Crystallization thermodynamics of 2,4(5)-dinitroimidazole in eleven pure solvents

doi:10.1016/j.cjche.2021.07.031

摘要/Abstract

摘要： 2,4(5)-Dinitroimidazole (2,4(5)-DNI) is an important energetic material, and it is also an important precursor for the preparation of drugs and energetic materials. In this study, the solubility of 2,4(5)-DNI in eleven pure solvents (chlorobenzene, benzene, 1,2-dichloroethane, toluene, water, isopropyl alcohol, ethyl acetate, acetonitrile, methanol, 1,4-dioxane and acetone) were measured by using a dynamic test method from 278.15?K to 323.15?K under 101.1?kPa. Four solubility models were used to fit the experimental data, which were ideal model, modified Apelblat equation, polynomial empirical equation, and λh equation. Meanwhile, the relative average deviation and root-mean-square deviation between the experimental data and the fitted data were also calculated. Furthermore, the three thermodynamic parameters, i.e., dissolution enthalpy, dissolution entropy and Gibbs energy were obtained based on solubility data. Finally, the crude product of 2,4(5)-DNI was crystallized with acetone as solvent, and the purity of the crystalline product was greater than 99.5%.

关键词: 2,4(5)-Dinitroimidazole, Solid-liquid equilibrium, Solubility model, Three thermodynamic parameters, Cooling crystallization

Abstract: 2,4(5)-Dinitroimidazole (2,4(5)-DNI) is an important energetic material, and it is also an important precursor for the preparation of drugs and energetic materials. In this study, the solubility of 2,4(5)-DNI in eleven pure solvents (chlorobenzene, benzene, 1,2-dichloroethane, toluene, water, isopropyl alcohol, ethyl acetate, acetonitrile, methanol, 1,4-dioxane and acetone) were measured by using a dynamic test method from 278.15?K to 323.15?K under 101.1?kPa. Four solubility models were used to fit the experimental data, which were ideal model, modified Apelblat equation, polynomial empirical equation, and λh equation. Meanwhile, the relative average deviation and root-mean-square deviation between the experimental data and the fitted data were also calculated. Furthermore, the three thermodynamic parameters, i.e., dissolution enthalpy, dissolution entropy and Gibbs energy were obtained based on solubility data. Finally, the crude product of 2,4(5)-DNI was crystallized with acetone as solvent, and the purity of the crystalline product was greater than 99.5%.

Key words: 2,4(5)-Dinitroimidazole, Solid-liquid equilibrium, Solubility model, Three thermodynamic parameters, Cooling crystallization

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]. 中国化学工程学报, 2022, 48(8): 236-243.

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