Journal article
A Pd-Catalyzed in situ domino process for mild and quantitative production of 2,5-dimethylfuran directly from carbohydrates
Guizhou University1
Department of Chemistry, Technical University of Denmark2
Centre for Catalysis and Sustainable Chemistry, Department of Chemistry, Technical University of Denmark3
Organic Chemistry, Department of Chemistry, Technical University of Denmark4
Centre of Innovative and Applied Bioprocessing5
Nanjing Agricultural University6
An in situ domino process has been developed to be highly efficient for direct and mild conversion of various hexose sugars to the biofuel 2,5-dimethylfuran in almost quantitative yields, without separation of unstable intermediates at 120 °C in n-butanol, by using polymethylhydrosiloxane and hydrophobic Pd/C as a H-donor and a bifunctional catalyst, respectively.
Among the cascade reactions, the hydrosilylation process was confirmed by deuterium-labeling and kinetic studies to be favorable for sugar dehydration and exclusively acts on deoxygenation of in situ formed intermediates including furanic alcohols and aldehydes to DMF via a hydride transfer process that was facilitated by an alcoholic solvent.
The catalytic system is more selective than the H2-participated counterpart, and could be scaled up with only 0.04 mol% catalyst loading, giving DMF in a comparable yield of 85%. Moreover, Pd(0) was demonstrated to be the active species for deoxygenation, and the heterogeneous catalyst exhibited good recyclability with little elemental leaching.
Language: | English |
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Publisher: | The Royal Society of Chemistry |
Year: | 2017 |
Pages: | 2101-2106 |
ISSN: | 14639270 and 14639262 |
Types: | Journal article |
DOI: | 10.1039/C7GC00580F |
ORCIDs: | Riisager, Anders and 0000-0003-1301-3030 |