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Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen
This paper discloses that inexpensive hydrobromic acid (HBr) is active and highly selective to the photo-oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF) with dioxygen (O(2)) or even with water under visible light illumination, which can achieve the highest 89.1% DFF yield in DM...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9036589/ https://www.ncbi.nlm.nih.gov/pubmed/35479798 http://dx.doi.org/10.1039/d1ra00865j |
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author | Hu, Wenwei She, Jialuo Fu, Zaihui Yang, Bo Zhang, Huanhuan Jiang, Dabo |
author_facet | Hu, Wenwei She, Jialuo Fu, Zaihui Yang, Bo Zhang, Huanhuan Jiang, Dabo |
author_sort | Hu, Wenwei |
collection | PubMed |
description | This paper discloses that inexpensive hydrobromic acid (HBr) is active and highly selective to the photo-oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF) with dioxygen (O(2)) or even with water under visible light illumination, which can achieve the highest 89.1% DFF yield in DMSO at 80 °C under pure O(2) atmosphere. More importantly, under bifunctional acid-photooxidation catalysis of HBr, fructose can be directly converted to DFF and its two-step cascade conversion in DMSO provides a far higher DFF yield (80.2%) than the one-step cascade conversion in MeCN (42.1%). The results of HMF photooxidation catalyzed by hydrohalic acids, free radical quenching tests and EPR spectrum support that the Br atom and superoxide (O(2)(−)˙) anion radicals generated by HBr photolysis in O(2) are active species for the oxidation of HMF to DFF and their activities are adjusted by the reaction medium. This photo-synthetic protocol is very simple and practical, especially with low operating costs, showing a good industrial application prospect. |
format | Online Article Text |
id | pubmed-9036589 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90365892022-04-26 Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen Hu, Wenwei She, Jialuo Fu, Zaihui Yang, Bo Zhang, Huanhuan Jiang, Dabo RSC Adv Chemistry This paper discloses that inexpensive hydrobromic acid (HBr) is active and highly selective to the photo-oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-diformylfuran (DFF) with dioxygen (O(2)) or even with water under visible light illumination, which can achieve the highest 89.1% DFF yield in DMSO at 80 °C under pure O(2) atmosphere. More importantly, under bifunctional acid-photooxidation catalysis of HBr, fructose can be directly converted to DFF and its two-step cascade conversion in DMSO provides a far higher DFF yield (80.2%) than the one-step cascade conversion in MeCN (42.1%). The results of HMF photooxidation catalyzed by hydrohalic acids, free radical quenching tests and EPR spectrum support that the Br atom and superoxide (O(2)(−)˙) anion radicals generated by HBr photolysis in O(2) are active species for the oxidation of HMF to DFF and their activities are adjusted by the reaction medium. This photo-synthetic protocol is very simple and practical, especially with low operating costs, showing a good industrial application prospect. The Royal Society of Chemistry 2021-07-02 /pmc/articles/PMC9036589/ /pubmed/35479798 http://dx.doi.org/10.1039/d1ra00865j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Hu, Wenwei She, Jialuo Fu, Zaihui Yang, Bo Zhang, Huanhuan Jiang, Dabo Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen |
title | Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen |
title_full | Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen |
title_fullStr | Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen |
title_full_unstemmed | Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen |
title_short | Highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using HBr and molecular oxygen |
title_sort | highly efficient and tunable visible-light-catalytic synthesis of 2,5-diformylfuran using hbr and molecular oxygen |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9036589/ https://www.ncbi.nlm.nih.gov/pubmed/35479798 http://dx.doi.org/10.1039/d1ra00865j |
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