59514-63-5Relevant articles and documents
Heteropoly acid catalysis for the isomerization of biomass-derived limonene oxide and kinetic separation of the trans-isomer in green solvents
Cotta, Rafaela F.,Martins, Rafael A.,Pereira, Matheus M.,da Silva Rocha, Kelly A.,Kozhevnikova, Elena F.,Kozhevnikov, Ivan V.,Gusevskaya, Elena V.
, (2019/08/02)
Terpenes are an abundant class of natural products, which is important for flavor and fragrance industry. Many acid catalyzed reactions used for upgrading terpenes still involve mineral acids as homogeneous catalysts and/or toxic solvents. Heteropoly acids represent a well-established eco-friendly alternative to conventional acid catalysts. As these reactions are usually performed in the liquid phase, solvents play a critical role for the process sustainability. In the present work, we developed a catalytic route to valuable fragrance ingredients, dihydrocarvone and carvenone, from limonene oxide by its isomerization using silica-supported tungstophosphoric acid as a heterogeneous catalyst and dialkylcarbonates as green solvents. The reaction pathway can be switched between dihydrocarvone and carvenone (obtained in 90% yield each) simply by changing the reaction temperature. In addition, we developed an efficient method for kinetic separation of trans-limonene oxide from commercial cis/trans-limonene oxide mixture and stereoselective synthesis of trans-dihydrocarvone.
Heteropoly acid catalysts for the synthesis of fragrance compounds from biorenewables: Isomerization of limonene oxide
Costa, Vinicius V.,Da Silva Rocha, Kelly A.,Kozhevnikov, Ivan V.,Kozhevnikova, Elena F.,Gusevskaya, Elena V.
, p. 244 - 250 (2013/04/10)
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. The Royal Society of Chemistry 2013.
Reactions of cis-and trans-epoxy derivatives of (+)-3-carene and limonene with aldehydes over askanite-bentonite clay
Volcho,Tatarova,Korchagina,Salakhutdinov,Barkhash
, p. 32 - 39 (2007/10/03)
cis-and trans-Epoxy derivatives of (+)-3-carene, limonene, and dipentene react with aldehydes in the presence of askanite-bentonite clay to give acetals. Hydrolysis of the latter selectively yields the corresponding cis-diols. The relative contribution of intra-and intermolecular processes in the reactions of epoxy derivatives with aldehydes is determined mainly by steric factor. * This study was financially supported by the Russian Foundation for Basic Research (project no. 97-03-32 952a).
Acidity and Catalytic Activity of Iron(II) Sulfate Heat-treated at High Temperatures
Arata, Kazushi,Hino, Makoto
, p. 535 - 536 (2007/10/02)
Acidity and catalytic activity of FeSO4 calcined at 500-900 deg C were studied.The product obtained by calcination at 700 deg C showed maximum acidity at Ho1.5 and activity for isomerization of d-limonene oxide, polymerization of isobutyl vinyl ether and dehydration of 2-propanol.When calcined at 750 deg C the product showed no acidity or activity.
