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Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst
5‐hydroxymethylfurfural (HMF) has been successfully valorized into 3‐hydroxymethylcyclopentylamine through a one‐pot cascade process in aqueous phase by coupling the hydrogenative ring‐rearrangement of HMF into 3‐hydroxymethylcyclopentanone (HCPN) with a subsequent reductive amination with ammonia....
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401071/ https://www.ncbi.nlm.nih.gov/pubmed/35362654 http://dx.doi.org/10.1002/cssc.202200194 |
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author | Hurtado, Beatriz Arias, Karen S. Climent, Maria J. Concepción, Patricia Corma, Avelino Iborra, Sara |
author_facet | Hurtado, Beatriz Arias, Karen S. Climent, Maria J. Concepción, Patricia Corma, Avelino Iborra, Sara |
author_sort | Hurtado, Beatriz |
collection | PubMed |
description | 5‐hydroxymethylfurfural (HMF) has been successfully valorized into 3‐hydroxymethylcyclopentylamine through a one‐pot cascade process in aqueous phase by coupling the hydrogenative ring‐rearrangement of HMF into 3‐hydroxymethylcyclopentanone (HCPN) with a subsequent reductive amination with ammonia. Mono‐ (Ni@C, Co@C) and bimetallic (NiCo@C) nanoparticles with different Ni/Co ratios partially covered by a thin carbon layer were prepared and characterized. Results showed that a NiCo catalyst, (molar ratio Ni/Co=1, Ni(0.5)Co(0.5)@C), displayed excellent performance in the hydrogenative ring‐rearrangement of HMF into HCPN (>90 % yield). The high selectivity of the catalyst was attributed to the formation of NiCo alloy structures as hydrogenating sites that limited competitive reactions such as the hydrogenation of furan ring and the over‐reduction of the formed HPCN. The subsequent reductive amination of HPCN with aqueous ammonia was performed giving the target cyclopentylaminoalcohol in 97 % yield. Moreover, the catalyst exhibited high stability maintaining its activity and selectivity for repeated reaction cycles. |
format | Online Article Text |
id | pubmed-9401071 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-94010712022-08-26 Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst Hurtado, Beatriz Arias, Karen S. Climent, Maria J. Concepción, Patricia Corma, Avelino Iborra, Sara ChemSusChem Research Articles 5‐hydroxymethylfurfural (HMF) has been successfully valorized into 3‐hydroxymethylcyclopentylamine through a one‐pot cascade process in aqueous phase by coupling the hydrogenative ring‐rearrangement of HMF into 3‐hydroxymethylcyclopentanone (HCPN) with a subsequent reductive amination with ammonia. Mono‐ (Ni@C, Co@C) and bimetallic (NiCo@C) nanoparticles with different Ni/Co ratios partially covered by a thin carbon layer were prepared and characterized. Results showed that a NiCo catalyst, (molar ratio Ni/Co=1, Ni(0.5)Co(0.5)@C), displayed excellent performance in the hydrogenative ring‐rearrangement of HMF into HCPN (>90 % yield). The high selectivity of the catalyst was attributed to the formation of NiCo alloy structures as hydrogenating sites that limited competitive reactions such as the hydrogenation of furan ring and the over‐reduction of the formed HPCN. The subsequent reductive amination of HPCN with aqueous ammonia was performed giving the target cyclopentylaminoalcohol in 97 % yield. Moreover, the catalyst exhibited high stability maintaining its activity and selectivity for repeated reaction cycles. John Wiley and Sons Inc. 2022-05-12 2022-07-07 /pmc/articles/PMC9401071/ /pubmed/35362654 http://dx.doi.org/10.1002/cssc.202200194 Text en © 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://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 | Research Articles Hurtado, Beatriz Arias, Karen S. Climent, Maria J. Concepción, Patricia Corma, Avelino Iborra, Sara Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst |
title | Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst |
title_full | Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst |
title_fullStr | Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst |
title_full_unstemmed | Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst |
title_short | Selective Conversion of HMF into 3‐Hydroxymethylcyclopentylamine through a One‐Pot Cascade Process in Aqueous Phase over Bimetallic NiCo Nanoparticles as Catalyst |
title_sort | selective conversion of hmf into 3‐hydroxymethylcyclopentylamine through a one‐pot cascade process in aqueous phase over bimetallic nico nanoparticles as catalyst |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401071/ https://www.ncbi.nlm.nih.gov/pubmed/35362654 http://dx.doi.org/10.1002/cssc.202200194 |
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