Jump to main content
Jump to site search


Sustainable Catalytic Protocols for the Solvent Free Epoxidation and (anti)-Dihydroxylation of the Alkene Bonds of Biorenewable Terpene Feedstocks Using H2O2 as Oxidant

Abstract

A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and a-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3- carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, a-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.

Back to tab navigation

Supplementary files

Publication details

The article was received on 11 Sep 2019, accepted on 26 Nov 2019 and first published on 26 Nov 2019


Article type: Paper
DOI: 10.1039/C9GC03208H
Green Chem., 2019, Accepted Manuscript
  • Open access: Creative Commons BY license
  •   Request permissions

    Sustainable Catalytic Protocols for the Solvent Free Epoxidation and (anti)-Dihydroxylation of the Alkene Bonds of Biorenewable Terpene Feedstocks Using H2O2 as Oxidant

    S. Bull, W. B. Cunningham, J. D. Tibbetts, M. Hutchby, K. A. Smug, M. G. Davidson, U. Hintermair and P. Plucinski, Green Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9GC03208H

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements