Measurement and correlation for solubility of dimethyl-2,6-naphthalene dicarboxylate in  organic solvents

Abstract

Abstract: Solubility of dimethyl-2,6-naphthalene dicarboxylate in acetic acid, N,N-dimethylformamide, N,N-dimethyl acetamide, dimethyl sulphoxide, and N-methyl-2-ketopyrrolidine were determined using a dynamic method. The measured systems were correlated by UNIFAC group contribution method. A new main group (aromatic ester, ACCOO) was defined to express the activity coefficients of the aromatic ester. New interaction parameters of the ACCOO group were expressed as the first-order function of temperature and were determined from the experimental data. The calculated results for the new interaction parameters were satisfactory. The measured systems were also correlated with the Wilson and λ-h models, and the results were compared with those of the UNIFAC model.

Key words: solid-liquid equilibrium, solubility, dimethyl-2, 6-naphthalene dicarboxylate, UNIFAC group contribution method, activity coefficient

摘要： Solubility of dimethyl-2,6-naphthalene dicarboxylate in acetic acid, N,N-dimethylformamide, N,N-dimethyl acetamide, dimethyl sulphoxide, and N-methyl-2-ketopyrrolidine were determined using a dynamic method. The measured systems were correlated by UNIFAC group contribution method. A new main group (aromatic ester, ACCOO) was defined to express the activity coefficients of the aromatic ester. New interaction parameters of the ACCOO group were expressed as the first-order function of temperature and were determined from the experimental data. The calculated results for the new interaction parameters were satisfactory. The measured systems were also correlated with the Wilson and λ-h models, and the results were compared with those of the UNIFAC model.

关键词: solid-liquid equilibrium;solubility;dimethyl-2;6-naphthalene dicarboxylate;UNIFAC group contribution method;activity coefficient

XIAQing,MAPeisheng. Measurement and correlation for solubility of dimethyl-2,6-naphthalene dicarboxylate in
organic solvents[J]. .

夏清, 马沛生. 2，6-萘二甲酸二甲酯在有机溶剂中溶解度的测定与关联[J]. CIESC Journal.

References

1    Shiroto, Y., Kato, T., “Trends of production technologies of naphthalene derivatives for functional polyesters”  Catalysts & Catalysis, 33(8),559—565(1991).
2    Xia, Q., Ruan, X.Q., Zheng, J.M., Ma, P.S., “The trend of the production of 2,6-naphthalene dicarboxylic acid by Co-Mn-Br catalytic oxidation of 2,6-dialkyl naphthalene”, Chem. Ind. and Eng., 14(4), 27—33(1997). (in Chinese)
3    Xia, Q., Ma, P.S., “Research for the process of esterify-ing 2,6-naphthalene dicarboxylic acid by methanol－Determination for the optimum catalyst and the reaction conditions”, Chinese Chem. Reaction Eng. and Process, 16(3), 32—37(2000). (in Chinese)
4    Jiao, N.N., “Progress in synthesis and application of di-methyl 2，6-naphthaIene dicarboxylate” China Synthetic Fiber Industry, 25(6), 34—38(2002). (in Chinese)
5    Xia, Q., Ma, P.S., “Advances in 2,6-naphthalene dicar-boxylic acid purification technology”, Chinese Petro-chem. Technol., 26(5), 325—331(1997).
6    Lu, E.X., “Preparation technology of dimethyl 2,6-naphthalene dicarboxylate”, Guangzhou Chem. Ind. and Technol., 22(3), 41—44(1994). (in Chinese)
7    Ye, Q.L., Guo, S.Z., Cao, F.H., Fang, D.Y., “A review on the preparation of 2. 6-naphthalene dicarboxylic acid”, Chemical World, 46(3), 181—185(2005). (in Chinese)
8    Ma, P.S., Xia, Q., “Determination and correlation for solubility of aromatic acids in solvents”, Chin. J. Chem. Eng., 9(1), 39—44(2001).
9    Stephen, H., Stephen, T., Solubilities of Inorganic and Organic Compounds, Oxford Pergamon, London (1963).
10    Gmehling, J., Anderson, T.F., Prausnitz, J.M., “Solid-liquid equilibria using UNIFAC”, Ind. Eng. Chem. Fundam., 17, 269—273(1978).
11    Tong, J.S., Li, J., Calculation of Fluid Thermophysic Properties, Tsinghua University Press, Beijing (1982).
12    Nelder, J.A., Mead, R. “A simplex method for function minimization”, Comput. J., 18(2), 308—313(1975).
13    Fredenslund, A., Gmehling, J., Rasmussen, P., Va-por-Liquid Equilibria Using UNIFAC, Elsevier, Amster-dam (1977).
14    Gmehling, J., Li, J., Schiller, M., “A modified UNIFAC model. 2. Present parameter matrix and results for dif-ferent thermodynamic properties” , Ind. Eng. Chem. Res., 32(1), 178—193(1993).
15    Domanska, U., Hofman, T., “Solubility correlation of monocarbonxylic acids in one-component solvents”, Ind. Eng. Chem. Process Des. Dev., 25(4), 996—1008(1986).
16    Domanska, U., Hofman, T., “Correlations for the solubility of normal akanoic acids and o-toluic acid in binary solvent mixture” J. Solution Chem., 14(7), 531—547(1985).
17    Buchowski, H., “Solubility of solids in liquids: One pa-rameter solubility equation”, Fluid Phase Equilibria, 25, 273—278(1986).
18    Ma, P.S., Chen, M.M., “Solid-liquid equilibrium of terephthalic acid in several solvents” Chin. J. Chem. Eng., 11(3), 334—337(2003).
19    Ma, P.S., Chen, M.M., Dong, Y., “Solid-liquid equilibria of several binary and ternary systems containing maleic an-hydride”, Chin. J. Chem. Eng., 10(3), 323—327(2002).
20    Domanska, U., “Solid-liquid phase relations of some normal long-chain fatty acids in selected organic one-and two-component solvents” Ind. Eng. Chem. Res., 26(6), 1153—1162(1987).
21    Domanska, U., “Solubility of n-paraffins hydrocarbons in binary solvent mixtures”, Fluid Phase Equilibria, 35(1-3), 217—236(1987).

Related Articles 15

[1]	Chao HU, Yuming DONG, Wei ZHANG, Hongling ZHANG, Peng ZHOU, Hongbin XU. Preparation of high-concentration positive electrolyte of vanadium redox flow battery by activating vanadium pentoxide with highly concentrated sulfuric acid [J]. CIESC Journal, 2023, 74(S1): 338-345.
[2]	Xudong YU, Qi LI, Niancu CHEN, Li DU, Siying REN, Ying ZENG. Phase equilibria and calculation of aqueous ternary system KCl + CaCl₂ + H₂O at 298.2, 323.2, and 348.2 K [J]. CIESC Journal, 2023, 74(8): 3256-3265.
[3]	Erqi WANG, Shuzhou PENG, Zhen YANG, Yuanyuan DUAN. Evaluation of vapor-liquid equilibrium models for mixtures containing HFOs [J]. CIESC Journal, 2023, 74(8): 3216-3225.
[4]	Ke CHEN, Li DU, Ying ZENG, Siying REN, Xudong YU. Phase equilibria and calculation of quaternary system LiCl+MgCl₂+CaCl₂+H₂O at 323.2 K [J]. CIESC Journal, 2023, 74(5): 1896-1903.
[5]	Wenting CHENG, Jie LI, Li XU, Fangqin CHENG, Guoji LIU. Experiment and prediction for the solubility of AlCl₃·6H₂O in FeCl₃, CaCl₂, KCl and KCl-FeCl₃solutions [J]. CIESC Journal, 2023, 74(2): 642-652.
[6]	Jin CAI, Xiaohui WANG, Han TANG, Guangjin CHEN, Changyu SUN. Prediction of the phase equilibrium of semi-clathrate hydrate in TBAB aqueous solution [J]. CIESC Journal, 2023, 74(1): 408-415.
[7]	Yuxin REN, Runfeng XU, Wanying WANG, Pengzhong CHEN, Xiaojun PENG. Synthesis and stability study of anthraquinone dyes for color photoresist [J]. CIESC Journal, 2022, 73(5): 2251-2261.
[8]	Yanlong JIANG, Ni ZHANG, Danran LI, Bingbing ZHU, Yichen JIANG, Haijun CHEN, Yuezhao ZHU. Selected ionic liquids by COSMO-RS method for tar removal [J]. CIESC Journal, 2022, 73(4): 1704-1713.
[9]	Siying REN, Xudong YU, Jun LUO, Xia FENG, Zhixing ZHAO, Zhihao YAO. Phase equilibria of aqueous quaternary system Li⁺, K⁺, $N H 4 +$ // Cl^- - H₂O at 298.2 K [J]. CIESC Journal, 2022, 73(10): 4335-4344.
[10]	Jianyuan XU, Yanyang WU, Jumei XU, Yangfeng PENG. Study on vapor-liquid equilibria and distillation simulation of 1,3,5-trimethylbenzene-1,2,4-trimethylbenzene and 1,3,5-trimethylbenzene-2-ethyltoluene at 2 kPa [J]. CIESC Journal, 2021, 72(9): 4504-4510.
[11]	Zhirong CHEN, Yun TONG, Shenfeng YUAN, Hong YIN. Dissociation constants and activity coefficients of methionine in KCl aqueous solutions [J]. CIESC Journal, 2021, 72(9): 4469-4478.
[12]	Xueping ZHANG, Ruizhi CUI, Shihua SANG. Experiment and calculation of phase equilibrium in ternary systems NaBr-CaBr₂-H₂O and KBr-CaBr₂-H₂O at 273.15 K [J]. CIESC Journal, 2021, 72(9): 4479-4486.
[13]	Shengzheng GUO, Songgu WU, Xin SU, Wei GAO, Zhiping NIU, Junbo GONG. Determination of solubility and metastable zone width of rebaudioside A and study on its crystallization process [J]. CIESC Journal, 2021, 72(8): 3997-4008.
[14]	Xian WANG, Yanxing ZHAO, Xueqiang DONG, Xiaogang CHEN, Maoqiong GONG. Prediction of solid-liquid equilibrium of binary mixtures containing methane [J]. CIESC Journal, 2021, 72(8): 4009-4018.
[15]	LUO Jun, WANG Lin, HUANG Qin, REN Siying, YU Xudong, ZENG Ying. Phase equilibria for ternary system CsCl-PEG8000-H₂O at 288.2, 298.2 and 308.2 K [J]. CIESC Journal, 2021, 72(6): 3140-3148.