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...
| Published in: | ChemSusChem |
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| Main Authors: | , , , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2014
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| Subjects: | |
| Online Access: | 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 |
| Summary: | 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). |
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