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

被引：49
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.
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页码：244 / 250
页数：7
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