Epoxidation, hydroxylation and oxidative fission

Epoxidation is the reaction by which a double bond is converted to an epoxide  

About a dozen natural epoxy acids have been identified (Section 1.10). 

Epoxidation is extensively employed, both as a laboratory procedure and on a commercial scale. Epoxidized oils are produced at the rate of about 10 Ib/year and used mainly as a combined stabilizer-plasticizer for polyvinyl chloride. 

Most epoxidations are effected by peroxy acids which are often preformed and used in situ for epoxidation though some can be stored and used as required. The peroxy acids are made by interaction of carboxylic acids, anhydrides or acid chlorides with hydrogen peroxide, with the first of these requiring an acidic catalyst such as sulphuric acid or a sulphonic acid. 

RCOOH + H2O2 RCO3H + H2O (RC0)20 + H202 -------- RCO3H +RCOOH 

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