Journal
ACS CATALYSIS
Volume 8, Issue 3, Pages 1843-1850Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03952
Keywords
biomass; cycloaddition; zeolite; synchrotron X-ray; modeling
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Funding
- Light Source Ltd (U.K.)
- Brazil CsF/CNPq
- Office of China Postdoctoral Council
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Herein, we report a synthetic strategy to convert biomass-derived unsubstituted furan to aromatics at high selectivity, especially to ethylbenzene via alkylation/Diels- Alder cycloaddition using ethanol, while greatly reducing the formation of the main side product, benzofuran, over zeolite catalysts. Using synchrotron X-ray powder diffraction and first principles calculations, it is shown that the above methodology favors the formation of aromatic products due to ready alkylation of furan by the first ethanol molecule, followed by Diels-Alder cycloaddition with ethylene derived from the second ethanol molecule on a Bronsted acid site in a one-pot synthesis. This gives a double-promoting effect: an alkyl substituent(s) on furan creates steric hindrance to inhibit self-coupling to benzofuran while an alkylated furan (diene) undergoes a Diels-Alder reaction more favorably due to higher HOMO energy.
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