Cargando…

One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation

Glutamic acid, an abundant nonessential amino acid, was converted into 2‐pyrrolidone in the presence of a supported Ru catalyst under a pressurized hydrogen atmosphere. This reaction pathway proceeded through the dehydration of glutamic acid into pyroglutamic acid, subsequent hydrogenation, and the...

Descripción completa

Detalles Bibliográficos
Autores principales: Suganuma, Satoshi, Otani, Akihiro, Joka, Shota, Asako, Hiroki, Takagi, Rika, Tsuji, Etsushi, Katada, Naonobu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155029/
https://www.ncbi.nlm.nih.gov/pubmed/30698350
http://dx.doi.org/10.1002/cssc.201802980
_version_ 1783521947546550272
author Suganuma, Satoshi
Otani, Akihiro
Joka, Shota
Asako, Hiroki
Takagi, Rika
Tsuji, Etsushi
Katada, Naonobu
author_facet Suganuma, Satoshi
Otani, Akihiro
Joka, Shota
Asako, Hiroki
Takagi, Rika
Tsuji, Etsushi
Katada, Naonobu
author_sort Suganuma, Satoshi
collection PubMed
description Glutamic acid, an abundant nonessential amino acid, was converted into 2‐pyrrolidone in the presence of a supported Ru catalyst under a pressurized hydrogen atmosphere. This reaction pathway proceeded through the dehydration of glutamic acid into pyroglutamic acid, subsequent hydrogenation, and the dehydrogenation–decarbonylation of pyroglutaminol into 2‐pyrrolidone. In the conversion of pyroglutaminol, Ru/Al(2)O(3) exhibited notably higher activity than supported Pt, Pd, and Rh catalysts. IR analysis revealed that Ru can hydrogenate the formed CO through dehydrogenation–decarbonylation of hydroxymethyl groups in pyroglutaminol and can also easily desorb CH(4) from the active sites on Ru. Furthermore, Ru/Al(2)O(3) showed the highest catalytic activity among the tested catalysts in the conversion of pyroglutamic acid. Consequently, the conversion of glutamic acid produced a high yield of 2‐pyrrolidone by using the supported Ru catalyst. This is the first report of this one‐pot reaction under mild reaction conditions (433 K, 2 MPa H(2))„ which avoids the degradation of unstable amino acids above 473 K.
format Online
Article
Text
id pubmed-7155029
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-71550292020-04-15 One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation Suganuma, Satoshi Otani, Akihiro Joka, Shota Asako, Hiroki Takagi, Rika Tsuji, Etsushi Katada, Naonobu ChemSusChem Full Papers Glutamic acid, an abundant nonessential amino acid, was converted into 2‐pyrrolidone in the presence of a supported Ru catalyst under a pressurized hydrogen atmosphere. This reaction pathway proceeded through the dehydration of glutamic acid into pyroglutamic acid, subsequent hydrogenation, and the dehydrogenation–decarbonylation of pyroglutaminol into 2‐pyrrolidone. In the conversion of pyroglutaminol, Ru/Al(2)O(3) exhibited notably higher activity than supported Pt, Pd, and Rh catalysts. IR analysis revealed that Ru can hydrogenate the formed CO through dehydrogenation–decarbonylation of hydroxymethyl groups in pyroglutaminol and can also easily desorb CH(4) from the active sites on Ru. Furthermore, Ru/Al(2)O(3) showed the highest catalytic activity among the tested catalysts in the conversion of pyroglutamic acid. Consequently, the conversion of glutamic acid produced a high yield of 2‐pyrrolidone by using the supported Ru catalyst. This is the first report of this one‐pot reaction under mild reaction conditions (433 K, 2 MPa H(2))„ which avoids the degradation of unstable amino acids above 473 K. John Wiley and Sons Inc. 2019-03-04 2019-04-05 /pmc/articles/PMC7155029/ /pubmed/30698350 http://dx.doi.org/10.1002/cssc.201802980 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Suganuma, Satoshi
Otani, Akihiro
Joka, Shota
Asako, Hiroki
Takagi, Rika
Tsuji, Etsushi
Katada, Naonobu
One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
title One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
title_full One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
title_fullStr One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
title_full_unstemmed One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
title_short One‐Step Conversion of Glutamic Acid into 2‐Pyrrolidone on a Supported Ru Catalyst in a Hydrogen Atmosphere: Remarkable Effect of CO Activation
title_sort one‐step conversion of glutamic acid into 2‐pyrrolidone on a supported ru catalyst in a hydrogen atmosphere: remarkable effect of co activation
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155029/
https://www.ncbi.nlm.nih.gov/pubmed/30698350
http://dx.doi.org/10.1002/cssc.201802980
work_keys_str_mv AT suganumasatoshi onestepconversionofglutamicacidinto2pyrrolidoneonasupportedrucatalystinahydrogenatmosphereremarkableeffectofcoactivation
AT otaniakihiro onestepconversionofglutamicacidinto2pyrrolidoneonasupportedrucatalystinahydrogenatmosphereremarkableeffectofcoactivation
AT jokashota onestepconversionofglutamicacidinto2pyrrolidoneonasupportedrucatalystinahydrogenatmosphereremarkableeffectofcoactivation
AT asakohiroki onestepconversionofglutamicacidinto2pyrrolidoneonasupportedrucatalystinahydrogenatmosphereremarkableeffectofcoactivation
AT takagirika onestepconversionofglutamicacidinto2pyrrolidoneonasupportedrucatalystinahydrogenatmosphereremarkableeffectofcoactivation
AT tsujietsushi onestepconversionofglutamicacidinto2pyrrolidoneonasupportedrucatalystinahydrogenatmosphereremarkableeffectofcoactivation
AT katadanaonobu onestepconversionofglutamicacidinto2pyrrolidoneonasupportedrucatalystinahydrogenatmosphereremarkableeffectofcoactivation