Synthesis of Biobased Succinonitrile from Glutamic Acid and Glutamine

Authors

  • Tijs M. Lammens,

    Corresponding author
    1. Valorisation of Plant Production Chains, Wageningen University, PO Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
    • Valorisation of Plant Production Chains, Wageningen University, PO Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
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  • Dr. Jérôme Le Nôtre,

    1. Valorisation of Plant Production Chains, Wageningen University, PO Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
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  • Dr. Maurice C. R. Franssen,

    1. Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB, Wageningen (The Netherlands)
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  • Dr. Elinor L. Scott,

    Corresponding author
    1. Valorisation of Plant Production Chains, Wageningen University, PO Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
    • Valorisation of Plant Production Chains, Wageningen University, PO Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
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  • Prof. Johan P. M. Sanders

    1. Valorisation of Plant Production Chains, Wageningen University, PO Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
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Abstract

Succinonitrile is the precursor of 1,4-diaminobutane, which is used for the industrial production of polyamides. This paper describes the synthesis of biobased succinonitrile from glutamic acid and glutamine, amino acids that are abundantly present in many plant proteins. Synthesis of the intermediate 3-cyanopropanoic amide was achieved from glutamic acid 5-methyl ester in an 86 mol % yield and from glutamine in a 56 mol % yield. 3-Cyanopropanoic acid can be converted into succinonitrile, with a selectivity close to 100 % and a 62 % conversion, by making use of a palladium(II)-catalyzed equilibrium reaction with acetonitrile. Thus, a new route to produce biobased 1,4-diaminobutane has been discovered.

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