Bio-Based Nitriles from the Heterogeneously Catalyzed Oxidative Decarboxylation of Amino Acids

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), NH4Br, and H2O2 as the terminal oxidant. Both halide oxidation and oxidative decarboxylati...

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Published in:ChemSusChem Vol. 8; no. 2; pp. 345 - 352
Main Authors: Claes, Laurens, Matthessen, Roman, Rombouts, Ine, Stassen, Ivo, De Baerdemaeker, Trees, Depla, Diederik, Delcour, Jan A., Lagrain, Bert, De Vos, Dirk E.
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 01.01.2015
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects:
Amino acids
Amino Acids - chemistry
Aqueous solutions
biomass
Catalysis
Decarboxylation
Glutens - chemistry
heterogeneous catalysis
Hydrolysis
Nitriles - chemistry
oxidation
Oxidation-Reduction
Triticum - chemistry
tungsten
oxidation
biomass
tungsten
heterogeneous catalysis
amino acids
ISSN:1864-5631, 1864-564X, 1864-564X
Online Access:Get full text
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Summary: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), NH4Br, and H2O2 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. Going the extra nitrile: A catalytic system that consists of a tungstate‐exchanged layered double hydroxide and a bromide salt is developed for the oxidative decarboxylation of amino acids under mild conditions using H2O2 as a green oxidant. Several functional groups are tolerated, and the nitrile selectivity is often 99 %. This strategy offers opportunities for protein‐rich biomass valorization.
Bibliography:IWT Flanders
BELSPO - No. IAP-PAI P7/05
ark:/67375/WNG-F3CTDSG5-J
ArticleID:CSSC201402801
istex:1070C567D19EB97A17F9F8F97CD1A469987376F7
KU Leuven - No. IOF-ZKC6712
Flemish government
FWO Flanders
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1864-5631
1864-564X
1864-564X
DOI:10.1002/cssc.201402801