Epoxidation of alkenes catalyzed by metal porphyrin complexes

Abstract

The epoxidation of alkenes by aldehyde/oxygen oxidant using metalloprphyrin as catalyst was studied. The catalytic activity of a series of metalloporphyrins was investigated by utilizing the epoxidation reaction of cyclohexene as test reaction. The productivity and selectivity of cyclohexene oxide over the catalysts revealed that (meso-tetrakis-4-chlorophenylporphyrinato)manganese(III) acted as the highest potential catalyst. The parameters affected the epoxidation reaction including type and amount of aldehye, type of solvent and amounts of alkene and catalyst were examined. Under this condition, cyclohexene was selectively transformed to cyclohexene oxide in the maximum yield, ca, 85%. In addition, the epoxidation system was developed for other epoxide productions. The good yield and selectivity of their corresponding epoxides were obtained from the epoxidations of styrene and even the aliphatic terminal alkene like 1-dodecene under mild conditions.