An Empirical Study of Phosphine Ligands for the Methoxycarbonylation of Medium-Chain Alkenes

Cedric Holzapfel, Tyler Bredenkamp

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

The methoxycarbonylation reaction provides a route to the synthesis of esters from medium-chain alkenes that may be used as fuel supplements. However, the known productive catalytic systems are expensive and/or unstable at elevated temperatures. Most of the data available on the methoxycarbonylation of alkenes is derived from ethylene and styrene as substrates. To broaden the scope, we conducted a comparative study of a range of phosphine ligands under comparable conditions for the methoxycarbonylation of 1-octene. The results demonstrate that a number of ligand structural motifs facilitate the process effectually. Furthermore, the critical importance of alkene isomerization and the acid/ligand and Pd/ligand ratios are presented.

Original languageEnglish
Pages (from-to)2598-2606
Number of pages9
JournalChemCatChem
Volume7
Issue number17
DOIs
Publication statusPublished - 1 Sept 2015

Keywords

  • alkenes
  • captodative
  • carbonylation
  • diesel
  • isomerization

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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