Synthesis of Glycerol 1-Monooleate by Condensation of Oleic Acid with Glycidol Catalyzed by Anion-Exchange Resin in Aqueous Organic Polymorphic System

Abstract

The condensation of technical-grade oleic acid (OA) (65%, 85%, and 90% oleic acid) with glycidol (Gly) was carried out in an aqueous medium in the presence of a macroporous anion-exchange resin containing ammonium groups. The reaction was optimized by a unifactorial method and by a 2 n −1 fractional factorial plan. The effects of the following main parameters were quantified from experiments based on a 2 (5−1) = 2 4 factorial design: OA/Gly molar ratio, concentration (mmol of OA/mL of H 2 O), catalytic efficiency (mequiv of X/mmol of OA), and temperature. The conditions were optimized for a discontinuous process in a stirred reactor for selective synthesis of glycerol 1-monooleate (1-GMO) in a polymorphic system (solid resin/emulsion or microemulsion) consisting of OA/Gly/H 2 O/1-GMO. The catalytic role of the Ambersep 900−X resin was demonstrated by conducting the reaction using the resin in the different functional forms Ambersep 900−OH − and Ambersep 900−HCO 3 − and in the nonfunctionalized form Ambersep 900−Cl − . The highest yield of 1-GMO (97%) was obtained with the nonfunctionalized form Ambersep 900−Cl − at 70 °C.