Heteropoly acid catalysts for the synthesis of fragrance compounds from biorenewables : isomerization of limonene oxide.

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2013
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The liquid-phase isomerization of limonene oxide was studied in the presence of heteropoly acid catalysts in aprotic solvents in homogeneous and heterogeneous systems. Among the catalysts were bulk and silica-supported tungstophosphoric acid H3PW12O40 and its acidic Cs salt Cs0.5H0.5PW12O40 (CsPW). The reaction gave dihydrocarvone, a valuable fragrance intermediate, as the main product with turnover numbers of up to 8000. The nature of the solvent had a strong effect on reaction rate and selectivity. CsPW (0.1 mol%) was found to be a highly efficient and truly heterogeneous catalyst for this reaction, providing 82% yield of dihydrocarvone in 1,4-dioxane as a solvent under ambient conditions. This simple catalytic method represents economically attractive route to industrially important compounds starting from bio-renewable substrates easily available from essential oils.
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COSTA, V. V. et al. Heteropoly acid catalysts for the synthesis of fragrance compounds from biorenewables: isomerization of limonene oxide. ChemCatChem, v. 5, p. 244-250, 2013. Disponível em: <http://onlinelibrary.wiley.com/doi/10.1002/cctc.201300208/abstract>. Acesso em: 20 mai. 2017.