论文信息 - An efficient reaction protocol for the ruthenium‐catalysed epoxidation of methyl oleate

An efficient reaction protocol for the ruthenium‐catalysed epoxidation of methyl oleate

The transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide was investigated using Ru(acac)3/dipicolinic acid as catalyst. Under optimised reaction conditions, the epoxidised methyl oleate 2 was obtained with a quantitative yield in short reaction time and under mild reaction conditions. Practical applications: Epoxidised fatty acids and their derivatives are produced by the Prilezhaev reaction and used in various applications in the chemical industry. Due to the known drawbacks of epoxidation with peroxy acids, such as hazardous handling of peracids in large quantities or the decrease of epoxide selectivity due to the formation of undesired by-products in the acidic medium, the epoxidation of fatty acid derivatives using more convenient oxidants is still a subject of research interest. Herein, we present a simple procedure for the transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide in quantitative yields, and under mild reaction conditions, as a potential alternative for the production of epoxidised fatty acid derivatives.

[1] A. Fulford,et al. Catalytic alkene epoxidation with ruthenium complexes and hydrogen peroxide , 1992 .

[2] G. Du,et al. Catalytic epoxidation of methyl linoleate , 2004 .

[3] W. Cheung,et al. A silica gel-supported ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxide. , 2002, The Journal of organic chemistry.

[4] Andreas Martin,et al. Oxidation of unsaturated fatty acid derivatives and vegetable oils , 2008 .

[5] M. Beller,et al. A convenient ruthenium-catalyzed alkene epoxidation with hydrogen peroxide as oxidant , 2004 .

[6] J. Metzger,et al. Synthesis and characterization of polyurethanes from epoxidized methyl oleate based polyether polyols as renewable resources , 2006 .

[7] Li-sheng Wang,et al. Catalytic Epoxidation of a Technical Mixture of Methyl Oleate and Methyl Linoleate in Ionic Liquids Using MoO(O2)2·2QOH (QOH = 8-quinilinol) as Catalyst and NaHCO3 as co-Catalyst , 2009, Molecules.

[8] M. Beller,et al. Synthetic, spectral and catalytic activity studies of ruthenium bipyridine and terpyridine complexes: Implications in the mechanism of the ruthenium(pyridine-2,6-bisoxazoline)(pyridine-2,6-dicarboxylate)-catalyzed asymmetric epoxidation of olefins utilizing H2O2 , 2006 .