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Cross metathesis of bio-sourced fatty nitriles with acrylonitrile

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Abstract

We report the cross metathesis of two olefinic partners containing different types of nitrile functionality. Thus, cross metathesis of fatty nitriles with acrylonitrile have been achieved with olefin metathesis ruthenium catalysts. 10-Undecenenitrile provides 2-dodecenedinitrile with a high turnover number of 13,280 in the green solvent, diethyl carbonate. Cross metathesis with the internal carbon–carbon double bond of oleonitrile gave the expected products, and the cleavage of the internal double bond proved to be more difficult probably owing to faster catalyst decomposition.

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Acknowledgments

The research leading to these results has received funding from the European Union Seventh Framework Programme (FP7/2007–2013) under grant agreement n° 241718 EuroBioRef. The authors thank Arkema for a fruitful collaboration and for providing 10-undecenenitrile and oleonitrile. The authors also thank Umicore Precious Metals Chemistry, Hanau, Germany, for a loan of ruthenium catalysts.

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Authors and Affiliations

  1. OMC-Organometallics : Materials and Catalysis, Center for Catalysis and Green Chemistry, Institut des Sciences chimiques de Rennes, UMR 6226 CNRS, Université de Rennes 1, Campus de Beaulieu, 35042, Rennes Cedex, France

    Johan Bidange, Cédric Fischmeister & Christian Bruneau

  2. ARKEMA France, Colombes, France

    Jean-Luc Dubois

  3. ARKEMA France, Pierre-Benite, France

    Jean-Luc Couturier

Authors
  1. Johan Bidange
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  2. Cédric Fischmeister
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  3. Christian Bruneau
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  4. Jean-Luc Dubois
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  5. Jean-Luc Couturier
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Corresponding author

Correspondence to Christian Bruneau.

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Dedicated to Franz Stelzer for his important contribution to polymer science.

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Bidange, J., Fischmeister, C., Bruneau, C. et al. Cross metathesis of bio-sourced fatty nitriles with acrylonitrile. Monatsh Chem 146, 1107–1113 (2015). https://doi.org/10.1007/s00706-015-1480-1

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  • DOI: https://doi.org/10.1007/s00706-015-1480-1

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