Ruthenium catalyzed ethenolysis of renewable oleonitrile

Authors

  • Johan Bidange,

    1. UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre for Catalysis and Green Chemistry, Rennes Cedex, France
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  • Jean-Luc Dubois,

    1. Arkema CRRA, Pierre Bénite, France
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  • Jean-Luc Couturier,

    1. Arkema CRRA, Pierre Bénite, France
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  • Cédric Fischmeister,

    Corresponding author
    1. UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre for Catalysis and Green Chemistry, Rennes Cedex, France
    • Correspondence: Dr. Cédric Fischmeister, UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre for Catalysis and Green Chemistry, 263, avenue du général Leclerc, Campus de Beaulieu, 35042 Rennes Cedex, France

      E-mail: cedric.fischmeister@univ-rennes1.fr

      Fax: +33 (0) 2 23236939

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  • Christian Bruneau

    Corresponding author
    1. UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre for Catalysis and Green Chemistry, Rennes Cedex, France
    • Correspondence: Dr. Cédric Fischmeister, UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre for Catalysis and Green Chemistry, 263, avenue du général Leclerc, Campus de Beaulieu, 35042 Rennes Cedex, France

      E-mail: cedric.fischmeister@univ-rennes1.fr

      Fax: +33 (0) 2 23236939

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    • Additional Corresponding author: Dr. Christian Bruneau, E-mail: christian.bruneau@univ-rennes1.fr

Abstract

Oleonitrile is a bio-sourced compound readily obtained by ammoniation of the renewable oleic acid. The production of the short chain undecenitrile by ethenolysis (cross-metathesis with ethylene) of oleonitrile is reported. Optimization of the reaction conditions led to promising TONs of 1400 with high selectivity for the ethenolysis products. From a series of catalysts tested, the bulky and activated M71 SiPr catalyst enabled the best performances. The influence of feed purification method was investigated in details and it was found that thermal treatment of the feed was required to ensure the highest productivity.

Practical applications: The selective ethenolysis of oleonitrile provides a direct access to bio-sourced 9-decenitrile and 1-decene. These two compounds of interest for the synthesis of polymers precursors have also some potential use as fuel additives.

ejlt201400184-gra-0001

The ruthenium catalyzed cross-metathesis of the bio-sourced oleonitrile with ethylene (ethenolysis) is presented. 9-Decenitrile and 1-decene were produced with high selectivity (88%) at low catalyst loading (0.0625 mol%).

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