Chemical Synthesis of Fully Biomass-Based Poly(butylene succinate) from Inedible-Biomass-Based Furfural and Evaluation of Its Biomass Carbon Ratio
We have produced fully biomass-based poly(butylene succinate) (PBS) from furfural produced from inedible agricultural cellulosic waste. Furfural was oxidized to give fumaric acid. Fumaric acid was hydrogenated under high pressure with a palladium−rhenium/carbon catalyst to give 1,4-butanediol, and w...
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| Veröffentlicht in: | Biomacromolecules 2010-10, Vol.11 (10), p.2760-2765 |
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| creator | Tachibana, Yuya Masuda, Takashi Funabashi, Masahiro Kunioka, Masao |
| description | We have produced fully biomass-based poly(butylene succinate) (PBS) from furfural produced from inedible agricultural cellulosic waste. Furfural was oxidized to give fumaric acid. Fumaric acid was hydrogenated under high pressure with a palladium−rhenium/carbon catalyst to give 1,4-butanediol, and with a palladium/carbon catalyst to give succinic acid. Dimethyl succinate was synthesized from fumaric acid by esterification and hydrogenation under normal pressure. Fully biomass-based PBS was obtained by polycondensation of biomass-based 1,4-butanediol and biomass-based succinic acid or dimethyl succinate. The biomass carbon ratio calculated from 14C concentrations measured by accelerator mass spectroscopy (AMS) verified that the PBS obtained in this study contained only biomass carbon. The polycondensation of biomass-based 1,4-butanediol and petroleum-based terephthalic acid or dimethyl terephthalate gave partially biomass-based poly(butylene terephthalate), which is an engineering plastic. |
| doi_str_mv | 10.1021/bm100820y |
| format | Article |
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Furfural was oxidized to give fumaric acid. Fumaric acid was hydrogenated under high pressure with a palladium−rhenium/carbon catalyst to give 1,4-butanediol, and with a palladium/carbon catalyst to give succinic acid. Dimethyl succinate was synthesized from fumaric acid by esterification and hydrogenation under normal pressure. Fully biomass-based PBS was obtained by polycondensation of biomass-based 1,4-butanediol and biomass-based succinic acid or dimethyl succinate. The biomass carbon ratio calculated from 14C concentrations measured by accelerator mass spectroscopy (AMS) verified that the PBS obtained in this study contained only biomass carbon. The polycondensation of biomass-based 1,4-butanediol and petroleum-based terephthalic acid or dimethyl terephthalate gave partially biomass-based poly(butylene terephthalate), which is an engineering plastic.</description><identifier>ISSN: 1525-7797</identifier><identifier>EISSN: 1526-4602</identifier><identifier>DOI: 10.1021/bm100820y</identifier><identifier>PMID: 20815381</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Agronomy. Soil science and plant productions ; Applied sciences ; Biodegradation, Environmental ; Biological and medical sciences ; Biomass ; Butylene Glycols - chemical synthesis ; Butylene Glycols - chemistry ; Carbon - analysis ; Cellulose - chemistry ; Esterification ; Exact sciences and technology ; Fundamental and applied biological sciences. Psychology ; Furaldehyde - chemistry ; General agronomy. Plant production ; Hydrogenation ; Mass Spectrometry ; Organic polymers ; Oxidation-Reduction ; Physicochemistry of polymers ; Polycondensation ; Polymers - chemical synthesis ; Polymers - chemistry ; Preparation, kinetics, thermodynamics, mechanism and catalysts ; Use of agricultural and forest wastes. Biomass use, bioconversion</subject><ispartof>Biomacromolecules, 2010-10, Vol.11 (10), p.2760-2765</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-b2e4ced6301cd009f100fd9a0e9a2f47e651866c1382293f2a5ec8850047de6f3</citedby><cites>FETCH-LOGICAL-a410t-b2e4ced6301cd009f100fd9a0e9a2f47e651866c1382293f2a5ec8850047de6f3</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/bm100820y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bm100820y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23407101$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20815381$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tachibana, Yuya</creatorcontrib><creatorcontrib>Masuda, Takashi</creatorcontrib><creatorcontrib>Funabashi, Masahiro</creatorcontrib><creatorcontrib>Kunioka, Masao</creatorcontrib><title>Chemical Synthesis of Fully Biomass-Based Poly(butylene succinate) from Inedible-Biomass-Based Furfural and Evaluation of Its Biomass Carbon Ratio</title><title>Biomacromolecules</title><addtitle>Biomacromolecules</addtitle><description>We have produced fully biomass-based poly(butylene succinate) (PBS) from furfural produced from inedible agricultural cellulosic waste. Furfural was oxidized to give fumaric acid. Fumaric acid was hydrogenated under high pressure with a palladium−rhenium/carbon catalyst to give 1,4-butanediol, and with a palladium/carbon catalyst to give succinic acid. Dimethyl succinate was synthesized from fumaric acid by esterification and hydrogenation under normal pressure. Fully biomass-based PBS was obtained by polycondensation of biomass-based 1,4-butanediol and biomass-based succinic acid or dimethyl succinate. The biomass carbon ratio calculated from 14C concentrations measured by accelerator mass spectroscopy (AMS) verified that the PBS obtained in this study contained only biomass carbon. The polycondensation of biomass-based 1,4-butanediol and petroleum-based terephthalic acid or dimethyl terephthalate gave partially biomass-based poly(butylene terephthalate), which is an engineering plastic.</description><subject>Agronomy. Soil science and plant productions</subject><subject>Applied sciences</subject><subject>Biodegradation, Environmental</subject><subject>Biological and medical sciences</subject><subject>Biomass</subject><subject>Butylene Glycols - chemical synthesis</subject><subject>Butylene Glycols - chemistry</subject><subject>Carbon - analysis</subject><subject>Cellulose - chemistry</subject><subject>Esterification</subject><subject>Exact sciences and technology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Furaldehyde - chemistry</subject><subject>General agronomy. Plant production</subject><subject>Hydrogenation</subject><subject>Mass Spectrometry</subject><subject>Organic polymers</subject><subject>Oxidation-Reduction</subject><subject>Physicochemistry of polymers</subject><subject>Polycondensation</subject><subject>Polymers - chemical synthesis</subject><subject>Polymers - chemistry</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Use of agricultural and forest wastes. Biomass use, bioconversion</subject><issn>1525-7797</issn><issn>1526-4602</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1TAQhS0EoqWw4AWQN4h2ERg7cX6W9KoXrlQJxM86cpyxmsqxiydGymvwxPWltwUkVmONP58jn8PYSwFvBUjxbpgFQCthfcSOhZJ1UdUgH_8-q6JpuuaIPSO6BoCurNRTdiShFapsxTH7tbnCeTLa8a-rX66QJuLB8m1ybuXnU5g1UXGuCUf-Obj1dEjL6tAjp2TM5PWCZ9zGMPOdx3EaHBb_PtqmaFPM8tqP_OKndkkvU_B7j91C9w58o-OQt1_2l8_ZE6sd4YvDPGHftxffNh-Ly08fdpv3l4WuBCzFILEyONYlCDPmn9mcgR07DdhpaasGayXaujaibKXsSiu1QtO2CqBqRqxtecLe3OnexPAjIS39PJFB57THkKhvVFOpru0gk2d3pImBKKLtb-I067j2Avp9A_1DA5l9dVBNw4zjA3kfeQZeHwBNOXcbtTcT_eHKChoBf3HaUH8dUvQ5jP8Y3gLSGJrA</recordid><startdate>20101011</startdate><enddate>20101011</enddate><creator>Tachibana, Yuya</creator><creator>Masuda, Takashi</creator><creator>Funabashi, Masahiro</creator><creator>Kunioka, Masao</creator><general>American Chemical Society</general><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>20101011</creationdate><title>Chemical Synthesis of Fully Biomass-Based Poly(butylene succinate) from Inedible-Biomass-Based Furfural and Evaluation of Its Biomass Carbon Ratio</title><author>Tachibana, Yuya ; Masuda, Takashi ; Funabashi, Masahiro ; Kunioka, Masao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-b2e4ced6301cd009f100fd9a0e9a2f47e651866c1382293f2a5ec8850047de6f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Applied sciences</topic><topic>Biodegradation, Environmental</topic><topic>Biological and medical sciences</topic><topic>Biomass</topic><topic>Butylene Glycols - chemical synthesis</topic><topic>Butylene Glycols - chemistry</topic><topic>Carbon - analysis</topic><topic>Cellulose - chemistry</topic><topic>Esterification</topic><topic>Exact sciences and technology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Furaldehyde - chemistry</topic><topic>General agronomy. Plant production</topic><topic>Hydrogenation</topic><topic>Mass Spectrometry</topic><topic>Organic polymers</topic><topic>Oxidation-Reduction</topic><topic>Physicochemistry of polymers</topic><topic>Polycondensation</topic><topic>Polymers - chemical synthesis</topic><topic>Polymers - chemistry</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Use of agricultural and forest wastes. Biomass use, bioconversion</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tachibana, Yuya</creatorcontrib><creatorcontrib>Masuda, Takashi</creatorcontrib><creatorcontrib>Funabashi, Masahiro</creatorcontrib><creatorcontrib>Kunioka, Masao</creatorcontrib><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>Biomacromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tachibana, Yuya</au><au>Masuda, Takashi</au><au>Funabashi, Masahiro</au><au>Kunioka, Masao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical Synthesis of Fully Biomass-Based Poly(butylene succinate) from Inedible-Biomass-Based Furfural and Evaluation of Its Biomass Carbon Ratio</atitle><jtitle>Biomacromolecules</jtitle><addtitle>Biomacromolecules</addtitle><date>2010-10-11</date><risdate>2010</risdate><volume>11</volume><issue>10</issue><spage>2760</spage><epage>2765</epage><pages>2760-2765</pages><issn>1525-7797</issn><eissn>1526-4602</eissn><abstract>We have produced fully biomass-based poly(butylene succinate) (PBS) from furfural produced from inedible agricultural cellulosic waste. Furfural was oxidized to give fumaric acid. Fumaric acid was hydrogenated under high pressure with a palladium−rhenium/carbon catalyst to give 1,4-butanediol, and with a palladium/carbon catalyst to give succinic acid. Dimethyl succinate was synthesized from fumaric acid by esterification and hydrogenation under normal pressure. Fully biomass-based PBS was obtained by polycondensation of biomass-based 1,4-butanediol and biomass-based succinic acid or dimethyl succinate. The biomass carbon ratio calculated from 14C concentrations measured by accelerator mass spectroscopy (AMS) verified that the PBS obtained in this study contained only biomass carbon. The polycondensation of biomass-based 1,4-butanediol and petroleum-based terephthalic acid or dimethyl terephthalate gave partially biomass-based poly(butylene terephthalate), which is an engineering plastic.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20815381</pmid><doi>10.1021/bm100820y</doi><tpages>6</tpages></addata></record> |
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| subjects | Agronomy. Soil science and plant productions Applied sciences Biodegradation, Environmental Biological and medical sciences Biomass Butylene Glycols - chemical synthesis Butylene Glycols - chemistry Carbon - analysis Cellulose - chemistry Esterification Exact sciences and technology Fundamental and applied biological sciences. Psychology Furaldehyde - chemistry General agronomy. Plant production Hydrogenation Mass Spectrometry Organic polymers Oxidation-Reduction Physicochemistry of polymers Polycondensation Polymers - chemical synthesis Polymers - chemistry Preparation, kinetics, thermodynamics, mechanism and catalysts Use of agricultural and forest wastes. Biomass use, bioconversion |
| title | Chemical Synthesis of Fully Biomass-Based Poly(butylene succinate) from Inedible-Biomass-Based Furfural and Evaluation of Its Biomass Carbon Ratio |
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