Measurement of the solubility and density of the saturated solution of 3-aminophenol in different pure solvents from 283.1 to 323.1 K: Correlative to pure predictive thermodynamic modeling and molecular dynamic simulation.

[Display omitted] • The solubility of 3-aminophenol was measured in different pure solvents from 283.1 to 323.1 K. • The density of pure solvents and the saturated 3-aminophenol solutions were measured. • The Wilson, NRTL, UNIQUAC, and NRTL-SAC models were used in the modeling. • The predictive models UNIFAC, UNIFAC-DMD, and COSMO-SAC were used. • The values of solvation free energy obtained by molecular dynamics are in agreement with the experimental data. The solubility of 3-aminophenol was measured in water, isopropanol, ethyl acetate, chloroform, and tert -butyl methyl ether (MTBE) from 283.1 to 323.1 K at atmospheric pressure. In addition, the density of pure solvents and the saturated 3-aminophenol solutions was measured. The experimental solubility data were correlated and predicted using four types of thermodynamic models, including correlative (Wilson, NRTL, and UNIQUAC), semi-predictive (NRTL-SAC, and UNIQAUC-SAC), predictive group contribution methods (UNIFAC, and UNIFAC-DMD), and pure predictive COSMO-SAC model. The NRTL-SAC and UNIQUAC-SAC as semi-predictive models were used to obtain 3-aminophenol conceptual segment numbers, and then, using the NRTL-SAC model, the solubility of 3-aminophenol was predicted in 58 FDA approved solvents in the pharmaceutical industry. The predictive models including UNIFAC and UNIFAC-DMD were also used to predict the 3-aminophenol solubility and compared with the experimental data. The results of the COSMO-SAC model have a large deviation from experimental data. In addition, the experimental solubility data were correlated using the PR equation of state with relative success. The segment-based models such as NRTL-SAC and UNIQUAC-SAC are suggested in the fast solvent screening procedure. Finally, the standard dissolution enthalpy (Δ dis H), the standard dissolution entropy (Δ dis S), and the standard dissolution Gibbs energy (Δ dis G) of 3-aminophenol in the selected solvents were calculated by the Van't Hoff model and the Gibbs-Helmholtz equation. These values imply that the solubility of 3-aminophenol is an entropy-driven non-spontaneous endothermic process in all chosen single solvents. Using the molecular dynamic (MD) simulation the solvation free energy of 3-aminophenol was calculated. The order of the absolute value of free energy of solvation is as ethyl acetate > isopropanol > MTBE > water > chloroform which is consistent with the order of solubility data. [ABSTRACT FROM AUTHOR]