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Issue 5, 2016
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Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene

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Abstract

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.

Graphical abstract: Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene

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Supplementary files

Article information


Submitted
12 Sep 2015
Accepted
07 Oct 2015
First published
27 Oct 2015

Green Chem., 2016,18, 1368-1376
Article type
Paper
Author version available

Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene

C. Chang, H. Je Cho, J. Yu, R. J. Gorte, J. Gulbinski, P. Dauenhauer and W. Fan, Green Chem., 2016, 18, 1368
DOI: 10.1039/C5GC02164B

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