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 journalArticlepeer-review

50 Scopus citations

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

Bibliographical note

Funding Information:
Financial support was provided from the Catalysis Center for Energy Innovation , a U.S. Department of Energy – Energy Frontiers Research Center (www.efrc.udel.edu) under Award DE-SC0001004 . This research used resources of the National Energy Research Scientific Computing Center (NERSC), a DOE Office of Science User Facility supported by the Office of Science of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231 .

Publisher Copyright:
© 2015 Elsevier B.V.

Keywords

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

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