Thermodynamic modelling and Hansen solubility parameter of N-hydroxy-5-norbornene-2,3-dicarboximide in twelve pure solvents at various temperatures

Abstract

Solubility of N-hydroxy-5-norbornene-2,3-dicarboximide (HONB) in methanol, ethanol, n-propanol, isopropanol, 2-methoxyethanol, 2-propoxyethanol, 2-ethoxyethanol, 2-butoxyethanol, acetonitrile, ethyl acetate, acetone at (278.15–323.15) K and 1,4-dioxane at (288.15–323.15) K was determined with a laser monitoring method at pressure of 0.1 MPa. The experimental results indicated that solubility of HONB increased positively with the increase of temperature in selected neat solvents. At 298.15 K, solubility data in studied solvents followed the sequence of 2-methoxyethanol (0.1412) > methanol (0.1108) > 2-ethoxyethanol (0.1007) > 1,4-dioxane (0.0963) > 2-propoxyethanol (0.0718) > 2-butoxyethanol (0.0601) > ethanol (0.0592) > acetone (0.0520) > isopropanol (0.0402) > n-propanol (0.0401) > acetonitrile (0.0298) > ethyl acetate (0.0156). The solubility behaviors of HONB in investigated solvents were analyzed by Hansen solubility parameter (Δδd, Δδp, Δδh, Δδt and Δδ), the consequences showed that solubility order of HONB resulted from the comprehensive function of several solubility parameters. Experimental solubility values were correlated with five thermodynamic models including Nonrandom Two-Liquids (NRTL), Two-Suffix Margules, Universal Quasi-chemical (UNIQUAC), Nonrandom Two-Liquid Segment Activity Coefficient (NRTL-SAC) and Wilson model. Results showed that the smallest average values of average relative deviation (ARD) and root-mean square deviation (104RMSD) were obtained by Wilson model with values of 1.06% and 8.73. Moreover, mixing properties (mixing enthalpy ΔmixH, entropy ΔmixS, Gibbs energy ΔmixG) were evaluated based on measured solubility and equation parameters of Wilson model. The positive values of ΔmixS and negative values of ΔmixG revealed that mixing process of HONB in considered solvents was entropy-driven and spontaneous.