Determination of the solubility profile of isophthalic acid in some aqueous solutions of betaine-based deep eutectic solvents: Study the extent of H-bonding interactions between starting materials of deep eutectic solvents in aqueous medium

The equilibrium solubility of isophthalic acid (IPA) in three aqueous solutions of betaine/propylene glycol (Bet/PG, 1:5 M ratio), betaine/ethylene glycol (Bet/EG, 1:3 M ratio) and betaine/glycerol (Bet/Gly, 1:3 M ratio) deep eutectic solvents (DESs) (1) was determined experimentally by utilizing a shake-flask method at 293.15–313.15 K covering the whole composition range at atmospheric pressure (≈85 kPa). For three investigated systems, an increase in solubility was observed by decreasing water mass fraction; so that, the lowest and highest solubilities were in water at 293.15 K and pure DESs at 323.15 K, respectively. Also, the mixtures containing PG presented the higher values of the solubility than that of EG or Gly which may be attributed to its lower dipole moment and dielectric constant (2.27 D, 32.0) than the others. By representation the derived equilibrium solubilities with models of Jouyban-Acree, Jouyban-Acree-van't Hoff, NRTL and Wilson a maximum overall mean relative deviation of 15.9% was achieved. Moreover, the solubilities of IPA in ternary (Bet + PG, EG or Gly + water) mixtures at 298.15 were measured to investigate the extent of H-bonding interactions of Bet with PG, EG or Gly into DESs in the presence of water by comparing IPA solubility data for each binary (DES + water) system and the corresponding ternary mixtures. The results suggested that the H-bonding interactions between two components of DESs were disappeared when the water content was exceeded 60% (g/g). This result more explored by recording 1H NMR spectra of diluted DESs with deuterium dioxide. Eventually, an endothermic and enthalpy-driven process in most mixtures was determined by thermodynamic analysis of IPA dissolution and mixing processes based on the modified van't Hoff equation. [Display omitted] •Measuring IPA solubility in three betaine-based DESs + water mixtures at 293.15–313.15 K.•Studying the stability of H-bonding interactions of DESs in aqueous medium by solubility measurements.•Disappearing the H-bonding interaction between DESs components at water mass fractions ≥60%.•Correlation of IPA solubility data by some cosolvency and activity coefficients models.•Obtaining an endothermic and enthalpy-driven process in all mixtures by the van't Hoff and Gibbs equations.