Rapid Synthesis of Cellulose Esters by Transesterification of Cellulose with Vinyl Esters under the Catalysis of NaOH or KOH in DMSO
Traditionally, a long reaction time was required in the synthesis of cellulose esters (CEs). In this work, dimethyl sulfoxide (DMSO)/aqueous NaOH or KOH was introduced as an efficient reaction system for rapidly synthesizing CEs by transesterification. Surprisingly, cellulose could react with vinyl...
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Veröffentlicht in: | Journal of agricultural and food chemistry 2013-03, Vol.61 (10), p.2489-2495 |
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creator | Cao, Xuefei Sun, Shaoni Peng, Xinwen Zhong, Linxin Sun, Runcang Jiang, Dan |
description | Traditionally, a long reaction time was required in the synthesis of cellulose esters (CEs). In this work, dimethyl sulfoxide (DMSO)/aqueous NaOH or KOH was introduced as an efficient reaction system for rapidly synthesizing CEs by transesterification. Surprisingly, cellulose could react with vinyl acetate, vinyl propionate, and vinyl butyrate and synthesized cellulose acetate, cellulose propionate, and cellulose butyrate with a high degree of substitution (2.14–2.34) in 5 min, which was in sharp contrast to hours of existing methods. The effects of solvents, catalysts, and esterifying agents on the synthesis of CEs were comparatively investigated to better understand this method. The structure and thermal properties of obtained CEs were characterized by Fourier transform infrared (FTIR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies and differential scanning calorimetry. Results from these spectra confirmed the successful synthesis of these CEs. Furthermore, these CEs showed similar thermal properties compared to products obtained from other methods. |
doi_str_mv | 10.1021/jf3055104 |
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In this work, dimethyl sulfoxide (DMSO)/aqueous NaOH or KOH was introduced as an efficient reaction system for rapidly synthesizing CEs by transesterification. Surprisingly, cellulose could react with vinyl acetate, vinyl propionate, and vinyl butyrate and synthesized cellulose acetate, cellulose propionate, and cellulose butyrate with a high degree of substitution (2.14–2.34) in 5 min, which was in sharp contrast to hours of existing methods. The effects of solvents, catalysts, and esterifying agents on the synthesis of CEs were comparatively investigated to better understand this method. The structure and thermal properties of obtained CEs were characterized by Fourier transform infrared (FTIR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies and differential scanning calorimetry. Results from these spectra confirmed the successful synthesis of these CEs. Furthermore, these CEs showed similar thermal properties compared to products obtained from other methods.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf3055104</identifier><identifier>PMID: 23414423</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; butyrates ; Catalysis ; catalytic activity ; cellulose ; Cellulose - chemistry ; cellulose acetate ; differential scanning calorimetry ; dimethyl sulfoxide ; Dimethyl Sulfoxide - chemistry ; Esterification ; Food industries ; Fourier transform infrared spectroscopy ; Fundamental and applied biological sciences. Psychology ; Hydroxides - chemistry ; Molecular Structure ; nuclear magnetic resonance spectroscopy ; Polymers - chemical synthesis ; Polymers - chemistry ; Potassium Compounds - chemistry ; propionic acid ; sodium hydroxide ; Sodium Hydroxide - chemistry ; thermal properties ; transesterification ; Vinyl Compounds - chemistry</subject><ispartof>Journal of agricultural and food chemistry, 2013-03, Vol.61 (10), p.2489-2495</ispartof><rights>Copyright © 2013 American Chemical Society</rights><rights>2014 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a369t-b0ae7c29ba269f800824f428b5fb550a6ef44f247a9084f9248eff7ad78cba013</citedby><cites>FETCH-LOGICAL-a369t-b0ae7c29ba269f800824f428b5fb550a6ef44f247a9084f9248eff7ad78cba013</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf3055104$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf3055104$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=27199475$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23414423$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cao, Xuefei</creatorcontrib><creatorcontrib>Sun, Shaoni</creatorcontrib><creatorcontrib>Peng, Xinwen</creatorcontrib><creatorcontrib>Zhong, Linxin</creatorcontrib><creatorcontrib>Sun, Runcang</creatorcontrib><creatorcontrib>Jiang, Dan</creatorcontrib><title>Rapid Synthesis of Cellulose Esters by Transesterification of Cellulose with Vinyl Esters under the Catalysis of NaOH or KOH in DMSO</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Traditionally, a long reaction time was required in the synthesis of cellulose esters (CEs). In this work, dimethyl sulfoxide (DMSO)/aqueous NaOH or KOH was introduced as an efficient reaction system for rapidly synthesizing CEs by transesterification. Surprisingly, cellulose could react with vinyl acetate, vinyl propionate, and vinyl butyrate and synthesized cellulose acetate, cellulose propionate, and cellulose butyrate with a high degree of substitution (2.14–2.34) in 5 min, which was in sharp contrast to hours of existing methods. The effects of solvents, catalysts, and esterifying agents on the synthesis of CEs were comparatively investigated to better understand this method. The structure and thermal properties of obtained CEs were characterized by Fourier transform infrared (FTIR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies and differential scanning calorimetry. Results from these spectra confirmed the successful synthesis of these CEs. Furthermore, these CEs showed similar thermal properties compared to products obtained from other methods.</description><subject>Biological and medical sciences</subject><subject>butyrates</subject><subject>Catalysis</subject><subject>catalytic activity</subject><subject>cellulose</subject><subject>Cellulose - chemistry</subject><subject>cellulose acetate</subject><subject>differential scanning calorimetry</subject><subject>dimethyl sulfoxide</subject><subject>Dimethyl Sulfoxide - chemistry</subject><subject>Esterification</subject><subject>Food industries</subject><subject>Fourier transform infrared spectroscopy</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydroxides - chemistry</subject><subject>Molecular Structure</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Polymers - chemical synthesis</subject><subject>Polymers - chemistry</subject><subject>Potassium Compounds - chemistry</subject><subject>propionic acid</subject><subject>sodium hydroxide</subject><subject>Sodium Hydroxide - chemistry</subject><subject>thermal properties</subject><subject>transesterification</subject><subject>Vinyl Compounds - chemistry</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0EFP2zAUB3ALMY3CduALgC-T2CHs2bET54g6NqaVVVpbrtFLalNXaVzsRCh3PviMWkBIOz1Z_vkvvz8hpwwuGXD2bW1SkJKBOCAjJjkkkjF1SEYQLxMlM3ZEjkNYA4CSOXwkRzwVTAiejsjTX9zaJZ0NbbfSwQbqDB3rpukbFzS9Dp32gVYDnXtsg34-WmNr7Kxr39NH263onW2H5uVV3y61pzGWjrHDZtin_8HpDXWe_o7DtvT77Wz6iXww2AT9eT9PyOLH9Xx8k0ymP3-NryYJplnRJRWgzmteVMizwqi4DRdGcFVJU0kJmGkjhOEixwKUMAUXShuT4zJXdYXA0hNyscvdevfQx23KjQ11XAFb7fpQMpExlck045F-3dHauxC8NuXW2w36oWRQPpdevpYe7dk-tq82evkqX1qO4MseYKixMbHL2oY3l7OiELmM7nznDLoS7300ixkHJgAYB1Xkb0lYh3Ltet_Gvv7zpX8ZiJ3m</recordid><startdate>20130313</startdate><enddate>20130313</enddate><creator>Cao, Xuefei</creator><creator>Sun, Shaoni</creator><creator>Peng, Xinwen</creator><creator>Zhong, Linxin</creator><creator>Sun, Runcang</creator><creator>Jiang, Dan</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>IQODW</scope><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>7X8</scope></search><sort><creationdate>20130313</creationdate><title>Rapid Synthesis of Cellulose Esters by Transesterification of Cellulose with Vinyl Esters under the Catalysis of NaOH or KOH in DMSO</title><author>Cao, Xuefei ; Sun, Shaoni ; Peng, Xinwen ; Zhong, Linxin ; Sun, Runcang ; Jiang, Dan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a369t-b0ae7c29ba269f800824f428b5fb550a6ef44f247a9084f9248eff7ad78cba013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Biological and medical sciences</topic><topic>butyrates</topic><topic>Catalysis</topic><topic>catalytic activity</topic><topic>cellulose</topic><topic>Cellulose - chemistry</topic><topic>cellulose acetate</topic><topic>differential scanning calorimetry</topic><topic>dimethyl sulfoxide</topic><topic>Dimethyl Sulfoxide - chemistry</topic><topic>Esterification</topic><topic>Food industries</topic><topic>Fourier transform infrared spectroscopy</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydroxides - chemistry</topic><topic>Molecular Structure</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Polymers - chemical synthesis</topic><topic>Polymers - chemistry</topic><topic>Potassium Compounds - chemistry</topic><topic>propionic acid</topic><topic>sodium hydroxide</topic><topic>Sodium Hydroxide - chemistry</topic><topic>thermal properties</topic><topic>transesterification</topic><topic>Vinyl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cao, Xuefei</creatorcontrib><creatorcontrib>Sun, Shaoni</creatorcontrib><creatorcontrib>Peng, Xinwen</creatorcontrib><creatorcontrib>Zhong, Linxin</creatorcontrib><creatorcontrib>Sun, Runcang</creatorcontrib><creatorcontrib>Jiang, Dan</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cao, Xuefei</au><au>Sun, Shaoni</au><au>Peng, Xinwen</au><au>Zhong, Linxin</au><au>Sun, Runcang</au><au>Jiang, Dan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rapid Synthesis of Cellulose Esters by Transesterification of Cellulose with Vinyl Esters under the Catalysis of NaOH or KOH in DMSO</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2013-03-13</date><risdate>2013</risdate><volume>61</volume><issue>10</issue><spage>2489</spage><epage>2495</epage><pages>2489-2495</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Traditionally, a long reaction time was required in the synthesis of cellulose esters (CEs). In this work, dimethyl sulfoxide (DMSO)/aqueous NaOH or KOH was introduced as an efficient reaction system for rapidly synthesizing CEs by transesterification. Surprisingly, cellulose could react with vinyl acetate, vinyl propionate, and vinyl butyrate and synthesized cellulose acetate, cellulose propionate, and cellulose butyrate with a high degree of substitution (2.14–2.34) in 5 min, which was in sharp contrast to hours of existing methods. The effects of solvents, catalysts, and esterifying agents on the synthesis of CEs were comparatively investigated to better understand this method. The structure and thermal properties of obtained CEs were characterized by Fourier transform infrared (FTIR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies and differential scanning calorimetry. Results from these spectra confirmed the successful synthesis of these CEs. Furthermore, these CEs showed similar thermal properties compared to products obtained from other methods.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>23414423</pmid><doi>10.1021/jf3055104</doi><tpages>7</tpages></addata></record> |
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subjects | Biological and medical sciences butyrates Catalysis catalytic activity cellulose Cellulose - chemistry cellulose acetate differential scanning calorimetry dimethyl sulfoxide Dimethyl Sulfoxide - chemistry Esterification Food industries Fourier transform infrared spectroscopy Fundamental and applied biological sciences. Psychology Hydroxides - chemistry Molecular Structure nuclear magnetic resonance spectroscopy Polymers - chemical synthesis Polymers - chemistry Potassium Compounds - chemistry propionic acid sodium hydroxide Sodium Hydroxide - chemistry thermal properties transesterification Vinyl Compounds - chemistry |
title | Rapid Synthesis of Cellulose Esters by Transesterification of Cellulose with Vinyl Esters under the Catalysis of NaOH or KOH in DMSO |
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