title: Synthesis of biobased succinonitrile from glutamic acid and glutamine.
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.
authors.affiliation: Valorisation of Plant Production Chains, Wageningen University, PO Box 17, 6700 AA Wageningen, The Netherlands. tijs.lammens@wur.nl
authors.forename: Tijs M
authors.initials: TM
authors.lastname: Lammens
authors.forename: Jérôme
authors.initials: J
authors.lastname: Le Nôtre
authors.forename: Maurice C R
authors.initials: MC
authors.lastname: Franssen
authors.forename: Elinor L
authors.initials: EL
authors.lastname: Scott
authors.forename: Johan P M
authors.initials: JP
authors.lastname: Sanders
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D055162:Biocatalysis; D018533:Biomass; D018698:Glutamic Acid / Q000378:metabolism*; D005973:Glutamine / Q000378:metabolism*; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry
chemical_list: D000097:Acetonitriles; D009570:Nitriles; D005973:Glutamine; C010337:succinonitrile; D018698:Glutamic Acid; D010165:Palladium; C032159:acetonitrile