Selective epoxidation of linear terminal olefins with metalloporphyrins under mild conditions

Abstract

The epoxidation of linear terminal olefins with metalloporphyrins in the presence of dioxygen and isobutyraldehyde under ambient temperature and atmospheric pressure was investigated. The results show that all olefins could be smoothly converted to epoxides with high selectivities (70%-90%). For the metalloporphyrins with different catalytic activities within 1-hexene epoxidation in the order of Fe>Mn>Co, T(o-Cl)PPFe(Ⅲ)Cl was most effective, with a 41.7% yield and 80.2% selectivity of 1,2-epoxyhexane. Various amounts of catalyst were investigated, and it was found that with only 10 ppm catalyst the yield of 1,2-epoxyhexane and turnover number (TON) could reach up to 41.9% and 41859, respectively.

Keywords

metalloporphyrins / olefins / dioxygen / epoxidation

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Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Beijing (No. 2061001) and the Project of the National Natural Science Foundation of China (Grant Nos. 20576005 and 20776003).

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2014 Higher Education Press and Springer-Verlag Berlin Heidelberg