From Biomass-Derived Furans to Aromatics with Ethanol over Zeolite

We report a novel catalytic conversion of biomass‐derived furans and alcohols to aromatics over zeolite catalysts. Aromatics are formed via Diels–Alder cycloaddition with ethylene, which is produced in situ from ethanol dehydration. The use of liquid ethanol instead of gaseous ethylene, as the sourc...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2016-10, Vol.55 (42), p.13061-13066
Main Authors: Teixeira, Ivo F., Lo, Benedict T. W., Kostetskyy, Pavlo, Stamatakis, Michail, Ye, Lin, Tang, Chiu C., Mpourmpakis, Giannis, Tsang, Shik Chi Edman
Format: Article
Language:English
Subjects:
Activation
Affinity
Alcohols
Aromatic compounds
Biomass
Catalysts
Catalytic converters
Conversion
Cycloaddition
Dehydration
Diffraction
Ethanol
Ethylene
Furans
High pressure
Mathematical analysis
Pesticides
Pressure
Protonation
Selectivity
structure elucidation
Zeolites
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Summary:We report a novel catalytic conversion of biomass‐derived furans and alcohols to aromatics over zeolite catalysts. Aromatics are formed via Diels–Alder cycloaddition with ethylene, which is produced in situ from ethanol dehydration. The use of liquid ethanol instead of gaseous ethylene, as the source of dienophile in this one‐pot synthesis, makes the aromatics production much simpler and renewable, circumventing the use of ethylene at high pressure. More importantly, both our experiments and theoretical studies demonstrate that the use of ethanol instead of ethylene, results in significantly higher rates and higher selectivity to aromatics, due to lower activation barriers over the solid acid sites. Synchrotron‐diffraction experiments and proton‐affinity calculations clearly suggest that a preferred protonation of ethanol over the furan is a key step facilitating the Diels–Alder and dehydration reactions in the acid sites of the zeolite. Liquid lunch: Ethylene produced in situ from ethanol dehydration over zeolite is used for the catalytic conversion of biomass‐derived furans to aromatics via Diels–Alder cycloaddition. The one‐pot synthesis using liquid ethanol instead of pressurized ethylene gas enables much faster production of aromatics in a renewable manner.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201604108