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Synthesis of Biobased Succinonitrile from Glutamic Acid and Glutamine
Author(s) -
Lammens Tijs M.,
Le Nôtre Jérôme,
Franssen Maurice C. R.,
Scott Elinor L.,
Sanders Johan P. M.
Publication year - 2011
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201100030
Subject(s) - succinonitrile , chemistry , glutamine , yield (engineering) , organic chemistry , amide , selectivity , glutamic acid , polyamide , catalysis , amino acid , biochemistry , materials science , electrode , electrolyte , metallurgy
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.