Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene
- Univ. of Massachusetts, Amherst, MA (United States); Univ. of Delaware, Newark, DE (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
- Univ. of Delaware, Newark, DE (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI); Univ. of Pennsylvania, Philadelphia, PA (United States)
- Univ. of Delaware, Newark, DE (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
- Univ. of Delaware, Newark, DE (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI); Univ. of Minnesota, Minneapolis, MN (United States)
In this work, Lewis acid zeolites including Zr-, Sn-, and Ti-BEA were examined for tandem [4 + 2] Diels–Alder cycloaddition of 2,5-dimethylfuran (DMF) and ethylene to oxanorbornene with subsequent dehydration to produce biorenewable p-xylene. Zr-BEA (Si/Zr = 168) exhibited superior performance with improved recalcitrance to deactivation, which was attributed to its low activity for the hydrolysis of DMF to 2,5-hexanedione and subsequent condensation. Zr-BEA also achieved the highest selectivity to p-xylene of 90% at 99% conversion of DMF. For low catalyst loading within a three-phase reactor, the reaction rate to form p-xylene was linearly proportional to the number of Lewis acid sites, while high catalyst loading exhibited zero order dependence on Lewis acid sites. A maximum achievable reaction rate was shown to be consistent with a transition in rate-limiting reactions from dehydration of oxanorbornene, the Diels–Alder product, to the Diels–Alder cycloaddition of DMF and ethylene.
- Research Organization:
- Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
- Sponsoring Organization:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- Grant/Contract Number:
- SC0001004
- OSTI ID:
- 1387601
- Journal Information:
- Green Chemistry, Vol. 18, Issue 5; Related Information: CCEI partners with the University of Delaware (lead); Brookhaven National Laboratory; California Institute of Technology; Columbia University; University of Delaware; Lehigh University; University of Massachusetts, Amherst; Massachusetts Institute of Technology; University of Minnesota; Pacific Northwest National Laboratory; University of Pennsylvania; Princeton University; Rutgers University; ISSN 1463-9262
- Publisher:
- Royal Society of ChemistryCopyright Statement
- Country of Publication:
- United States
- Language:
- English
Web of Science
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