Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Yu.S. Demidova, E.V. Suslov, O.A. Simakova, K.P. Volcho, N.F. Salakhutdinov, I.L. Simakova, D.Yu. Murzin
Publication year: 2016
Journal: Journal of Molecular Catalysis A: Chemical
Volume number: 420
Start page: 142
End page: 148
eISSN: 1873-314X


Abstract

It was shown for the first time that dihydrocarvone can be selectively produced by gold-catalyzed one-pot transformation of carvone oxime. This reaction was carried out at 100 °C under hydrogen pressure of 9 bar over 1.9 wt.% Au/TiO2 catalyst using methanol as a solvent. Dihydrocarvone synthesis was shown to occur via carvone formation with the subsequent hydrogenation of its conjugated Cdouble bond; length as m-dashC double bond. Application of Au/TiO2 catalyst for both deoximation and selective hydrogenation of olefinic Cdouble bond; length as m-dashC functional group is reported for the first time. The combination of these steps provides optimization of the synthetic method for dihydrocarvone production from carvone oxime which is a key intermediate in carvone synthesis from limonene. Despite a lower reaction rate than in the case of carvone, a significant increase in the stereoselectivity towards trans-dihydrocarvone was observed in the case of carvone oxime hydrogenation. The ratio between trans- and cis-dihydrocarvone was close to 4.0 compared to 1.8 achieved in the case of carvone hydrogenation.


Keywords

engineering education

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