Measurement and correlation of solubility of dodecanedioic acid in different pure solvents from T = (288.15 to 323.15) K
Introduction
Dodecanedioic acid (DDDA, C12H22O4, CAS registry No. 693-23-3, figure 1) has achieved industrial importance in the manufacturing of polyamides, polyesters, lubricating oils and plasticizers [1], [2], [3]. DDDA is usually obtained by oxidizing cyclododecanol or cyclododecanone with nitric acid or via an increasingly important method of microbiological fermentation [4], during which by-products such as dicarboxylic acids having less than 11 carbon atoms and nitrogen-containing metabolites are inevitable [5]. In industry, solution crystallization is the most common and efficient purification method to get commercial DDDA [6]. However, the DDDA homologues and the metabolites are extremely difficult to be separated from aqueous solution because the extreme poor aqueous solubility of DDDA [7] and homologues leads to uncontrolled crystallization process. Therefore, to realize a good control of crystallization process and thus high purity, organic solvents need to be applied in the process of crystallization of DDDA. To select suitable solvents and to design an optimal production process, it is important to know the solubility of DDDA in the organic solvents. Unfortunately, the solubility data of DDDA in commonly used organic solvents at different temperature are not available in the literature.
In this work, a static analytic method was employed to determine the solubility of DDDA in ethanol, acetic acid, acetone, butanone, 3-pentanone and ethyl acetate at atmospheric pressure over the temperature range from (288.15 to 323.15) K. The molecular modeling was carried out to understand the striking difference of solubility in various solvents. Moreover, the modified Apelblat equation was chosen to fit the measured solubility data. The molar Gibbs energies, enthalpies, and entropies of solutions in pure solvents were derived using the parameters of modified Apelblat equation. Actually, we have also tried to correlate the experimental data with van’t Hoff, λh (Buchowski), Wilson and NRTL models [8], [9]. The modified Apelblat equation showed the best agreement, so the correlation results with other equations were not reported here for brevity reason.
Section snippets
Materials
The DDDA was supplied by Huaian Qingjiang Petrochemical Co., Ltd. (Jiangsu, China) with a minimum mass fraction purity 0.990. The crystal structure of DDDA was identified by powder X-ray diffraction (PXRD, D/MAX 2500 Japan) pattern. The PXRD pattern was shown in figure 2. All of the organic solvents used for the experiments, including ethanol, acetic acid, acetone, ethyl acetate, butanone, 3-pentanone (purchased from Tianjin Kewei Co. of China) were of analytic reagent grade and were used
Solubility in the selected solvents
The solubility of DDDA in the selected pure solvents is presented in the table 2. Within the temperature range of the measurements, the solubility of DDDA increases with increasing temperature in all selected solvents. At a given temperature, the order of solubility is ethanol > acetic acid > acetone > butanone > 3-pentanone > ethyl acetate.
The order of polarities of the solvents is ethanol > acetone > butanone > 3-pentanone > acetic acid > ethyl acetate. Unexpectedly, the solubility does not increase with
Conclusions
The solubility of DDDA in ethanol, acetic acid, acetone, butanone, 3-pentanone and ethyl acetate was measured over the temperature range from (288.15 to 323.15) K by a static analytic method at atmospheric pressure. The solubility monotonically increased with increasing temperature and was, at the same temperature, in the order of ethanol > acetic acid > acetone > butanone > 3-pentanone > ethyl acetate. Further, the molecular modeling studies indicated that this behavior is due to the different hydrogen
Acknowledgment
This work was supported by the National high technology research and development program (863 Program No. 2012AA021202).
References (27)
- et al.
Fluid Phase Equilib.
(2012) - et al.
J. Chem. Thermodyn.
(1999) - et al.
Fluid Phase Equilib.
(2011) - et al.
Fluid Phase Equilib.
(2012) - M. A. Emanuel, K.N. James, US Patent No. 3417138,...
- Y. Okada, US Patent No. 3903152,...
- Ullmann’s Encyclopedia of Industrial Chemistry, Dicarboxylic Acids, Aliphatic,...
- Y. Okada, US Patent No. 3714244,...
- S.C. Zhang, US Patent No. 6218574,...
- C.H. Norman, US Patent No. 2858335,...
J. Chem. Soc.
Ind. Eng. Chem. Res.
Ind. Eng. Chem. Res.
Cited by (51)
Solubility measurement and correlation of 2-aminoterephthalic acid in eight alcoholic solvents at different temperatures
2023, Journal of Chemical ThermodynamicsSolubility measurements and thermodynamic modelling of organoaluminum supported by unsymmetrical β-diketimine ligand
2022, Journal of Molecular LiquidsSolubility determination and dissolution thermodynamic properties of dodecanedioic acid in binary-mixed solvents from T = (288.15–328.15) K
2022, Journal of Chemical ThermodynamicsCitation Excerpt :Meanwhile, when the mole fraction of ethyl acetate gets larger continuously and exceeds the certain value, the polarity of the mixed solution decreases due to the low polarity of ethyl acetate, and the solubility of DDDA will decrease. For the purpose of checking the reliability of the experimental method employed in this paper, the solubility we obtained of DDDA in ethanol, acetic acid, acetone and ethyl acetate are compared with those published in the literature [5]. The solubility of DDDA in four solvents in the literature are listed in Table S1 and the relative deviation between the literature value and experimental value of DDDA mole solubility are listed in Table S2.
Solubility determination and thermodynamic analysis of organic zinc supported by β-diimine ligands in pure solvents
2022, Journal of Molecular LiquidsCitation Excerpt :It meant that the smaller ΔGosol is, the greater solubility of compounds in the solvent is, and the easier the reaction is to go ahead. This trend of ΔGosol with solubility was reported in the previous literature [31,32]. The dissolution process of the three compounds all proves this rule.
Thermodynamic analysis and molecular dynamic simulation of the solubility of 2,2-Bis(hydroxymethyl)propionic acid in 12 monosolvents
2022, Journal of Chemical ThermodynamicsCitation Excerpt :As a polyurethane chain extender and chemical raw material [10], DMPA is often used in such solvents including ethanol, water, DMF, and acetone. As the basic data of industrial production and scientific research, DMPA solubility is crucial for developing new crystallization process and obtaining new applications [11]. However, there is no solubility data of DMPA reported in these systems.