A highly efficient, green and recoverable catalytic system for the epoxidation of fatty esters and biodiesel with H2O2

A highly efficient and green strategy for the epoxidation of fatty esters, combining a green oxidant (aqueous hydrogen peroxide) and a recyclable catalyst (a seleninic acid derivative) is presented. The possibility of integrating renewable solvents derived from glycerol in the productive cycle of biodiesel commodities is also explored. Fluorinated solvents (both commercial and glycerol-derived) play a double key role on this methodology: on the one hand, they strongly accelerate epoxidation reaction with respect to common non-fluorinated solvents and, on the other hand, some of them allow catalyst recycling. Mono- and polyunsaturated fatty esters, as well as soy biodiesel have been epoxidized with excellent yields and selectivities towards epoxide under the optimal conditions and with minimum catalyst loads.

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► Fluoroalcohols strongly accelerate the epoxidation reaction of fatty esters with H2O2.
► Diselenides are very efficient catalysts for the epoxidation of fatty esters with H2O2.
► Quantitative yields and complete stereoselectivity are obtained under mild conditions.
► Se catalyst can be recovered and reused after extracting the products with isooctane.
► Removal of water from the catalytic phase allows reusing it up to seven times.