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A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics
Renewable aromatics can be conveniently synthesized from furanics by introducing an intermediate hydrogenation step in the Diels–Alder (DA) aromatization route, to effectively block retro‐DA activity. Aromatization of the hydrogenated DA adducts requires tandem catalysis, using a metal‐based dehydro...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4737293/ https://www.ncbi.nlm.nih.gov/pubmed/26684008 http://dx.doi.org/10.1002/anie.201509346 |
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author | Thiyagarajan, Shanmugam Genuino, Homer C. van der Waal, Jan C. de Jong, Ed Weckhuysen, Bert M. van Haveren, Jacco Bruijnincx, Pieter C. A. van Es, Daan S. |
author_facet | Thiyagarajan, Shanmugam Genuino, Homer C. van der Waal, Jan C. de Jong, Ed Weckhuysen, Bert M. van Haveren, Jacco Bruijnincx, Pieter C. A. van Es, Daan S. |
author_sort | Thiyagarajan, Shanmugam |
collection | PubMed |
description | Renewable aromatics can be conveniently synthesized from furanics by introducing an intermediate hydrogenation step in the Diels–Alder (DA) aromatization route, to effectively block retro‐DA activity. Aromatization of the hydrogenated DA adducts requires tandem catalysis, using a metal‐based dehydrogenation catalyst and solid acid dehydration catalyst in toluene. Herein it is demonstrated that the hydrogenated DA adducts can instead be conveniently converted into renewable aromatics with up to 80 % selectivity in a solid‐phase reaction with shorter reaction times using only an acidic zeolite, that is, without solvent or dehydrogenation catalyst. Hydrogenated adducts from diene/dienophile combinations of (methylated) furans with maleic anhydride are efficiently converted into renewable aromatics with this new route. The zeolite H‐Y was found to perform the best and can be easily reused after calcination. |
format | Online Article Text |
id | pubmed-4737293 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-47372932016-02-12 A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics Thiyagarajan, Shanmugam Genuino, Homer C. van der Waal, Jan C. de Jong, Ed Weckhuysen, Bert M. van Haveren, Jacco Bruijnincx, Pieter C. A. van Es, Daan S. Angew Chem Int Ed Engl Communications Renewable aromatics can be conveniently synthesized from furanics by introducing an intermediate hydrogenation step in the Diels–Alder (DA) aromatization route, to effectively block retro‐DA activity. Aromatization of the hydrogenated DA adducts requires tandem catalysis, using a metal‐based dehydrogenation catalyst and solid acid dehydration catalyst in toluene. Herein it is demonstrated that the hydrogenated DA adducts can instead be conveniently converted into renewable aromatics with up to 80 % selectivity in a solid‐phase reaction with shorter reaction times using only an acidic zeolite, that is, without solvent or dehydrogenation catalyst. Hydrogenated adducts from diene/dienophile combinations of (methylated) furans with maleic anhydride are efficiently converted into renewable aromatics with this new route. The zeolite H‐Y was found to perform the best and can be easily reused after calcination. John Wiley and Sons Inc. 2015-12-18 2016-01 /pmc/articles/PMC4737293/ /pubmed/26684008 http://dx.doi.org/10.1002/anie.201509346 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Thiyagarajan, Shanmugam Genuino, Homer C. van der Waal, Jan C. de Jong, Ed Weckhuysen, Bert M. van Haveren, Jacco Bruijnincx, Pieter C. A. van Es, Daan S. A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics |
title | A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics |
title_full | A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics |
title_fullStr | A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics |
title_full_unstemmed | A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics |
title_short | A Facile Solid‐Phase Route to Renewable Aromatic Chemicals from Biobased Furanics |
title_sort | facile solid‐phase route to renewable aromatic chemicals from biobased furanics |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4737293/ https://www.ncbi.nlm.nih.gov/pubmed/26684008 http://dx.doi.org/10.1002/anie.201509346 |
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