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 journalArticlepeer-review

315 Scopus citations

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

Keywords

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

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