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

被引：46

作者：

Costa, Vinicius V. ^{[1
]}

da Silva Rocha, Kelly A. ^{[2
]}

Kozhevnikov, Ivan V. ^{[3
]}

Kozhevnikova, Elena F. ^{[3
]}

Gusevskaya, Elena V. ^{[1
]}

机构：

[1] Univ Fed Minas Gerais, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil

[2] Univ Fed Ouro Preto, Dept Quim, BR-35400000 Ouro Preto, MG, Brazil

[3] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

CATALYSIS SCIENCE & TECHNOLOGY | 2013年 / 3卷 / 01期

关键词：

ALPHA-PINENE OXIDE; HETEROGENEOUS CATALYST; ALLYLIC ALCOHOLS; ESSENTIAL OILS; ACETOXYLATION; REARRANGEMENT; HYDRATION; EPOXIDES; CAMPHENE;

D O I：

10.1039/c2cy20526b

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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.

引用

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页码：244 / 250

页数：7

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