Prileshajev epoxidation

Fatty acid epoxides have numerous uses. In particular, oils and fats of vegetable and animal origin represent the greatest proportion of current consumption of renewable raw materials in the chemical industry, providing applications that cannot be met by petrochemicals [64]. Polyether polyols produced from methyl oleate by the Prileshajev epoxidation (using peracetic acid) are an example. Epoxidized soybean oil (ESBO) is a mixture of the glycerol esters of epoxidized linoleic, linolenic, and oleic acids. It is used as a plasticizer and stabilizer for poly (vinyl chloride) (PVC) [1] and as a stabilizer for PVC resins to improve flexibility, elasticity, and toughness [65]. The ESBO market is second to that of epoxy resins and its world wide production... 

Another early discovery was that CALB accepts H202 as nucleophile to produce peroxycarboxylic acids from esters or carboxylic acids (perhydrolysis activity can also be found in other serine hydrolases) [46, 47]. The in situ formed peracid can subsequently be used to epoxidize an alkene by (non-enzymatic) Prileshajev epoxidation. Hence, oleic acid incubated with CALB and H202 will produce 9,10-epoxyoctadecanoic acid [48]. Other alkenes can be epoxidized by H202 and a catalytic amount of carboxylic acid (and CALB) (Scheme 13.2) [49],... 

The oxidative cleavage of the olefin and especially the following oxidation of the aldehydes to carboxylic acids by peracetic acid are fast reactions. The side reaction (Prileshajev-reaction) to the epoxide proceeds much slower under the... 

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