Hydrogenation of (–)-Carvone in the Presence of Gold Catalysts: the Role of Support

Liquid phase hydrogenation of biomass derived (–)-carvone into industrially valuable dihydrocarvone was studied over monometallic Au catalysts supported on alumina, titania and zirconia, as well as on mesoporous carbon support Sibunit in methanol as a solvent (100 °C, hydrogen pressure 9 bar). It was shown that among the three types of functional groups present in carvone, which can be hydrogenated, namely C=O, conjugated and isolated C=C groups, hydrogenation of the latter was predominant. The catalytic activity was found to depend on the catalyst support type. Under comparative reaction conditions conversion of carvone increased in the following sequence: Au/C << Au/ZrO₂ < Au/Al₂O₃ << Au/TiO₂. Higher activity of Au catalysts over metal oxides compared to Au/C can be caused by the presence of acid sites as well as oxygen vacancies in their structure allowing strong adsorption of carvone through its carbonyl moiety. All catalysts supported on oxides showed similar selectivity to trans- and cis-dihydrocarvone with the ratio between isomers (trans- : cis-isomer) being about 1.8, while this value for Au/C is close to 3.9, which can be related to much low carvone conversion in the latter case.

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