Evidence contrary to the accepted Diels-Alder mechanism in the thermal modification of vegetable oil

Mert Arca, Brajendra K. Sharma, Neil P.J. Price, Joseph Manuel Sr Perez, Kenneth M. Doll

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

A fatty methyl ester product has been made using two routes. Soybean oil was thermally polymerized anaerobically without a catalyst at 330 °C and the material was then transesterified using base catalyst and methanol. Alternatively, a similar product can be obtained by heating methyl linoleate to the same temperature in a pressure reactor. The product structure was studied by NMR spectroscopy, gel permeation chromatography and mass spectrometry. It is a dimeric product which does not contain substituted cyclohexane structures. This evidence shows that the Diels-Alder reaction has not occurred under these conditions. This is in contradiction to many literature reports, but in agreement with a neglected paper from 1971. This correction has implications in both biodiesel and industrial oil products.

Original languageEnglish (US)
Pages (from-to)987-994
Number of pages8
JournalJAOCS, Journal of the American Oil Chemists' Society
Volume89
Issue number6
DOIs
StatePublished - Jun 1 2012

All Science Journal Classification (ASJC) codes

  • Chemical Engineering(all)
  • Organic Chemistry

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