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Stereoselective Hydrogenation of (-)-Menthone and (+)-Isomenthone Mixture Using Nickel Catalysts

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The catalytic hydrogenation of an optically active mixture of (-)-menthone and (+)-isomenthone was studied. The catalysts Raney nickel and Ni/SiO2 were used for these hydrogenations. Catalysts modified with (2R, 3R)-(+)-tartaric acid were tested as well. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol. (-)-Menthol was produced during these reactions to a limited extent; the production of (-)-isomenthol was barely existent. Isomerization of (-)-menthone and (+)-isomenthone occurred during these reactions. Isomerizations among individual isomers were barely detectable. The catalysts used showed a very low activity under the given reaction conditions.

Affiliations: 1: Department of Organic Technology, Institute of Chemical Technology - ICT Prague, Technická 5, 166 28 Prague 6, CZECH REPUBLIC


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