Synthesis of Biobased Succinonitrile from Glutamic Acid and Glutamine

T.M. Lammens, J. Le Nôtre, M.C.R. Franssen, E.L. Scott, J.P.M. Sanders

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32 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)785-791
JournalChemSusChem
Volume4
Issue number6
DOIs
Publication statusPublished - 2011

Keywords

  • primary amides
  • amino-acids
  • nitriles
  • suzuki
  • dehydration
  • complexes
  • catalysts

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