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

Steven Bull, William Cunningham, Joshua Tibbetts, Marc Hutchby, Katarzyna A. Smug, Matthew Davidson, Ulrich Hintermair, Pawel Plucinski

Research output: Contribution to journalArticlepeer-review

42 Citations (SciVal)

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 α-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, α-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.
Original languageEnglish
Pages (from-to)513-524
Number of pages12
JournalGreen Chemistry
Volume22
Issue number2
Early online date26 Nov 2019
DOIs
Publication statusPublished - 21 Jan 2020

Bibliographical note

Funding Information:
We would like to thank EPSRC for funding through “Terpene-based Manufacturing for Sustainable Chemical Feedstocks” EP/K014889 and the Centre for Doctoral Training in Sustainable Chemical Technologies (EP/L016354/1). Södra Forestry Cooperative are thanked for supplying an authentic industrial sample of CST.

Publisher Copyright:
© 2020 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

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