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...
Autores principales: | , , , , , , |
---|---|
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 |