Oxidation of olefins with H2O2 catalyzed by gallium(III) nitrate and aluminum(III) nitrate in solution

Dalmo Mandelli, Yuriy N. Kozlov, Cezar A R da Silva, Wagner A. Carvalho, Paolo P. Pescarmona, Daniele de A Cella, Polyana T. de Paiva, Georgiy B. Shul'pin*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

7 Citations (Scopus)

Abstract

Soluble gallium and aluminum nitrates (simple salts of non-transition metals) are good catalysts for the epoxidation of olefins (cyclooctene, dec-1-ene) including terpenes (carvone, limonene) with hydrogen peroxide in ethyl acetate or tetrahydrofurane (THF). Typically, the gallium salt is more efficient in comparison with the aluminum derivative. Products are formed in yields up to 93%, turnover numbers (TONs) attained 40. Addition of trifluoroacetic acid or pyrazine-2-carboxylic acid (PCA) accelerates the reaction and improves the yield. In striking contrast, added 2,2′-bipyridine or phenanthroline dramatically inhibit the oxidation.

Original languageEnglish
Pages (from-to)216-220
Number of pages5
JournalJournal of Molecular Catalysis A: Chemical
Volume422
DOIs
Publication statusPublished - 2016

Keywords

  • Carvone
  • Epoxidation
  • Limonene
  • Olefins
  • Terpenes

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