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Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids

(2015) CHEMSUSCHEM. 8(2). p.345-352
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Abstract
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.
Keywords
biomass, amino acids, heterogeneous catalysis, oxidation, tungsten, LAYERED DOUBLE HYDROXIDES, GLUTAMIC-ACID, BIOMASS, BROMINATION, CHEMISTRY, BROMOPEROXIDASE, HALOGENATION, CONVERSION, CHEMICALS, TUNGSTATE

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MLA
Claes, Laurens et al. “Bio-based Nitriles from the Heterogeneously Catalyzed Oxidative Decarboxylation of Amino Acids.” CHEMSUSCHEM 8.2 (2015): 345–352. Print.
APA
Claes, L., Matthessen, R., Rombouts, I., Stassen, I., De Baerdemaeker, T., Depla, D., Delcour, J. A., et al. (2015). Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids. CHEMSUSCHEM, 8(2), 345–352.
Chicago author-date
Claes, Laurens, Roman Matthessen, Ine Rombouts, Ivo Stassen, Trees De Baerdemaeker, Diederik Depla, Jan A Delcour, Bert Lagrain, and Dirk E De Vos. 2015. “Bio-based Nitriles from the Heterogeneously Catalyzed Oxidative Decarboxylation of Amino Acids.” Chemsuschem 8 (2): 345–352.
Chicago author-date (all authors)
Claes, Laurens, Roman Matthessen, Ine Rombouts, Ivo Stassen, Trees De Baerdemaeker, Diederik Depla, Jan A Delcour, Bert Lagrain, and Dirk E De Vos. 2015. “Bio-based Nitriles from the Heterogeneously Catalyzed Oxidative Decarboxylation of Amino Acids.” Chemsuschem 8 (2): 345–352.
Vancouver
1.
Claes L, Matthessen R, Rombouts I, Stassen I, De Baerdemaeker T, Depla D, et al. Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids. CHEMSUSCHEM. 2015;8(2):345–52.
IEEE
[1]
L. Claes et al., “Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids,” CHEMSUSCHEM, vol. 8, no. 2, pp. 345–352, 2015.
@article{6837765,
  abstract     = {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.},
  author       = {Claes, Laurens and Matthessen, Roman and Rombouts, Ine and Stassen, Ivo and De Baerdemaeker, Trees and Depla, Diederik and Delcour, Jan A and Lagrain, Bert and De Vos, Dirk E},
  issn         = {1864-5631},
  journal      = {CHEMSUSCHEM},
  keywords     = {biomass,amino acids,heterogeneous catalysis,oxidation,tungsten,LAYERED DOUBLE HYDROXIDES,GLUTAMIC-ACID,BIOMASS,BROMINATION,CHEMISTRY,BROMOPEROXIDASE,HALOGENATION,CONVERSION,CHEMICALS,TUNGSTATE},
  language     = {eng},
  number       = {2},
  pages        = {345--352},
  title        = {Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids},
  url          = {http://dx.doi.org/10.1002/cssc.201402801},
  volume       = {8},
  year         = {2015},
}

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