Phase equilibria of phenolic compounds in water or ethanol

The mutual solubilities of water and eight phenolic compounds (i.e. phenol, guaiacol, syringol, pyrocatechol, o-, m-, p-cresol and vanillin) were investigated between 293.15 and 323.15K. The solubility of the phenolic compounds in water increases as follows: vanillin < syringol < guaiacol < p-cresol < m-cresol < o-cresol < phenol < pyrocatechol. For the molecules presenting liquid-liquid equilibria, the solubility of water into the phenolic phase increases as follows: guaiacol < o-cresol < m-cresol < p-cresol < syringol. The vapor-liquid equilibria of binary mixtures composed of ethanol and phenol or guaiacol or o-cresol were measured in a range of pressure from 0.09 bar to atmospheric pressure. Finally, the mixing enthalpies of the phenolic compounds with ethanol indicate that the reactions are exothermic. It was found that NRTL model is suitable for the representation of phase diagrams of systems containing phenolic compounds and water or ethanol.