Cycloaddition of biomass-derived furans for catalytic production of renewable p -xylene

C. Luke Williams, Chun Chih Chang, Phuong Do, Nima Nikbin, Stavros Caratzoulas, Dionisios G. Vlachos, Raul F. Lobo, Wei Fan, Paul J. Dauenhauer

Research output: Contribution to journalArticle

258 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)935-939
Number of pages5
JournalACS Catalysis
Volume2
Issue number6
DOIs
StatePublished - Jun 1 2012

Fingerprint

Furans
Cycloaddition
Xylene
Biomass
Dehydration
Zeolites
Ethylene
Microporous materials
Energy barriers
Alkylation
Reaction rates
Hydrolysis
Polymerization
4-xylene
Catalysts
Acids
Water
ethylene

Keywords

  • Diels?Alder
  • ethylene
  • furan
  • xylene
  • zeolite

Cite this

Williams, C. L., Chang, C. C., Do, P., Nikbin, N., Caratzoulas, S., Vlachos, D. G., ... Dauenhauer, P. J. (2012). Cycloaddition of biomass-derived furans for catalytic production of renewable p -xylene. ACS Catalysis, 2(6), 935-939. https://doi.org/10.1021/cs300011a

Cycloaddition of biomass-derived furans for catalytic production of renewable p -xylene. / Williams, C. Luke; Chang, Chun Chih; Do, Phuong; Nikbin, Nima; Caratzoulas, Stavros; Vlachos, Dionisios G.; Lobo, Raul F.; Fan, Wei; Dauenhauer, Paul J.

In: ACS Catalysis, Vol. 2, No. 6, 01.06.2012, p. 935-939.

Research output: Contribution to journalArticle

Williams, CL, Chang, CC, Do, P, Nikbin, N, Caratzoulas, S, Vlachos, DG, Lobo, RF, Fan, W & Dauenhauer, PJ 2012, 'Cycloaddition of biomass-derived furans for catalytic production of renewable p -xylene', ACS Catalysis, vol. 2, no. 6, pp. 935-939. https://doi.org/10.1021/cs300011a
Williams CL, Chang CC, Do P, Nikbin N, Caratzoulas S, Vlachos DG et al. Cycloaddition of biomass-derived furans for catalytic production of renewable p -xylene. ACS Catalysis. 2012 Jun 1;2(6):935-939. https://doi.org/10.1021/cs300011a
Williams, C. Luke ; Chang, Chun Chih ; Do, Phuong ; Nikbin, Nima ; Caratzoulas, Stavros ; Vlachos, Dionisios G. ; Lobo, Raul F. ; Fan, Wei ; Dauenhauer, Paul J. / Cycloaddition of biomass-derived furans for catalytic production of renewable p -xylene. In: ACS Catalysis. 2012 ; Vol. 2, No. 6. pp. 935-939.
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