Complete and partial epoxidation of plant oils by lipase-catalyzed perhydrolysis

Epoxidation of unsaturated plant oils is industrially carried out by the Pr ileshajev-epoxidation using either preformed or in-situ-generated short cha in peroxy acids. The need of a strong acid to catalyze peroxy acid formatio n in these processes often results in unsatisfactory selectivities. Chemo-e nzymatic 'self'-epoxidation by the lipase-catalyzed in-situ-formation of pe roxy fatty acids is a highly selective method for the epoxidation of plant oils. Rapeseed, sunflower, soybean and linseed oil were epoxidized with sel ectivities and conversions well above 90%. Beside complete epoxidation the high selectivity of the chemo-enzymatic 'self-'epoxidation renders an accur ate prediction of iodine values and oxirane oxygen contents of partially ep oxidized plant oils possible. Thus, it is possible to produce tailor-made p artially epoxidized plant oil, e.g. a synthetic substitute for vernonia oil . (C) 1999 Elsevier Science B.V. All rights reserved.