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Bio‐Based Nitriles from the Heterogeneously Catalyzed Oxidative Decarboxylation of Amino Acids
Author(s) -
Claes Laurens,
Matthessen Roman,
Rombouts Ine,
Stassen Ivo,
De Baerdemaeker Trees,
Depla Diederik,
Delcour Jan A.,
Lagrain Bert,
De Vos Dirk E.
Publication year - 2015
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.201402801
Subject(s) - chemistry , decarboxylation , oxidative decarboxylation , nitrile , catalysis , amide , organic chemistry , amine gas treating , amino acid , hydroxide , aqueous solution , biochemistry
The oxidative decarboxylation of amino acids to nitriles was achieved in aqueous solution by in situ halide oxidation using catalytic amounts of tungstate exchanged on a [Ni,Al] layered double hydroxide (LDH), NH 4 Br, and H 2 O 2 as the terminal oxidant. Both halide oxidation and oxidative decarboxylation were facilitated by proximity effects between the reactants and the LDH catalyst. A wide range of amino acids was converted with high yields, often >90 %. The nitrile selectivity was excellent, and the system is compatible with amide, alcohol, and in particular carboxylic acid, amine, and guanidine functional groups after appropriate neutralization. This heterogeneous catalytic system was applied successfully to convert a protein‐rich byproduct from the starch industry into useful bio‐based N‐containing chemicals.