Solubility measurement and thermodynamic modeling of carbamazepine (form III) in five pure solvents at various temperatures

doi:10.1016/j.cjche.2020.09.054

Chinese Journal of Chemical Engineering ›› 2021, Vol. 33 ›› Issue (5): 231-235.DOI: 10.1016/j.cjche.2020.09.054

• Chemical Engineering Thermodynamics • Previous Articles Next Articles

Solubility measurement and thermodynamic modeling of carbamazepine (form III) in five pure solvents at various temperatures

Wenju Liu, Zehua Bao, Yanmin Shen, Tiantian Yao, Hongjuan Bai, Xinyu Jin

School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, China

Received:2020-06-01 Revised:2020-09-22 Online:2021-08-19 Published:2021-05-28
Contact: Wenju Liu
Supported by:
The authors would like to thank the Science Foundation of Henan University of Technology (2017RCJH09, 2017QNJH29), Science Foundation of Henan Province (202102310208, 182102210399) for their financial assistance in this project.

Solubility measurement and thermodynamic modeling of carbamazepine (form III) in five pure solvents at various temperatures

Wenju Liu, Zehua Bao, Yanmin Shen, Tiantian Yao, Hongjuan Bai, Xinyu Jin

School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, China

通讯作者: Wenju Liu
基金资助:
The authors would like to thank the Science Foundation of Henan University of Technology (2017RCJH09, 2017QNJH29), Science Foundation of Henan Province (202102310208, 182102210399) for their financial assistance in this project.

Abstract

Abstract: In this work, the solubilities of carbamazepine (CBZ) (form III) in ethyl acetate, methyl acetate, ethylene glycol, chloroform and cyclohexylamine were determined by laser monitoring techniques at pressure above sea level, and the solubility data of CBZ (form III) in different pure solvents were fitted by the Modified Apelblat model and λh model. The result shows that the solubility of CBZ (form III) in five solvents increases as temperature rises, and the solubility in chloroform was the largest. The experimental solubility values of CBZ (form III) in ethyl acetate, methyl acetate, chloroform and cyclohexylamine were in better agreement with the simulated fitting values of the λh model. For ethylene glycol, the r value was much larger than the other four solvents, and it can be seen from the λh model that ethylene glycol was closer to the ideal solution system than the other four solvents.

Key words: Solubility, Carbamazepine (form III), Modified Apelblat model, λh model

摘要： In this work, the solubilities of carbamazepine (CBZ) (form III) in ethyl acetate, methyl acetate, ethylene glycol, chloroform and cyclohexylamine were determined by laser monitoring techniques at pressure above sea level, and the solubility data of CBZ (form III) in different pure solvents were fitted by the Modified Apelblat model and λh model. The result shows that the solubility of CBZ (form III) in five solvents increases as temperature rises, and the solubility in chloroform was the largest. The experimental solubility values of CBZ (form III) in ethyl acetate, methyl acetate, chloroform and cyclohexylamine were in better agreement with the simulated fitting values of the λh model. For ethylene glycol, the r value was much larger than the other four solvents, and it can be seen from the λh model that ethylene glycol was closer to the ideal solution system than the other four solvents.

关键词: Solubility, Carbamazepine (form III), Modified Apelblat model, λh model

Wenju Liu, Zehua Bao, Yanmin Shen, Tiantian Yao, Hongjuan Bai, Xinyu Jin. Solubility measurement and thermodynamic modeling of carbamazepine (form III) in five pure solvents at various temperatures[J]. Chinese Journal of Chemical Engineering, 2021, 33(5): 231-235.

References

[1] S.L. Childs, P.A. Wood, N. Rodríguez-Hornedo, L.S. Reddy, K.I. Hardcastle, Analysis of 50 Crystal structures containing carbamazepine using the Materials Module of Mercury CSD, Cryst. Growth Des. 9(4) (2009) 1869-1888.
[2] A.L. Grzesiak, M.D. Lang, K. Kim, A.J. Matzger, Comparison of the four anhydrous polymorphs of carbamazepine and the crystal structure of form I, J. Pharm. Sci. 92(11) (2003) 2260-2271.
[3] M.D. Lang, J.W. Kampf, A.J. Matzger, Form IV of carbamazepine, J. Pharm. Sci. 91(4) (2002) 1186-1190.
[4] Y. Kobayashi, S. Ito, S. Itai, K. Yamamoto, Physicochemical properties and bioavailability of carbamazepine polymorphs and dihydrate, Int. J. Pharm. 193(2) (2000) 137-146.
[5] H.Y. Qu, M. Louhi-Kultanen, J. Kallas, Solubility and stability of anhydrate/ hydrate in solvent mixtures, Int. J. Pharm. 321(1-2) (2006) 101-107.
[6] H.Y. Qu, M. Louhi-Kultanen, J. Kallas, Additive effects on the solvent-mediated anhydrate/hydrate phase transformation in a mixed solvent, Cryst. Growth Des. 7(4) (2007) 724-729.
[7] D. Murphy, F. Rodríguez-Cintrón, B. Langevin, R.C. Kelly, N. RodríguezHornedo, Solution-mediated phase transformation of anhydrous to dihydrate carbamazepine and the effect of lattice disorder, Int. J. Pharm. 246(2002) 121-134.
[8] W.J. Lu, L.P. Dang, S. Black, H.Y. Wei, Solubility of carbamazepine (Form III) in different solvents from (275 to 343) K, J. Chem. Eng. Data. 53(2008) 2204-2206.
[9] J.A. Dean, Lange’s Handbook of Chemistry, 13th ed., McGraw-Hill, New York, USA, 1985.
[10] A. Apelblat, E. Manzurola, Solubilities of L-aspartic, DL-aspartic, DL-glutamic, p-hydroxybenzoic, o-anisic, p-anisic, and itaconic acids in water from T = 278 K to T = 345 K, J. Chem. Thermodyn. 29(1997) 1527-1533.
[11] H. Buchowski, A. Ksiazczak, S. Pietrzyk, Solvent activity along a saturation line and solubility of hydrogen-bonding solids, J. Phys. Chem. 84(1980) 975-979.
[12] Y. Wang, W.F. Ge, M.M. Wang, X.Q. Wang, Studies on dissolution equilibrium of chlorfenapyr in five mono-solvents and two mixed solvents ranging from 288.15 to 328.15K, Fluid Phase Equilib. 514(2020) 112560.
[13] D. Li, R.Y. He, K.P. Yang, J. Sha, Y.M. Wan, Y. Li, X.D. Yao, T. Li, B.Z. Ren, Thermodynamic studies of thiamethoxam in nine pure solvents and one mixed solvent, solubility and correlation ranged from 278.15 to 323.15 K, J. Chem. Thermodyn. 146(2020) 106116.
[14] L.F. Ning, X.F. Gong, P. Li, X.F. Chen, H.P. Wang, J. Xu, Measurement and correlation of the solubility of estradiol and estradiol-urea co-crystal in fourteen pure solvents at temperatures from 273.15 K to 318.15 K, J. Mol. Liq. 304(2020) 112599.
[15] X.Y. Hao, X.R. Wu, G.P. Shen, L.F. Wen, H.C. Li, Q. Huang, Thermodynamic models for determination of the solubility of (-)-shikimic acid in different pure solvents and in (H₂O+ethanol) binary solvent mixtures, J. Chem. Thermodyn. 88(2015) 8-14.
[16] Y. Cheng, Z.H. Wang, S.Z. Ding, J.C. Li, Determination and correlation of the solubility of tricin in water and ethanol mixtures, J. Chem. Thermodyn. 89(2015) 89-92.
[17] T. Li, Z.X. Jiang, F.X. Chen, B.Z. Ren, Solubilities of d -xylose in water +(acetic acid or propionic acid) mixtures at atmospheric pressure and different temperatures, Fluid Phase Equilib. 65(2013) 7-10.
[18] Y.M. Wan, H.X. He, P.S. Zhang, Z.B. Huang, R. Zhao, J. Sha, T. Li, B.Z. Ren, Solidliquid equilibrium solubility and thermodynamic properties of cis-5-norbornene-endo-2,3-dicarboxylic anhydride in fourteen pure solvents and three binary solvents at various temperatures, J. Mol. Liq. 297(2020) 111396.
[19] W.E. Acree, Mathematical representation of thermodynamic properties. Part 2. Derivation of the combined nearly ideal binary solvent (NIBS)/Redlich-Kister mathematical representation from a two-body and three-body interactional mixing model, Thermochim. Acta 198(1992) 71-79.
[20] W.E. Acree, Comments concerning ‘model for solubility estimation in mixed solvent systems’, Int. J. Pharm. 127(1996) 27-30.
[21] M. Barzegar-Jalali, E.M.H. Agha, K. Adibkia, F. Martinez, A. Jouyban, The solubility of ketoconazole in binary carbitol + water mixtures at T = (293.2-313.2) K, J. Mol. Liq. 297(2020) 111756.
[22] J.Q. Zhu, Y.S. Yu, C.H. He, Calculation of solid’s solubilities in mixed liquid solvents by the kh equation using mixing rules, Fluid Phase Equilib. 155(1) (1999) 85-94.

Solubility measurement and thermodynamic modeling of carbamazepine (form III) in five pure solvents at various temperatures

Solubility measurement and thermodynamic modeling of carbamazepine (form III) in five pure solvents at various temperatures

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jingzhou Guo, Yuanzuo Zou, Bo Shi, Yuan Pu, Jiexin Wang, Dan Wang, Jianfeng Chen. Experimental verification of nanonization enhanced solubility for poorly soluble optoelectronic molecules [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 8-15.
[2]	Xingjuan Liang, Dehua Xu, Zhengjuan Yan, Jingxu Yang, Xinlong Wang, Zhiye Zhang, Jingli Wu, Honggang Zhen. Solid-liquid phase equilibrium for the system ammonium polyphosphate-urea ammonium nitrate-potassium chloride-water at 273.2 K [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 131-142.
[3]	Huiqi Wang, Jianpo Ren, Shihao Zhang, Jiayu Dai, Yue Niu, Ketao Shi, Qiuxiang Yin, Ling Zhou. Measurement and correlation of solubility of 9-fluorenone in 11 pure organic solvents from T = 283.15 to 323.15 K [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 235-241.
[4]	Wen Yu, Yiyang Bo, Yiling Luo, Xiyan Huang, Rixiang Zhang, Jiaheng Zhang. Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 160-168.
[5]	Zhonghao Li, Yuanyuan Yang, Huanong Cheng, Yun Teng, Chao Li, Kangkang Li, Zhou Feng, Hongwei Jin, Xinshun Tan, Shiqing Zheng. Measurement and model of density, viscosity, and hydrogen sulfide solubility in ferric chloride/trioctylmethylammonium chloride ionic liquid [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 210-221.
[6]	Yun-Zhang Liu, Lu-Yao Zhang, Dan He, Li-Zhen Chen, Zi-Shuai Xu, Jian-Long Wang. Solubility measurement, correlation and thermodynamic properties of 2, 3, 4-trichloro-1, 5-dinitrobenzene in fifteen mono-solvents at temperatures from 278.15 to 323.15 K [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 224-233.
[7]	Pengbao Lian, Lizhen Chen, Dan He, Guangyuan Zhang, Zishuai Xu, Jianlong Wang. Crystallization thermodynamics of 2,4(5)-dinitroimidazole in binary solvents [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 173-182.
[8]	Peng Yang, Shengzhe Jia, Yan Wang, Zongqiu Li, Songgu Wu, Jingkang Wang, Junbo Gong. Dissolution behavior, thermodynamic and kinetic analysis of malonamide by experimental measurement and molecular simulation [J]. Chinese Journal of Chemical Engineering, 2023, 53(1): 260-269.
[9]	Pengbao Lian, Lizhen Chen, Daozhen Huang, Jianxin Xu, Zishuai Xu, Cai Cao, Jiaxiang Zhao, Jianlong Wang. Crystallization thermodynamics of 2,4(5)-dinitroimidazole in eleven pure solvents [J]. Chinese Journal of Chemical Engineering, 2022, 48(8): 236-243.
[10]	Haoyu Yao, Dongxia Yan, Xingmei Lu, Qing Zhou, Yinan Bao, Junli Xu. Solubility determination and thermodynamic modeling of bis-2-hydroxyethyl terephthalate (BHET) in different solvents [J]. Chinese Journal of Chemical Engineering, 2022, 45(5): 294-300.
[11]	Fanfan Shen, Lizhen Chen, Pengbao Lian, Jianlong Wang, Duanlin Cao. Solubility and metastable zone width measurement of 2,4-diaminobenzenesulfonic acid in (H₂SO₄ + H₂O) system [J]. Chinese Journal of Chemical Engineering, 2022, 44(4): 384-391.
[12]	Xi Wu, Shuaishuai Yang, Shiming Xu, Xinjie Zhang, Yujie Ren. Measurement and correlation of the solubility of sodium acetate in eight pure and binary solvents [J]. Chinese Journal of Chemical Engineering, 2022, 44(4): 474-484.
[13]	Alireza Afsharpour. A new approach for correlating of H₂S solubility in [emim][Lac], [bmim][ac] and [emim][pro] ionic liquids using two-parts combined models [J]. Chinese Journal of Chemical Engineering, 2022, 44(4): 521-527.
[14]	Yu Dong, Tiantian Ping, Shufeng Shen. Solubility of CO₂ in nonaqueous system of 2-(butylamino)ethanol with 2-butoxyethanol: Experimental data and model representation [J]. Chinese Journal of Chemical Engineering, 2022, 41(1): 441-448.
[15]	Jipeng Li, Huan Xu, Jingqi Wang, Yujun Wang, Diannan Lu, Jichang Liu, Jianzhong Wu. Theoretical insights on the hydration of quinones as catholytes in aqueous redox flow batteries [J]. Chinese Journal of Chemical Engineering, 2021, 37(9): 72-78.