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
Hauptverfasser: Cao, Xuefei, Sun, Shaoni, Peng, Xinwen, Zhong, Linxin, Sun, Runcang, Jiang, Dan
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container_end_page 2495
container_issue 10
container_start_page 2489
container_title Journal of agricultural and food chemistry
container_volume 61
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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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&amp;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. 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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. 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source MEDLINE; ACS Publications
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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