The hydrogenation of 2-butyne-1,4-diol in propan-2-ol over a carbon-supported palladium catalyst has been investigated in a batch reactor. At low conversions complete selectivity to cis-but-2-ene-1,4-diol is observed. However, further hydrogenation leads to a wide variety of products, most notably 2-isopropoxy-tetrahydrofuran and butane, neither of which have previously been associated with this reaction system. The former is thought to occur as a result of a surface-mediated process, involving the insertion of dissociatively adsorbed solvent molecules. Butane formation is attributed to the double condensation and hydrogenation of a chemisorbed cis-but-2-ene-1,4-diol intermediate. The alkane preferentially partitions in the gaseous phase, which results in an marked mass imbalance for the liquid phase. A reaction scheme is presented to rationalise these observations.
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I.W. Sutherland, I.T. Duncanson, B. Cullen, S.D. Jackson and D. Lennon, to be published
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Duncanson, I.T., Sutherland, I.W., Cullen, B. et al. The Hydrogenation of 2-butyne-1,4-diol over a Carbon-supported Palladium Catalyst. Catal Lett 103, 195–199 (2005). https://doi.org/10.1007/s10562-005-7154-6
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DOI: https://doi.org/10.1007/s10562-005-7154-6