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Novel Two‐Phase Catalysis with Organometallic Compounds for Epoxidation of Vegetable Oils by Hydrogen Peroxide
Author(s) -
Jiang Pingping,
Chen Min,
Dong Yuming,
Lu Yun,
Ye Xia,
Zhang Weijie
Publication year - 2010
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-009-1469-1
Subject(s) - catalysis , chemistry , hydrogen peroxide , selectivity , adduct , solvent , organic chemistry , soybean oil , organometallic chemistry , imidazole , peroxide , epoxidized soybean oil , medicinal chemistry , raw material , food science
A series of new organometallic catalysts for epoxidized vegetable oils using H 2 O 2 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 [(C 18 H 37 ) 2 N(CH 3 ) 2 ] 3 {PO 4 [WO(O 2 ) 2 ] 4 } was used as the catalyst. When methyltrioxorhenium (MTO), imidazole and CH 3 CN 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 H 2 O 2 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.