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Electrocatalytic hydrogenation of alkyl-substituted phenols in aqueous solutions at a Raney nickel electrode in the presence of a non-micelle-forming cationic surfactant

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Abstract

The electrocatalytic hydrogenation (ECH) of 2,6-dimethylphenol and 2-tert-butylphenol was performed at RaNi cathodes in aqueous buffers containing various amounts of didodecyldimethylammonium bromide (DDAB). Without surfactant, 2,6-dimethylcyclohexanol, 2-tert-butylcyclohexanone and 2-tert-butylcyclohexanol were obtained, at 65 °C, with very low yields. The surfactant effect on the yields, the selectivity of the reaction and the diastereoisomeric composition of alkylcyclohexanols produced was studied in acidic and basic solutions in relation to the substrate adsorption. At pH 9 the efficiency of the hydrogenation reaction was significantly improved by low amounts of DDAB, which led to an increase of the alkylcyclohexanols formation. In particular, cis-2-tert-butylcyclohexanol was obtained with a high diastereoselectivity.

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Authors and Affiliations

  1. Laboratoire de chimie et d'électrochimie organique, Département de Chimie, Faculté des Sciences, Université des Sciences et des Technologies d'Oran, BP 1505, En Manaouer Oran, Algéria

    H. Ilikti

  2. Laboratoire CERCOF, UMR CNRS 5622, Université, Claude Bernard Lyon I, 43 Bd 11 Novembre 1918, 69622, Villeurbanne Cedex, France

    N. Rekik & M. Thomalla

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  1. H. Ilikti
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  2. N. Rekik
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  3. M. Thomalla
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Correspondence to M. Thomalla.

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Ilikti, H., Rekik, N. & Thomalla, M. Electrocatalytic hydrogenation of alkyl-substituted phenols in aqueous solutions at a Raney nickel electrode in the presence of a non-micelle-forming cationic surfactant. Journal of Applied Electrochemistry 34, 127–136 (2004). https://doi.org/10.1023/B:JACH.0000009932.06652.a0

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