”⁵ is estimated as

τ^{2} = \frac{Q - d f}{c},

(9)

where, for ln x₁,

Q = \sum_{i = 1}^{k} w_{i} {(\ln x_{1})}_{i}^{2} - \frac{{(\sum_{i = 1}^{k} w_{i} {(\ln x_{1})}_{i})}^{2}}{\sum_{i = 1}^{k} w_{i}},

(10)

d f = k - 1,

(11)

c = \sum_{i = 1}^{k} w_{i} - \frac{\sum_{i = 1}^{k} w_{i}^{2}}{\sum_{i = 1}^{k} w_{i}} .

Here, k is the number of studies compared and df is the number of degrees of freedom. In the random effects model, the weight assigned to study i is

w_{i}^{*} = \frac{1}{u_{i}^{2} + τ^{2}},

(12)

where u_i is the standard error of datum i. The consensus values of ln x₁ (the summary estimates) are computed as

\ln x_{1, c o n s \cdot} = \frac{\sum_{i = 0}^{k} w_{i}^{*} {(\ln x_{1})}_{i}}{\sum_{i = 0}^{k} w_{i}^{*}} .

(13)

The variance of the consensus value is

u (\ln x_{1, c o n s}) = \frac{1}{\sum_{i = 1}^{k} w_{i}^{*}} .

(14)

This analysis requires comparable data, in this case, ln x₁ values at the same temperatures, but the reported solubilities are commonly reported at different temperatures. The process adopted was to calculate values of ln x₁ at specified temperatures, using the A, B, and C parameters of Eq. , for each data set, i.

The consensus values, derived from Eq. (13), were also fitted to Eq. (8), and the resulting coefficients A_cons, B_cons, and C_cons are reported for each system, allowing calculation of consensus and their uncertainties at different temperatures. It should be noted that these parameters will reproduce the consensus values within the temperature range where there is overlap of data sets but values calculated at temperatures outside of this range are likely to carry greater uncertainties.

Evaluation reports. Only systems for which there are two or more independent sets of experimental data were evaluated. In some cases, solubilities were reported in mass fractions, and these were converted to amount fractions by the evaluator using the latest release of the Periodic Table (dated 1 December 2018).⁶ Where solubilities were reported as concentrations (mol l⁻¹), the data were not converted to amount fractions as this requires the solution densities.

To allow consensus values to be estimated at different temperatures, these were fitted to Eq. (8) and the corresponding parameters, A_cons, B_cons, and C_cons are reported in the system evaluation along with the estimated uncertainty of the consensus value. The temperature range, ΔT, where there are overlapping data sets is also noted.

A plot of the experimental data against temperature is provided in the following evaluation tables, along with the locus of the derived equation and an error channel defined by ±3u(ln x_1,cons), where u(ln x₁) is calculated using Eq. (14).

The derived equation provides the basis for calculating consensus x₁ values; that is, consensus values are those calculated using Eq. (8) and the recovered values of A_cons, B_cons, and C_cons.

2.2. Evaluation of the solubility data for hexanedioic acid in oxepan-2-one

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Oxepan-2-one (ε-caprolactone), C₆H₁₀O₂ [502-44-3]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

306–335

A_cons

−92.2853

B_cons

614.672

C_cons

15.1115

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets^7,8 were measured using turbidometry with

a laser detection system. The quoted uncertainties of the

temperature are 0.13 and 0.12 K.

Consensus values at integral temperatures

T (K)

310

320

330

340

ln x_1,cons ± u(ln x₁)

−3.51 ± 0.13

−3.20 ± 0.15

−2.79 ± 0.15

−2.39 ± 0.12

τ

0.18

0.22

0.21

0.17

x_1,cons ± u(x₁)%

0.027 ± 13%

0.041 ± 15%

0.061 ± 15%

0.091 ± 12%

Evaluation:

Only data between 306 and 336 K were included in the analysis.

Original measurements:

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

⁸W. Luo, D. Ruan, D. Liu, K. Xie, X. Li, W. Deng, and C. Guo, J. Chem. Eng. Data 61, 2474 (2016).

2.3. Evaluation of the solubility data for hexanedioic acid in trichloromethane

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Trichloromethane, CHCl₃ [67-66-3]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

302–323

A_cons

184.575

B_cons

−10 732.4

C_cons

−27.1619

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C \ln T

⁠, where T is expressed in K.

Comments:

Both data sets^9,10 were measured by titrating the equilibrated solution

with calibrated NaOH solution.

The quoted uncertainties of the temperature are 0.05 K in both cases.

Consensus values at integral temperatures

T (K)

300

310

320

ln x_1,cons ± u(ln x₁)

−6.125 ± 0.003

−5.862 ± 0.001

−5.643 ± 0.002

τ

0

x_1,cons ± u(x₁)%

0.002 19 ± 0.3%

0.002 83 ± 0.1%

0.003 54 ± 0.2%

Evaluation:

Data between 300 and 323 K were included in the analysis.

Original measurements:

⁹D. Wei and W. Cao, J. Chem. Eng. Data 54, 152 (2009).

¹⁰Z. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

2.4. Evaluation of the solubility data for hexanedioic acid in methanol

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Methanol, CH₄O [67-56-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

283–324

A_cons

−52.588 7

B_cons

−165.920

C_cons

8.792 83

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Two methods, determination of the masses of solvent and solute

in an equilibrated sample by evaporation of the solvent¹¹ and turbidometry

with laser detection,^12,13 were used to determine the solubilities.

The quoted uncertainties of the temperature are 0.13 K or better.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−3.31 ± 0.03

−2.99 ± 0.02

−2.68 ± 0.02

−2.39 ± 0.02

τ

0.05

0.04

0.03

x_1,cons ± u(x₁)%

0.037 ± 2.8%

0.050 ± 2.3%

0.068 ± 2.1%

0.092 ± 2.0%

Evaluation:

Data between 283 and 324 K were included in the analysis.

Original measurements:

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

2.5. Evaluation of the solubility data for hexanedioic acid in ethanol

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–340

A_cons

−79.9987

B_cons

735.123

C_cons

13.0373

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Three methods were used to determine the solubilities: By mass and

evaporation of the solvent,^11,15 by titration of the equilibrated liquid,¹²

and by differential scanning calorimetry.¹⁴

The quoted uncertainties of the temperature are 0.1 K or better.

Consensus values at integral temperatures

T (K)

290

305

320

335

ln x_1,cons ± u(ln x₁)

−3.54 ± 0.02

−3.01 ± 0.03

−2.49 ± 0.02

−2.04± 0.05

τ

0.03

0.04

0.07

x_1,cons ± u(x₁)%

0.029 ± 2.0%

0.049 ± 2.7%

0.082 ± 2.4%

0.13 ± 5.1%

Evaluation:

Mohan et al.¹⁴ reported data at only three temperatures, and so these were excluded from the analysis. The values are included in the graph.

Data between 283 and 324 K were included in the analysis.

Original measurements:

¹⁰Z. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

¹⁴R. Mohan, H. Lorentz, and A. S. Myerson, Ind. Eng. Chem. Res. 41, 4854 (2002).

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

2.6. Evaluation of the solubility data for hexanedioic acid in 1-butanol

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) 1-Butanol, C₄H₁₀O [71-36-3]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

298–333

A_cons

−55.891 9

B_cons

−496.932

C_cons

9.463 41

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The solubilities were determined by analysis of equilibrated solutions by

mass with evaporation of solvent¹¹ or titration of the solute with NaOH.¹⁰

The quoted uncertainties of the temperature are 0.1 K or better.

Consensus values at integral temperatures

T (K)

300

310

320

330

ln x_1,cons ± u(ln x₁)

−3.57 ± 0.11

−3.21± 0.10

−2.86 ± 0.09

−2.52 ± 0.08

τ

0.15

0.14

0.13

0.12

x_1,cons ± u(x₁)%

0.028 ± 11%

0.040 ± 10%

0.057 ± 8.9%

0.081 ± 8.2%

Evaluation:

Only data between 293 and 334 K were included in the analysis.

Original measurements:

¹⁰L. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

2.7. Evaluation of the solubility data for hexanedioic acid in cyclohexanol

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Cyclohexanol, C₆H₁₂O [108-93-0]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

300–353

A_cons

746.1984

B_cons

−39 712.6

C_cons

−108.338

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Three of the data sets were measured by turbidometry^16,18,19 and the fourth

was by high-performance liquid chromatographic (HPLC) analysis

of the equilibrated solution.¹⁷

The quoted uncertainties of the temperature are 0.12 K or better.

Consensus values at integral temperatures

T (K)

300

315

330

345

ln x_1,cons ± u(ln x₁)

−4.11 ± 0.5

−3.09± 0.2

−2.40 ± 0.04

−1.98 ± 0.02

τ

0.8

0.3

0.06

0.02

x_1,cons ± u(x₁)%

0.016± 48%

0.045 ± 18%

0.090 ± 4.0%

0.137 ± 1.6%

Evaluation:

References 18 and 19 report the same data, except that Ref. 18 reports one extra datum. Thus, the data from Luo et al.¹⁹ were

excluded from the analysis.

Data between 301 and 353 K were included in the analysis.

Original measurements:

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

¹⁷S. Suren, N. Sunsandee, M. Stolcova, M. Hronec, N. Leepipatpiboon, U. Pancharoen, and S. Kheawhom, Fluid Phase Equilib. 360, 332 (2013).

¹⁸X. Sheng, Q. Wang, Z. Xiong, and C. Chen, Fluid Phase Equilib. 415, 8 (2016).

¹⁹W. Luo, M. Yan, X.-X. Sheng, B. Tao, S. Shi, W. Deng, W. Yang, and S. Luo, Ind. Eng. Chem. Res. 58, 10018 (2019).

2.8. Evaluation of the solubility data for hexanedioic acid in propanone

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

285–323

A_cons

−280.224

B_cons

9835.14

C_cons

42.6770

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Four methods were used: Acid–base titration,^9,10 gravimetry by

evaporation of solvent,^11,15 a combination of ATR–FTIR and heat

flow calorimetry,²⁰ and turbidometry²¹ were applied to equilibrated solutions.

The quoted uncertainties of the temperature are 0.12 K or better.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−4.34 ± 0.01

−4.02 ± 0.01

−3.68 ± 0.01

−3.31 ± 0.02

τ

0.03

0.02

0.05

x_1,cons ± u(x₁)%

0.013 ± 1.3%

0.018 ± 1.1%

0.025 ± 1.0%

0.036 ± 2.2%

Evaluation:

Data from 283 to 326 K were included.

Original measurements:

⁹D. Wei and W. Cao, J. Chem. Eng. Data 54, 152 (2009).

¹⁰Z. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

²⁰A. d. P. M. da Silva and J. F. Cajaiba da Silva, Org. Process Res. Dev. 15, 893 (2011).

²¹Y. Li, Y. Wang, Z. Ning, J. Gui, Q. Wu, and X. Wang, J. Chem. Eng. Data 59, 4062 (2014).

2.9. Evaluation of the solubility data for hexanedioic acid in cyclohexanone

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

292–355

A_cons

−149.011

B_cons

3655.23

C_cons

23.2611

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

One data set was determined by gravimetry,¹⁷ while the others were

determined by turbidometry.^{7,12,13,16,18,19} The quoted

uncertainties in T were 0.12 K or less.

Consensus values at integral temperatures

T (K)

295

315

335

355

ln x_1,cons ± u(ln x₁)

−4.335 ± 0.001

−3.595 ± 0.004

−2.844 ± 0.001

−2.12 ± 0.003

τ

0

x_1,cons ± u(x₁)%

0.0131 ± 0.1%

0.0275± 0.04%

0.0582 ± 0.1%

0.120 ± 0.3%

Evaluation:

Two of the references^19,12 report the same data except that Ref. 19 reports four extra data points; only one of these sets of data¹⁹

was included in the evaluation.

Data between 292 and 355 K were included in the analysis.

Original measurements:

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

¹⁷S. Suren, N. Sunsandee, M. Stolcova, M. Hronec, N. Leepipatpiboon, U. Pancharoen, and S. Kheawhom, Fluid Phase Equilib. 360, 332 (2013).

¹⁸X. Sheng, Q. Wang, Z. Xiong, and C. Chen, Fluid Phase Equilib. 415, 8 (2016).

¹⁹W. Luo, D. Ruan, D. Liu, K. Xie, X. Li, W. Deng, and C. Guo, J. Chem. Eng. Data 61, 2474 (2016).

2.10. Evaluation of the solubility data for hexanedioic acid in ethanoic acid

Components:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

297–347

A_cons

−81.6336

B_cons

532.620

C_cons

13.3357

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Five of the data sets were determined by turbidometry,^{8,16,19,23,24} two were

determined by gravimetry,^11,15 and two were determined by HPLC

analysis of saturated solutions.^17,22 The quoted uncertainties

in T were 0.12 K of less.

Consensus values at integral temperatures

T (K)

300

315

330

345

ln x_1,cons ± u(ln x₁)

−3.79 ± 0.01

−3.23 ± 0.01

−2.69 ± 0.01

−2.18 ± 0.02

τ

0.04

0.03

0.04

0.05

x_1,cons ± u(x₁)%

0.022 ± 1.4%

0.038± 1.1%

0.068 ± 1.4%

0.113 ± 2.0%

Evaluation:

Data between 293 and 353 K were included in the analysis.

Original measurements:

⁸W. Luo, D. Ruan, D. Liu, K. Xie, X. Li, W. Deng, and C. Guo, J. Chem. Eng. Data 61, 2474 (2016).

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

¹⁷S. Suren, N. Sunsandee, M. Stolcova, M. Hronec, N. Leepipatpiboon, U. Pancharoen, and S. Kheawhom, Fluid Phase Equilib. 360, 332 (2013).

¹⁹W. Luo, M. Yan, X.-X. Sheng, B. Tao, S. Shi, W. Deng, W. Yang, and S. Luo, Ind. Eng. Chem. Res. 58, 10018 (2019).

²²B. Shen, Q. Wang, Y. Wang, X. Ye, F. Lei, and X. Gong, J. Chem. Eng. Data 58, 938 (2013).

²³W. Luo, M. Yan. B. Tao, S. Shi, and B. Chen, J. Chem. Thermodyn. 138, 332 (2019).

²⁴W. Luo, X. Li, D. Ruan, D. Liu, K. Xie, J. Wang, W. Deng, Q. Liu, and Z. Chen, J. Chem. Eng. Data 62, 1269 (2017).

2.11. Evaluation of the solubility data for nonanedioic acid in ethanol

Components:

(1) Nonanedioic acid (azelaic acid), C₉H₁₆O₄ [123-99-9]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

292–323

A_cons

−186.149

B_cons

5391.25

C_cons

29.0338

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Different methods were used for the measurements, turbidometry,²⁵ and

gravimetry.¹⁵ The stated uncertainties in T were 0.1 K or less.

Consensus values at integral temperatures

T (K)

300

310

320

ln x_1,cons ± u(ln x₁)

−2.68 ± 0.09

−2.30 ± 0.08

−1.92 ± 0.09

τ

0.1

x_1,cons ± u(x₁)%

0.069 ± 8.7%

0.10 ± 7.0%

0.146 ± 8.6%

Evaluation:

Data between 292 and 325 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

²⁵S. Chen, Q. Xia, D. Li, W.-G. Yuan, F.-B. Zhang, and G.-L Zhang, J. Chem. Eng. Data 54, 1395 (2009).

2.12. Evaluation of the solubility data for nonanedioic acid in propanone

Components:

(1) Nonanedioic acid (azelaic acid), C₉H₁₆O₄ [123-99-9]

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–323

A_cons

−584.208

B_cons

22 465.4

C_cons

88.7144

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both sets of data were determined by gravimetry.^15,26 The stated uncertainties

in T were 0.1 K or better.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−3.74 ± 0.25

−3.32± 0.16

−2.82 ± 0.12

−2.27 ± 0.11

τ

0.35

0.23

0.16

0.15

x_1,cons ± u(x₁)%

0.023 ± 21%

0.036 ± 16%

0.059 ± 12%

0.103 ± 11%

Evaluation:

Data between 286 and 326 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

²⁶B. Long, T. Li, Y. Xia, X. Y. Li, and Y. Ding, J. Mol. Liq. 272, 930 (2018).

2.13. Evaluation of the solubility data for nonanedioic acid ethanoic acid

Components:

(1) Nonanedioic acid (azelaic acid), C₉H₁₆O₄ [123-99-9]

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

290–325

A_cons

−50.0612

B_cons

−1376.49

C_cons

9.0402

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both sets of data were determined by gravimetry.^15,26 The stated uncertainties

in T were 0.1 K or better.

Consensus values at integral temperatures

T (K)

295

305

315

325

ln x_1,cons ± u(ln x₁)

−3.32 ± 0.21

−2.86 ± 0.16

−2.43 ± 0.10

−2.01 ± 0.03

τ

0.28

0.22

0.14

0.04

x_1,cons ± u(x₁)%

0.036 ± 21%

0.057 ± 16%

0.088 ± 9.9%

0.134 ± 3.3%

Evaluation:

Data between 288 and 326 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

²⁶B. Long, T. Li, Y. Xia, X. Y. Li, and Y. Ding, J. Mol. Liq. 272, 930 (2018).

2.14. Evaluation of the solubility data for pentanedioic acid in oxepan-2-one

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Oxepan-2-one (ε-caprolactone), C₆H₁₀O₂ [502-44-3]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

295–325

A_cons

159.446

B_cons

−9400.11

C_cons

−22.7158

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were determined by turbidometry with laser detection.^7,27

The quoted uncertainties in T were 0.12 K or less.

Consensus values at integral temperatures

T (K)

300

310

320

ln x_1,cons ± u(ln x₁)

−1.45 ± 0.1

−1.19 ± 0.06

−0.96 ± 0.05

τ

0.14

0.09

0.07

x_1,cons ± u(x₁)%

0.23 ± 10%

0.31 ± 6.8%

0.38 ± 5.2%

Evaluation:

Data between 296 and 329 K were included in the analysis.

Original measurements:

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

²⁷W. Luo, X. Li, D. Ruan, K. Xie, B. Tao, and C. Guo, J. Chem. Eng. Data 63, 298 (2018).

2.15. Evaluation of the solubility data for pentanedioic acid in trichloromethane

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Trichloromethane, CHCl₃ [67-66-3]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

305–325

A_cons

⋯

B_cons

⋯

C_cons

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

One data set was determined by titration of the saturated solutions²⁸

and the other was determined by gravimetry.²⁹ The reported

uncertainties in T were 0.1 K or less.

Evaluation:

The x₁ values reported by Sun et al. are approximately three times those reported by Zhang et al. within the temperature range where

there is overlap of the data sets. Thus, since at least one of the data sets must be significantly incorrect, it is impossible to evaluate

the solubilities in this system.

Original measurements:

²⁸X. Sun, K. Ren, Z. Mao, Z. Wang, and G. Liu, J. East China Univ. Sci. Technol. 33, 629 (2007).

²⁹S. Zhang and A. C. Rasmuson, Cryst. Growth Des. 13, 1153 (2013).

2.16. Evaluation of the solubility data for pentanedioic acid in methanol

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Methanol, CH₄O [67-56-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

295–325

A_cons

−173.493

B_cons

6300.66

C_cons

26.4947

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were determined by turbidometry using laser detection.^12,13

The quoted uncertainties in T were 0.13 K.

Consensus values at integral temperatures

T (K)

300

310

320

ln x_1,cons ± u(ln x₁)

−1.37 ± 0.02

−1.18 ± 0.02

−0.97 ± 0.04

τ

0.03

0.06

x_1,cons ± u(x₁)%

0.254 ± 1.8%

0.308 ± 2.4%

0.378 ± 3.9%

Evaluation:

Data between 293 and 322 K were included in the analysis.

Original measurements:

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

2.17. Evaluation of the solubility data for pentanedioic acid in ethanol

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

304–323

A_cons

334.045

B_cons

−18 473.0

C_cons

−48.0841

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

One data set was determined by titration of the saturated solutions²⁸ and the

other was determined by gravimetry.¹⁵ The reported uncertainties

in T were 0.1 K or less.

Consensus values at integral temperatures

T (K)

300

310

320

ln x_1,cons ± u(ln x₁)

−1.79 ± 0.1

−1.38 ± 0.03

−1.04 ± 0.08

τ² (τ)

0.14

0.04

0.11

x_1,cons ± u(x₁)%

0.17 ± 10%

0.25 ± 3.1%

0.35 ± 7.8%

Evaluation:

Only data between 304 and 326 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

²⁸X. Sun, K. Ren, Z. Mao, Z. Wang, and G. Liu, J. East China Univ. Sci. Technol. 33, 629 (2007).

2.18. Evaluation of the solubility data for pentanedioic acid in cyclohexanol

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Cyclohexanol, C₆H₁₂O [108-93-0]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

305–335

A_cons

1477.15

B_cons

11.7888

C_cons

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

One data set was determined by titration of the solute³⁰ and the other was

determined by turbidometry with laser detection.¹⁹ The quoted

uncertainties in T were 0.05 K.

Consensus values at integral temperatures

T (K)

300

315

330

345

ln x_1,cons ± u(ln x₁)

−1.57 ± 0.02

−1.23 ± 0.02

−0.88± 0.02

−0.544 ± 0.04

τ² (τ)

0.02

0.03

0.02

0

x_1,cons ± u(x₁)%

0.2.08 ± 1.6%

0.292 ± 2.1%

0.412 ± 1.5%

0.581 ± 0.4%

Evaluation:

Only data between 305 and 345 K were included in the analysis.

Original measurements:

¹⁹W. Luo, M. Yan, X.-X. Sheng, B. Tao, S. Shi, W. Deng, W. Yang, and S. Luo, Ind. Eng. Chem. Res. 58, 10018 (2019).

³⁰W. Song, P. Ma, L. Fan, and Z. Xiang, Chin. J. Chem. Eng. 15, 228 (2007).

2.19. Evaluation of the solubility data for pentanedioic acid in propanone

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

285–325

A_cons

−54.987 1

B_cons

477.215

C_cons

9.108 21

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The data were determined by titration²⁸ and gravimetry¹⁵ of saturated

solutions. The quoted uncertainties in T were 0.05 K.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−1.69 ± 0.04

−1.45 ± 0.03

−1.21 ± 0.01

−0.93 ± 0.01

τ

0.06

0.03

0.004

0

x_1,cons ± u(x₁)%

0.18 ± 4.2%

0.235 ± 2.6%

0.299 ± 0.7%

0.385 ± 0.6%

Evaluation:

All data were included in the analysis. There is a clear anomaly in the Zhang et al.¹⁵ datum at 308.15 K, but this was retained in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

²⁸X. Sun, K. Ren, Z. Mao, Z. Wang, and G. Liu, J. East China Univ. Sci. Technol. 33, 629 (2007).

2.20. Evaluation of the solubility data for pentanedioic acid in cyclohexanone

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

295–335

A_cons

−122.059

B_cons

3277.60

C_cons

19.1876

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

All data were determined by turbidometry with laser detection.^7,12,13,30

The reported uncertainties in T were 0.13 K or less.

Consensus values at integral temperatures

T (K)

295

305

315

325

ln x_1,cons ± u(ln x₁)

−1.83 ± 0.02

−1.56 ± 0.02

−1.28 ± 0.01

−0.993± 0.003

τ

0.04

0.02

0

x_1,cons ± u(x₁)%

0.160 ± 2.1%

0.210 ± 1.9%

0.279 ± 1.1%

0.370 ± 0.3%

Evaluation:

Only data between 294 and 336 K were included in the analysis.

Original measurements:

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

³⁰W. Song, P. Ma, L. Fan, and Z. Xiang, Chin. J. Chem. Eng. 15, 228 (2007).

2.21. Evaluation of the solubility data for pentanedioic acid in ethanoic acid

Components:

(1) Pentanedioic acid (glutaric acid), C₅H₈O₄ [110-94-1]

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

290–340

A_cons

−66.3553

B_cons

1055.65

C_cons

10.7431

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

One data set¹⁵ was measured by gravimetry and the other five were measured

by turbidometry with laser detection.^{19,23,24,27,30} The quoted uncertainties

in T were 0.14 K or less.

Consensus values at integral temperatures

T (K)

295

310

325

340

ln x_1,cons ± u(ln x₁)

−1.68 ± 0.04

−1.32 ± 0.02

−0.97 ± 0.01

−0.62 ± 0.01

τ

0.08

0.03

0.02

x_1,cons ± u(x₁)%

0.186 ± 3.6%

0.266 ± 1.4%

0.379 ± 1.0%

0.539 ± 1.1%

Evaluation:

Data between 292 and 342 K were included in the analysis. References 24 and 27 report the same data; only one of these was included

in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

¹⁹W. Luo, M. Yan, X.-X. Sheng, B. Tao, S. Shi, W. Deng, W. Yang, and S. Luo, Ind. Eng. Chem. Res. 58, 10018 (2019).

²³W. Luo, M. Yan. B. Tao, S. Shi, and B. Chen, J. Chem. Thermodyn. 138, 332 (2019).

²⁴W. Luo, X. Li, D. Ruan, D. Liu, K. Xie, J. Wang, W. Deng, Q. Liu, and Z. Chen, J. Chem. Eng. Data 62, 1269 (2017).

²⁷W. Luo, X. Li, D. Ruan, K. Xie, B. Tao, and C. Guo, J. Chem. Eng. Data 63, 298 (2018).

³⁰W. Song, P. Ma, L. Fan, and Z. Xiang, Chin. J. Chem. Eng. 15, 228 (2007).

2.22. Evaluation of the solubility data for (±) hydroxybutanedioic acid in ethanol

Components:

(1) (±) Hydroxybutanedioic acid (malic acid), C₄H₆O₅ [6915-15-7]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

300–333

A_cons

130.307

B_cons

−7863.00

C_cons

−18.6696

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were determined by gravimetry.^31,32 The quoted uncertainties

in T were 0.1 K or less.

Consensus values at integral temperatures

T (K)

300

310

320

330

ln x_1,cons ± u(ln x₁)

−2.39 ± 0.21

−2.16 ± 0.19

−1.96 ± 0.20

−1.79 ± 0.24

τ

0.30

0.26

0.28

0.34

x_1,cons ± u(x₁)%

0.09 ± 21%

0.12 ± 19%

0.14 ± 20%

0.17 ± 24%

Evaluation:

All data were included in the analysis.

Original measurements:

³¹A. Daneshfar, M. Baghlani, R. S. Sarabi, R. Sahraei, S. Abassi, H. Kaviyan, and T. Khezeli, Fluid Phase Equilib. 313, 11 (2012).

³²Y. Yuan, Y. Leng, H. Shao, C. Huang, and K. Shan, Fluid Phase Equilib. 377, 27 (2014).

2.23. Evaluation of the solubility data for propanedioic acid in ethanol

Components:

(1) Propanedioic acid (malonic acid), C₃H₄O₄ [141-82-2]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

303–323

A_cons

56.607 1

B_cons

−4225.73

C_cons

−7.869 01

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

All three data sets were determined by gravimetry.^15,31,33 The quoted

uncertainties in T were 0.1 K or less.

Consensus values at integral temperatures

T (K)

305

315

325

ln x_1,cons ± u(ln x₁)

−2.27± 0.05

−2.08 ± 0.03

−1.90 ± 0.02

τ

0.08

0.04

0.03

x_1,cons ± u(x₁)%

0.104 ± 5.3%

0.125 ± 3.0%

0.150 ± 2.4%

Evaluation:

The values of the data of Yu et al.³³ are around three times those of the other two data sets and were excluded from the analysis.

Data between 303 and 323 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³¹A. Daneshfar, M. Baghlani, R. S. Sarabi, R. Sahraei, S. Abassi, H. Kaviyan, and T. Khezeli, Fluid Phase Equilib. 313, 11 (2012).

³³X. Yu, W. Wu, J. Wang, and J. Ulrich, Chem. Eng. Technol. 41, 1098 (2018).

2.24. Evaluation of the solubility data for propanedioic acid in propanone

Components:

(1) Propanedioic acid (malonic acid), C₃H₄O₄ [141-82-2]

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

⋯

A_cons

⋯

B_cons

⋯

C_cons

⋯

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were measured by gravimetry. The quoted uncertainties

in T were 0.1 K or less.

Evaluation:

The data reported by Zhang et al.¹⁵ are approximately about 0.14 mole fraction higher than those of Yu et al.³³

Thus, since at least one of the data sets must be significantly incorrect, it is impossible to evaluate the solubilities in this system.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³³X. Yu, W. Wu, J. Wang, and J. Ulrich, Chem. Eng. Technol. 41, 1098 (2018).

2.25. Evaluation of the solubility data for propanedioic acid in ethanenitrile

Components:

(1) Propanedioic acid (malonic acid), C₃H₄O₄ [141-82-2]

(2) Ethanenitrile, C₂H₃N [75-05-8]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

303–313

A_cons

⋯

B_cons

⋯

C_cons

⋯

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

All data were determined by gravimetry.^31,33 The quoted

uncertainties in T were 0.1 K.

Evaluation:

There is only an overlap of three data points from each data set, which is too few for a meaningful analysis, so the data were not analyzed.

Original measurements:

³¹A. Daneshfar, M. Baghlani, R. S. Sarabi, R. Sahraei, S. Abassi, H. Kaviyan, and T. Khezeli, Fluid Phase Equilib. 313, 11 (2012).

³³X. Yu, W. Wu, J. Wang, and J. Ulrich, Chem. Eng. Technol. 41, 1098 (2018).

2.26. Evaluation of the solubility data for heptanedioic acid in ethanol

Components:

(1) Heptanedioic acid (pimelic acid), C₇H₁₂O₄ [111-16-0]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

298–323

A_cons

39.648 0

B_cons

−4467.76

C_cons

−4.713 79

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The data sere determined by turbidometry³⁴ and gravimetry.¹⁵

The quoted uncertainties in T were 0.1 K or less.

Consensus values at integral temperatures

T (K)

300

310

320

ln x_1,cons ± u(ln x₁)

−2.13 ± 0.06

−1.81± 0.05

−1.51 ± 0.04

τ

0.08

0.07

0.05

x_1,cons ± u(x₁)%

0.119 ± 5.7%

0.164 ± 4.9%

0.223 ± 3.5%

Evaluation:

Data between 298 and 326 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³⁴H. Li, J. Liu, J. Zhu, L. Zhao, H. Wang, and Y. Zhang, Russ. J. Phys. Chem. A 86, 314 (2012).

2.27. Evaluation of the solubility data for decanedioic acid in ethanol

Components:

(1) Decanedioic acid (sebacic acid), C₁₀H₁₈O₄ [111-20-6]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–323

A_cons

−125.521

B_cons

2015.79

C_cons

20.1566

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The data were measured by turbidometry with laser detection³⁵

and gravimetry.¹⁵ The quoted uncertainties in T were 0.1 K or less

(Ref. 15 reports ±1 K; however, in other papers by the authors, the

reported uncertainty in the temperature was ±0.1 K).

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−4.28 ± 0.09

−3.83± 0.03

−3.39 ± 0.01

−2.95 ± 0.03

τ

0.12

0.04

0.008

0.03

x_1,cons ± u(x₁)%

0.014 ± 8.8%

0.022 ± 3.2%

0.034 ± 0.9%

0.052 ± 2.5%

Evaluation:

Data between 288 and 326 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³⁵Q. Xia, F.-B. Zhang, G.-L. Zhang, J.-C. Ma, and L. Zhao, J. Chem. Eng. Data 53, 838 (2008).

2.28. Evaluation of the solubility data for octanedioic acid in ethyl ethanoate

Components:

(1) Octanedioic acid (suberic acid), C₈H₁₄O₄ [505-48-6]

(2) Ethyl ethanoate, C₄H₈O₂ [141-78-6]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–323

A_cons

−9.465 38

B_cons

−3599.38

C_cons

2.795 87

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both sets of data were determined by gravimetry.^15,36

The quoted uncertainties in T were 0.05 K for both data sets.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−6.02 ± 0.07

−5.52 ± 0.07

−5.04 ± 0.05

−4.58 ± 0.02

τ

0.10

0.07

0.02

x_1,cons ± u(x₁)%

0.0024 ± 7.4%

0.0040 ± 7.1%

0.0065 ± 5.2%

0.0101 ± 1.9%

Evaluation:

Data between 288 and 325 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³⁶Q. Yu, X. Ma, and W. Gao, Fluid Phase Equilib. 330, 44 (2012).

2.29. Evaluation of the solubility data for octanedioic acid in ethanol

Components:

(1) Octanedioic acid (suberic acid), C₈H₁₄O₄ [505-48-6]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–323

A_cons

−58.4065

B_cons

−624.925

C_cons

10.0032

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were measured by gravimetry.^15,36 The quoted uncertainties

in T were 0.05 K in both cases.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−3.84 ± 0.05

−3.43₉ ± 0.003

−3.03₈ ± 0.003

−2.66 ± 0.03

τ

0.06

0

0.04

x_1,cons ± u(x₁)%

0.021 ± 4.6%

0.0321 ± 0.3%

0.047₉ ± 0.3%

0.070 ± 2.9%

Evaluation:

Data between 288 and 325 K were analyzed.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³⁶Q. Yu, X. Ma, and W. Gao, Fluid Phase Equilib. 330, 44 (2012).

2.30. Evaluation of the solubility data for octanedioic acid in propanone

Components:

(1) Octanedioic acid (suberic acid), C₈H₁₄O₄ [505-48-6]

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–323

A_cons

186.241

B_cons

−12 044.7

C_cons

−26.3474

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were measured by gravimetry.^15,36 The quoted

uncertainties in T were 0.05 K in both cases.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−4.68 ± 0.13

−4.19 ± 0.17

−3.76 ± 0.15

−3.38 ± 0.07

τ

0.17

0.24

0.21

0.010 (0.10)

x_1,cons ± u(x₁)%

0.0093 ± 13%

0.015 ± 17%

0.023 ± 15%

0.034 ± 7.4%

Evaluation:

Data between 288 and 324 K were included in the analysis.

Original measurements:

¹⁵ H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³⁶Q. Yu, X. Ma, and W. Gao, Fluid Phase Equilib. 330, 44 (2012).

2.31. Evaluation of the solubility data for butanedioic acid in oxepan-2-one

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) Oxepan-2-one (ε-caprolactone), C₆H₁₀O₂ [502-44-3]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

298–328

A_cons

108.984

B_cons

−8555.81

C_cons

−14.8218

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were measured by turbidometry with laser detection.^7,27

The quoted uncertainties in T were 0.13 K or better.

Consensus values at integral temperatures

T (K)

300

310

320

330

ln x_1,cons ± u(ln x₁)

−4.08 ± 0.03

−3.64 ± 0.02

−3.25 ± 0.02

−2.90 ± 0.01

τ

0.04

0.03

0.02

x_1,cons ± u(x₁)%

0.017 ± 2.5%

0.026 ± 2.4%

0.039 ± 2.0%

0.055 ± 1.3%

Evaluation:

Data from 298 to 333 K were included in the analysis.

Original measurements:

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

²⁷W. Luo, X. Li, D. Ruan, K. Xie, B. Tao, and C. Guo, J. Chem. Eng. Data 63, 298 (2018).

2.32. Evaluation of the solubility data for butanedioic acid in methanol

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) Methanol, CH₄O [67-56-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

293–324

A_cons

−41.153 1

B_cons

−141.675

C_cons

6.783 55

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were measured by turbidometry with laser detection.^12,13

The quoted uncertainties in T were 0.13 K in both cases.

Consensus values at integral temperatures

T (K)

295

305

315

325

ln x_1,cons ± u(ln x₁)

−3.06 ± 0.02

−2.81₃ ± 0.004

−2.58 ± 0.01

−2.35 ± 0.03

τ

0.02

0

0.01

0.05

x_1,cons ± u(x₁)%

0.047 ± 1.6%

0.060₀ ± 0.4%

0.076 ± 0.9%

0.095 ± 3.3%

Evaluation:

Data between 290 and 327 K were included in the analysis.

Original measurements:

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

2.33. Evaluation of the solubility data for butanedioic acid in ethanol

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–332

A_cons

−252.875

B_cons

9098.08

C_cons

38.4884

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The data were determined by turbidometry with laser detection,^37,38

gravimetry,^15,39 and gas chromatographic analysis of saturated solutions.⁴⁰

The quoted uncertainties in T were 0.1 K or better.

Consensus values at integral temperatures

T (K)

295

305

315

325

ln x_1,cons ± u(ln x₁)

−3.15 ± 0.1

−2.88 ± 0.07

−2.58 ± 0.07

−2.27 ± 0.1

τ

0.19

0.13

0.14

0.22

x_1,cons ± u(x₁)%

0.043 ± 9.5%

0.056 ± 6.7%

0.075 ± 6.9%

0.10 ± 10.9%

Evaluation:

Data between 283 and 334 K were included in the analysis. Xu et al.⁴⁰ reported data at only two temperatures,

and so these data were not analyzed; the data points are included on the graph.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³⁷Q. Yu, S. Black, and H. Wei, J. Chem. Eng. Data 54, 2123 (2009).

³⁸Y.-H. Hu, Z-G. Chen, W.-G. Yang, Y. Shi, H.-L. Sun, and Y.-L. Li, J. Solution Chem. 42, 102 (2013).

³⁹M. L. N. Oliveira and M. R. Franco, Jr., Fluid Phase Equilib. 326, 50 (2012).

⁴⁰S. Xu, L. Dang, and H. Wei, J. Chem. Eng. Data 56, 2746 (2011).

2.34. Evaluation of the solubility data for butanedioic acid in 1-propanol

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) 1-Propanol, C₃H₈O [71-23-8]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–323

A_cons

−495.672

B_cons

19 740.2

C_cons

74.7333

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Data were determined by gravimetry³⁹ and turbidometry with laser

detection.³⁷ The quoted uncertainties in T were 0.05 K in both cases.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−3.88 ± 0.03

−3.61 ± 0.01

−3.28 ± 0.07

−2.90 ± 0.1

τ

0

0.09

0.20

x_1,cons ± u(x₁)%

0.020 ± 3.2%

0.027 ± 1.4%

0.038 ± 6.6%

0.055 ± 14%

Evaluation:

Data from 298 to 334 K were included in the analysis.

Original measurements:

³⁷Q. Yu, S. Black, and H. Wei, J. Chem. Eng. Data 54, 2123 (2009).

³⁹M. L. N. Oliveira and M. R. Franco, Jr., Fluid Phase Equilib. 326, 50 (2012).

2.35. Evaluation of the solubility data for butanedioic acid in cyclohexanol

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) Cyclohexanol, C₆H₁₂O [108-93-0]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

307–346

A_cons

218.400

B_cons

−13 415.6

C_cons

−31.1367

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

Both data sets were measured by turbidometry with laser detection.^20,41

The quoted uncertainties in T were 0.12 K or better.

Consensus values at integral temperatures

T (K)

310

320

330

340

ln x_1,cons ± u(ln x₁)

−3.49 ± 0.24

−3.13 ± 0.16

−2.82 ± 0.14

−2.55 ± 0.08

τ

0.34

0.23

0.17

0.12

x_1,cons ± u(x₁)%

0.030 ± 24%

0.044 ± 17%

0.060 ± 12%

0.078 ± 8.3%

Evaluation:

Data between 307 and 350 K were included in the analysis.

Original measurements:

²⁰W. Luo, M. Yan, X.-X. Sheng, B. Tao, S. Shi, W. Deng, W. Yang, and S. Luo, Ind. Eng. Chem. Res. 58, 10018 (2019).

⁴¹W. W. Song, P.-S. Ma, and Z.-L. Xiang, J. Chem. Eng. Chin. Univ. 21, 341 (2007).

2.36. Evaluation of the solubility data for butanedioic acid in propanone

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

288–320

A_cons

−22.561 2

B_cons

−1247.36

C_cons

3.979 18

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The data were determined by turbidometry with laser detection,^31,37 analysis

of the equilibrated solution by high-performance liquid chromatography,⁴⁰

and gravimetry.¹⁵ The quoted uncertainties in T were 0.1 K or better.

Consensus values at integral temperatures

T (K)

290

300

310

320

ln x_1,cons ± u(ln x₁)

−4.30 ± 0.03

−4.02 ± 0.03

−3.76 ± 0.04

−3.51 ± 0.06

τ

0.06

0.08

0.10

x_1,cons ± u(x₁)%

0.014 ± 3.4%

0.018 ± 3.3%

0.023± 4.4%

0.030 ± 5.7%

Evaluation:

Only data between 287 and 319 K were included in the analysis. Xu et al.⁴⁰ report only two data points,

and these were not included in the analysis but are shown on the graph.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

³¹Y. Li, Y. Wang, Z. Ning, J. Gui, Q. Wu, and X. Wang, J. Chem. Eng. Data 59, 4062 (2014).

³⁷Q. Yu, S. Black, and H. Wei, J. Chem. Eng. Data 54, 2123 (2009).

⁴⁰S. Xu, L. Dang, and H. Wei, J. Chem. Eng. Data 56, 2746 (2011).

2.37. Evaluation of the solubility data for butanedioic acid in cyclohexanone

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

295–340

A_cons

134.724

B_cons

−9456.61

C_cons

−18.8689

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

where T is expressed in K.

Comments:

All data sets were measured by turbidometry with laser

detection.^{7,12,13,24,27,41} The quoted uncertainties in T were 0.13 K or better.

Consensus values at integral temperatures

T (K)

295

310

325

340

ln x_1,cons ± u(ln x₁)

−4.64 ± 0.05

−4.02 ± 0.02

−3.51 ± 0.02

−3.08₃ ± 0.006

τ

0.09

0.03

0.007

x_1,cons ± u(x₁)%

0.0097 ± 4.7%

0.018 ± 1.6%

0.029 ± 1.7%

0.046 ± 0.6%

Evaluation:

Two data sets were reported twice (Refs. 12 and 24 and Refs. 13 and 27) but were included only once in the analysis.

Data between 293 and 341 K were included in the analysis.

Original measurements:

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

²⁴W. Luo, X. Li, D. Ruan, D. Liu, K. Xie, J. Wang, W. Deng, Q. Liu, and Z. Chen, J. Chem. Eng. Data 62, 1269 (2017).

²⁷W. Luo, X. Li, D. Ruan, K. Xie, B. Tao, and C. Guo, J. Chem. Eng. Data 63, 298 (2018).

⁴¹W. W. Song, P.-S. Ma, and Z.-L. Xiang, J. Chem. Eng. Chin. Univ. 21, 341 (2007).

2.38. Evaluation of the solubility data for butanedioic acid in ethanoic acid

Components:

(1) Butanedioic acid (succinic acid), C₄H₆O₄ [110-15-6]

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

290–345

A_cons

−8.245 83

B_cons

−2245.17

C_cons

2.019 97

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The solubilities were determined by turbidometry with laser

detection,^{20,23,24,27,37,41} analysis of saturated solutions by high-performance

liquid chromatography,⁴² and gravimetry.¹⁵ The quoted uncertainties in T

were 0.12 K or better.

Consensus values at integral temperatures

T (K)

295

310

325

340

ln x_1,cons ± u(ln x₁)

−4.36 ± 0.06

−3.90 ± 0.03

−3.47 ± 0.01

−3.05 ± 0.02

τ

0.15

0.08

0.02

0.06

x_1,cons ± u(x₁)%

0.013 ± 5.7%

0.020 ± 3.1%

0.031 ± 0.7%

0.047 ± 2.2%

Evaluation:

Two papers from the same authors^24,27 report solubilities at the same temperatures but marginally different solubilities.

It was assumed that the later data set²⁷ reported corrected solubilities and was included in the analysis, while the earlier set²⁴

was excluded. Data in the range 288–347 K were included in the analysis.

Original measurements:

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

²⁰W. Luo, M. Yan, X.-X. Sheng, B. Tao, S. Shi, W. Deng, W. Yang, and S. Luo, Ind. Eng. Chem. Res. 58, 10018 (2019).

²³W. Luo, M. Yan. B. Tao, S. Shi, and B. Chen, J. Chem. Thermodyn. 138, 332 (2019).

²⁴W. Luo, X. Li, D. Ruan, D. Liu, K. Xie, J. Wang, W. Deng, Q. Liu, and Z. Chen, J. Chem. Eng. Data 62, 1269 (2017).

²⁷W. Luo, X. Li, D. Ruan, K. Xie, B. Tao, and C. Guo, J. Chem. Eng. Data 63, 298 (2018).

³⁷Q. Yu, S. Black, and H. Wei, J. Chem. Eng. Data 54, 2123 (2009).

⁴¹W. W. Song, P.-S. Ma, and Z.-L. Xiang, J. Chem. Eng. Chin. Univ. 21, 341 (2007).

⁴²F. Lei, Q. Wang, X. Gong, B. Shen, W. Zhang, and Q. Han, J. Chem. Eng. Data 59, 1714 (2014).

2.39. Evaluation of the solubility data for (R,R)-(±)-2,3-dihydroxybutanedioc acid in ethanol

Components:

(1) (R*,R*)-(±)-2,3-Dihydroxybutanedioc acid (DL-tartaric acid), C₄H₆O₆ [133-37-9]

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Waghorne

Temperature range ΔT (K)

⋯

A_cons

⋯

B_cons

⋯

C_cons

⋯

\ln x_{1, c o n s} = A_{cons} + \frac{B_{cons}}{T} + C_{cons} \ln T

⁠, where T is expressed in K.

Comments:

The solubilities were determined by turbidometry⁴³ with laser

detection and titration of saturated solutions.⁴⁴ The quoted

uncertainties in T were 0.1 K or better.

Evaluation:

The data reported by Tan et al.⁴⁴ are approximately three times those of Li et al.⁴³ Thus, since at least one of the data

sets must be significantly incorrect, it is impossible to evaluate the solubilities in this system.

Original measurements:

⁴³Q. S. Li, Z. D. Feng, Y. Zhao, and B. H. Wang, J. Beijing Univ. Chem. Technol. 39, 6 (2012).

⁴⁴Q. Tan, Y. Leng, J. Wang, C. Huang, and Y. Yan, J. Mol. Liq. 216, 476 (2016).

3. Solubility of Hexanedioic Acid in Organic Solvents

Hexanedioic acid (also called adipic acid) is a valuable chemical reagent used in the manufacture of nylon-66 through the polycondensation reaction with hexamethylene diamine, and it is a monomer for the production of polyurethane. Hexanedioic acid is used in controlled-release drug formulations in order to achieve a pH-dependent release of both weakly acidic and weakly basic drug molecules,^45,46 and like other alkanedioic acids, it is known to form cocrystals with several active pharmaceutical ingredients.^47–49 Cocrystals provide a means to increase the solubility and oral bioavailability of poorly water-soluble drugs that lack functional groups capable of salt formation.

The experimental solubility data for hexanedioic acid dissolved in organic mono-solvents and aqueous–organic solvent mixtures are given in Secs. 3.1–3.9.

3.1. Hexanedioic acid solubility data in aromatic hydrocarbons

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁹D. Wei and W. Cao, J. Chem. Eng. Data 54, 152 (2009).

(2) Methylbenzene, C₇H₈ [108-88-3]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
298.15	0.9999	0.000 045 3
300.15	0.9999	0.000 056 4
302.15	0.9999	0.000 071 6
304.15	0.9999	0.000 094 1
306.15	0.9999	0.000 114
308.15	0.9999	0.000 146
310.15	0.9998	0.000 182
312.15	0.9998	0.000 223
314.15	0.9997	0.000 268
316.15	0.9997	0.000 324
318.15	0.9996	0.000 391
323.15	0.9994	0.000 614
328.15	0.9990	0.000 959
333.15	0.9985	0.001 46

Experimental values
T (K)	x₂a	x₁b
298.15	0.9999	0.000 045 3
300.15	0.9999	0.000 056 4
302.15	0.9999	0.000 071 6
304.15	0.9999	0.000 094 1
306.15	0.9999	0.000 114
308.15	0.9999	0.000 146
310.15	0.9998	0.000 182
312.15	0.9998	0.000 223
314.15	0.9997	0.000 268
316.15	0.9997	0.000 324
318.15	0.9996	0.000 391
323.15	0.9994	0.000 614
328.15	0.9990	0.000 959
333.15	0.9985	0.001 46

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Constant temperature water bath, water-jacketed glass equilibrium vessel, analytical balance, and magnetic stirrer.

Solubilities were determined by a static analytical method. The solvent and excess solute were placed in a water-jacketed glass equilibrium vessel and allowed to equilibrate in a constant temperature bath with stirring for at least three days. An aliquot of the clear saturated solution was withdrawn and the concentration of the dissolved acid was determined by acid–base titration using an aqueous sodium hydroxide solution. The attainment of equilibrium was verified by repetitive measurements after three additional days of equilibration and by approaching equilibrium from supersaturation by pre-equilibrating the solutions at a higher temperature. The reported solubility represented the average of five independent determinations.

Source and Purity of Chemicals:

(1) Purity not given, Beijing Qingshengda Chemical Technology Company, Ltd., Beijing, China, was recrystallized twice from water and dried at 393 K prior to use.

(2) 99.96%, Analytical grade, Tianjin Kewei Chemical Reagent Company, China, was refluxed over freshly activated calcium oxide for 2 h, and then fractionally distilled and stored over freshly activated molecular sieves prior to use. Solvent purity determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±1.2% (relative error).

3.2. Hexanedioic acid solubility data in esters

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

(2) Ethyl ethanoate, C₄H₈O₂ [141-78-6]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁a
288.15	0.9981	0.001 858
293.15	0.9963	0.003 679
298.15	0.9950	0.004 964
303.15	0.9933	0.006 707
308.15	0.9914	0.008 552
315.15	0.9896	0.010 41
318.15	0.9882	0.011 82
323.15	0.9857	0.014 28

Experimental values
T (K)	x₂a	x₁a
288.15	0.9981	0.001 858
293.15	0.9963	0.003 679
298.15	0.9950	0.004 964
303.15	0.9933	0.006 707
308.15	0.9914	0.008 552
315.15	0.9896	0.010 41
318.15	0.9882	0.011 82
323.15	0.9857	0.014 28

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Analytical balance, magnetic stirrer, dual-wall flask, and a thermostatically controlled constant temperature bath.

Solubilities were determined by a gravimetric method. The solvent and excess solute were placed in a specially designed sealed dual-wall flask and allowed to equilibrate in a constant temperature bath with stirring. The stirring was later discontinued and the suspended solid allowed to settle to the bottom of the flask. A clear aliquot of the saturated solution was removed, filtered, and then transferred to a tared container. The container and its contents were weighed. The solvent was evaporated, and the solubility determined from the mass of the solid residue and mass of the sample analyzed. The reported value represented the average of three measurements.

Source and Purity of Chemicals:

99%, Tianjin Xi’ensi Company Ltd., China, no purification details given in Ref. 15.
99.5%, Analytical Reagent grade, Tianjin Kewei Chemical Company, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

(2) Dimethyl hexanedioate (dimethyl adipate), C₈H₁₄O₄ [627-93-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
293.15	0.9955	0.0045
298.15	0.9947	0.0053
303.15	0.9937	0.0063
308.15	0.9928	0.0072
313.15	0.9908	0.0092
318.15	0.9885	0.0115
323.15	0.9860	0.0140

Experimental values
T (K)	x₂a	x₁b
293.15	0.9955	0.0045
298.15	0.9947	0.0053
303.15	0.9937	0.0063
308.15	0.9928	0.0072
313.15	0.9908	0.0092
318.15	0.9885	0.0115
323.15	0.9860	0.0140

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.13 K.

x₁: ±0.10 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

(2) Dimethyl pentanedioate (dimethyl glutarate), C₇H₁₂O₄ [1119-40-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
294.15	0.9963	0.0037
299.15	0.0057	0.0047
305.65	0.9935	0.0065
311.35	0.9921	0.0079
315.25	0.9903	0.0097
320.35	0.9879	0.0121
325.05	0.9855	0.0145
328.05	0.9833	0.0167
331.35	0.9807	0.0193
334.25	0.9776	0.0224
337.35	0.9737	0.0263

Experimental values
T (K)	x₂a	x₁b
294.15	0.9963	0.0037
299.15	0.0057	0.0047
305.65	0.9935	0.0065
311.35	0.9921	0.0079
315.25	0.9903	0.0097
320.35	0.9879	0.0121
325.05	0.9855	0.0145
328.05	0.9833	0.0167
331.35	0.9807	0.0193
334.25	0.9776	0.0224
337.35	0.9737	0.0263

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 125-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.13 K.

x₁: ±0.10 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

(2) ε-Caprolactone, C₆H₁₀O₂ [502-44-3]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
290.15	0.9891	0.0109
296.35	0.9861	0.0139
302.05	0.9827	0.0173
306.35	0.9793	0.0207
310.35	0.9759	0.0241
314.05	0.9724	0.0276
319.95	0.9654	0.0346
324.45	0.9576	0.0424
329.15	0.9486	0.0514
334.15	0.9373	0.0627

Experimental values
T (K)	x₂a	x₁b
290.15	0.9891	0.0109
296.35	0.9861	0.0139
302.05	0.9827	0.0173
306.35	0.9793	0.0207
310.35	0.9759	0.0241
314.05	0.9724	0.0276
319.95	0.9654	0.0346
324.45	0.9576	0.0424
329.15	0.9486	0.0514
334.15	0.9373	0.0627

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.12 K.

x₁: ±0.04 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁸W. Luo, D. Ruan, D. Liu, K. Xie, X. Li, W. Deng, and C. Guo, J. Chem. Eng. Data 61, 2474 (2016).

(2) ε-Caprolactone, C₆H₁₀O₂ [502-44-3]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
306.05	0.9746	0.0254
310.15	0.9691	0.0309
314.35	0.9633	0.0367
317.55	0.9568	0.0432
321.05	0.9500	0.0500
323.95	0.9430	0.0570
327.35	0.9358	0.0642
330.45	0.9283	0.0717
332.65	0.9208	0.0792
335.35	0.9127	0.0873

Experimental values
T (K)	x₂a	x₁b
306.05	0.9746	0.0254
310.15	0.9691	0.0309
314.35	0.9633	0.0367
317.55	0.9568	0.0432
321.05	0.9500	0.0500
323.95	0.9430	0.0570
327.35	0.9358	0.0642
330.45	0.9283	0.0717
332.65	0.9208	0.0792
335.35	0.9127	0.0873

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.10 (relative error).

3.3. Hexanedioic acid solubility data in ethers

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) 1,4-Dioxane, C₄H₈O₂ [123-91-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
283.15	0.9758	0.0242
293.15	0.9653	0.0347
303.15	0.9513	0.0487
313.15	0.9330	0.0670
333.15	0.8785	0.1215

Experimental values
T (K)	x₂a	x₁b
283.15	0.9758	0.0242
293.15	0.9653	0.0347
303.15	0.9513	0.0487
313.15	0.9330	0.0670
333.15	0.8785	0.1215

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glassstopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was stored over potassium hydroxide for two weeks, refluxed over sodium metal for one day, and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

3.4. Hexanedioic acid solubility data in haloalkanes, haloalkenes, and haloaromatic hydrocarbons

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁹D. Wei and W. Cao, J. Chem. Eng. Data 54, 152 (2009).

(2) Trichloromethane, CHCl₃ [67-66-3]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
298.15	0.9979	0.002 095
300.15	0.9978	0.002 205
302.15	0.9977	0.002 308
304.15	0.9975	0.002 450
306.15	0.9974	0.002 590
308.15	0.9973	0.002 725
310.15	0.9971	0.002 858
312.15	0.9970	0.002 994
314.15	0.9969	0.003 141
316.15	0.9967	0.003 262
318.15	0.9966	0.003 402
323.15	0.9962	0.003 767

Experimental values
T (K)	x₂a	x₁b
298.15	0.9979	0.002 095
300.15	0.9978	0.002 205
302.15	0.9977	0.002 308
304.15	0.9975	0.002 450
306.15	0.9974	0.002 590
308.15	0.9973	0.002 725
310.15	0.9971	0.002 858
312.15	0.9970	0.002 994
314.15	0.9969	0.003 141
316.15	0.9967	0.003 262
318.15	0.9966	0.003 402
323.15	0.9962	0.003 767

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Constant temperature water bath, water-jacketed glass equilibrium vessel, analytical balance, and magnetic stirrer.

Solubilities were determined by a static analytical method. The solvent and excess solute were placed in a water-jacketed glass equilibrium vessel and allowed to equilibrate in a constant temperature bath with stirring for at least three days. An aliquot of the clear saturated solution was withdrawn, and the concentration of the dissolved acid was determined by acid–base titration using an aqueous sodium hydroxide solution. The attainment of equilibrium was verified by repetitive measurements after three additional days of equilibration and by approaching equilibrium from supersaturation by pre-equilibrating the solutions at a higher temperature. The reported solubility represented the average of five independent determinations.

Source and Purity of Chemicals:

Purity not given, Beijing Qingshengda Chemical Technology Company, Ltd., Beijing, China, was recrystallized twice from water and dried at 393 K prior to use.
99.93%, Analytical grade, Tianjin Kewei Chemical Reagent Company, China, was refluxed over freshly activated calcium oxide for 2 h, and then fractionally distilled and stored over freshly activated molecular sieves prior to use. Solvent purity determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±1.2% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁰Z. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

(2) Trichloromethane, CHCl₃ [67-66-3]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
302.65	0.9976	0.002 370
306.35	0.9974	0.002 569
309.55	0.9972	0.002 806
313.45	0.9969	0.003 102
316.35	0.9967	0.003 304
319.70	0.9965	0.003 482
323.05	0.9962	0.003 819
326.70	0.9960	0.003 991
331.55	0.9955	0.004 509

Experimental values
T (K)	x₂a	x₁b
302.65	0.9976	0.002 370
306.35	0.9974	0.002 569
309.55	0.9972	0.002 806
313.45	0.9969	0.003 102
316.35	0.9967	0.003 304
319.70	0.9965	0.003 482
323.05	0.9962	0.003 819
326.70	0.9960	0.003 991
331.55	0.9955	0.004 509

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed glass dissolution flask equipped with a condenser to prevent solvent loss from evaporation, electronic balance, precision thermometer, constant temperature recirculating water bath, and magnetic mixer.

Solubilities were determined by a static method. The solvent and excess solute were placed in a 100-ml jacketed glass dissolution flask and allowed to equilibrate with stirring for 60–150 min. The stirring was then discontinued, and the solution was allowed to sit for 60–180 min so that the suspended solid could settle to the bottom of the flask. A known aliquot of the clear solution was removed. The concentration of the dissolved solute was determined by titration using a standardized sodium hydroxide solution with phenolphthalein as the indicator.

Source and Purity of Chemicals:

99.6%, chemical source not given, no purification details were provided in the paper.
Analytical Reagent grade, chemical source not given, no purification details were provided in Ref. 10.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2% (relative error, estimated by compiler).

3.5. Hexanedioic acid solubility data in alcohols

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii, and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) Methanol, CH₄O [67-56-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
273.15	0.9782	0.0218
283.15	0.9694	0.0306
293.15	0.9578	0.0422
303.15	0.9424	0.0576
313.15	0.9225	0.0775

Experimental values
T (K)	x₂a	x₁b
273.15	0.9782	0.0218
283.15	0.9694	0.0306
293.15	0.9578	0.0422
303.15	0.9424	0.0576
313.15	0.9225	0.0775

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was dried over Drierite for one day and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵⁰M. K. Chantooni and I. M. Kolthoff, J. Phys. Chem. 79, 1176 (1975).

(2) Methanol, CH₄O [67-56-1]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 1.12 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Very few experimental details were provided. Solubility was determined by titrating a filtered aliquot of the saturated solution alkalimetrically in an aqueous-ethanol mixture using phenolphthalein as the acid–base indicator.

Source and Purity of Chemicals:

99.5%, White Label, Eastman Kodak Chemical Company, Rochester, NY, USA, was dried for 2 h at 333 K before use. Purity determined by alkalimetric titration in water.
Purity not given, chemical source not given, was dehydrated and then distilled over sulfanilic acid to remove alkaline impurities.

Estimated Error:

Temperature: ±0.1 K.

c₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

(2) Methanol, CH₄O [67-56-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
284.85	0.9702	0.0298
288.95	0.9661	0.0339
291.45	0.9620	0.0380
296.45	0.9560	0.0440
299.45	0.9512	0.0488
302.95	0.9460	0.0540
306.95	0.9390	0.0610
309.55	0.9332	0.0668
313.55	0.9248	0.0752
318.65	0.9134	0.0866

Experimental values
T (K)	x₂a	x₁b
284.85	0.9702	0.0298
288.95	0.9661	0.0339
291.45	0.9620	0.0380
296.45	0.9560	0.0440
299.45	0.9512	0.0488
302.95	0.9460	0.0540
306.95	0.9390	0.0610
309.55	0.9332	0.0668
313.55	0.9248	0.0752
318.65	0.9134	0.0866

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99.9%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.13 K.

x₁: ±0.10 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

(2) Methanol, CH₄O [67-56-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
287.95	0.9659	0.0341
294.45	0.9590	0.0410
298.35	0.9523	0.0477
302.95	0.9459	0.0541
307.15	0.9395	0.0605
310.15	0.9332	0.0668
313.15	0.9266	0.0734
316.35	0.9196	0.0804
319.95	0.9124	0.0876
323.15	0.9043	0.0957
328.25	0.8906	0.1094

Experimental values
T (K)	x₂a	x₁b
287.95	0.9659	0.0341
294.45	0.9590	0.0410
298.35	0.9523	0.0477
302.95	0.9459	0.0541
307.15	0.9395	0.0605
310.15	0.9332	0.0668
313.15	0.9266	0.0734
316.35	0.9196	0.0804
319.95	0.9124	0.0876
323.15	0.9043	0.0957
328.25	0.8906	0.1094

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 125-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99.9%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.13 K.

x₁: ±0.10 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
273.15	0.9838	0.016 19
283.15	0.9788	0.021 2
293.15	0.9674	0.032 6
303.15	0.9547	0.045 3
313.15	0.9376	0.062 4
333.15	0.8854	0.114 6

Experimental values
T (K)	x₂a	x₁b
273.15	0.9838	0.016 19
283.15	0.9788	0.021 2
293.15	0.9674	0.032 6
303.15	0.9547	0.045 3
313.15	0.9376	0.062 4
333.15	0.8854	0.114 6

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was dried over Drierite for one day and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁰Z. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
302.00	0.9540	0.0460
304.90	0.9486	0.0514
309.65	0.9403	0.0597
311.55	0.9362	0.0638
315.40	0.9281	0.0719
318.70	0.9192	0.0808
321.35	0.9146	0.0854
325.25	0.9052	0.0948
328.75	0.8959	0.1041
333.25	0.8828	0.1172
337.45	0.8644	0.1356
340.95	0.8508	0.1492

Experimental values
T (K)	x₂a	x₁b
302.00	0.9540	0.0460
304.90	0.9486	0.0514
309.65	0.9403	0.0597
311.55	0.9362	0.0638
315.40	0.9281	0.0719
318.70	0.9192	0.0808
321.35	0.9146	0.0854
325.25	0.9052	0.0948
328.75	0.8959	0.1041
333.25	0.8828	0.1172
337.45	0.8644	0.1356
340.95	0.8508	0.1492

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed glass dissolution flask equipped with a condenser to prevent solvent loss from evaporation, electronic balance, precision thermometer, constant temperature recirculating water bath, and magnetic mixer.

Solubilities were determined by a static method. The solvent and excess solute were placed in a 100-ml jacketed glass dissolution flask and allowed to equilibrate with stirring for 60–150 min. The stirring was then discontinued, and the solution was allowed to sit for 60–180 min so that the suspended solid could settle to the bottom of the flask. A known aliquot of the clear solution was removed. The concentration of the dissolved solute was determined by titration using a standardized sodium hydroxide solution with phenolphthalein as the indicator.

Source and Purity of Chemicals:

99.6%, chemical source not given, no purification details were provided in Ref. 10.
Analytical Reagent grade, chemical source not given, no purification details were provided in Ref. 10.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁴R. Mohan, H. Lorentz, and A. S. Myerson, Ind. Eng. Chem. Res. 41, 4854 (2002).

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁^b,c
302.83	0.9580	0.0420
328.61	0.9028	0.0972
340.39	0.8552	0.1448

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

^c

Solubilities were given in the paper as mass fractions. The mole fraction values were calculated by the compiler.

Auxiliary Information

Method/Apparatus/Procedure:

Analytical balance and a differential scanning calorimeter.

Solubilities were determined using a differential scanning calorimetric method that is described in detail in Ref. 14.

Source and Purity of Chemicals:

99+%, Aldrich Chemical Company, Milwaukee, WI, USA, no purification details were given in Ref. 14.
Purity not given, HPLC grade, chemical source not given, no purification details were given in Ref. 14.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±3% (relative error, estimated by the compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

(2) Ethanol, C₂H₆O [64-17-5]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
288.15	0.9716	0.028 35
293.15	0.9660	0.033 95
298.15	0.9609	0.039 05
303.15	0.9577	0.042 25
308.15	0.9449	0.055 07
315.15	0.9327	0.067 27
318.15	0.9186	0.081 36
323.15	0.8964	0.103 6

Experimental values
T (K)	x₂a	x₁b
288.15	0.9716	0.028 35
293.15	0.9660	0.033 95
298.15	0.9609	0.039 05
303.15	0.9577	0.042 25
308.15	0.9449	0.055 07
315.15	0.9327	0.067 27
318.15	0.9186	0.081 36
323.15	0.8964	0.103 6

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Analytical balance, magnetic stirrer, dual-wall flask, and a thermostatically controlled constant temperature bath.

Solubilities were determined by a gravimetric method. The solvent and excess solute were placed in a specially designed sealed dual-wall flask and allowed to equilibrate in a constant temperature bath with stirring. The stirring was later discontinued, and the suspended solid was allowed to settle at the bottom of the flask. A clear aliquot of the saturated solution was removed, filtered, and then transferred to a tared container. The container and its contents were weighed. The solvent was evaporated, and the solubility determined from the mass of the solid residue and mass of the sample analyzed. The reported value represented the average of three measurements.

Source and Purity of Chemicals:

99%, Tianjin Xi’ensi Company Ltd., China, no purification details given in Ref. 15.
99.5%, Analytical Reagent grade, Tianjin Kewei Chemical Company, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) 1-Propanol, C₃H₈O [71-23-8]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
273.15	0.9899	0.010 14
283.15	0.9843	0.015 69
293.15	0.9768	0.023 2
303.15	0.9662	0.033 8
313.15	0.9515	0.048 5
333.15	0.9047	0.095 3

Experimental values
T (K)	x₂a	x₁b
273.15	0.9899	0.010 14
283.15	0.9843	0.015 69
293.15	0.9768	0.023 2
303.15	0.9662	0.033 8
313.15	0.9515	0.048 5
333.15	0.9047	0.095 3

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was dried over Drierite for one day and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) 2-Propanol, C₃H₈O [67-63-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
273.15	0.9876	0.012 38
283.15	0.9809	0.019 13
293.15	0.9713	0.028 7
303.15	0.9578	0.042 2
313.15	0.9399	0.060 1
333.15	0.8875	0.112 5

Experimental values
T (K)	x₂a	x₁b
273.15	0.9876	0.012 38
283.15	0.9809	0.019 13
293.15	0.9713	0.028 7
303.15	0.9578	0.042 2
313.15	0.9399	0.060 1
333.15	0.8875	0.112 5

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was dried over Drierite for one day and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) 1-Butanol, C₄H₁₀O [71-36-3]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
273.15	0.9914	0.008 61
283.15	0.9869	0.013 05
293.15	0.9807	0.019 34
303.15	0.9716	0.028 4
313.15	0.9589	0.041 1
333.15	0.9171	0.082 9

Experimental values
T (K)	x₂a	x₁b
273.15	0.9914	0.008 61
283.15	0.9869	0.013 05
293.15	0.9807	0.019 34
303.15	0.9716	0.028 4
313.15	0.9589	0.041 1
333.15	0.9171	0.082 9

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was dried over Drierite for one day and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁰L. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

(2) 1-Butanol, C₄H₁₀O [71-36-3]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
298.85	0.9696	0.0304
303.85	0.9645	0.0355
308.25	0.9576	0.0424
312.50	0.9524	0.0476
317.15	0.9428	0.0572
321.05	0.9339	0.0661
324.95	0.9249	0.0751
328.35	0.9176	0.0824
332.90	0.9039	0.0961
339.15	0.8856	0.1144
343.15	0.8740	0.1260
347.15	0.8576	0.1424
353.35	0.8324	0.1676
358.15	0.8052	0.1948

Experimental values
T (K)	x₂a	x₁b
298.85	0.9696	0.0304
303.85	0.9645	0.0355
308.25	0.9576	0.0424
312.50	0.9524	0.0476
317.15	0.9428	0.0572
321.05	0.9339	0.0661
324.95	0.9249	0.0751
328.35	0.9176	0.0824
332.90	0.9039	0.0961
339.15	0.8856	0.1144
343.15	0.8740	0.1260
347.15	0.8576	0.1424
353.35	0.8324	0.1676
358.15	0.8052	0.1948

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed glass dissolution flask equipped with a condenser to prevent solvent loss from evaporation, electronic balance, precision thermometer, constant temperature recirculating water bath, and magnetic mixer.

Solubilities were determined by a static method. The solvent and excess solute were placed in a 100-ml jacketed glass dissolution flask and allowed to equilibrate with stirring for 60–150 min. The stirring was then discontinued, and the solution was allowed to sit for 60–180 min so that the suspended solid could settle to the bottom of the flask. A known aliquot of the clear solution was removed. The concentration of the dissolved solute was determined by titration using a standardized sodium hydroxide solution with phenolphthalein as the indicator.

Source and Purity of Chemicals:

99.6%, chemical source not given, no purification details were provided in Ref. 10.
Analytical Reagent grade, chemical source not given, no purification details were provided in Ref. 10.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) 2-Methyl-2-propanol, C₄H₁₀O [75-65-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
293.15	0.9497	0.0503
303.15	0.9351	0.0649
313.15	0.9175	0.0825
333.15	0.8741	0.1259

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was dried over Drierite for one day and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

(2) Cyclohexanol, C₆H₁₂O [108-93-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
298.80	0.9983	0.0017
301.35	0.9893	0.0107
306.43	0.9817	0.0183
308.75	0.9732	0.0268
311.95	0.9613	0.0387
317.65	0.9459	0.0541
322.90	0.9323	0.0677
329.45	0.9149	0.0851
334.75	0.9011	0.0989
340.10	0.8862	0.1138
344.90	0.8702	0.1298
352.47	0.8449	0.1551

Experimental values
T (K)	x₂a	x₁b
298.80	0.9983	0.0017
301.35	0.9893	0.0107
306.43	0.9817	0.0183
308.75	0.9732	0.0268
311.95	0.9613	0.0387
317.65	0.9459	0.0541
322.90	0.9323	0.0677
329.45	0.9149	0.0851
334.75	0.9011	0.0989
340.10	0.8862	0.1138
344.90	0.8702	0.1298
352.47	0.8449	0.1551

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, constant temperature thermostat, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 50-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.1 K per 10 min near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The solid–liquid equilibrium temperature was recorded when the last piece of solid dissolved.

Source and Purity of Chemicals:

99.8%, Tianjin Guangfu Fine Chemical Plant, China, was used as received.
99.5%, The First Chemical Reagent Plant of Tianjin, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.0001.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁷S. Suren, N. Sunsandee, M. Stolcova, M. Hronec, N. Leepipatpiboon, U. Pancharoen, and S. Kheawhom, Fluid Phase Equilib. 360, 332 (2013).

(2) Cyclohexanol, C₆H₁₂O [108-93-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
303.0	0.985	0.015
313.0	0.966	0.034
323.0	0.936	0.064
333.0	0.913	0.087
343.0	0.875	0.125
353.0	0.846	0.154
363.0	0.805	0.195
373.0	0.763	0.237
383.0	0.713	0.287
393.0	0.669	0.331

Experimental values
T (K)	x₂a	x₁b
303.0	0.985	0.015
313.0	0.966	0.034
323.0	0.936	0.064
333.0	0.913	0.087
343.0	0.875	0.125
353.0	0.846	0.154
363.0	0.805	0.195
373.0	0.763	0.237
383.0	0.713	0.287
393.0	0.669	0.331

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatted silicone oil bath, magnetic stirring rotor, and a high-performance liquid chromatographic (HPLC) system equipped with a photodiode array detector.

The solvent and excess solute were placed in sealed container and equilibrated with stirring in a thermostatted silicone oil bath for 90 min. The stirring was then discontinued, and the solution was allowed to sit for 180 min to allow the suspended solid particles to settle to the bottom of the container. An aliquot of the saturated solution was removed and weighed. The concentration of the dissolved solute was determined by HPLC analysis with photodiode array detection.

Source and Purity of Chemicals:

99%, Sigma-Aldrich Chemical Company, St. Louis, MO, USA, was used as received.
95%, Mikrochem, Slovak, was used as received.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁸X. Sheng, Q. Wang, Z. Xiong, and C. Chen, Fluid Phase Equilib. 415, 8 (2016).

(2) Cyclohexanol, C₆H₁₂O [108-93-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁^b,c
307.75	0.9528	0.0472
312.55	0.9448	0.0552
316.65	0.9368	0.0632
320.55	0.9288	0.0712
324.35	0.9207	0.0793
327.55	0.9126	0.0874
330.45	0.9048	0.0952
333.75	0.8970	0.1030
337.35	0.9856	0.1144
342.65	0.8691	0.1309
346.95	0.8537	0.1463

Experimental values
T (K)	x₂a	x₁^b,c
307.75	0.9528	0.0472
312.55	0.9448	0.0552
316.65	0.9368	0.0632
320.55	0.9288	0.0712
324.35	0.9207	0.0793
327.55	0.9126	0.0874
330.45	0.9048	0.0952
333.75	0.8970	0.1030
337.35	0.9856	0.1144
342.65	0.8691	0.1309
346.95	0.8537	0.1463

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

^c

Solubilities were reported in Ref. 18 as grams of 1,6-hexanedioic acid per 100 g of solvent. Mole fraction solubilities were calculated by the compiler.

Auxiliary Information

Method/Apparatus/Procedure:

Analytical balance, magnetic stirring rotor, thermocouple, and a laser transmitting and receiving system.

The solvent and excess solute were placed in a 125 ml solid–liquid equilibrium tank with an attached reflux condenser. The equilibrium tank was then placed in a thermostatted water bath. The solid–liquid mixture was continuously stirred while the temperature was gradually increased at a rate of 2.5 K/h. Near the point of complete dissolution, the rate of heating was reduced to 0.2 K/h. The temperature at which the solid completely dissolved was observed using a laser transmitting and receiving system. Each experimental datum was measured at least twice.

Source and Purity of Chemicals:

99.0%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
97.0%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±4% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁹W. Luo, M. Yan, X.-X. Sheng, B. Tao, S. Shi, W. Deng, W. Yang, and S. Luo, Ind. Eng. Chem. Res. 58, 10018 (2019).

(2) Cyclohexanol, C₆H₁₂O [108-93-0]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
307.75	0.9642	0.0358
312.55	0.9577	0.0423
316.65	0.9509	0.0491
320.55	0.9429	0.0571
324.35	0.9366	0.0634
327.55	0.9274	0.0726
330.45	0.9188	0.0812
333.75	0.9112	0.0888
337.35	0.8999	0.1001
342.65	0.8847	0.1153

Experimental values
T (K)	x₂a	x₁b
307.75	0.9642	0.0358
312.55	0.9577	0.0423
316.65	0.9509	0.0491
320.55	0.9429	0.0571
324.35	0.9366	0.0634
327.55	0.9274	0.0726
330.45	0.9188	0.0812
333.75	0.9112	0.0888
337.35	0.8999	0.1001
342.65	0.8847	0.1153

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.12 K.

x₁: ±0.04 (relative error).

3.6. Hexanedioic acid solubility data in ketones

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁹D. Wei and W. Cao, J. Chem. Eng. Data 54, 152 (2009).

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
298.15	0.9831	0.016 87
300.15	0.9820	0.018 01
302.15	0.9807	0.019 29
304.15	0.9793	0.020 69
306.15	0.9779	0.022 13
308.15	0.9765	0.023 54
310.15	0.9747	0.025 27
312.15	0.9728	0.027 15
314.15	0.9705	0.029 45
316.15	0.9683	0.031 72
318.15	0.9655	0.034 53
323.15	0.9570	0.043 02

Experimental values
T (K)	x₂a	x₁b
298.15	0.9831	0.016 87
300.15	0.9820	0.018 01
302.15	0.9807	0.019 29
304.15	0.9793	0.020 69
306.15	0.9779	0.022 13
308.15	0.9765	0.023 54
310.15	0.9747	0.025 27
312.15	0.9728	0.027 15
314.15	0.9705	0.029 45
316.15	0.9683	0.031 72
318.15	0.9655	0.034 53
323.15	0.9570	0.043 02

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Constant temperature water bath, water-jacketed glass equilibrium vessel, analytical balance, and magnetic stirrer.

Solubilities were determined by a static analytical method. The solvent and excess solute were placed in a water-jacketed glass equilibrium vessel and allowed to equilibrate at a constant temperature with stirring for at least three days. An aliquot of the clear saturated solution was withdrawn, and the concentration of the dissolved acid was determined by acid–base titration using an aqueous sodium hydroxide solution. The attainment of equilibrium was verified by repetitive measurements after three additional days of equilibration and by approaching equilibrium from supersaturation by pre-equilibrating the solutions at a higher temperature. The reported solubility represented the average of five independent determinations.

Source and Purity of Chemicals:

Purity not given, Beijing Qingshengda Chemical Technology Company, Ltd., Beijing, China, was recrystallized twice from water and dried at 393 K prior to use.
99.95%, Analytical grade, Tianjin Kewei Chemical Reagent Company, China, was refluxed over freshly activated calcium oxide for 2 h, and then fractionally distilled and stored over freshly activated molecular sieves prior to use. Solvent purity determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±1.2% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁰Z. Mao, X. Sun, X. Luan, Y. Wang, and G. Liu, Chin. J. Chem. Eng. 17, 473 (2009).

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
288.05	0.9868	0.0132
293.05	0.9831	0.0169
297.95	0.9813	0.0187
302.35	0.9780	0.0220
303.45	0.9774	0.0226
305.90	0.9752	0.0248
309.60	0.9722	0.0278
315.65	0.9654	0.0346
317.60	0.9633	0.0367
321.95	0.9564	0.0436
325.85	0.9472	0.0528

Experimental values
T (K)	x₂a	x₁b
288.05	0.9868	0.0132
293.05	0.9831	0.0169
297.95	0.9813	0.0187
302.35	0.9780	0.0220
303.45	0.9774	0.0226
305.90	0.9752	0.0248
309.60	0.9722	0.0278
315.65	0.9654	0.0346
317.60	0.9633	0.0367
321.95	0.9564	0.0436
325.85	0.9472	0.0528

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed glass dissolution flask equipped with a condenser to prevent solvent loss from evaporation, electronic balance, precision thermometer, constant temperature recirculating water bath, and magnetic mixer.

Solubilities were determined by a static method. The solvent and excess solute were placed in a 100-ml jacketed glass dissolution flask and allowed to equilibrate with stirring for 60–150 min. The stirring was then discontinued, and the solution was allowed to sit for 60–180 min so that the suspended solid could settle to the bottom of the flask. A known aliquot of the clear solution was removed. The concentration of the dissolved solute was determined by titration using a standardized sodium hydroxide solution with phenolphthalein as the indicator.

Source and Purity of Chemicals:

99.6%, chemical source not given, no purification details were provided in Ref. 10.
Analytical Reagent grade, chemical source not given, no purification details were provided in Ref. 10.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
273.15	0.9935	0.006 50
283.15	0.9906	0.009 41
293.15	0.9865	0.013 51
303.15	0.9807	0.019 3
313.15	0.9726	0.027 4

Experimental values
T (K)	x₂a	x₁b
273.15	0.9935	0.006 50
283.15	0.9906	0.009 41
293.15	0.9865	0.013 51
303.15	0.9807	0.019 3
313.15	0.9726	0.027 4

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was dried over Drierite for one day and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

²⁰A. d. P. M. da Silva and J. F. Cajaiba da Silva, Org. Process Res. Dev. 15, 893 (2011).

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental valuesa
T (K)	x₂b	x₁c
297.9	0.9832	0.016 81
301.9	0.9810	0.019 03
304.0	0.9797	0.020 27
309.9	0.9761	0.023 87
311.9	0.9740	0.026 03
313.9	0.9720	0.027 95
315.8	0.9692	0.030 81
317.8	0.9670	0.033 00
322.8	0.9613	0.038 67

Experimental valuesa
T (K)	x₂b	x₁c
297.9	0.9832	0.016 81
301.9	0.9810	0.019 03
304.0	0.9797	0.020 27
309.9	0.9761	0.023 87
311.9	0.9740	0.026 03
313.9	0.9720	0.027 95
315.8	0.9692	0.030 81
317.8	0.9670	0.033 00
322.8	0.9613	0.038 67

^a

Based on the ATR-FTR spectrophotometric measurements.

^b

x₂: mole fraction of component 2 in the saturated solution.

^c

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Attenuated Total Reflectance (ATR) Fourier transform infrared (FTIR), analytical balance and heat flow calorimeter.

Solubilities were determined by ATR FTIR and heat flow calorimetry. In the case of the ATR-FTIR spectrophotometric measurements, the solubility was evaluated by analyzing the area of the C–O (1100–1300 cm⁻¹), the C=O (1600–1750 cm⁻¹), and the O–H (2600–3600 cm⁻¹) absorption bands as incremental amounts of the solute were added to the solution. In the case of the heat flow calorimetric measurements, the enthalpy differences between the additions were obtained by calculating the heat flow peak areas. The experimental procedure is described in greater detail in Ref. 20.

Source and Purity of Chemicals:

99.6%, chemical source not given, no purification details were provided in Ref. 20.
Analytical Reagent grade, chemical source not given, no purification details were provided in Ref. 20.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2.5% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁵H. Zhang, Q. Yin, Z. Liu, J. Gong, Y. Bao, M. Zhang, H. Hao, B. Hou, and C. Xie, J. Chem. Thermodyn. 77, 91 (2014).

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
288.15	0.9838	0.016 24
293.15	0.9810	0.019 03
298.15	0.9771	0.022 88
303.15	0.9739	0.026 05
308.15	0.9679	0.032 06
315.15	0.9640	0.036 02
318.15	0.9597	0.040 32
323.15	0.9483	0.051 70

Experimental values
T (K)	x₂a	x₁b
288.15	0.9838	0.016 24
293.15	0.9810	0.019 03
298.15	0.9771	0.022 88
303.15	0.9739	0.026 05
308.15	0.9679	0.032 06
315.15	0.9640	0.036 02
318.15	0.9597	0.040 32
323.15	0.9483	0.051 70

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Analytical balance, magnetic stirrer, dual-wall flask and a thermostatically controlled constant temperature bath.

Solubilities were determined by a gravimetric method. The solvent and excess solute were placed in a specially designed sealed dual-wall flask and allowed to equilibrate in a constant temperature bath with stirring. The stirring was later discontinued, and the suspended solid allowed to settle to the bottom of the flask. A clear aliquot of the saturated solution was removed, filtered, and then transferred to a tared container. The container and its contents were weighed. The solvent was evaporated, and the solubility was determined from the mass of the solid residue and mass of the sample analyzed. The reported value represented the average of three measurements.

Source and Purity of Chemicals:

99%, Tianjin Xi’ensi Company Ltd., China, no purification details given in Ref. 15.
99.5%, Analytical Reagent grade, Tianjin Kewei Chemical Company, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±2% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

²¹Y. Li, Y. Wang, Z. Ning, J. Gui, Q. Wu, and X. Wang, J. Chem. Eng. Data 59, 4062 (2014).

(2) Propanone, C₃H₆O [67-64-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
284.95	0.9896	0.0104
286.65	0.9889	0.0111
289.05	0.9882	0.0118
290.55	0.9874	0.0126
292.55	0.9866	0.0134
294.25	0.9857	0.0143
296.35	0.9847	0.0153
298.75	0.9835	0.0165
301.10	0.9820	0.0180
303.85	0.9801	0.0199
306.65	0.9780	0.0220
309.85	0.9756	0.0244
313.00	0.9728	0.0272

Experimental values
T (K)	x₂a	x₁b
284.95	0.9896	0.0104
286.65	0.9889	0.0111
289.05	0.9882	0.0118
290.55	0.9874	0.0126
292.55	0.9866	0.0134
294.25	0.9857	0.0143
296.35	0.9847	0.0153
298.75	0.9835	0.0165
301.10	0.9820	0.0180
303.85	0.9801	0.0199
306.65	0.9780	0.0220
309.85	0.9756	0.0244
313.00	0.9728	0.0272

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Electronic analytical balance, magnetic stirrer, jacketed glass equilibrium vessel, a constant temperature circulating water bath, and a laser monitoring system.

Solubilities were determined using a dynamic method. Weighed amounts of solute and solvent were placed in a jacketed glass vessel with a magnetic stirrer. The temperature of the water circulating through the jacket was controlled by a constant temperature water circulating bath. The temperature was slowly increased until the solid completely disappeared. A laser monitoring system was used to determine the temperature at which complete dissolution occurred.

Source and Purity of Chemicals:

99.5%, China Pingmei Shenma Group, China, no purification details given in Ref. 21.
99.5%, Tianjin Fengchuan Chemical Reagent Company, Ltd., China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.0004.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵¹J. N. Starr and C. J. King, Ind. Eng. Chem. Res. 31, 2572 (1992).

(2) 2-Heptanone, C₇H₁₄O [110-43-0]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.0271 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Constant-temperature shaker bath.

Excess solute and organic solvent were added to a 125-ml Erlenmeyer flask. The closed flask was placed in a constant-temperature shaker water bath and allowed to equilibrate for at least 10 days. An aliquot of the saturated solution was removed, and the concentration of the dissolved solute was determined by back extraction of the acid into an aqueous solution of known sodium hydroxide concentration. The resulting aqueous solution was back titrated with aqueous hydrochloric acid with phenolphthalein being used as the indicator.

Source and Purity of Chemicals:

Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.
Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.

Estimated Error:

Temperature: ±0.1 K (estimated by compiler).

c₁: ±1% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵¹J. N. Starr and C. J. King, Ind. Eng. Chem. Res. 31, 2572 (1992).

(2) 3-Heptanone, C₇H₁₄O [106-35-3]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.0150 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Constant-temperature shaker bath.

Excess solute and organic solvent were added to a 125-ml Erlenmeyer flask. The closed flask was placed in a constant-temperature shaker water bath and allowed to equilibrate for at least 10 days. An aliquot of the saturated solution was removed, and the concentration of the dissolved solute was determined by back extraction of the acid into an aqueous solution of known sodium hydroxide concentration. The resulting aqueous solution was back titrated with aqueous hydrochloric acid with phenolphthalein being used as the indicator.

Source and Purity of Chemicals:

Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.
Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.

Estimated Error:

Temperature: ±0.1 K (estimated by compiler).

c₁: ±1% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵¹J. N. Starr and C. J. King, Ind. Eng. Chem. Res. 31, 2572 (1992).

(2) 4-Heptanone, C₇H₁₄O [123-19-3]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.0118 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Constant-temperature shaker bath.

Excess solute and organic solvent were added to a 125-ml Erlenmeyer flask. The closed flask was placed in a constant-temperature shaker water bath and allowed to equilibrate for at least 10 days. An aliquot of the saturated solution was removed, and the concentration of the dissolved solute was determined by back extraction of the acid into an aqueous solution of known sodium hydroxide concentration. The resulting aqueous solution was back titrated with aqueous hydrochloric acid with phenolphthalein being used as the indicator.

Source and Purity of Chemicals:

Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.
Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.

Estimated Error:

Temperature: ±0.1 K (estimated by compiler).

c₁: ±1% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
292.75	0.9896	0.0104
294.55	0.9890	0.0110
297.23	0.9860	0.0140
298.75	0.9852	0.0148
302.35	0.9837	0.0163
304.09	0.9828	0.0172
312.55	0.9760	0.0240
318.40	0.9657	0.0343
327.55	0.9548	0.0452
339.05	0.9322	0.0678
349.85	0.8980	0.1020
355.15	0.8717	0.1283

Experimental values
T (K)	x₂a	x₁b
292.75	0.9896	0.0104
294.55	0.9890	0.0110
297.23	0.9860	0.0140
298.75	0.9852	0.0148
302.35	0.9837	0.0163
304.09	0.9828	0.0172
312.55	0.9760	0.0240
318.40	0.9657	0.0343
327.55	0.9548	0.0452
339.05	0.9322	0.0678
349.85	0.8980	0.1020
355.15	0.8717	0.1283

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, constant temperature thermostat, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 50-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.1 K per 10 min near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The solid–liquid equilibrium temperature was recorded when the last piece of solid dissolved.

Source and Purity of Chemicals:

99.8%, Tianjin Guangfu Fine Chemical Plant, China, was used as received.
99.5%, The First Chemical Reagent Plant of Tianjin, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.0001.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁷S. Suren, N. Sunsandee, M. Stolcova, M. Hronec, N. Leepipatpiboon, U. Pancharoen, and S. Kheawhom, Fluid Phase Equilib. 360, 332 (2013).

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
303.0	0.987	0.013
313.0	0.981	0.019
323.0	0.968	0.032
333.0	0.951	0.049
343.0	0.926	0.074
353.0	0.900	0.100
363.0	0.864	0.136
373.0	0.822	0.178
383.0	0.786	0.214
393.0	0.748	0.252

Experimental values
T (K)	x₂a	x₁b
303.0	0.987	0.013
313.0	0.981	0.019
323.0	0.968	0.032
333.0	0.951	0.049
343.0	0.926	0.074
353.0	0.900	0.100
363.0	0.864	0.136
373.0	0.822	0.178
383.0	0.786	0.214
393.0	0.748	0.252

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatted silicone oil bath, magnetic stirring rotor, and a HPLC system equipped with a photodiode array detector.

The solvent and excess solute were placed in sealed container and equilibrated with stirring in a thermostatted silicone oil bath for 90 min. The stirring was then discontinued, and the solution was allowed to sit for 180 min to allow the suspended solid particles to settle to the bottom of the container. An aliquot of the saturated solution was removed and weighed. The concentration of the dissolved solute was determined by HPLC analysis with photodiode array detection.

Source and Purity of Chemicals:

99%, Sigma-Aldrich Chemical Company, St. Louis, MO, USA, was used as received.
99%, Mikrochem, Slovak, was used as received.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵¹J. N. Starr and C. J. King, Ind. Eng. Chem. Res. 31, 2572 (1992).

(2) Cyclohexanone, C₆H₁₂O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.163 mol dm⁻³ at 298.15 K and c₁ = 0.290 mol dm⁻³ at 313.15 K.

Auxiliary Information

Method/Apparatus/Procedure:

Constant-temperature shaker bath.

Excess solute and organic solvent were added to a 125-ml Erlenmeyer flask. The closed flask was placed in a constant-temperature shaker water bath and allowed to equilibrate for at least 10 days. An aliquot of the saturated solution was removed, and the concentration of the dissolved solute was determined by back extraction of the acid into an aqueous solution of known sodium hydroxide concentration. The resulting aqueous solution was back titrated with aqueous hydrochloric acid with phenolphthalein being used as the indicator.

Source and Purity of Chemicals:

Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.
Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.

Estimated Error:

Temperature: ±0.1 K (estimated by compiler).

c₁: ±1% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁸X. Sheng, Q. Wang, Z. Xiong, and C. Chen, Fluid Phase Equilib. 415, 8 (2016).

(2) Cyclohexanone, C₆H₁₂O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁^b,c
305.05	0.9786	0.0214
309.35	0.9746	0.0254
313.35	0.9706	0.0294
316.85	0.9666	0.0334
321.95	0.9597	0.0403
326.35	0.9527	0.0473
330.85	0.9446	0.0554
334.65	0.9362	0.0638
338.90	0.9247	0.0753
343.15	0.9133	0.0867
346.95	0.9021	0.0979

Experimental values
T (K)	x₂a	x₁^b,c
305.05	0.9786	0.0214
309.35	0.9746	0.0254
313.35	0.9706	0.0294
316.85	0.9666	0.0334
321.95	0.9597	0.0403
326.35	0.9527	0.0473
330.85	0.9446	0.0554
334.65	0.9362	0.0638
338.90	0.9247	0.0753
343.15	0.9133	0.0867
346.95	0.9021	0.0979

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

^c

Solubilities were reported in Ref. 18 as grams of hexanedioic acid per 100 g of solvent. Mole fraction solubilities were calculated by the compiler.

Auxiliary Information

Method/Apparatus/Procedure:

An analytical balance, magnetic stirring rotor, thermocouple, and a laser transmitting and receiving system.

The solvent and excess solute were placed in a 125 ml solid–liquid equilibrium tank with an attached reflux condenser. The equilibrium tank was then placed in a thermostatted water bath. The solid–liquid mixture was continuously stirred while the temperature was gradually increased at a rate of 2.5 K/h. Near the point of complete dissolution, the rate of heating was reduced to 0.2 K/h. The temperature at which the solid completely dissolved was observed using a laser transmitting and receiving system. Each experimental datum was measured at least twice.

Source and Purity of Chemicals:

99.0%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99.0%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±4% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹²W. Luo, K. Xie, D. Liu, X. Li, B. Tao, J. Hao, W. Deng, Q. Liu, and C. Guo, J. Chem. Eng. Data 62, 3124 (2017).

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
301.25	0.9853	0.0147
305.45	0.9815	0.0185
309.95	0.9773	0.0227
314.45	0.9726	0.0274
318.25	0.9679	0.0321
321.15	0.9631	0.0369
324.35	0.9578	0.0422
327.65	0.9522	0.0478
331.65	0.9458	0.0542
334.75	0.9384	0.0616

Experimental values
T (K)	x₂a	x₁b
301.25	0.9853	0.0147
305.45	0.9815	0.0185
309.95	0.9773	0.0227
314.45	0.9726	0.0274
318.25	0.9679	0.0321
321.15	0.9631	0.0369
324.35	0.9578	0.0422
327.65	0.9522	0.0478
331.65	0.9458	0.0542
334.75	0.9384	0.0616

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99.5%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.13 K.

x₁: ±0.10 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁷M. Yan, X. Li, B. Tao, L. Yang, and W. Luo, J. Mol. Liq. 272, 106 (2018).

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
294.15	0.9875	0.0125
298.45	0.9849	0.0151
302.45	0.9822	0.0178
307.15	0.9789	0.0211
312.45	0.9753	0.0247
317.05	0.9716	0.0284
321.75	0.9655	0.0345
326.36	0.9592	0.0408
331.55	0.9496	0.0504
335.25	0.9399	0.0601

Experimental values
T (K)	x₂a	x₁b
294.15	0.9875	0.0125
298.45	0.9849	0.0151
302.45	0.9822	0.0178
307.15	0.9789	0.0211
312.45	0.9753	0.0247
317.05	0.9716	0.0284
321.75	0.9655	0.0345
326.36	0.9592	0.0408
331.55	0.9496	0.0504
335.25	0.9399	0.0601

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99.5%, Sinopharm Chemical Reagent Co, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.12 K.

x₁: ±0.04 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹³B. Chen, M. Yan, B. Tao, L. Yang, and W. Luo, J. Chem. Eng. Data 65, 56 (2020).

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
293.75	0.9875	0.0125
297.75	0.9855	0.0145
302.05	0.9830	0.0170
306.65	0.9799	0.0201
310.55	0.9768	0.0232
314.75	0.9729	0.0271
319.15	0.9681	0.0319
323.15	0.9630	0.0370
327.25	0.9570	0.0430
331.15	0.9504	0.0496

Experimental values
T (K)	x₂a	x₁b
293.75	0.9875	0.0125
297.75	0.9855	0.0145
302.05	0.9830	0.0170
306.65	0.9799	0.0201
310.55	0.9768	0.0232
314.75	0.9729	0.0271
319.15	0.9681	0.0319
323.15	0.9630	0.0370
327.25	0.9570	0.0430
331.15	0.9504	0.0496

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 125-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99.5%, Sinopharm Chemical Reagent Co., China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.12 K.

x₁: ±0.10 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁸W. Luo, D. Ruan, D. Liu, K. Xie, X. Li, W. Deng, and C. Guo, J. Chem. Eng. Data 61, 2474 (2016).

(2) Cyclohexanone, C₆H₁₀O [108-94-1]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
301.25	0.9853	0.0147
305.45	0.9812	0.0188
309.95	0.9770	0.0230
314.45	0.9726	0.0274
318.25	0.9679	0.0321
321.15	0.9631	0.0369
324.35	0.9578	0.0422
327.65	0.9522	0.0478
331.65	0.9458	0.0542
334.75	0.9384	0.0616
338.55	0.9310	0.0690
341.35	0.9236	0.0764
342.85	0.9163	0.0837
344.95	0.9090	0.0910

Experimental values
T (K)	x₂a	x₁b
301.25	0.9853	0.0147
305.45	0.9812	0.0188
309.95	0.9770	0.0230
314.45	0.9726	0.0274
318.25	0.9679	0.0321
321.15	0.9631	0.0369
324.35	0.9578	0.0422
327.65	0.9522	0.0478
331.65	0.9458	0.0542
334.75	0.9384	0.0616
338.55	0.9310	0.0690
341.35	0.9236	0.0764
342.85	0.9163	0.0837
344.95	0.9090	0.0910

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatic water–circulator bath, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 100-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.2 K/h near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The intensities of the transmitted laser beam were expressed by output photovoltages recorded by a computer. When the solute just completely dissolved, the laser intensity would be the strongest. The corresponding temperature was recorded and regarded as the one at which solid–liquid equilibrium would be achieved.

Source and Purity of Chemicals:

99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by HPLC analysis.
99%, Aladdin Chemistry Company, China, was used as received. Purity was determined by gas-liquid chromatographic analysis.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.10 (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵¹J. N. Starr and C. J. King, Ind. Eng. Chem. Res. 31, 2572 (1992).

(2) Methylcyclohexanone, C₇H₁₄O (isomer was not specified)

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.102 mol dm⁻³ at 298.15 K and c₁ = 0.195 mol dm⁻³ at 313.15 K.

Auxiliary Information

Method/Apparatus/Procedure:

Constant-temperature shaker bath.

Excess solute and organic solvent were added to a 125-ml Erlenmeyer flask. The closed flask was placed in a constant-temperature shaker water bath and allowed to equilibrate for at least 10 days. An aliquot of the saturated solution was removed, and the concentration of the dissolved solute was determined by back extraction of the acid into an aqueous solution of known sodium hydroxide concentration. The resulting aqueous solution was back titrated with aqueous hydrochloric acid with phenolphthalein being used as the indicator.

Source and Purity of Chemicals:

Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.
Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.

Estimated Error:

Temperature: ±0.1 K (estimated by compiler).

c₁: ±1% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵¹J. N. Starr and C. J. King, Ind. Eng. Chem. Res. 31, 2572 (1992).

(2) Acetophenone, C₈H₈O [98-86-2]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.0382 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Constant-temperature shaker bath.

Excess solute and organic solvent were added to a 125-ml Erlenmeyer flask. The closed flask was placed in a constant-temperature shaker water bath and allowed to equilibrate for at least 10 days. An aliquot of the saturated solution was removed, and the concentration of the dissolved solute was determined by back extraction of the acid into an aqueous solution of known sodium hydroxide concentration. The resulting aqueous solution was back titrated with aqueous hydrochloric acid with phenolphthalein being used as the indicator.

Source and Purity of Chemicals:

Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.
Purity not given, chemical supplier not given, no purification details were provided in Ref. 51.

Estimated Error:

Temperature: ±0.1 K (estimated by compiler).

c₁: ±1% (relative error, estimated by compiler).

3.7. Hexanedioic acid solubility data in miscellaneous organic solvents

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

(2) N,N-Dimethylformamide, C₃H₇NO [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
290.80	0.7583	0.2417
295.05	0.7518	0.2482
301.25	0.7440	0.2560
304.45	0.7379	0.2621
307.27	0.7334	0.2666
311.10	0.7248	0.2752
316.75	0.7140	0.2860
323.85	0.6999	0.3001
329.35	0.6870	0.3130
335.25	0.6755	0.3245

Experimental values
T (K)	x₂a	x₁b
290.80	0.7583	0.2417
295.05	0.7518	0.2482
301.25	0.7440	0.2560
304.45	0.7379	0.2621
307.27	0.7334	0.2666
311.10	0.7248	0.2752
316.75	0.7140	0.2860
323.85	0.6999	0.3001
329.35	0.6870	0.3130
335.25	0.6755	0.3245

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, constant temperature thermostat, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 50-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.1 K per 10 min near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The solid–liquid equilibrium temperature was recorded when the last piece of solid dissolved.

Source and Purity of Chemicals:

99.8%, Tianjin Guangfu Fine Chemical Plant, China, was used as received.
99.5%, The First Chemical Reagent Plant of Tianjin, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.0001.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵⁰M. K. Chantooni and I. M. Kolthoff, J. Phys. Chem. 79, 1176 (1975).

(2) N,N-Dimethylformamide, C₃H₇NO [64-19-7]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 2.86 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Very few experimental details were provided. Solubility was determined by titrating a filtered aliquot of the saturated solution alkalimetrically in an aqueous-ethanol mixture using phenolphthalein as the acid–base indicator.

Source and Purity of Chemicals:

99.5%, White Label, Eastman Kodak Chemical Company, Rochester, NY, USA, was dried for 2 h at 333 K before use. Purity determined by alkalimetric titration in water.
Purity not given, chemical source not given, was shaken first with phosphorous pentoxide and then with potassium hydroxide pellets. Solvent was distilled shortly before use.

Estimated Error:

Temperature: ±0.1 K.

c₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵²H. Smagowski, Zesz. Nauk. Wydz. Mat., Fiz., Chem., [Ser.]: Chem. (Uniw. Gdanski) 3, 45 (1974).

(2) N,N-Dimethylformamide, C₃H₇NO [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 2.48 mol dm⁻³ at T (K) = 273.15, c₁ = 5.68 mol dm⁻³ at T (K) = 288.15, and c₁ = 6.95 mol dm⁻³ at T (K) = 298.15.

Auxiliary Information

Method/Apparatus/Procedure:

Very few experimental details were provided. Solubility was determined by titrating an aliquot of the saturated solution alkalimetrically using phenolphthalein as the acid–base indicator.

Source and Purity of Chemicals:

Purity not given, chemical source not given, recrystallized from ethyl acetate before use.
Purity not given, chemical source not given, purified by distillation with benzene under reduced pressure.

Estimated Error:

Temperature: Insufficient information given to determine.

c₁: Insufficient information given to determine.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

(2) N,N-Dimethylacetamide, C₄H₉NO [127-19-5]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
294.55	0.7061	0.2939
301.09	0.6995	0.3005
306.05	0.6906	0.3094
311.70	0.6820	0.3180
313.35	0.6796	0.3204
317.43	0.6741	0.3259
321.45	0.6688	0.3312
325.05	0.6609	0.3391
329.09	0.6512	0.3488
332.80	0.6429	0.3571
336.73	0.6341	0.3659

Experimental values
T (K)	x₂a	x₁b
294.55	0.7061	0.2939
301.09	0.6995	0.3005
306.05	0.6906	0.3094
311.70	0.6820	0.3180
313.35	0.6796	0.3204
317.43	0.6741	0.3259
321.45	0.6688	0.3312
325.05	0.6609	0.3391
329.09	0.6512	0.3488
332.80	0.6429	0.3571
336.73	0.6341	0.3659

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, constant temperature thermostat, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 50-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.1 K per 10 min near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The solid–liquid equilibrium temperature was recorded when the last piece of solid dissolved.

Source and Purity of Chemicals:

99.8%, Tianjin Guangfu Fine Chemical Plant, China, was used as received.
99.5%, The First Chemical Reagent Plant of Tianjin, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.0001.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

(2) Dimethyl sulfoxide, C₂H₆OS [67-68-5]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
292.95	0.6868	0.3132
296.15	0.6824	0.3176
299.35	0.6774	0.3226
301.35	0.6753	0.3247
305.45	0.6680	0.3320
309.85	0.6602	0.3398
314.47	0.6528	0.3472
320.25	0.6425	0.3575
324.95	0.6354	0.3646
328.95	0.6267	0.3733
334.70	0.6162	0.3838

Experimental values
T (K)	x₂a	x₁b
292.95	0.6868	0.3132
296.15	0.6824	0.3176
299.35	0.6774	0.3226
301.35	0.6753	0.3247
305.45	0.6680	0.3320
309.85	0.6602	0.3398
314.47	0.6528	0.3472
320.25	0.6425	0.3575
324.95	0.6354	0.3646
328.95	0.6267	0.3733
334.70	0.6162	0.3838

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, constant temperature thermostat, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 50-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.1 K per 10 min near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The solid–liquid equilibrium temperature was recorded when the last piece of solid dissolved.

Source and Purity of Chemicals:

99.8%, Tianjin Guangfu Fine Chemical Plant, China, was used as received.
99.5%, The First Chemical Reagent Plant of Tianjin, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.0001.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵⁰M. K. Chantooni and I. M. Kolthoff, J. Phys. Chem. 79, 1176 (1975).

(2) Dimethyl sulfoxide, C₂H₆OS [67-68-5]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 3.69 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Very few experimental details were provided. Solubility was determined by titrating a filtered aliquot of the saturated solution alkalimetrically in an aqueous-ethanol mixture using phenolphthalein as the acid–base indicator.

Source and Purity of Chemicals:

99.5%, White Label, Eastman Kodak Chemical Company, Rochester, NY, USA, was dried for 2 h at 333 K before use. Purity determined by alkalimetric titration in water.
Purity not given, chemical source not given, was shaken with activated alumina and then distilled before use.

Estimated Error:

Temperature: ±0.1 K.

c₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵⁰M. K. Chantooni and I. M. Kolthoff, J. Phys. Chem. 79, 1176 (1975).

(2) Ethanenitrile, C₂H₃N [75-05-8]

Variables:

Prepared by:

T (K) = 298.15

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.039 mol dm⁻³.

Auxiliary Information

Method/Apparatus/Procedure:

Very few experimental details were provided. Solubility was determined by titrating a filtered aliquot of the saturated solution alkalimetrically in an aqueous-ethanol mixture using phenolphthalein as the acid–base indicator.

Source and Purity of Chemicals:

99.5%, White Label, Eastman Kodak Chemical Company, Rochester, NY, USA, was dried for 2 h at 333 K before use. Purity determined by alkalimetric titration in water.
Purity not given, chemical source not given, was purified by shaking with saturated potassium hydroxide, followed by activated alumina, and then anhydrous calcium chloride to remove water. Ethanenitrile was further dried over anhydrous magnesium sulfate and then phosphorous pentoxide. The sample was distilled shortly before use.

Estimated Error:

Temperature: ±0.1 K.

c₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵²H. Smagowski, Zesz. Nauk. Wydz. Mat., Fiz., Chem., [Ser.]: Chem. (Uniw. Gdanski) 3, 45 (1974).

(2) Ethanenitrile, C₂H₃N [75-05-8]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.068 mol dm⁻³ at T (K) = 273.15 K, c₁ = 0.089 mol dm⁻³ at T (K) = 288.15, c₁ = 0.13 mol dm⁻³ at T (K) = 298.15, and c₁ = 0.18 mol dm⁻³ at T (K) = 308.15.

Auxiliary Information

Method/Apparatus/Procedure:

Very few experimental details were provided. Solubility was determined by titrating an aliquot of the saturated solution alkalimetrically using phenolphthalein as the acid–base indicator.

Source and Purity of Chemicals:

Purity not given, chemical source not given, recrystallized from ethyl acetate before use.
Purity not given, chemical source not given, was dried over potassium carbonate and distilled from phosphorous pentoxide under reduced pressure.

Estimated Error:

Temperature: Insufficient information given to determine.

c₁: Insufficient information given to determine.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

⁵²H. Smagowski, Zesz. Nauk. Wydz. Mat., Fiz., Chem., [Ser.]: Chem. (Uniw. Gdanski) 3, 45 (1974).

(2) Nitromethane, CH₃NO₂ [75-52-5]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental Values

The measured solubility was reported to be c₁ = 0.005 mol dm⁻³ at T (K) = 273.15, c₁ = 0.007 mol dm⁻³ at T (K) = 288.15, c₁ = 0.012 mol dm⁻³ at T (K) = 298.15, and c₁ = 0.018 mol dm⁻³ at T (K) = 308.15.

Auxiliary Information

Method/Apparatus/Procedure:

Very few experimental details were provided. Solubility was determined by titrating an aliquot of the saturated solution alkalimetrically using bromothymol blue as the acid–base indicator.

Source and Purity of Chemicals:

Purity not given, chemical source not given, recrystallized from ethyl acetate before use.
Purity not given, chemical source not given, purified by distillation from phosphorous pentoxide under reduced pressure.

Estimated Error:

Temperature: Insufficient information given to determine.

c₁: Insufficient information given to determine.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁶L. Fan, P. Ma, and Z. Xiang, Chin. J. Chem. Eng. 15, 110 (2007).

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
297.93	0.9803	0.0197
302.70	0.9754	0.0246
306.65	0.9720	0.0280
311.67	0.9663	0.0337
315.20	0.9614	0.0386
319.33	0.9558	0.0442
323.49	0.9488	0.0512
326.57	0.9432	0.0568
329.30	0.9378	0.0622
332.85	0.9306	0.0694
335.77	0.9200	0.0800
339.55	0.9098	0.0902
344.53	0.8984	0.1016
347.65	0.8881	0.1119

Experimental values
T (K)	x₂a	x₁b
297.93	0.9803	0.0197
302.70	0.9754	0.0246
306.65	0.9720	0.0280
311.67	0.9663	0.0337
315.20	0.9614	0.0386
319.33	0.9558	0.0442
323.49	0.9488	0.0512
326.57	0.9432	0.0568
329.30	0.9378	0.0622
332.85	0.9306	0.0694
335.77	0.9200	0.0800
339.55	0.9098	0.0902
344.53	0.8984	0.1016
347.65	0.8881	0.1119

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, constant temperature thermostat, and laser monitoring system.

Solubilities were determined by a dynamic method. A known amount of solute and solvent were placed in a 50-ml jacketed equilibrium cell. A condenser attached to the top of the equilibrium cell prevented the evaporation of the organic solvent. The temperature of the solution was slowly increased (at a rate of less than 0.1 K per 10 min near the solid–liquid equilibrium temperature), and the dissolution of the solid solute was monitored with a laser detection system. The power of the laser light that passed through the solution increased as the solid dissolved. The solid–liquid equilibrium temperature was recorded when the last piece of solid dissolved.

Source and Purity of Chemicals:

99.8%, Tianjin Guangfu Fine Chemical Plant, China, was used as received.
99.5%, Kewei Company of Tianjin University, China, was used as received.

Estimated Error:

Temperature: ±0.05 K.

x₁: ±0.0001.

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹¹A. N. Gaivoronskii and V. A. Granzhan, Russ. J. Appl. Chem. 78, 404 (2005).

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

293.15

0.9827

0.017 31

303.15

0.9750

0.025 0

313.15

0.9638

0.036 2

333.15

0.9269

0.073 1

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Flask with ground-glass stopper, electronic balance, precision thermometer, constant temperature thermostat, and a synchronous electric motor for stirring.

Solubilities were determined by an isothermal method. The solvent and excess solute were placed in a flask with a ground-glass stopper and allowed to equilibrate with stirring in a constant temperature thermostat bath. After suitable equilibration, an aliquot of the saturated solution was removed, filtered, and transferred into a tared beaker for determining the mass of the sample analyzed. The solvent was then evaporated at 323 K using a temperature-controlled plate placed in an exhaust hood. The remaining solid residue was dried at 353 K until a constant mass was attained. The solubility was calculated from the mass of the solid residue and the mass of the saturated solution analyzed.

Source and Purity of Chemicals:

Analytical grade, chemical source not given, was recrystallized twice from water and dried at 393 K before use.
Analytical grade, chemical source not given, was purified by twofold freezing before use.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±0.5% (relative error).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

¹⁷S. Suren, N. Sunsandee, M. Stolcova, M. Hronec, N. Leepipatpiboon, U. Pancharoen, and S. Kheawhom, Fluid Phase Equilib. 360, 332 (2013).

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	x₂a	x₁b
303.0	0.974	0.026
313.0	0.963	0.037
323.0	0.941	0.059
333.0	0.915	0.085
343.0	0.884	0.116
353.0	0.853	0.147
363.0	0.793	0.207
373.0	0.737	0.263
383.0	0.678	0.322

Experimental values
T (K)	x₂a	x₁b
303.0	0.974	0.026
313.0	0.963	0.037
323.0	0.941	0.059
333.0	0.915	0.085
343.0	0.884	0.116
353.0	0.853	0.147
363.0	0.793	0.207
373.0	0.737	0.263
383.0	0.678	0.322

^a

x₂: mole fraction of component 2 in the saturated solution.

^b

x₁: mole fraction solubility of the solute.

Auxiliary Information

Method/Apparatus/Procedure:

Jacketed solubility cell, analytical balance, thermostatted silicone oil bath, magnetic stirring rotor, and HPLC equipped with a photodiode array detector.

The solvent and excess solute were placed in sealed container and equilibrated with stirring in a thermostatted silicone oil bath for 90 min. The stirring was then discontinued, and the solution was allowed to sit for 180 min to allow the suspended solid particles to settle to the bottom of the container. An aliquot of the saturated solution was removed and weighed. The concentration of the dissolved solute was determined by HPLC analysis with photodiode array detection.

Source and Purity of Chemicals:

99%, Sigma-Aldrich Chemical Company, St. Louis, MO, USA, was used as received.
99%, Sigma-Aldrich Chemical Company, St. Louis, MO, USA, was used as received.

Estimated Error:

Temperature: ±0.1 K.

x₁: ±2% (relative error, estimated by compiler).

Components:

Original measurements:

(1) Hexanedioic acid (adipic acid), C₆H₁₀O₄ [124-04-9]

²²B. Shen, Q. Wang, Y. Wang, X. Ye, F. Lei, and X. Gong, J. Chem. Eng. Data 58, 938 (2013).

(2) Ethanoic acid, C₂H₄O₂ [64-19-7]

Variables:

Prepared by:

Temperature

W. E. Acree, Jr.

Experimental values
T (K)	s₁a
303.2	5.80
313.2	8.41
323.2	11.89
333.2	17.10
343.2	23.01

^a

s₁: solubility of the solute, expressed as grams of solute per 100 g of either solvent or solution. While the authors do not explicitly state the basis of the solubility measurement, the compiler believes that the solubility is likely grams of solute per 100 g of solution based on the experimental description.

Auxiliary Information

IUPAC-NIST Solubility Data Series. 105. Solubility of Solid Alkanoic Acids, Alkenoic Acids, Alkanedioic Acids, and Alkenedioic Acids Dissolved in Neat Organic Solvents, Organic Solvent Mixtures, and Aqueous–Organic Solvent Mixtures. III. Alkanedioic Acids and Alkenedioic Acids

1. Preface

1.1. Scope of this volume

1.2. Concentration units used to report solubility data

2. Critical Evaluation of Solubility Data

2.1. Methodology used in the critical evaluations

2.2. Evaluation of the solubility data for hexanedioic acid in oxepan-2-one

2.3. Evaluation of the solubility data for hexanedioic acid in trichloromethane

2.4. Evaluation of the solubility data for hexanedioic acid in methanol

2.5. Evaluation of the solubility data for hexanedioic acid in ethanol

2.6. Evaluation of the solubility data for hexanedioic acid in 1-butanol

2.7. Evaluation of the solubility data for hexanedioic acid in cyclohexanol

2.8. Evaluation of the solubility data for hexanedioic acid in propanone

2.9. Evaluation of the solubility data for hexanedioic acid in cyclohexanone

2.10. Evaluation of the solubility data for hexanedioic acid in ethanoic acid

2.11. Evaluation of the solubility data for nonanedioic acid in ethanol

2.12. Evaluation of the solubility data for nonanedioic acid in propanone

2.13. Evaluation of the solubility data for nonanedioic acid ethanoic acid

2.14. Evaluation of the solubility data for pentanedioic acid in oxepan-2-one

2.15. Evaluation of the solubility data for pentanedioic acid in trichloromethane

2.16. Evaluation of the solubility data for pentanedioic acid in methanol

2.17. Evaluation of the solubility data for pentanedioic acid in ethanol

2.18. Evaluation of the solubility data for pentanedioic acid in cyclohexanol

2.19. Evaluation of the solubility data for pentanedioic acid in propanone

2.20. Evaluation of the solubility data for pentanedioic acid in cyclohexanone

2.21. Evaluation of the solubility data for pentanedioic acid in ethanoic acid

2.22. Evaluation of the solubility data for (±) hydroxybutanedioic acid in ethanol

2.23. Evaluation of the solubility data for propanedioic acid in ethanol

2.24. Evaluation of the solubility data for propanedioic acid in propanone

2.25. Evaluation of the solubility data for propanedioic acid in ethanenitrile

2.26. Evaluation of the solubility data for heptanedioic acid in ethanol

2.27. Evaluation of the solubility data for decanedioic acid in ethanol

2.28. Evaluation of the solubility data for octanedioic acid in ethyl ethanoate

2.29. Evaluation of the solubility data for octanedioic acid in ethanol

2.30. Evaluation of the solubility data for octanedioic acid in propanone

2.31. Evaluation of the solubility data for butanedioic acid in oxepan-2-one

2.32. Evaluation of the solubility data for butanedioic acid in methanol

2.33. Evaluation of the solubility data for butanedioic acid in ethanol

2.34. Evaluation of the solubility data for butanedioic acid in 1-propanol

2.35. Evaluation of the solubility data for butanedioic acid in cyclohexanol

2.36. Evaluation of the solubility data for butanedioic acid in propanone

2.37. Evaluation of the solubility data for butanedioic acid in cyclohexanone

2.38. Evaluation of the solubility data for butanedioic acid in ethanoic acid

2.39. Evaluation of the solubility data for (R*,R*)-(±)-2,3-dihydroxybutanedioc acid in ethanol

3. Solubility of Hexanedioic Acid in Organic Solvents

3.1. Hexanedioic acid solubility data in aromatic hydrocarbons

3.2. Hexanedioic acid solubility data in esters

3.3. Hexanedioic acid solubility data in ethers

3.4. Hexanedioic acid solubility data in haloalkanes, haloalkenes, and haloaromatic hydrocarbons

3.5. Hexanedioic acid solubility data in alcohols

3.6. Hexanedioic acid solubility data in ketones

3.7. Hexanedioic acid solubility data in miscellaneous organic solvents

2.39. Evaluation of the solubility data for (R,R)-(±)-2,3-dihydroxybutanedioc acid in ethanol