Direct catalytic conversion of biomass-derived furan and ethanol to ethylbenzene
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...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Published: |
American Chemical Society
2018
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| _version_ | 1797090408215347200 |
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| author | Teixeira, I Lo, B Kostetskyy, P Ye, L Tang, C Mpourmpakis, G Tsang, S |
| author_facet | Teixeira, I Lo, B Kostetskyy, P Ye, L Tang, C Mpourmpakis, G Tsang, S |
| author_sort | Teixeira, I |
| collection | OXFORD |
| description | 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 readily alkylation of furan by the first ethanol molecule, followed by Diels-Alder cycloaddition with derived ethylene from the second ethanol molecule on a Brønsted acid site in a one pot synthesis. This gives a double promoting effect: alkyl substituent(s) on furan creates steric hindrance to inhibit self-coupling to benzofuran while alkylated furan (diene) undergoes Diels-Alder reaction more favorably due to higher HOMO energy. |
| first_indexed | 2024-03-07T03:18:10Z |
| format | Journal article |
| id | oxford-uuid:b6852d1c-9348-4696-b4b2-8b03a78416be |
| institution | University of Oxford |
| last_indexed | 2024-03-07T03:18:10Z |
| publishDate | 2018 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:b6852d1c-9348-4696-b4b2-8b03a78416be2022-03-27T04:41:30ZDirect catalytic conversion of biomass-derived furan and ethanol to ethylbenzeneJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b6852d1c-9348-4696-b4b2-8b03a78416beSymplectic Elements at OxfordAmerican Chemical Society2018Teixeira, ILo, BKostetskyy, PYe, LTang, CMpourmpakis, GTsang, SHerein, 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 readily alkylation of furan by the first ethanol molecule, followed by Diels-Alder cycloaddition with derived ethylene from the second ethanol molecule on a Brønsted acid site in a one pot synthesis. This gives a double promoting effect: alkyl substituent(s) on furan creates steric hindrance to inhibit self-coupling to benzofuran while alkylated furan (diene) undergoes Diels-Alder reaction more favorably due to higher HOMO energy. |
| spellingShingle | Teixeira, I Lo, B Kostetskyy, P Ye, L Tang, C Mpourmpakis, G Tsang, S Direct catalytic conversion of biomass-derived furan and ethanol to ethylbenzene |
| title | Direct catalytic conversion of biomass-derived furan and ethanol to ethylbenzene |
| title_full | Direct catalytic conversion of biomass-derived furan and ethanol to ethylbenzene |
| title_fullStr | Direct catalytic conversion of biomass-derived furan and ethanol to ethylbenzene |
| title_full_unstemmed | Direct catalytic conversion of biomass-derived furan and ethanol to ethylbenzene |
| title_short | Direct catalytic conversion of biomass-derived furan and ethanol to ethylbenzene |
| title_sort | direct catalytic conversion of biomass derived furan and ethanol to ethylbenzene |
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