Epoxidation of α-pinene catalyzed by methyltrioxorhenium(VII): Influence of additives, oxidants and solvents

Typhne Michel, Daniel Betz, Mirza Cokoja, Volker Sieber, Fritz E. Kühn

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34 Scopus citations

Abstract

The epoxidation of α-pinene employing methyltrioxorhenium as catalyst is examined. The influence of mono- and bidentate Lewis basic additives (e.g. tbutylpyridine, 4,4′-dimethyl-2,2′-bipyridine, and Schiff-bases) is investigated. Additionally the impact of the oxidant (H 2O2 in water or urea-hydrogen peroxide (UHP)) on the catalytic performance is studied. The effect of the solvent is also examined in order to determine the optimal conditions for the epoxidation of α-pinene. The best and straightforwardly applicable result is obtained when a ratio α-pinene:MTO:tbutylpyridine:UHP of 200:1:40:600 is applied at 0 °C in nitromethane. In this case, α-pinene oxide is formed with 95% yield after 3 h with a turnover frequency (TOF) of 610 h-1.

Original languageEnglish
Pages (from-to)9-14
Number of pages6
JournalJournal of Molecular Catalysis A: Chemical
Volume340
Issue number1-2
DOIs
StatePublished - 23 Apr 2011

Keywords

  • Epoxidation
  • Homogeneous catalysis
  • Methyltrioxorhenium
  • Pinene oxide
  • Terpenes

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