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Mild catalytic oxidations of unsaturated fatty acid methyl esters (FAMEs) by oxovanadium complexes

Paper ID Volume ID Publish Year Pages File Format Full-Text
39098 45806 2016 9 PDF Available
Title
Mild catalytic oxidations of unsaturated fatty acid methyl esters (FAMEs) by oxovanadium complexes
Abstract

•A selection of fatty acid methyl esters has been oxidized by exploiting the activity showed by a series of oxovanadium(IV) complexes.•The oxidation of substrates using TBHP as main oxidant showed high conversions of starting materials and high selectivities toward mono- di- and tri-epoxides.•The results furnish a further opportunity for the selective oxyfunctionalization of bio-renewable resources like FAMEs.

A selection of unsaturated fatty acid methyl esters, namely methyl oleate (C18:1), methyl linoleate (C18:2) and methyl linolenate (C18:3) has been oxidized under mild homogeneous catalytic conditions, using a series of oxovanadium(IV) complexes containing 4-acyl-5-pyrazolone donor ligands with different substituents on acyl residue. The main goal was to evaluate the catalytic role exerted by oxovanadium(IV) metal center, as precursor complex, in the selective oxyfunctionalization of carbon-carbon double bonds of these bio-renewable resources, as a greener alternative to more drastic processes currently used at the industrial level. The three substrates, oxidized using tert-butylhydroperoxide as main oxidant, with or without solvents, showed high conversions of starting materials and high selectivities in the formation of corresponding mono- di- and tri-epoxides, especially under solvent-less conditions. Investigations on a probable catalytic cycle mechanism operative in the tert-butylhydroperoxide oxidation of a simple FAME model substrate, have been performed by means of ESI-MS.

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Keywords
Oxovanadium complexes; Epoxidation; t-butyl hydroperoxide; ESI-MS
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Mild catalytic oxidations of unsaturated fatty acid methyl esters (FAMEs) by oxovanadium complexes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 517, 5 May 2016, Pages 120–128
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Don't Miss Today's Special Offer
Price was $35.95
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Price after discount Only $4.95
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Full-text PDF Download
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