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Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 406843
Title Synthesis of Biobased Succinonitrile from Glutamic Acid and Glutamine
Author(s) Lammens, T.M.; Nôtre, J. Le; Franssen, M.C.R.; Scott, E.L.; Sanders, J.P.M.
Source ChemSusChem 4 (2011)6. - ISSN 1864-5631 - p. 785 - 791.
Department(s) Biobased Chemistry and Technology
Laboratory for Organic Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2011
Keyword(s) primary amides - amino-acids - nitriles - suzuki - dehydration - complexes - catalysts
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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