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

Epoxidation of unsaturated plant oils is industrially carried out by the Prileshajev-epoxidation using either preformed or in-situ-generated short chain peroxy acids. The need of a strong acid to catalyze peroxy acid formation in these processes often results in unsatisfactory selectivities. Chemo-enzymatic `self'-epoxidation by the lipase-catalyzed in-situ-formation of peroxy fatty acids is a highly selective method for the epoxidation of plant oils. Rapeseed, sunflower, soybean and linseed oil were epoxidized with selectivities and conversions well above 90%. Beside complete epoxidation the high selectivity of the chemo-enzymatic `self-'epoxidation renders an accurate prediction of iodine values and oxirane oxygen contents of partially epoxidized plant oils possible. Thus, it is possible to produce tailor-made partially epoxidized plant oil, e.g. a synthetic substitute for vernonia oil.