Diels-Alder cycloaddition of 2-methylfuran and ethylene for renewable toluene

Sara K. Green, Ryan E. Patet, Nima Nikbin, C. Luke Williams, Chun Chih Chang, Jingye Yu, Raymond J. Gorte, Stavros Caratzoulas, Wei Fan, Dionisios G. Vlachos, Paul J. Dauenhauer

Research output: Contribution to journalArticle

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Abstract

Diels-Alder cycloaddition of biomass-derived 2-methylfuran and ethylene provides a thermochemical pathway to renewable toluene. In this work, the kinetics and reaction pathways of toluene formation have been evaluated with H-BEA and Sn-BEA catalysts. Kinetic analysis of the main reaction chemistries reveals the existence of two rate-controlling reactions: (i) Diels-Alder cycloaddition of 2-methylfuran and ethylene where the production rate is independent of the Brønsted acid site concentration, and (ii) dehydration of the Diels-Alder cycloadduct where the production rate is dependent on the Brønsted acid site concentration. Application of a reduced kinetic model supports the interplay of these two regimes with the highest concentration of toluene measured at a catalyst loading equal to the transition region between the two kinetic regimes. Selectivity to toluene never exceeded 46%, as 2-methylfuran was consumed by several newly identified reactions to side products, including dimerization of 2-methylfuran, the formation of a trimer following hydrolysis and ring-opening of 2-methylfuran, and the incomplete dehydration of the Diels-Alder cycloadduct of 2-methylfuran and ethylene.

Original languageEnglish (US)
Pages (from-to)487-496
Number of pages10
JournalApplied Catalysis B: Environmental
Volume180
DOIs
StatePublished - Jan 1 2016

Fingerprint

Cycloaddition
Toluene
toluene
ethylene
Ethylene
kinetics
Kinetics
Dehydration
dehydration
catalyst
Catalysts
Dimerization
Acids
acid
Reaction rates
hydrolysis
Hydrolysis
Biomass
2-methylfuran
biomass

Keywords

  • Biomass
  • Diels-Alder
  • Furan
  • Toluene
  • Zeolite

Cite this

Diels-Alder cycloaddition of 2-methylfuran and ethylene for renewable toluene. / Green, Sara K.; Patet, Ryan E.; Nikbin, Nima; Williams, C. Luke; Chang, Chun Chih; Yu, Jingye; Gorte, Raymond J.; Caratzoulas, Stavros; Fan, Wei; Vlachos, Dionisios G.; Dauenhauer, Paul J.

In: Applied Catalysis B: Environmental, Vol. 180, 01.01.2016, p. 487-496.

Research output: Contribution to journalArticle

Green, SK, Patet, RE, Nikbin, N, Williams, CL, Chang, CC, Yu, J, Gorte, RJ, Caratzoulas, S, Fan, W, Vlachos, DG & Dauenhauer, PJ 2016, 'Diels-Alder cycloaddition of 2-methylfuran and ethylene for renewable toluene', Applied Catalysis B: Environmental, vol. 180, pp. 487-496. https://doi.org/10.1016/j.apcatb.2015.06.044
Green, Sara K. ; Patet, Ryan E. ; Nikbin, Nima ; Williams, C. Luke ; Chang, Chun Chih ; Yu, Jingye ; Gorte, Raymond J. ; Caratzoulas, Stavros ; Fan, Wei ; Vlachos, Dionisios G. ; Dauenhauer, Paul J. / Diels-Alder cycloaddition of 2-methylfuran and ethylene for renewable toluene. In: Applied Catalysis B: Environmental. 2016 ; Vol. 180. pp. 487-496.
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