Polyoxyethylene esters of fatty acids: an alternative synthetic route for high selectivity of monoesters

Abstract

Esterification reaction of fatty acids with polyoxyethylenes has been studied in the presence of solid acid catalysts and the results are compared with those obtained with a classical homogeneous catalyst, p-toluene sulphonic acid. Solid acid catalysts showed very high selectivities for monoesters even under less favorable reaction conditions of 1:1 molar ratios of oleic acid to PEG. Excess amount of PEG is normally required to ensure high selectivity for monoesters in the presence of homogeneous catalysts. The yields for monoesters given by heterogeneous catalysts such as zeolites, HPA and nafion were comparable to that with p-toluene sulphonic acid after 24 h of reaction. Results suggest that solid acid catalysts are potential catalysts for selective synthesis of monoesters from oleic acids and PEG even under severe reaction conditions. A screening study of different solid acid catalysts showed ZSM-5, zeolite-β, and nafion to be better catalysts than zeolite USY and mordenite, the former giving higher selectivity and yield to monoesters. The results suggest that the most important parameters in optimization catalyst performance for monoesters production is the acid strength and less so on other properties such as shape selectivity and concentration of active sites.