Direct Catalytic Conversion of Furfural to Furan‐derived Amines in the Presence of Ru‐based Catalyst
The production of amine intermediates from biomass is capturing increasing attention. Herein, a simple and efficient preparation of l furan‐derived amines was developed [e.g., 1‐(furan‐2‐yl)‐4‐methylpentan‐2‐amine] with high yield (up to 95 %) from (E)‐1‐(furan‐2‐yl)‐5‐methylhex‐1‐en‐3‐one. The cata...
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| Veröffentlicht in: | ChemSusChem 2020-04, Vol.13 (7), p.1699-1704 |
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| creator | Jiang, Shi Ramdani, Wahiba Muller, Eric Ma, Changru Pera‐Titus, Marc Jerôme, François De Oliveira Vigiera, Karine |
| description | The production of amine intermediates from biomass is capturing increasing attention. Herein, a simple and efficient preparation of l furan‐derived amines was developed [e.g., 1‐(furan‐2‐yl)‐4‐methylpentan‐2‐amine] with high yield (up to 95 %) from (E)‐1‐(furan‐2‐yl)‐5‐methylhex‐1‐en‐3‐one. The catalyst used was Ru/C, and it was recyclable up to the fourth cycle. To further realize cost‐efficiency, a one‐reactor tandem concept was attempted. To this aim direct reaction from furfural was investigated. A high yield (74 %) towards 1‐(furan‐2‐yl)‐4‐methylpentan‐2‐amine could be achieved starting directly from furfural in the presence of methyl isobutyl ketone, NH3, H2, and Ru/C catalyst.
Green amines: Catalytic conversion of furfural to primary amines is achieved with high yield (74 %) by a one‐reactor two‐step process in the presence of Amberlyst 16 and Ru/C based catalysts. The hydrogenation of C=C bonds together with the reductive amination of carbonyl groups at mild reaction conditions is performed using ammonia and hydrogen. |
| doi_str_mv | 10.1002/cssc.202000003 |
| format | Article |
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Green amines: Catalytic conversion of furfural to primary amines is achieved with high yield (74 %) by a one‐reactor two‐step process in the presence of Amberlyst 16 and Ru/C based catalysts. The hydrogenation of C=C bonds together with the reductive amination of carbonyl groups at mild reaction conditions is performed using ammonia and hydrogen.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.202000003</identifier><identifier>PMID: 31944561</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Amines ; Ammonia ; biomass ; Catalysis ; catalyst ; Catalysts ; Catalytic converters ; Chemical Sciences ; Furfural ; ketones</subject><ispartof>ChemSusChem, 2020-04, Vol.13 (7), p.1699-1704</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5503-52316d72f85e4c6e2352872fec9f9c1a43052f45253614c52713f0f28e56043a3</citedby><cites>FETCH-LOGICAL-c5503-52316d72f85e4c6e2352872fec9f9c1a43052f45253614c52713f0f28e56043a3</cites><orcidid>0000-0003-3613-7992 ; 0000-0001-7335-1424 ; 0000-0002-8324-0119</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%2Fcssc.202000003$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcssc.202000003$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1416,27915,27916,45565,45566</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31944561$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03015522$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Jiang, Shi</creatorcontrib><creatorcontrib>Ramdani, Wahiba</creatorcontrib><creatorcontrib>Muller, Eric</creatorcontrib><creatorcontrib>Ma, Changru</creatorcontrib><creatorcontrib>Pera‐Titus, Marc</creatorcontrib><creatorcontrib>Jerôme, François</creatorcontrib><creatorcontrib>De Oliveira Vigiera, Karine</creatorcontrib><title>Direct Catalytic Conversion of Furfural to Furan‐derived Amines in the Presence of Ru‐based Catalyst</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>The production of amine intermediates from biomass is capturing increasing attention. Herein, a simple and efficient preparation of l furan‐derived amines was developed [e.g., 1‐(furan‐2‐yl)‐4‐methylpentan‐2‐amine] with high yield (up to 95 %) from (E)‐1‐(furan‐2‐yl)‐5‐methylhex‐1‐en‐3‐one. The catalyst used was Ru/C, and it was recyclable up to the fourth cycle. To further realize cost‐efficiency, a one‐reactor tandem concept was attempted. To this aim direct reaction from furfural was investigated. A high yield (74 %) towards 1‐(furan‐2‐yl)‐4‐methylpentan‐2‐amine could be achieved starting directly from furfural in the presence of methyl isobutyl ketone, NH3, H2, and Ru/C catalyst.
Green amines: Catalytic conversion of furfural to primary amines is achieved with high yield (74 %) by a one‐reactor two‐step process in the presence of Amberlyst 16 and Ru/C based catalysts. The hydrogenation of C=C bonds together with the reductive amination of carbonyl groups at mild reaction conditions is performed using ammonia and hydrogen.</description><subject>Amines</subject><subject>Ammonia</subject><subject>biomass</subject><subject>Catalysis</subject><subject>catalyst</subject><subject>Catalysts</subject><subject>Catalytic converters</subject><subject>Chemical Sciences</subject><subject>Furfural</subject><subject>ketones</subject><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqF0c9LHDEUB_AgLWptrx4l4KUeds3vzRyXsVZhoVJb6C3E7AsbmZ1oMrNlb_0T_Bv7lzTD6Apemktewud9SXgIHVMypYSwc5ezmzLCyLD4HjqkWomJVOLXu13N6QH6kPM9IYpUSu2jA04rIaSih2h1ERK4Dte2s822Cw7Xsd1AyiG2OHp82SffJ9vgLg61bf_-eVpCChtY4vk6tJBxaHG3AnyTIEPrYOj63hd2Z3NBY3DuPqL33jYZPj3vR-jn5Zcf9dVk8e3rdT1fTJyUhE8k41QtZ8xrCcIpYFwyXY7gKl85agUnknkhmeSKCifZjHJPPNMgFRHc8iN0NuaubGMeUljbtDXRBnM1X5jhjnBCpWRsQ4v9PNqHFB97yJ1Zh-ygaWwLsc-GcV7NtNZVVejpG3of-9SWnxSlFRNqJnVR01G5FHNO4HcvoMQM8zLDvMxuXqXh5Dm2v1vDcsdfBlRANYLfoYHtf-JMfXtbv4b_AxbfoLw</recordid><startdate>20200407</startdate><enddate>20200407</enddate><creator>Jiang, Shi</creator><creator>Ramdani, Wahiba</creator><creator>Muller, Eric</creator><creator>Ma, Changru</creator><creator>Pera‐Titus, Marc</creator><creator>Jerôme, François</creator><creator>De Oliveira Vigiera, Karine</creator><general>Wiley Subscription Services, Inc</general><general>ChemPubSoc Europe/Wiley</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0003-3613-7992</orcidid><orcidid>https://orcid.org/0000-0001-7335-1424</orcidid><orcidid>https://orcid.org/0000-0002-8324-0119</orcidid></search><sort><creationdate>20200407</creationdate><title>Direct Catalytic Conversion of Furfural to Furan‐derived Amines in the Presence of Ru‐based Catalyst</title><author>Jiang, Shi ; Ramdani, Wahiba ; Muller, Eric ; Ma, Changru ; Pera‐Titus, Marc ; Jerôme, François ; De Oliveira Vigiera, Karine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5503-52316d72f85e4c6e2352872fec9f9c1a43052f45253614c52713f0f28e56043a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amines</topic><topic>Ammonia</topic><topic>biomass</topic><topic>Catalysis</topic><topic>catalyst</topic><topic>Catalysts</topic><topic>Catalytic converters</topic><topic>Chemical Sciences</topic><topic>Furfural</topic><topic>ketones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Shi</creatorcontrib><creatorcontrib>Ramdani, Wahiba</creatorcontrib><creatorcontrib>Muller, Eric</creatorcontrib><creatorcontrib>Ma, Changru</creatorcontrib><creatorcontrib>Pera‐Titus, Marc</creatorcontrib><creatorcontrib>Jerôme, François</creatorcontrib><creatorcontrib>De Oliveira Vigiera, Karine</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>ChemSusChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Shi</au><au>Ramdani, Wahiba</au><au>Muller, Eric</au><au>Ma, Changru</au><au>Pera‐Titus, Marc</au><au>Jerôme, François</au><au>De Oliveira Vigiera, Karine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Catalytic Conversion of Furfural to Furan‐derived Amines in the Presence of Ru‐based Catalyst</atitle><jtitle>ChemSusChem</jtitle><addtitle>ChemSusChem</addtitle><date>2020-04-07</date><risdate>2020</risdate><volume>13</volume><issue>7</issue><spage>1699</spage><epage>1704</epage><pages>1699-1704</pages><issn>1864-5631</issn><eissn>1864-564X</eissn><abstract>The production of amine intermediates from biomass is capturing increasing attention. Herein, a simple and efficient preparation of l furan‐derived amines was developed [e.g., 1‐(furan‐2‐yl)‐4‐methylpentan‐2‐amine] with high yield (up to 95 %) from (E)‐1‐(furan‐2‐yl)‐5‐methylhex‐1‐en‐3‐one. The catalyst used was Ru/C, and it was recyclable up to the fourth cycle. To further realize cost‐efficiency, a one‐reactor tandem concept was attempted. To this aim direct reaction from furfural was investigated. A high yield (74 %) towards 1‐(furan‐2‐yl)‐4‐methylpentan‐2‐amine could be achieved starting directly from furfural in the presence of methyl isobutyl ketone, NH3, H2, and Ru/C catalyst.
Green amines: Catalytic conversion of furfural to primary amines is achieved with high yield (74 %) by a one‐reactor two‐step process in the presence of Amberlyst 16 and Ru/C based catalysts. The hydrogenation of C=C bonds together with the reductive amination of carbonyl groups at mild reaction conditions is performed using ammonia and hydrogen.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31944561</pmid><doi>10.1002/cssc.202000003</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-3613-7992</orcidid><orcidid>https://orcid.org/0000-0001-7335-1424</orcidid><orcidid>https://orcid.org/0000-0002-8324-0119</orcidid><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Amines Ammonia biomass Catalysis catalyst Catalysts Catalytic converters Chemical Sciences Furfural ketones |
| title | Direct Catalytic Conversion of Furfural to Furan‐derived Amines in the Presence of Ru‐based Catalyst |
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