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Methyl Ricinoleate as Platform Chemical for Simultaneous Production of Fine Chemicals and Polymer Precursors

Authors

  • Antoine Dupé,

    1. Institut des Sciences Chimiques de Rennes, Organométalliques: Matériaux et Catalyse, UMR 6226-CNRS-Université de Rennes 1, Campus de Beaulieu, 263, avenue du général Leclerc. 35042 Rennes (France), Fax: (+33) 223236939
    2. ADEME, 20, avenue du Grésillé, 49004 Angers cedex 01 (France)
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  • Dr. Mathieu Achard,

    1. Institut des Sciences Chimiques de Rennes, Organométalliques: Matériaux et Catalyse, UMR 6226-CNRS-Université de Rennes 1, Campus de Beaulieu, 263, avenue du général Leclerc. 35042 Rennes (France), Fax: (+33) 223236939
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  • Dr. Cédric Fischmeister,

    Corresponding author
    1. Institut des Sciences Chimiques de Rennes, Organométalliques: Matériaux et Catalyse, UMR 6226-CNRS-Université de Rennes 1, Campus de Beaulieu, 263, avenue du général Leclerc. 35042 Rennes (France), Fax: (+33) 223236939
    • Institut des Sciences Chimiques de Rennes, Organométalliques: Matériaux et Catalyse, UMR 6226-CNRS-Université de Rennes 1, Campus de Beaulieu, 263, avenue du général Leclerc. 35042 Rennes (France), Fax: (+33) 223236939
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  • Dr. Christian Bruneau

    Corresponding author
    1. Institut des Sciences Chimiques de Rennes, Organométalliques: Matériaux et Catalyse, UMR 6226-CNRS-Université de Rennes 1, Campus de Beaulieu, 263, avenue du général Leclerc. 35042 Rennes (France), Fax: (+33) 223236939
    • Institut des Sciences Chimiques de Rennes, Organométalliques: Matériaux et Catalyse, UMR 6226-CNRS-Université de Rennes 1, Campus de Beaulieu, 263, avenue du général Leclerc. 35042 Rennes (France), Fax: (+33) 223236939
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Abstract

The modification of methyl ricinoleate by etherification of the hydroxyl group was accomplished by using a nonclassical ruthenium-catalyzed allylation reaction and also by esterification. Methyl ricinoleate derivatives were engaged in ring-closing metathesis (RCM) reactions leading to biosourced 3,6-dihydropyran and α,β-unsaturated lactone derivatives with concomitant production of polymer precursors. Sequential RCM/hydrogenation and RCM/cross-metathesis were also implemented as a straightforward method for the synthesis of tetrahydropyran and lactone derivatives as well as valuable monomers (i.e., polyamide precursors).

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