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Cycloaddition of Biomass-Derived Furans for Catalytic Production of Renewable p-Xylene
Abstract
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 °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 Brønsted 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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Metadata
- Authors
- Williams, C. L., Chang, C.-C., Do, P., Nikbin, N., Caratzoulas, S., Vlachos, D. G., Lobo, R. F., Fan, W., & Dauenhauer, P. J.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-04-26
- Volume
- 2
- Issue
- 6
- Pages
- 935-939
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2332824798
- Cited by
- 439
- References
- 1
- FWCI
- 18.14
- Type
- journal article
- Language
- en
- Open access
- closed
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