Synthesis of Biobased Succinonitrile from Glutamic Acid and Glutamine

• DOI: 10.1002/cssc.201100030
• Publication Date: 2011-05-10T11:46:44Z
• Authors: Tijs M. Lammens; Jérôme Le Nôtre; Maurice C. R. Fra...; Elinor L. Scott; Johan P. M. Sanders
• Keywords: Succinonitrile; Amide; Glutamic acid

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