Journal
ACS CATALYSIS
Volume 2, Issue 6, Pages 935-939Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs300011a
Keywords
xylene; furan; Diels-Alder; zeolite; ethylene
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Funding
- Catalysis Center for Energy Innovation, an Energy Frontier Research Center
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001004]
- Direct For Biological Sciences
- Div Of Biological Infrastructure [0923105] Funding Source: National Science Foundation
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A renewable route to p-xylene from biomass-derived dimethylfuran and ethylene is investigated with zeolite catalysts. Cycloaddition of ethylene and 2,5-dimethylfuran and subsequent dehydration to p-xylene has been achieved with 75% selectivity using H-Y zeolite and an aliphatic solvent at 300 degrees C. Competitive side reactions include hydrolysis of dimethylfuran to 2,5-hexanedione, alkylation of p-xylene, and polymerization of 2,5-hexanedione. The observed reaction rates and computed energy barriers are consistent with a two-step reaction that proceeds through a bicyclic adduct prior to dehydration to p-xylene. Cycloaddition of ethylene and dimethylfuran occurs without a catalytic active site, but the reaction is promoted by confinement within microporous materials. The presence of Bronsted acid sites catalyzes dehydration of the Diels-Alder cycloadduct (to produce p-xylene and water), and this ultimately causes the rate-determining step to be the initial cycloaddition.
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