Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates
Abstract The one‐pot production of industrially valuable diketone derivatives from carbohydrates is achieved through a bifunctional catalytic process. In particular, Pd/C‐catalyzed hydrogenation of HMF in water and under CO 2 affords 1‐hydroxypentane‐2,5‐dione with up to 77 % yield. The process is a...
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crwiley:10.1002/cssc.201402221 2024-09-15T18:01:38+00:00 Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates Liu, Fei Audemar, Maïté De Oliveira Vigier, Karine Clacens, Jean‐Marc De Campo, Floryan Jérôme, François 2014 http://dx.doi.org/10.1002/cssc.201402221 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcssc.201402221 http://onlinelibrary.wiley.com/wol1/doi/10.1002/cssc.201402221/fullpdf en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor ChemSusChem volume 7, issue 8, page 2089-2093 ISSN 1864-5631 1864-564X journal-article 2014 crwiley https://doi.org/10.1002/cssc.201402221 2024-07-04T04:27:54Z Abstract The one‐pot production of industrially valuable diketone derivatives from carbohydrates is achieved through a bifunctional catalytic process. In particular, Pd/C‐catalyzed hydrogenation of HMF in water and under CO 2 affords 1‐hydroxypentane‐2,5‐dione with up to 77 % yield. The process is also eligible starting from fructose and inulin, affording 1‐hydroxyhexane‐2,5‐dione with 36 % and 15 % yield, respectively. The key of the process is reversible in situ formation of carbonic acid, which is capable of assisting Pd/C during the hydrogenation reaction by promoting the dehydration of carbohydrates and the ring‐opening of furanic intermediates. Interestingly, by changing the reaction medium from H 2 O to a H 2 O/THF mixture (1:9), it is possible to switch the selectivity of the reaction and to produce 2,5‐hexanadione with 83 % yield. Within the framework of sustainable chemistry, reactions presented in this report show 100 % carbon economy, involve CO 2 to generate acidity, require water as a solvent, and are conducted under rather low hydrogen pressures (10 bar). Article in Journal/Newspaper Carbonic acid Wiley Online Library ChemSusChem 7 8 2089 2093 |
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Wiley Online Library |
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English |
description |
Abstract The one‐pot production of industrially valuable diketone derivatives from carbohydrates is achieved through a bifunctional catalytic process. In particular, Pd/C‐catalyzed hydrogenation of HMF in water and under CO 2 affords 1‐hydroxypentane‐2,5‐dione with up to 77 % yield. The process is also eligible starting from fructose and inulin, affording 1‐hydroxyhexane‐2,5‐dione with 36 % and 15 % yield, respectively. The key of the process is reversible in situ formation of carbonic acid, which is capable of assisting Pd/C during the hydrogenation reaction by promoting the dehydration of carbohydrates and the ring‐opening of furanic intermediates. Interestingly, by changing the reaction medium from H 2 O to a H 2 O/THF mixture (1:9), it is possible to switch the selectivity of the reaction and to produce 2,5‐hexanadione with 83 % yield. Within the framework of sustainable chemistry, reactions presented in this report show 100 % carbon economy, involve CO 2 to generate acidity, require water as a solvent, and are conducted under rather low hydrogen pressures (10 bar). |
format |
Article in Journal/Newspaper |
author |
Liu, Fei Audemar, Maïté De Oliveira Vigier, Karine Clacens, Jean‐Marc De Campo, Floryan Jérôme, François |
spellingShingle |
Liu, Fei Audemar, Maïté De Oliveira Vigier, Karine Clacens, Jean‐Marc De Campo, Floryan Jérôme, François Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates |
author_facet |
Liu, Fei Audemar, Maïté De Oliveira Vigier, Karine Clacens, Jean‐Marc De Campo, Floryan Jérôme, François |
author_sort |
Liu, Fei |
title |
Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates |
title_short |
Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates |
title_full |
Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates |
title_fullStr |
Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates |
title_full_unstemmed |
Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates |
title_sort |
palladium/carbon dioxide cooperative catalysis for the production of diketone derivatives from carbohydrates |
publisher |
Wiley |
publishDate |
2014 |
url |
http://dx.doi.org/10.1002/cssc.201402221 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcssc.201402221 http://onlinelibrary.wiley.com/wol1/doi/10.1002/cssc.201402221/fullpdf |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
ChemSusChem volume 7, issue 8, page 2089-2093 ISSN 1864-5631 1864-564X |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/cssc.201402221 |
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ChemSusChem |
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7 |
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8 |
container_start_page |
2089 |
op_container_end_page |
2093 |
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1810438747202781184 |