Palladium-catalysed hydroalkoxycarbonylation of styrene in [BMIM][BF 4] and [BMIM][PF6] ionic liquids

Gábor Rangits, László Kollár

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The hydroalkoxycarbonylation of styrene was carried out by using various alcohols (ethanol, n- and i-propyl alcohol, benzyl alcohol, n-octyl alcohol) in imidazolium-based ionic liquids. In addition to the formation of the expected 2-phenyl- and 3-phenyl-propionates, the oligomerization of the substrate depending on the reaction conditions was also observed in [BMIM][PF6] and in [BMIM][BF4] (to a small extent) ionic liquids. Moderate to high regioselectivities towards branched esters have been obtained in [BMIM][BF4]. The highest regioselectivities towards branched ester have been observed with 'preformed' PdCl2(PPh3) 2 catalyst. The addition of diphosphines favoured the formation of the linear isomer. The application of [BMIM][PF6] ionic liquid results mainly in the formation of the linear esters. The regioselectivity is strongly dependent also on the alcohol: for example, while the application of ethanol resulted in branched regioselectivities up to 50 and 81% in [BMIM][PF6] and [BMIM][BF4], respectively, 100% linear and 83% branched selectivities were obtained in the presence of n-octyl alcohol as a nucleophile.

Original languageEnglish
Pages (from-to)156-160
Number of pages5
JournalJournal of Molecular Catalysis A: Chemical
Volume242
Issue number1-2
DOIs
Publication statusPublished - Dec 1 2005

Keywords

  • Carbonylation
  • Hydroalkoxycarbonylation
  • Imidazolium
  • Ionic liquid
  • Palladium

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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