Diels–Alder cycloaddition of 2-methylfuran and ethylene for renewable toluene
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.
- Research Organization:
- Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
- Sponsoring Organization:
- USDOE SC Office of Basic Energy Sciences (SC-22)
- DOE Contract Number:
- SC0001004
- OSTI ID:
- 1386755
- Journal Information:
- Applied Catalysis. B, Environmental, Journal Name: Applied Catalysis. B, Environmental Journal Issue: C Vol. 180; ISSN 0926-3373
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
Similar Records
Tandem Diels-Alder Reaction of Dimethylfuran and Ethylene and Dehydration to para -Xylene Catalyzed by Zeotypic Lewis Acids
Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene
Related Subjects
bio-inspired
biofuels (including algae and biomass)
catalysis (heterogeneous)
catalysis (homogeneous)
hydrogen and fuel cells
materials and chemistry by design
synthesis (novel materials)
synthesis (scalable processing)
synthesis (self-assembly)