Hydrogenation of levoglucosenone to renewable chemicals
We have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 degree C) over a Pd/Al2O3 catalyst, LGO is select...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2017, Vol.19 (5), p.1278-1285 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Krishna, Siddarth H McClelland, Daniel J Rashke, Quinn A Dumesic, James A Huber, George W |
| description | We have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 degree C) over a Pd/Al2O3 catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 degree C) over a Pd/Al2O3 catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 degree C) over a bifunctional Pd/SiO2-Al2O3 catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM. |
| doi_str_mv | 10.1039/c6gc03028a |
| format | Article |
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At low temperature (40 degree C) over a Pd/Al2O3 catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 degree C) over a Pd/Al2O3 catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 degree C) over a bifunctional Pd/SiO2-Al2O3 catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/c6gc03028a</identifier><language>eng</language><subject>Aluminum oxide ; Catalysis ; Catalysts ; Hydrogenation ; Isomers ; Palladium ; Precursors ; Selectivity</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2017, Vol.19 (5), p.1278-1285</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c477t-93dbe0a9948437526f686b3641b60c292623c70f4739b4443062825a1aaa92a53</citedby><cites>FETCH-LOGICAL-c477t-93dbe0a9948437526f686b3641b60c292623c70f4739b4443062825a1aaa92a53</cites><orcidid>0000-0002-7838-6893</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids></links><search><creatorcontrib>Krishna, Siddarth H</creatorcontrib><creatorcontrib>McClelland, Daniel J</creatorcontrib><creatorcontrib>Rashke, Quinn A</creatorcontrib><creatorcontrib>Dumesic, James A</creatorcontrib><creatorcontrib>Huber, George W</creatorcontrib><title>Hydrogenation of levoglucosenone to renewable chemicals</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>We have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 degree C) over a Pd/Al2O3 catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 degree C) over a Pd/Al2O3 catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 degree C) over a bifunctional Pd/SiO2-Al2O3 catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM.</description><subject>Aluminum oxide</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Hydrogenation</subject><subject>Isomers</subject><subject>Palladium</subject><subject>Precursors</subject><subject>Selectivity</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNkM1Kw0AYRQdRsFY3PkGWIkS_-cn8LEvQVii40fUwmX6JkSRTZxKlb29rxbWrcxeHy-USck3hjgI39142Hjgw7U7IjArJc8MUnP5lyc7JRUrvAJQqKWZErXabGBoc3NiGIQt11uFnaLrJh4RDGDAbQxZxwC9XdZj5N-xb77p0Sc7qPfDql3Py-vjwUq7y9fPyqVyscy-UGnPDNxWCM0ZowVXBZC21rLgUtJLg2WEQ9wpqobiphBAcJNOscNQ5Z5gr-JzcHHu3MXxMmEbbt8lj17kBw5Qs1YZrLVnxH1UpLQoKZq_eHlUfQ0oRa7uNbe_izlKwhyNtKZflz5EL_g2AUmOW</recordid><startdate>2017</startdate><enddate>2017</enddate><creator>Krishna, Siddarth H</creator><creator>McClelland, Daniel J</creator><creator>Rashke, Quinn A</creator><creator>Dumesic, James A</creator><creator>Huber, George W</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7ST</scope><scope>7U6</scope><scope>C1K</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-7838-6893</orcidid></search><sort><creationdate>2017</creationdate><title>Hydrogenation of levoglucosenone to renewable chemicals</title><author>Krishna, Siddarth H ; McClelland, Daniel J ; Rashke, Quinn A ; Dumesic, James A ; Huber, George W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c477t-93dbe0a9948437526f686b3641b60c292623c70f4739b4443062825a1aaa92a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aluminum oxide</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Hydrogenation</topic><topic>Isomers</topic><topic>Palladium</topic><topic>Precursors</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krishna, Siddarth H</creatorcontrib><creatorcontrib>McClelland, Daniel J</creatorcontrib><creatorcontrib>Rashke, Quinn A</creatorcontrib><creatorcontrib>Dumesic, James A</creatorcontrib><creatorcontrib>Huber, George W</creatorcontrib><collection>CrossRef</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krishna, Siddarth H</au><au>McClelland, Daniel J</au><au>Rashke, Quinn A</au><au>Dumesic, James A</au><au>Huber, George W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrogenation of levoglucosenone to renewable chemicals</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2017</date><risdate>2017</risdate><volume>19</volume><issue>5</issue><spage>1278</spage><epage>1285</epage><pages>1278-1285</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>We have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 degree C) over a Pd/Al2O3 catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 degree C) over a Pd/Al2O3 catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 degree C) over a bifunctional Pd/SiO2-Al2O3 catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM.</abstract><doi>10.1039/c6gc03028a</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-7838-6893</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2017, Vol.19 (5), p.1278-1285 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1893886255 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Aluminum oxide Catalysis Catalysts Hydrogenation Isomers Palladium Precursors Selectivity |
| title | Hydrogenation of levoglucosenone to renewable chemicals |
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