Heteropoly acid catalysts for the synthesis of fragrance compounds from biorenewables: isomerization of limonene oxide
- 4 September 2012
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Catalysis Science & Technology
- Vol. 3 (1) , 244-250
Abstract
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.Keywords
This publication has 28 references indexed in Scilit:
- Esterification of camphene over heterogeneous heteropoly acid catalysts: Synthesis of isobornyl carboxylatesApplied Catalysis A: General, 2011
- Isomerization of α-pinene oxide over cerium and tin catalysts: Selective synthesis of trans-carveol and trans-sobrerolJournal of Molecular Catalysis A: Chemical, 2011
- Heteropoly acid catalysts in the valorization of the essential oils: Acetoxylation of β-caryophylleneApplied Catalysis A: General, 2010
- Phosphotungstic heteropoly acid as efficient heterogeneous catalyst for solvent-free isomerization of α-pinene and longifoleneApplied Catalysis A: General, 2009
- Phosphotungstic Acid as a Versatile Catalyst for the Synthesis of Fragrance Compounds by α‐Pinene Oxide Isomerization: Solvent‐Induced ChemoselectivityChemistry – A European Journal, 2008
- Pd–heteropoly acid as a bifunctional heterogeneous catalyst for one-pot conversion of citronellal to mentholApplied Catalysis A: General, 2007
- Hydration and acetoxylation of dihydromyrcene catalyzed by heteropoly acidJournal of Molecular Catalysis A: Chemical, 1997
- ISOMERIZATION OF d-LIMONENE OXIDE OVER ALUMINASChemistry Letters, 1976
- Isomerization of d-limonene oxide over solid acids and bases*1Journal of Catalysis, 1976
- Essential oils and their constituents. XLII. Isomerization of epoxides on active aluminaCanadian Journal of Chemistry, 1968