A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5-(Hydroxymethyl)furfural using Lewis Acid Zeolites

Hf‐, Zr‐ and Sn‐Beta zeolites effectively catalyze the coupled transfer hydrogenation and etherification of 5‐(hydroxymethyl)furfural with primary and secondary alcohols into 2,5‐bis(alkoxymethyl)furans, thus making it possible to generate renewable fuel additives without the use of external hydroge...

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Bibliographic Details
Published in:ChemSusChem 2014-08, Vol.7 (8), p.2255-2265
Main Authors: Lewis, Jennifer D., Van de Vyver, Stijn, Crisci, Anthony J., Gunther, William R., Michaelis, Vladimir K., Griffin, Robert G., Román-Leshkov, Yuriy
Format: Article
Language:English
Subjects:
biomass conversion
Butanols - chemistry
cascade reactions
Catalysis
Ethers - chemistry
Furaldehyde - analogs & derivatives
Furaldehyde - chemistry
hydrogen transfer
Hydrogenation
Lewis Acids - chemistry
solid lewis acids
Water - chemistry
Zeolites
Zeolites - chemistry
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Summary:Hf‐, Zr‐ and Sn‐Beta zeolites effectively catalyze the coupled transfer hydrogenation and etherification of 5‐(hydroxymethyl)furfural with primary and secondary alcohols into 2,5‐bis(alkoxymethyl)furans, thus making it possible to generate renewable fuel additives without the use of external hydrogen sources or precious metals. Continuous flow experiments reveal nonuniform changes in the relative deactivation rates of the transfer hydrogenation and etherification reactions, which impact the observed product distribution over time. We found that the catalysts undergo a drastic deactivation for the etherification step while maintaining catalytic activity for the transfer hydrogenation step. 119Sn and 29Si magic angle spinning (MAS) NMR studies show that this deactivation can be attributed to changes in the local environment of the metal sites. Additional insights were gained by studying effects of various alcohols and water concentration on the catalytic reactivity. Go with the continuous flow: The title reaction was investigated under continuous flow conditions in the presence of Hf‐, Zr‐, and Sn‐Beta zeolites. Product distribution studies and a thorough characterization of the catalysts reveal that their deactivation can be correlated to changes in the local environment of the metal sites.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.201402100