Organocatalytic Stereoselective Cyclic Polylactide Synthesis in Supercritical Carbon Dioxide under Plasticizing Conditions
Cyclic polylactide ( PLA) is a structural isomer of linear polylactide (PLA) although it possesses unique functionalities in comparison to its linear counterpart. Hitherto, the control of stereochemical purity in conventional PLA synthesis has not been achieved. In this study, highly stereochemicall...
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| Veröffentlicht in: | Polymers 2018-06, Vol.10 (7), p.713 |
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| creator | Mase, Nobuyuki Yamamoto, Shoji Nakaya, Yoshitaka Sato, Kohei Narumi, Tetsuo |
| description | Cyclic polylactide (
PLA) is a structural isomer of linear polylactide (PLA) although it possesses unique functionalities in comparison to its linear counterpart. Hitherto, the control of stereochemical purity in conventional
PLA synthesis has not been achieved. In this study, highly stereochemically pure
PLA was synthesized in the absence of a metal catalyst and organic solvent, which required high consumption of the residual monomer. The synthesis was conducted in supercritical carbon dioxide under CO₂ plasticizing polymerization conditions in the presence of an organocatalyst and thiourea additives. In comparison with the stereocomplexes synthesized through conventional methods,
PLA from l-lactide (
PLLA) and
PLA from d-lactide (
PDLA) were synthesized with higher stereochemical purity and improved thermal stability. Moreover, the method presented herein is environmentally friendly and thus, applicable on an industrial level. |
| doi_str_mv | 10.3390/polym10070713 |
| format | Article |
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PLA) is a structural isomer of linear polylactide (PLA) although it possesses unique functionalities in comparison to its linear counterpart. Hitherto, the control of stereochemical purity in conventional
PLA synthesis has not been achieved. In this study, highly stereochemically pure
PLA was synthesized in the absence of a metal catalyst and organic solvent, which required high consumption of the residual monomer. The synthesis was conducted in supercritical carbon dioxide under CO₂ plasticizing polymerization conditions in the presence of an organocatalyst and thiourea additives. In comparison with the stereocomplexes synthesized through conventional methods,
PLA from l-lactide (
PLLA) and
PLA from d-lactide (
PDLA) were synthesized with higher stereochemical purity and improved thermal stability. Moreover, the method presented herein is environmentally friendly and thus, applicable on an industrial level.</description><identifier>ISSN: 2073-4360</identifier><identifier>EISSN: 2073-4360</identifier><identifier>DOI: 10.3390/polym10070713</identifier><identifier>PMID: 30960638</identifier><language>eng</language><publisher>Switzerland: MDPI</publisher><ispartof>Polymers, 2018-06, Vol.10 (7), p.713</ispartof><rights>2018 by the authors. 2018</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c497t-e738fb2dd0ef5247405e5027b5bbbf61f44f7822031ac3f337528da884284b9c3</citedby><cites>FETCH-LOGICAL-c497t-e738fb2dd0ef5247405e5027b5bbbf61f44f7822031ac3f337528da884284b9c3</cites><orcidid>0000-0001-6244-4916 ; 0000-0001-6877-9223</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/PMC6404224/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6404224/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27915,27916,53782,53784</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30960638$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mase, Nobuyuki</creatorcontrib><creatorcontrib>Yamamoto, Shoji</creatorcontrib><creatorcontrib>Nakaya, Yoshitaka</creatorcontrib><creatorcontrib>Sato, Kohei</creatorcontrib><creatorcontrib>Narumi, Tetsuo</creatorcontrib><creatorcontrib>Moniruzzaman</creatorcontrib><title>Organocatalytic Stereoselective Cyclic Polylactide Synthesis in Supercritical Carbon Dioxide under Plasticizing Conditions</title><title>Polymers</title><addtitle>Polymers (Basel)</addtitle><description>Cyclic polylactide (
PLA) is a structural isomer of linear polylactide (PLA) although it possesses unique functionalities in comparison to its linear counterpart. Hitherto, the control of stereochemical purity in conventional
PLA synthesis has not been achieved. In this study, highly stereochemically pure
PLA was synthesized in the absence of a metal catalyst and organic solvent, which required high consumption of the residual monomer. The synthesis was conducted in supercritical carbon dioxide under CO₂ plasticizing polymerization conditions in the presence of an organocatalyst and thiourea additives. In comparison with the stereocomplexes synthesized through conventional methods,
PLA from l-lactide (
PLLA) and
PLA from d-lactide (
PDLA) were synthesized with higher stereochemical purity and improved thermal stability. Moreover, the method presented herein is environmentally friendly and thus, applicable on an industrial level.</description><issn>2073-4360</issn><issn>2073-4360</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpVkc1LxDAQxYMoKurRq-TopZomadNeBKmfIOzC6jmk6XSNZJM1aRfrX2_EDzSXCTO_eW_gIXSckzPGanK-9nZa5YQIInK2hfYpESzjrCTbf_576CjGF5IeL8oyF7toj5G6JCWr9tH7LCyV81oNyk6D0XgxQAAfwYIezAZwM2mb2vPkZFVqdYAXkxueIZqIjcOLcQ1BB5N2lcWNCq13-Mr4t09ydB0EPLcqprF5N26JG--6BHsXD9FOr2yEo-96gJ5urh-bu-xhdnvfXD5kmtdiyECwqm9p1xHoC8oFJwUUhIq2aNu2L_Oe815UlBKWK816xkRBq05VFacVb2vNDtDFl-56bFfQaXBDUFaug1mpMEmvjPw_ceZZLv1GlpxwSnkSOP0WCP51hDjIlYkarFUO_Bhl8i4ppXVBE5p9oTr4GAP0vzY5kZ-RyX-RJf7k722_9E9A7AN1WpZv</recordid><startdate>20180628</startdate><enddate>20180628</enddate><creator>Mase, Nobuyuki</creator><creator>Yamamoto, Shoji</creator><creator>Nakaya, Yoshitaka</creator><creator>Sato, Kohei</creator><creator>Narumi, Tetsuo</creator><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-6244-4916</orcidid><orcidid>https://orcid.org/0000-0001-6877-9223</orcidid></search><sort><creationdate>20180628</creationdate><title>Organocatalytic Stereoselective Cyclic Polylactide Synthesis in Supercritical Carbon Dioxide under Plasticizing Conditions</title><author>Mase, Nobuyuki ; Yamamoto, Shoji ; Nakaya, Yoshitaka ; Sato, Kohei ; Narumi, Tetsuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c497t-e738fb2dd0ef5247405e5027b5bbbf61f44f7822031ac3f337528da884284b9c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mase, Nobuyuki</creatorcontrib><creatorcontrib>Yamamoto, Shoji</creatorcontrib><creatorcontrib>Nakaya, Yoshitaka</creatorcontrib><creatorcontrib>Sato, Kohei</creatorcontrib><creatorcontrib>Narumi, Tetsuo</creatorcontrib><creatorcontrib>Moniruzzaman</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mase, Nobuyuki</au><au>Yamamoto, Shoji</au><au>Nakaya, Yoshitaka</au><au>Sato, Kohei</au><au>Narumi, Tetsuo</au><aucorp>Moniruzzaman</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organocatalytic Stereoselective Cyclic Polylactide Synthesis in Supercritical Carbon Dioxide under Plasticizing Conditions</atitle><jtitle>Polymers</jtitle><addtitle>Polymers (Basel)</addtitle><date>2018-06-28</date><risdate>2018</risdate><volume>10</volume><issue>7</issue><spage>713</spage><pages>713-</pages><issn>2073-4360</issn><eissn>2073-4360</eissn><abstract>Cyclic polylactide (
PLA) is a structural isomer of linear polylactide (PLA) although it possesses unique functionalities in comparison to its linear counterpart. Hitherto, the control of stereochemical purity in conventional
PLA synthesis has not been achieved. In this study, highly stereochemically pure
PLA was synthesized in the absence of a metal catalyst and organic solvent, which required high consumption of the residual monomer. The synthesis was conducted in supercritical carbon dioxide under CO₂ plasticizing polymerization conditions in the presence of an organocatalyst and thiourea additives. In comparison with the stereocomplexes synthesized through conventional methods,
PLA from l-lactide (
PLLA) and
PLA from d-lactide (
PDLA) were synthesized with higher stereochemical purity and improved thermal stability. Moreover, the method presented herein is environmentally friendly and thus, applicable on an industrial level.</abstract><cop>Switzerland</cop><pub>MDPI</pub><pmid>30960638</pmid><doi>10.3390/polym10070713</doi><orcidid>https://orcid.org/0000-0001-6244-4916</orcidid><orcidid>https://orcid.org/0000-0001-6877-9223</orcidid><oa>free_for_read</oa></addata></record> |
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| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; MDPI - Multidisciplinary Digital Publishing Institute; PubMed Central |
| title | Organocatalytic Stereoselective Cyclic Polylactide Synthesis in Supercritical Carbon Dioxide under Plasticizing Conditions |
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