Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin
5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2019-12, Vol.24 (24), p.4623 |
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| creator | Huynh, Nhan Thanh Thien Lee, Kyung Won Cho, Jin Ku Kim, Yong Jin Bae, Se Won Shin, Jong Shik Shin, Seunghan |
| description | 5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while soluble H
SO
was found to be the best acidic catalyst (yielding 86.6% AMF), we opted to utilize heterogeneous cation exchange resin (Amberlyst 15) together with recyclable industrial solvents (1,4-dioxane) for a more sustainable AMF synthesis procedure. Although the total yield of AMF was a little lower, both the enzyme and the solid acid catalyst could be recycled for five cycles without a significant loss of activity, which has a major contribution to the cost-efficient aspect of the entire process. |
| doi_str_mv | 10.3390/molecules24244623 |
| format | Article |
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SO
was found to be the best acidic catalyst (yielding 86.6% AMF), we opted to utilize heterogeneous cation exchange resin (Amberlyst 15) together with recyclable industrial solvents (1,4-dioxane) for a more sustainable AMF synthesis procedure. Although the total yield of AMF was a little lower, both the enzyme and the solid acid catalyst could be recycled for five cycles without a significant loss of activity, which has a major contribution to the cost-efficient aspect of the entire process.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules24244623</identifier><identifier>PMID: 31861157</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acylation ; Biomass ; Catalysis ; Cation exchange ; Cation Exchange Resins - chemistry ; Cation exchanging ; Cationic polymerization ; Chromatography ; Dehydration ; Enzymes, Immobilized ; Esterification ; Fructose ; Fructose - chemistry ; Furaldehyde - chemistry ; Furfural ; High performance liquid chromatography ; Ionic liquids ; Lipase ; Lipase - chemistry ; Liquid chromatography ; Nonrenewable resources ; Organic chemicals ; Organic chemistry ; Refractivity ; Renewable resources ; Sensors ; Solvents ; Solvents - chemistry ; Sulfolane ; Sustainable yield ; Temperature ; Vacuum distillation</subject><ispartof>Molecules (Basel, Switzerland), 2019-12, Vol.24 (24), p.4623</ispartof><rights>2019. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2019 by the authors. 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c427t-9b54e521c0e60bb335b410e4a6ef125805e84db39d33b6271c3a62aac80822e13</citedby><cites>FETCH-LOGICAL-c427t-9b54e521c0e60bb335b410e4a6ef125805e84db39d33b6271c3a62aac80822e13</cites><orcidid>0000-0003-1926-5466 ; 0000-0002-6904-8956 ; 0000-0001-5522-8561</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943744/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6943744/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,315,728,781,785,865,886,27928,27929,53795,53797</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31861157$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huynh, Nhan Thanh Thien</creatorcontrib><creatorcontrib>Lee, Kyung Won</creatorcontrib><creatorcontrib>Cho, Jin Ku</creatorcontrib><creatorcontrib>Kim, Yong Jin</creatorcontrib><creatorcontrib>Bae, Se Won</creatorcontrib><creatorcontrib>Shin, Jong Shik</creatorcontrib><creatorcontrib>Shin, Seunghan</creatorcontrib><title>Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while soluble H
SO
was found to be the best acidic catalyst (yielding 86.6% AMF), we opted to utilize heterogeneous cation exchange resin (Amberlyst 15) together with recyclable industrial solvents (1,4-dioxane) for a more sustainable AMF synthesis procedure. Although the total yield of AMF was a little lower, both the enzyme and the solid acid catalyst could be recycled for five cycles without a significant loss of activity, which has a major contribution to the cost-efficient aspect of the entire process.</description><subject>Acylation</subject><subject>Biomass</subject><subject>Catalysis</subject><subject>Cation exchange</subject><subject>Cation Exchange Resins - chemistry</subject><subject>Cation exchanging</subject><subject>Cationic polymerization</subject><subject>Chromatography</subject><subject>Dehydration</subject><subject>Enzymes, Immobilized</subject><subject>Esterification</subject><subject>Fructose</subject><subject>Fructose - chemistry</subject><subject>Furaldehyde - chemistry</subject><subject>Furfural</subject><subject>High performance liquid chromatography</subject><subject>Ionic liquids</subject><subject>Lipase</subject><subject>Lipase - chemistry</subject><subject>Liquid chromatography</subject><subject>Nonrenewable resources</subject><subject>Organic chemicals</subject><subject>Organic chemistry</subject><subject>Refractivity</subject><subject>Renewable resources</subject><subject>Sensors</subject><subject>Solvents</subject><subject>Solvents - chemistry</subject><subject>Sulfolane</subject><subject>Sustainable yield</subject><subject>Temperature</subject><subject>Vacuum distillation</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNplkUlrHDEQhUVIiLf8gFyMIBdf2pFUUi-XQBivMBAI8Vmo1dUzMt3SWOoePP71lvGCk0CJKtD3HlU8Qr5ydgrQsO9jGNDOAyYhhZSlgA9kn0vBCmCy-fhu3iMHKd0yJrjk6jPZA16XnKtqn7hF8FuMyQVPQ0_Pij7OdgoJ6RSoKozFKdzvRpzWu6EQRT_HXGagN8n5Fb0ex9C6wT1gR5duY7LM-I4uzPTkd35v18avkP7GTB-RT70ZEn556Yfk5uL8z-KqWP66vF78XBZWimoqmlZJVIJbhiVrWwDVSs5QmhJ7LlTNFNaya6HpANpSVNyCKYUxtma1EMjhkPx49t3M7YidRT_lhfUmutHEnQ7G6b9_vFvrVdjqspFQSZkNTl4MYribMU16dMniMBiPYU5agGgqqJlQGf32D3ob5ujzeZkCkMDzyxR_pmwMKUXs35bhTD8Fqf8LMmuO31_xpnhNDh4B_mycTg</recordid><startdate>20191217</startdate><enddate>20191217</enddate><creator>Huynh, Nhan Thanh Thien</creator><creator>Lee, Kyung Won</creator><creator>Cho, Jin Ku</creator><creator>Kim, Yong Jin</creator><creator>Bae, Se Won</creator><creator>Shin, Jong Shik</creator><creator>Shin, Seunghan</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-1926-5466</orcidid><orcidid>https://orcid.org/0000-0002-6904-8956</orcidid><orcidid>https://orcid.org/0000-0001-5522-8561</orcidid></search><sort><creationdate>20191217</creationdate><title>Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin</title><author>Huynh, Nhan Thanh Thien ; Lee, Kyung Won ; Cho, Jin Ku ; Kim, Yong Jin ; Bae, Se Won ; Shin, Jong Shik ; Shin, Seunghan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c427t-9b54e521c0e60bb335b410e4a6ef125805e84db39d33b6271c3a62aac80822e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Acylation</topic><topic>Biomass</topic><topic>Catalysis</topic><topic>Cation exchange</topic><topic>Cation Exchange Resins - chemistry</topic><topic>Cation exchanging</topic><topic>Cationic polymerization</topic><topic>Chromatography</topic><topic>Dehydration</topic><topic>Enzymes, Immobilized</topic><topic>Esterification</topic><topic>Fructose</topic><topic>Fructose - chemistry</topic><topic>Furaldehyde - chemistry</topic><topic>Furfural</topic><topic>High performance liquid chromatography</topic><topic>Ionic liquids</topic><topic>Lipase</topic><topic>Lipase - chemistry</topic><topic>Liquid chromatography</topic><topic>Nonrenewable resources</topic><topic>Organic chemicals</topic><topic>Organic chemistry</topic><topic>Refractivity</topic><topic>Renewable resources</topic><topic>Sensors</topic><topic>Solvents</topic><topic>Solvents - chemistry</topic><topic>Sulfolane</topic><topic>Sustainable yield</topic><topic>Temperature</topic><topic>Vacuum distillation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huynh, Nhan Thanh Thien</creatorcontrib><creatorcontrib>Lee, Kyung Won</creatorcontrib><creatorcontrib>Cho, Jin Ku</creatorcontrib><creatorcontrib>Kim, Yong Jin</creatorcontrib><creatorcontrib>Bae, Se Won</creatorcontrib><creatorcontrib>Shin, Jong Shik</creatorcontrib><creatorcontrib>Shin, Seunghan</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Access via ProQuest (Open Access)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huynh, Nhan Thanh Thien</au><au>Lee, Kyung Won</au><au>Cho, Jin Ku</au><au>Kim, Yong Jin</au><au>Bae, Se Won</au><au>Shin, Jong Shik</au><au>Shin, Seunghan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2019-12-17</date><risdate>2019</risdate><volume>24</volume><issue>24</issue><spage>4623</spage><pages>4623-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while soluble H
SO
was found to be the best acidic catalyst (yielding 86.6% AMF), we opted to utilize heterogeneous cation exchange resin (Amberlyst 15) together with recyclable industrial solvents (1,4-dioxane) for a more sustainable AMF synthesis procedure. Although the total yield of AMF was a little lower, both the enzyme and the solid acid catalyst could be recycled for five cycles without a significant loss of activity, which has a major contribution to the cost-efficient aspect of the entire process.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>31861157</pmid><doi>10.3390/molecules24244623</doi><orcidid>https://orcid.org/0000-0003-1926-5466</orcidid><orcidid>https://orcid.org/0000-0002-6904-8956</orcidid><orcidid>https://orcid.org/0000-0001-5522-8561</orcidid><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; DOAJ Directory of Open Access Journals; MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Acylation Biomass Catalysis Cation exchange Cation Exchange Resins - chemistry Cation exchanging Cationic polymerization Chromatography Dehydration Enzymes, Immobilized Esterification Fructose Fructose - chemistry Furaldehyde - chemistry Furfural High performance liquid chromatography Ionic liquids Lipase Lipase - chemistry Liquid chromatography Nonrenewable resources Organic chemicals Organic chemistry Refractivity Renewable resources Sensors Solvents Solvents - chemistry Sulfolane Sustainable yield Temperature Vacuum distillation |
| title | Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin |
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