Novel Two-Phase Catalysis with Organometallic Compounds for Epoxidation of Vegetable Oils by Hydrogen Peroxide

A series of new organometallic catalysts for epoxidized vegetable oils using H2O2 in a biphasic system were investigated. The effect of reaction parameters such as the amount of hydrogen peroxide, reaction time and temperature in the epoxidation of soybean oil are discussed in detail. A selectivity of 83.8% was obtained in 4 h at 60 °C, when [(C18H37)2N(CH3)2]3{PO4[WO(O2)2]4} was used as the catalyst. When methyltrioxorhenium (MTO), imidazole and CH3CN were used as the catalyst, adduct, and solvent respectively, a selectivity of 99.90% was achieved in 4 h at 20 °C. The catalytic system was used for the epoxidation of other oils, whose results showed it was active in the epoxidation of long-chain unsaturated compounds. Furthermore, the reaction of H2O2 with methyltrioxorhenium was studied by UV–Vis spectroscopy, which revealed the active peroxorhenium complexes formed during the reaction. Epoxidation of these oils with organometallic compounds occurred through the interactions between the oils unsaturated sites HOMO π(C–C) and the unoccupied peroxo σ*(O–O) orbital.