Solubility, molecular simulation, Hansen solubility parameter and thermodynamic properties of citiolone in thirteen organic pure solvents at different temperatures

Abstract

The solubility of citiolone (CIT) in 13 mono-solvents, including {methanol, 2-methoxyethanol, ethanol, 2-ethoxyethanol, n-propanol, 2-propoxyethanol, n-butanol, 2-butoxyethanol, n-pentanol, n-butyl acetate, ethyl acetate, methyl acetate, n-propyl acetate} was determined under 0.1 MPa from 278.15 K to 323.15 K by laser detection method. The results show that as the temperature increases, the solubility of CIT gradually increases. The order of solubility values (10x1) of CIT in 13 mono-solvents at 298.15 K is: 2-methoxyethanol (2.098) > methanol (1.650) > 2-ethoxyethanol (1.579) > 2-propoxyethanol (1.226) > 2-butoxyethanol (1.016) > ethanol (0.8658) > n-propanol (0.6781) > n-butanol (0.5739) > n-pentanol (0.5320) > methyl acetate (0.4785) > ethyl acetate (0.3252) > n-propyl acetate (0.2570) > n-butyl acetate (0.2276). In addition, the Hansen solubility parameter (HSP) was employed to further discuss the miscibility of CIT in the studied solvents. Molecular dynamics simulation explored the intermolecular interaction between solute and solvents. And the solvent effect of CIT in the tested pure solvents was explained by the KAT-LSER model. The basic data of experimental solubility of CIT were correlated with five thermodynamic models, including NRTL, λh, modified Apelblat, UNIQUAC and two-Suffix Margules. Furthermore, the van't Hoff equation was applied to analyze the dissolution thermodynamic properties of CIT in 13 particular solvents, including ΔdisHo, ΔdisSo and ΔdisGo.