Transformation of Unsaturated Fatty Acids/Esters to Corresponding Keto Fatty Acids/Esters by Aerobic Oxidation with Pd(II)/Lewis Acid Catalyst

J Agric Food Chem. 2017 Aug 16;65(32):6912-6918. doi: 10.1021/acs.jafc.7b02017. Epub 2017 Aug 1.

Abstract

Utilization of renewable biomass to partly replace the fossil resources in industrial applications has attracted attention due to the limited fossil feedstock with the increased environmental concerns. This work introduced a modified Wacker-type oxidation for transformation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, in which Cu2+ cation was replaced with common nonredox metal ions, that is, a novel Pd(II)/Lewis acid (LA) catalyst. It was found that adding nonredox metal ions can effectively promote Pd(II)-catalyzed oxidation of unsaturated fatty acids/esters to the corresponding keto fatty acids/esters, even much better than Cu2+, and the promotional effect is highly dependent on the Lewis acidity of added nonredox metal ions. The improved catalytic efficiency is attributed to the formation of heterobimetallic Pd(II)/LA species, and the oxidation mechanism of this Pd(II)/LA catalyst is also briefly discussed.

Keywords: Lewis acid; biomass valorization; oxidation; palladium(II); unsaturated fatty acid.

MeSH terms

  • Aerobiosis
  • Catalysis
  • Esters / chemistry*
  • Fatty Acids, Unsaturated / chemistry*
  • Lewis Acids / chemistry*
  • Oxidation-Reduction
  • Palladium / chemistry*

Substances

  • Esters
  • Fatty Acids, Unsaturated
  • Lewis Acids
  • Palladium