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

doi:10.1016/j.cjche.2022.10.022

摘要/Abstract

摘要： The solubility of 2,3,4-trichloro-1,5-dinitrobenzene (TCDNB) was measured by a laser dynamic method over the temperature range from 278.15 K to 323.15 K under 0.1 MPa in fifteen mono-solvents (methanol, ethanol, isopropanol, n-butanol, toluene, dichloromethane, chloroform, tetrachloromethane, 1,2-dichloroethane, acetone, ethyl acetate, acetonitrile, N-methylpyrrolidone (NMP), N,N-dimethylformamide dimethyl sulfoxide (DMF), dimethyl sulfoxide (DMSO). The solubility of TCDNB could be increased with increasing temperature in fifteen mono-solvents. TCDNB solubility is in the following order at 298.15 K: NMP>DMF>DMSO>toluene>acetone>ethyl acetate>dichloromethane>1,2-dichloroethane>chloroform>acetonitrile>tetrachloromethane>methanol>ethanol>n-butanol>isopropanol. The KAT-LSER model was used to investigate the solvent effect, which revealed that the hydrogen bond acidity of solvents has a greater effect on TCDNB solubility. The van't Hoff model, the modified Apelblat model, the λh model, and the non-random two liquid (NRTL) model were used to correlate the solubility of TCDNB. The calculated solubility data agreed well with the experimental data, and the modified Apelblat model fit best. Furthermore, the van't Hoff and Gibbs equations were also used to calculate the dissolution thermodynamic properties of TCDNB in various solvents. TCDNB dissolution could be an enthalpy-driven, non-spontaneous, and endothermic process in fifteen mono-solvents. The determination and fitting solubility of TCDNB, as well as the calculation of its thermodynamic properties, would be critical in the purification and crystallization of its preparation process research.

关键词: 2,3,4-Trichloro-1,5-dinitrobenzene (TCDNB), Solid-liquid equilibrium, Laser dynamic method, Solubility model, Thermodynamics properties

Abstract: The solubility of 2,3,4-trichloro-1,5-dinitrobenzene (TCDNB) was measured by a laser dynamic method over the temperature range from 278.15 K to 323.15 K under 0.1 MPa in fifteen mono-solvents (methanol, ethanol, isopropanol, n-butanol, toluene, dichloromethane, chloroform, tetrachloromethane, 1,2-dichloroethane, acetone, ethyl acetate, acetonitrile, N-methylpyrrolidone (NMP), N,N-dimethylformamide dimethyl sulfoxide (DMF), dimethyl sulfoxide (DMSO). The solubility of TCDNB could be increased with increasing temperature in fifteen mono-solvents. TCDNB solubility is in the following order at 298.15 K: NMP>DMF>DMSO>toluene>acetone>ethyl acetate>dichloromethane>1,2-dichloroethane>chloroform>acetonitrile>tetrachloromethane>methanol>ethanol>n-butanol>isopropanol. The KAT-LSER model was used to investigate the solvent effect, which revealed that the hydrogen bond acidity of solvents has a greater effect on TCDNB solubility. The van't Hoff model, the modified Apelblat model, the λh model, and the non-random two liquid (NRTL) model were used to correlate the solubility of TCDNB. The calculated solubility data agreed well with the experimental data, and the modified Apelblat model fit best. Furthermore, the van't Hoff and Gibbs equations were also used to calculate the dissolution thermodynamic properties of TCDNB in various solvents. TCDNB dissolution could be an enthalpy-driven, non-spontaneous, and endothermic process in fifteen mono-solvents. The determination and fitting solubility of TCDNB, as well as the calculation of its thermodynamic properties, would be critical in the purification and crystallization of its preparation process research.

Key words: 2,3,4-Trichloro-1,5-dinitrobenzene (TCDNB), Solid-liquid equilibrium, Laser dynamic method, Solubility model, Thermodynamics properties

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]. 中国化学工程学报, 2023, 58(6): 224-233.

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