Esterification synthesis of ethyl oleate catalyzed by Brønsted acid-surfactant-combined ionic liquid

Abstract

3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulfate ([SB3-12][HSO4]), a Brønsted acidic-surfactant-combined ionic liquid, was successfully prepared from cheap materials and applied to catalyze the esterification synthesis of ethyl oleate using oleic acid and ethanol as precursors. The produced condition of oleic acid ethyl ester was optimized including the amount of catalyst, reaction time, molar ratio and content of water. Under optimal condition (ethanol to oleic acid molar ratio, 3:1; amount of the catalyst, 5 wt% (based on the mass of oleic acid); reaction time, 3 h; reaction temperature, 78°C; and content of water, 0.4 wt%), the conversion of oleic acid was over 97%. Due to the reverse micelles formed by [SB3-12][HSO4], the microreactor not only promoted the esterification toward the desired side of the ester, but also avoided the hydrolysis of ester. Moreover, the [SB3-12][HSO4] could be reused by a simple decantation separating process and noticeable loss of catalytic activity was not observed even after being recycled for five cycles. The green system offers several advantages, such as excellent yield, efficient catalytic activity, free-solvent and simple operational procedure.