Hydrolysis of Mono- and Diepoxyoctadecanoates by Alumina

901 JAOCS, Vol. 80, no. 9 (2003) ABSTRACT: In this study it is shown that the epoxide derivative of oleic acid, methyl 9,10-epoxyoctadecanoate, is readily hydrolyzed to a diol when exposed to a commercial preparation of neutral alumina. Comparison of 1H and 13C NMR spectra of the diol with those of standards showed that the product was the threo isomer. When methyl 9,10-12,13-diepoxyoctadecanoate was treated with alumina, a mixture of dihydroxytetrahydrofuran regioisomers, methyl 9,12-epoxy-10,13-dihydroxystearate and methyl 10,13-epoxy-9,12-dihydroxystearate, was obtained. These results show that alumina is an unsuitable support for epoxidation catalysts. However, alumina-catalyzed hydrolysis of fatty epoxides is an efficient way to synthesize polyhydroxy materials, and these materials are suitable for several industrial applications. Paper no. J10561 in JAOCS 80, 901–904 (September 2003).