Sustainable catalytic protocols for the solvent free epoxidation and anti-dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant
| Autor: | Katarzyna A. Maltby, Steven D. Bull, Marc Hutchby, Matthew G. Davidson, Joshua D. Tibbetts, Pawel Plucinski, Ulrich Hintermair, William B. Cunningham |
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| Rok vydání: | 2020 |
| Předmět: | |
| Zdroj: | Green Chemistry. 22:513-524 |
| ISSN: | 1463-9270 1463-9262 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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