Revealing dissolution behavior of o-methoxybenzoic acid in twelve pure solvents using thermodynamic analysis and molecular simulation

Abstract The solubility of o-methoxybenzoic acid (OMBA) in twelve pure solvents range from 283.15 to 323.15 K was investigated by the experiments and molecular simulations. The result of gravimetric method showed that OMBA has the highest solubility in acetone and the lowest solubility in water. Molecular simulations of MPI, MEPs, HS and SFE were employed to understand the dissolution behavior. In particular, MPI had proved to be an uncommon but effective parameter, which can provide a better explanation based on the polarity of “like dissolves like”. Moreover, the intermolecular interactions derived from HS analysis indicated that the H-H contacts as well as the C=O∙∙∙H-O hydrogen bonding interactions were dominant in the crystal packing of OMBA. Six thermodynamic models were further selected to correlate experimental solubility results successfully as the A R D % values of the six models were less than 7%. The mixing thermodynamic properties obtained from the correlated results of the NRTL model, indicating that the dissolution process is spontaneous and entropy-driven. The experimental data can be used as a useful basis for the industrial production of intermediate product OMBA.