Structural and reactivity effects in the copper-catalyzed hydrogenolysis of aliphatic esters

J. W. Evans, M. S. Wainwright, N. W. Cant, D. L. Trimm

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The hydrogenolysis of a series of alkyl esters to their corresponding alcohols has been studied over a Raney copper catalyst in the temperature range 210-280 °C. Generally, the rate of hydrogen-olysis was found to increase with molecular weight while the selectivity to alcohol, derived from the acyl part of the ester, decreased due to transesterification reactions. The rate data correlated well to a Taft equation in which inductive effects were more important than steric effects, provided the equation included a term to account for the hydrogens on the α-carbon atoms. Reaction kinetics for ethyl acetate hydrogenolysis were found to be first order in hydrogen and -0.5 order in ethyl acetate.

Original languageEnglish
Pages (from-to)203-213
Number of pages11
JournalJournal of Catalysis
Issue number1
Publication statusPublished - 1984


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