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.
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).