Synthesis of mono- and dioleoyl erythritols through immobilized-lipase-catalyzed condensation of erythritol and oleic acid in acetone

Abstract

Erythritol was condensed with oleic acid using immobilized lipase from Candida antarctica in acetone. The effects of the molar ratio of oleic acid to erythritol on the formation of mono- and dioleoyl erythritols were examined in the absence or presence of 3A molecular sieves. A conversion to monooleoyl erythritol of ca. 0.5 was achieved at ratios of 2 and 3 without addition of the molecular sieves. A high ratio promoted the formation of dioleoyl erythritol, especially in the presence of the molecular sieves. The surface tensions of aqueous solutions of monooleoyl erythritol were measured at various concentrations and different temperatures, and the critical micelle concentrations (CMCs) were determined. The enthalpy of micellization was estimated to be 7.1 kJ/mol from the temperature-dependence of the CMC.