One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts
A new type of biomass‐derived non‐ionic surfactants has been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For instance, 5‐(octyloxymethyl)furfural glyceryl acetal can be obtained in a one‐pot process by etherification of HMF with fatty alcohols followed by acetaliz...
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Veröffentlicht in: | ChemSusChem 2018-09, Vol.11 (17), p.2870-2880 |
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description | A new type of biomass‐derived non‐ionic surfactants has been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For instance, 5‐(octyloxymethyl)furfural glyceryl acetal can be obtained in a one‐pot process by etherification of HMF with fatty alcohols followed by acetalization with glycerol. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation owing to the different adsorption characteristics of the reactant molecules. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives, which include a highly polar reactant such as glycerol. The scope of the reaction is good and a variety of new stable surfactant molecules can be obtained that present hydrophilic–lipophilic balance (HLB ) values in the range 4.9 to 6.6, which are of interest for water in oil emulsions.
Washing with biomass: New biomass‐derived non‐ionic surfactants have been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives. |
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Washing with biomass: New biomass‐derived non‐ionic surfactants have been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.201801132</identifier><identifier>PMID: 29975011</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alcohol ; Alcohols ; Aluminum ; Biomass ; Catalysis ; Catalysts ; Deactivation ; Emulsions ; Furfural ; Glycerol ; Hydroxymethylfurfural ; one-pot synthesis ; Polarity ; Silicon ; solid acid catalysts ; Surfactants ; Zeolites</subject><ispartof>ChemSusChem, 2018-09, Vol.11 (17), p.2870-2880</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5162-8d759c9ce22c2839c39ffd89223760d253bd80b3a08e71f084977bfd7a6882783</citedby><cites>FETCH-LOGICAL-c5162-8d759c9ce22c2839c39ffd89223760d253bd80b3a08e71f084977bfd7a6882783</cites><orcidid>0000-0002-2232-3527</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.201801132$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcssc.201801132$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,782,786,1419,27933,27934,45583,45584</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29975011$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Garcia‐Ortiz, Andrea</creatorcontrib><creatorcontrib>Arias, Karen S.</creatorcontrib><creatorcontrib>Climent, Maria J.</creatorcontrib><creatorcontrib>Corma, Avelino</creatorcontrib><creatorcontrib>Iborra, Sara</creatorcontrib><title>One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>A new type of biomass‐derived non‐ionic surfactants has been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For instance, 5‐(octyloxymethyl)furfural glyceryl acetal can be obtained in a one‐pot process by etherification of HMF with fatty alcohols followed by acetalization with glycerol. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation owing to the different adsorption characteristics of the reactant molecules. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives, which include a highly polar reactant such as glycerol. The scope of the reaction is good and a variety of new stable surfactant molecules can be obtained that present hydrophilic–lipophilic balance (HLB ) values in the range 4.9 to 6.6, which are of interest for water in oil emulsions.
Washing with biomass: New biomass‐derived non‐ionic surfactants have been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives.</description><subject>Alcohol</subject><subject>Alcohols</subject><subject>Aluminum</subject><subject>Biomass</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Deactivation</subject><subject>Emulsions</subject><subject>Furfural</subject><subject>Glycerol</subject><subject>Hydroxymethylfurfural</subject><subject>one-pot synthesis</subject><subject>Polarity</subject><subject>Silicon</subject><subject>solid acid catalysts</subject><subject>Surfactants</subject><subject>Zeolites</subject><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkctu1DAUhi0EoqWwZYkssWHBDLaT-LIcQm9SpSICEjvLsR0mlRMX24F6xwOw4Bl5krqaMkhs2JyLznf-c6QfgOcYrTFC5I2OUa8JwhxhXJEH4BBzWq8aWn9-uK8rfACexHiFEEWC0sfggAjBmrJxCH5ezvb3j1_vfYJdntPWxjFCP8C3o59UjGX0zobxmzWwW8KgdFJzirDP8IMtzTh_gWfZBH-TJ5u22Q0FWoJyr-Gpy9oGXyo1G3iiUspw47TfelcOzLDzbjRwo0toVVIuxxSfgkeDctE-u89H4NPJ8cf2bHVxeXrebi5WusGUrLhhjdBCW0I04ZXQlRgGwwUhFaPIkKbqDUd9pRC3DA-I14KxfjBMUc4J49UReLXTvQ7-62JjktMYtXVOzdYvURJEa0Y5qnFBX_6DXvklzOU7STDCjHFe14Va7ygdfIzBDvI6jJMKWWIk73ySdz7JvU9l4cW97NJP1uzxP8YUQOyA76Oz-T9ysu269q_4LRk2oec</recordid><startdate>20180911</startdate><enddate>20180911</enddate><creator>Garcia‐Ortiz, Andrea</creator><creator>Arias, Karen S.</creator><creator>Climent, Maria J.</creator><creator>Corma, Avelino</creator><creator>Iborra, Sara</creator><general>Wiley Subscription Services, Inc</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><orcidid>https://orcid.org/0000-0002-2232-3527</orcidid></search><sort><creationdate>20180911</creationdate><title>One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts</title><author>Garcia‐Ortiz, Andrea ; Arias, Karen S. ; Climent, Maria J. ; Corma, Avelino ; Iborra, Sara</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5162-8d759c9ce22c2839c39ffd89223760d253bd80b3a08e71f084977bfd7a6882783</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alcohol</topic><topic>Alcohols</topic><topic>Aluminum</topic><topic>Biomass</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Deactivation</topic><topic>Emulsions</topic><topic>Furfural</topic><topic>Glycerol</topic><topic>Hydroxymethylfurfural</topic><topic>one-pot synthesis</topic><topic>Polarity</topic><topic>Silicon</topic><topic>solid acid catalysts</topic><topic>Surfactants</topic><topic>Zeolites</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Garcia‐Ortiz, Andrea</creatorcontrib><creatorcontrib>Arias, Karen S.</creatorcontrib><creatorcontrib>Climent, Maria J.</creatorcontrib><creatorcontrib>Corma, Avelino</creatorcontrib><creatorcontrib>Iborra, Sara</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><jtitle>ChemSusChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Garcia‐Ortiz, Andrea</au><au>Arias, Karen S.</au><au>Climent, Maria J.</au><au>Corma, Avelino</au><au>Iborra, Sara</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts</atitle><jtitle>ChemSusChem</jtitle><addtitle>ChemSusChem</addtitle><date>2018-09-11</date><risdate>2018</risdate><volume>11</volume><issue>17</issue><spage>2870</spage><epage>2880</epage><pages>2870-2880</pages><issn>1864-5631</issn><eissn>1864-564X</eissn><abstract>A new type of biomass‐derived non‐ionic surfactants has been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For instance, 5‐(octyloxymethyl)furfural glyceryl acetal can be obtained in a one‐pot process by etherification of HMF with fatty alcohols followed by acetalization with glycerol. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation owing to the different adsorption characteristics of the reactant molecules. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives, which include a highly polar reactant such as glycerol. The scope of the reaction is good and a variety of new stable surfactant molecules can be obtained that present hydrophilic–lipophilic balance (HLB ) values in the range 4.9 to 6.6, which are of interest for water in oil emulsions.
Washing with biomass: New biomass‐derived non‐ionic surfactants have been obtained by reacting hydroxymethylfurfural (HMF), glycerol, and fatty alcohols. For a successful solid catalyst, acidity and polarity have to be optimized to improve conversion, selectivity, and catalyst deactivation. Accordingly, Beta zeolite with a high Si/Al ratio and practically free of connectivity defects showed good results when dealing with these biomass derivatives.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29975011</pmid><doi>10.1002/cssc.201801132</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-2232-3527</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Alcohol Alcohols Aluminum Biomass Catalysis Catalysts Deactivation Emulsions Furfural Glycerol Hydroxymethylfurfural one-pot synthesis Polarity Silicon solid acid catalysts Surfactants Zeolites |
title | One‐Pot Synthesis of Biomass‐Derived Surfactants by Reacting Hydroxymethylfurfural, Glycerol, and Fatty Alcohols on Solid Acid Catalysts |
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