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Selective Conversion of Polyenes to Monoenes by RuCl3-Catalyzed Transfer Hydrogenation: The Case of Cashew Nutshell Liquid

Authors

  • Sébastien Perdriau,

    1. Stratingh Institute of Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-3634296
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  • Prof. Dr. Sjoerd Harder,

    Corresponding author
    1. Stratingh Institute of Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-3634296
    • Stratingh Institute of Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-3634296
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  • Prof. Dr. Hero J. Heeres,

    Corresponding author
    1. Department of Chemical Engineering, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands)
    • Department of Chemical Engineering, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands)
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  • Prof. Dr. Johannes G. de Vries

    Corresponding author
    1. Stratingh Institute of Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-3634296
    2. DSM Innovative Synthesis BV, P.O. Box 18, 6160 MD Geleen (The Netherlands)
    • Stratingh Institute of Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31) 50-3634296
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Abstract

Cardanol, a constituent of cashew nutshell liquid (CNSL), was subjected to transfer hydrogenation catalyzed by RuCl3 using isopropanol as a reductant. The side chain of cardanol, which is a mixture of a triene, a diene, and a monoene, was selectively reduced to the monoene. Surprisingly, it is the C8[BOND]C9 double bond that is retained with high selectivity. A similar transfer hydrogenation of linoleic acid derivatives succeeded only if the substrate contained an aromatic ring, such as a benzyl ester. TEM and a negative mercury test showed that the catalyst was homogeneous. By using ESI-MS, ruthenium complexes were identified that contained one, two, or even three molecules of substrate, most likely as allyl complexes. The interaction between ruthenium and the aromatic ring determines selectivity in the hydrogenation reaction.

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