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From Biomass-Derived Furans to Aromatics with Ethanol over Zeolite
We report a novel catalytic conversion of biomass‐derived furans and alcohols to aromatics over zeolite catalysts. Aromatics are formed via Diels–Alder cycloaddition with ethylene, which is produced in situ from ethanol dehydration. The use of liquid ethanol instead of gaseous ethylene, as the sourc...
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Published in: | Angewandte Chemie (International ed.) 2016-10, Vol.55 (42), p.13061-13066 |
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creator | Teixeira, Ivo F. Lo, Benedict T. W. Kostetskyy, Pavlo Stamatakis, Michail Ye, Lin Tang, Chiu C. Mpourmpakis, Giannis Tsang, Shik Chi Edman |
description | We report a novel catalytic conversion of biomass‐derived furans and alcohols to aromatics over zeolite catalysts. Aromatics are formed via Diels–Alder cycloaddition with ethylene, which is produced in situ from ethanol dehydration. The use of liquid ethanol instead of gaseous ethylene, as the source of dienophile in this one‐pot synthesis, makes the aromatics production much simpler and renewable, circumventing the use of ethylene at high pressure. More importantly, both our experiments and theoretical studies demonstrate that the use of ethanol instead of ethylene, results in significantly higher rates and higher selectivity to aromatics, due to lower activation barriers over the solid acid sites. Synchrotron‐diffraction experiments and proton‐affinity calculations clearly suggest that a preferred protonation of ethanol over the furan is a key step facilitating the Diels–Alder and dehydration reactions in the acid sites of the zeolite.
Liquid lunch: Ethylene produced in situ from ethanol dehydration over zeolite is used for the catalytic conversion of biomass‐derived furans to aromatics via Diels–Alder cycloaddition. The one‐pot synthesis using liquid ethanol instead of pressurized ethylene gas enables much faster production of aromatics in a renewable manner. |
doi_str_mv | 10.1002/anie.201604108 |
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Liquid lunch: Ethylene produced in situ from ethanol dehydration over zeolite is used for the catalytic conversion of biomass‐derived furans to aromatics via Diels–Alder cycloaddition. The one‐pot synthesis using liquid ethanol instead of pressurized ethylene gas enables much faster production of aromatics in a renewable manner.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201604108</identifier><identifier>PMID: 27490584</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Activation ; Affinity ; Alcohols ; Aromatic compounds ; Biomass ; Catalysts ; Catalytic converters ; Conversion ; Cycloaddition ; Dehydration ; Diffraction ; Ethanol ; Ethylene ; Furans ; High pressure ; Mathematical analysis ; Pesticides ; Pressure ; Protonation ; Selectivity ; structure elucidation ; Zeolites</subject><ispartof>Angewandte Chemie (International ed.), 2016-10, Vol.55 (42), p.13061-13066</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5168-a9568f49276d8a072f54ec2396defd37955fbb54c9b7cb6c6d1e1c57a6e458413</citedby><cites>FETCH-LOGICAL-c5168-a9568f49276d8a072f54ec2396defd37955fbb54c9b7cb6c6d1e1c57a6e458413</cites><orcidid>0000-0002-8796-3146 ; 0000-0002-4853-0196 ; 0000-0002-4356-061X ; 0000-0002-3063-0607 ; 0000-0001-8338-8706</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201604108$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201604108$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,786,790,27957,27958,50923,51032</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27490584$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Teixeira, Ivo F.</creatorcontrib><creatorcontrib>Lo, Benedict T. W.</creatorcontrib><creatorcontrib>Kostetskyy, Pavlo</creatorcontrib><creatorcontrib>Stamatakis, Michail</creatorcontrib><creatorcontrib>Ye, Lin</creatorcontrib><creatorcontrib>Tang, Chiu C.</creatorcontrib><creatorcontrib>Mpourmpakis, Giannis</creatorcontrib><creatorcontrib>Tsang, Shik Chi Edman</creatorcontrib><title>From Biomass-Derived Furans to Aromatics with Ethanol over Zeolite</title><title>Angewandte Chemie (International ed.)</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>We report a novel catalytic conversion of biomass‐derived furans and alcohols to aromatics over zeolite catalysts. Aromatics are formed via Diels–Alder cycloaddition with ethylene, which is produced in situ from ethanol dehydration. The use of liquid ethanol instead of gaseous ethylene, as the source of dienophile in this one‐pot synthesis, makes the aromatics production much simpler and renewable, circumventing the use of ethylene at high pressure. More importantly, both our experiments and theoretical studies demonstrate that the use of ethanol instead of ethylene, results in significantly higher rates and higher selectivity to aromatics, due to lower activation barriers over the solid acid sites. Synchrotron‐diffraction experiments and proton‐affinity calculations clearly suggest that a preferred protonation of ethanol over the furan is a key step facilitating the Diels–Alder and dehydration reactions in the acid sites of the zeolite.
Liquid lunch: Ethylene produced in situ from ethanol dehydration over zeolite is used for the catalytic conversion of biomass‐derived furans to aromatics via Diels–Alder cycloaddition. The one‐pot synthesis using liquid ethanol instead of pressurized ethylene gas enables much faster production of aromatics in a renewable manner.</description><subject>Activation</subject><subject>Affinity</subject><subject>Alcohols</subject><subject>Aromatic compounds</subject><subject>Biomass</subject><subject>Catalysts</subject><subject>Catalytic converters</subject><subject>Conversion</subject><subject>Cycloaddition</subject><subject>Dehydration</subject><subject>Diffraction</subject><subject>Ethanol</subject><subject>Ethylene</subject><subject>Furans</subject><subject>High pressure</subject><subject>Mathematical analysis</subject><subject>Pesticides</subject><subject>Pressure</subject><subject>Protonation</subject><subject>Selectivity</subject><subject>structure elucidation</subject><subject>Zeolites</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkUtv1DAURi0EoqWwZYkisWGTwe_HclpmSksZFoCQurEc50Z1SeJiJy3993g0ZYRYwOpauuc7uvKH0EuCFwRj-taNARYUE4k5wfoROiSCkpopxR6XN2esVlqQA_Qs5-vCa43lU3RAFTdYaH6IjtcpDtVxiIPLuX4HKdxCW63n5MZcTbFalrWbgs_VXZiuqtV05cbYV_EWUnUJsQ8TPEdPOtdnePEwj9DX9erLyfv64tPp2cnyovaCSF07I6TuuKFKttphRTvBwVNmZAtdy5QRomsawb1plG-kly0B4oVyEng5lbAj9GbnvUnxxwx5skPIHvrejRDnbImmUnGGtSno67_Q6zinsVxnicGSS6Mo-ydVXNhISreuxY7yKeacoLM3KQwu3VuC7bYDu-3A7jsogVcP2rkZoN3jvz-9AGYH3IUe7v-js8vN2epPeb3LhjzBz33Wpe9WKqaE_bY5tR8u5cfNOftsz9kvllWfiA</recordid><startdate>20161010</startdate><enddate>20161010</enddate><creator>Teixeira, Ivo F.</creator><creator>Lo, Benedict T. 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W. ; Kostetskyy, Pavlo ; Stamatakis, Michail ; Ye, Lin ; Tang, Chiu C. ; Mpourmpakis, Giannis ; Tsang, Shik Chi Edman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5168-a9568f49276d8a072f54ec2396defd37955fbb54c9b7cb6c6d1e1c57a6e458413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Activation</topic><topic>Affinity</topic><topic>Alcohols</topic><topic>Aromatic compounds</topic><topic>Biomass</topic><topic>Catalysts</topic><topic>Catalytic converters</topic><topic>Conversion</topic><topic>Cycloaddition</topic><topic>Dehydration</topic><topic>Diffraction</topic><topic>Ethanol</topic><topic>Ethylene</topic><topic>Furans</topic><topic>High pressure</topic><topic>Mathematical analysis</topic><topic>Pesticides</topic><topic>Pressure</topic><topic>Protonation</topic><topic>Selectivity</topic><topic>structure elucidation</topic><topic>Zeolites</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Teixeira, Ivo F.</creatorcontrib><creatorcontrib>Lo, Benedict T. W.</creatorcontrib><creatorcontrib>Kostetskyy, Pavlo</creatorcontrib><creatorcontrib>Stamatakis, Michail</creatorcontrib><creatorcontrib>Ye, Lin</creatorcontrib><creatorcontrib>Tang, Chiu C.</creatorcontrib><creatorcontrib>Mpourmpakis, Giannis</creatorcontrib><creatorcontrib>Tsang, Shik Chi Edman</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Teixeira, Ivo F.</au><au>Lo, Benedict T. W.</au><au>Kostetskyy, Pavlo</au><au>Stamatakis, Michail</au><au>Ye, Lin</au><au>Tang, Chiu C.</au><au>Mpourmpakis, Giannis</au><au>Tsang, Shik Chi Edman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>From Biomass-Derived Furans to Aromatics with Ethanol over Zeolite</atitle><jtitle>Angewandte Chemie (International ed.)</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-10-10</date><risdate>2016</risdate><volume>55</volume><issue>42</issue><spage>13061</spage><epage>13066</epage><pages>13061-13066</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><notes>ArticleID:ANIE201604108</notes><notes>EPSRC (UK)</notes><notes>SINOPEC (China)</notes><notes>istex:75C69B5E7AE4094EB37CAA039B473E4EA8FAEE7C</notes><notes>ark:/67375/WNG-KZ6MNJ3S-J</notes><notes>These authors contributed equally to this work.</notes><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>We report a novel catalytic conversion of biomass‐derived furans and alcohols to aromatics over zeolite catalysts. Aromatics are formed via Diels–Alder cycloaddition with ethylene, which is produced in situ from ethanol dehydration. The use of liquid ethanol instead of gaseous ethylene, as the source of dienophile in this one‐pot synthesis, makes the aromatics production much simpler and renewable, circumventing the use of ethylene at high pressure. More importantly, both our experiments and theoretical studies demonstrate that the use of ethanol instead of ethylene, results in significantly higher rates and higher selectivity to aromatics, due to lower activation barriers over the solid acid sites. Synchrotron‐diffraction experiments and proton‐affinity calculations clearly suggest that a preferred protonation of ethanol over the furan is a key step facilitating the Diels–Alder and dehydration reactions in the acid sites of the zeolite.
Liquid lunch: Ethylene produced in situ from ethanol dehydration over zeolite is used for the catalytic conversion of biomass‐derived furans to aromatics via Diels–Alder cycloaddition. The one‐pot synthesis using liquid ethanol instead of pressurized ethylene gas enables much faster production of aromatics in a renewable manner.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27490584</pmid><doi>10.1002/anie.201604108</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-8796-3146</orcidid><orcidid>https://orcid.org/0000-0002-4853-0196</orcidid><orcidid>https://orcid.org/0000-0002-4356-061X</orcidid><orcidid>https://orcid.org/0000-0002-3063-0607</orcidid><orcidid>https://orcid.org/0000-0001-8338-8706</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Activation Affinity Alcohols Aromatic compounds Biomass Catalysts Catalytic converters Conversion Cycloaddition Dehydration Diffraction Ethanol Ethylene Furans High pressure Mathematical analysis Pesticides Pressure Protonation Selectivity structure elucidation Zeolites |
title | From Biomass-Derived Furans to Aromatics with Ethanol over Zeolite |
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