A simple and effective catalytic system for epoxidation of aliphatic terminal alkenes with manganese(II) as the catalyst

Kam Piu Ho, Wing Leung Wong, Kin Ming Lam, Cheuk Piu Lai, Tak Hang Chan, Kwok Yin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

32 Citations (Scopus)

Abstract

A simple catalytic system that uses commercially available manganese(II) Perchlorate as the catalyst and peracetic acid as the oxidant is found to be very effective in the epoxidation of aliphatic terminal alkenes with high product selectivity at ambient temperature. Many terminal alkenes are epoxidised efficiently on a gram scale in less than an hour to give excellent yields of isolated product (>90%) of epoxides in high purity. Kinetic studies with some C9-alkenes show that the catalytic system is more efficient in epoxidising terminal alkenes than internal alkenes, which is contrary to most commonly known epoxidation systems. The reaction rate for epoxidation decreases in the order: 1-nonene>cis-3-nonene> trans-3-nonene. ESI-MS and EPR spectroscopic studies suggest that the active form of the catalyst is a high-valent oligonuclear manganese species, which probably functions as the oxygen atomtransfer agent in the epoxidation reaction. KGaA.
Original languageEnglish
Pages (from-to)7988-7996
Number of pages9
JournalChemistry - A European Journal
Volume14
Issue number26
DOIs
Publication statusPublished - 8 Sep 2008

Keywords

  • Alkenes
  • Epoxidation
  • Homogeneous catalysis
  • Manganese
  • Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

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