Journal of Chemical and Engineering Data, Vol.63, No.10, 3715-3726, 2018
Solubility Measurement and Modeling of 2-Amino-4,6-dichoropyrimidine in Ten Pure Solvents and (Ethyl Acetate plus Ethanol) Solvent Mixtures
The basis of purification and further theoretical studies of 2-amino-4,6-dichoropyrimidine is the solubility and solution thermodynamics in different solvents. In this paper, the solubility of 2-amino-4,6-dichoropyrimidine in 10 neat solvents (methanol, ethanol, n-propanol, isopropanol, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, toluene, and cyclohexane) and binary liquid mixtures (ethyl acetate + ethanol) was measured by the isothermal saturation method at temperatures range from 278.15 to 318.15 K, at p = 101.2 kPa. High-performance liquid chromatography (HPLC) was used to analyze the solubility of 2-amino-4,6-dichoropyrimidine in selected solvents. To sum up, the equilibrium mole fraction solubility was highest in 1,4-dioxane (2.619 x 10(-2) at 318.15 K) and lowest in cyclohexane (0.02238 x 10(-2) at 318.15 K), and ranked as 1,4-dioxane (2.619 x 10(-2) at 318.15 K) > acetone (1.630 x 10(-2) at 318.15 K) ethyl acetate (1.471 x 10(-2) at 318.15 K) > acetonitrile (0.5048 x 10(-2) at 318.15 K) methanol (0.3888 x 10(-2) at 318.15 K) > ethanol (0.3391 x 10(-2) at 318.15 K) > n-propanol (0.3133 x 10(-2) at 318.15 K) > toluene (0.2737 x 10(-2) at 318.15 K) > isopropanol (0.2574 x 10(-2) at 318.15 K) > cyclohexane (0.02238 x 10(-2) at 318.15 K). The achieved solubility values in monosolvents were correlated by the modified Apelblat equation, lambda h equation, Wilson model, and NRTL model and in solvent mixtures by three cosolvency models including Jouyban-Acree model, van't Hoff-Jouyban-Acree model, and Apelblat-Jouyban-Acree model. Calculated results fitted well with experimental data. Consequently, for the monosolvents, the values of root mean-square deviation (RMSD) and relative average deviation (RAD) were less than 0.58 x 10(-4) and 0.80%, respectively, and for the binary solvent mixtures were 0.49 x 10(-4) and 0.46%. Furthermore, the Gibbs energy, mixing enthalpy, mixing entropy, activity coefficient at infinitesimal concentration (gamma(infinity)(1)) and reduced excess enthalpy (H-1(E,infinity)) in monosolvents, and dissolution property in mixed solvents were computed. The mixing process of 2-amino-4,6-dichoropyrimidine in the studied solvents was spontaneous and endothermic. The obtained solubility and thermodynamic studies would be used to optimize the purification process of 2-amino-4,6-dichoropyrimidine.