Organocatalytic depolymerization of poly(trimethylene carbonate)
Aliphatic polycarbonates have attracted attention as degradable and sustainable materials contributing to the circular plastic economy. Their chemical recycling has not been sufficiently studied. In this study, the efficacy of organocatalysts for depolymerization of poly(trimethylene carbonate) (PTM...
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Veröffentlicht in: | Journal of polymer science (2020) 2022-12, Vol.60 (24), p.3489-3500 |
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description | Aliphatic polycarbonates have attracted attention as degradable and sustainable materials contributing to the circular plastic economy. Their chemical recycling has not been sufficiently studied. In this study, the efficacy of organocatalysts for depolymerization of poly(trimethylene carbonate) (PTMC), a representative aliphatic polycarbonate, is investigated using several organic acids and bases. The hydrolysis of PTMC produces the water‐soluble degradates propane‐1,3‐diol (PD) and CO2. A phosphazene base P2‐t‐Bu shows high activity for the hydrolysis, yielding up to 31% and 89% of PD in the homogeneous reaction at around 27°C and the inhomogeneous reaction under the reflux condition, respectively. By contrast, 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) exhibits exceptionally high catalytic activity for the methanolysis of PTMC, producing PD and dimethyl carbonate. This is because of dual hydrogen‐bonding activation, which completes the inhomogeneous reaction in a few hours at around 27°C while yielding more than 90% of PD. The reaction rate of the TBD‐catalyzed methanolysis depends on the concentration of the nucleophile and catalyst, and the ratio of the nucleophile to the substrate affects the PD yield. These results provide a highly promising standard for chemical recycling of functionalized aliphatic polycarbonates that could potentially be applied to sustainable materials in the future. |
doi_str_mv | 10.1002/pol.20220551 |
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Their chemical recycling has not been sufficiently studied. In this study, the efficacy of organocatalysts for depolymerization of poly(trimethylene carbonate) (PTMC), a representative aliphatic polycarbonate, is investigated using several organic acids and bases. The hydrolysis of PTMC produces the water‐soluble degradates propane‐1,3‐diol (PD) and CO2. A phosphazene base P2‐t‐Bu shows high activity for the hydrolysis, yielding up to 31% and 89% of PD in the homogeneous reaction at around 27°C and the inhomogeneous reaction under the reflux condition, respectively. By contrast, 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) exhibits exceptionally high catalytic activity for the methanolysis of PTMC, producing PD and dimethyl carbonate. This is because of dual hydrogen‐bonding activation, which completes the inhomogeneous reaction in a few hours at around 27°C while yielding more than 90% of PD. The reaction rate of the TBD‐catalyzed methanolysis depends on the concentration of the nucleophile and catalyst, and the ratio of the nucleophile to the substrate affects the PD yield. These results provide a highly promising standard for chemical recycling of functionalized aliphatic polycarbonates that could potentially be applied to sustainable materials in the future.</description><identifier>ISSN: 2642-4150</identifier><identifier>EISSN: 2642-4169</identifier><identifier>DOI: 10.1002/pol.20220551</identifier><language>eng</language><publisher>Hoboken, USA: John Wiley & Sons, Inc</publisher><subject>Aliphatic compounds ; aliphatic polycarbonates ; Catalytic activity ; Depolymerization ; Hydrolysis ; methanolysis ; Nucleophiles ; Organic acids ; organocatalysts ; Phosphazene ; Polycarbonate resins ; Recycling ; Substrates ; Sustainable materials</subject><ispartof>Journal of polymer science (2020), 2022-12, Vol.60 (24), p.3489-3500</ispartof><rights>2022 The Authors. published by Wiley Periodicals LLC.</rights><rights>2022. This article is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). 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Their chemical recycling has not been sufficiently studied. In this study, the efficacy of organocatalysts for depolymerization of poly(trimethylene carbonate) (PTMC), a representative aliphatic polycarbonate, is investigated using several organic acids and bases. The hydrolysis of PTMC produces the water‐soluble degradates propane‐1,3‐diol (PD) and CO2. A phosphazene base P2‐t‐Bu shows high activity for the hydrolysis, yielding up to 31% and 89% of PD in the homogeneous reaction at around 27°C and the inhomogeneous reaction under the reflux condition, respectively. By contrast, 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) exhibits exceptionally high catalytic activity for the methanolysis of PTMC, producing PD and dimethyl carbonate. This is because of dual hydrogen‐bonding activation, which completes the inhomogeneous reaction in a few hours at around 27°C while yielding more than 90% of PD. The reaction rate of the TBD‐catalyzed methanolysis depends on the concentration of the nucleophile and catalyst, and the ratio of the nucleophile to the substrate affects the PD yield. These results provide a highly promising standard for chemical recycling of functionalized aliphatic polycarbonates that could potentially be applied to sustainable materials in the future.</description><subject>Aliphatic compounds</subject><subject>aliphatic polycarbonates</subject><subject>Catalytic activity</subject><subject>Depolymerization</subject><subject>Hydrolysis</subject><subject>methanolysis</subject><subject>Nucleophiles</subject><subject>Organic acids</subject><subject>organocatalysts</subject><subject>Phosphazene</subject><subject>Polycarbonate resins</subject><subject>Recycling</subject><subject>Substrates</subject><subject>Sustainable materials</subject><issn>2642-4150</issn><issn>2642-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNp9kE9LAzEQxYMoWGpvfoAFLwpuTTJJdvdmKf6DQj3oOaTZiW7Zbmo2RdZPb0rVo6cZhh9v3nuEnDM6ZZTym61vp5xyTqVkR2TEleC5YKo6_tslPSWTvl_ThINUgqoRuV2GN9N5a6Jph9jYrMYkNGwwNF8mNr7LvMv2l8sYmg3G96HFDjNrwsp3JuLVGTlxpu1x8jPH5PX-7mX-mC-WD0_z2SK3IBjLJXOusJUQzgJHqLAoi7qgRWkLiWBccm2BCiNYbZzidbkSqmaqBobWsNLAmFwcdLfBf-ywj3rtd6FLLzUvpIASKiYTdX2gbPB9H9DpbbJtwqAZ1fuadMqif2tKOBzwz6bF4V9WPy8XM6ASGHwDKZBqTQ</recordid><startdate>20221215</startdate><enddate>20221215</enddate><creator>Fukushima, Kazuki</creator><creator>Watanabe, Yuya</creator><creator>Ueda, Tetsuya</creator><creator>Nakai, So</creator><creator>Kato, Takashi</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-3753-7800</orcidid><orcidid>https://orcid.org/0000-0001-8250-3258</orcidid><orcidid>https://orcid.org/0000-0002-0571-0883</orcidid><orcidid>https://orcid.org/0000-0002-6980-9663</orcidid></search><sort><creationdate>20221215</creationdate><title>Organocatalytic depolymerization of poly(trimethylene carbonate)</title><author>Fukushima, Kazuki ; Watanabe, Yuya ; Ueda, Tetsuya ; Nakai, So ; Kato, Takashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3411-51ff7c944fc32e39e787d7078c75e3af055c304a41daf62d8b46d16d31eca18a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aliphatic compounds</topic><topic>aliphatic polycarbonates</topic><topic>Catalytic activity</topic><topic>Depolymerization</topic><topic>Hydrolysis</topic><topic>methanolysis</topic><topic>Nucleophiles</topic><topic>Organic acids</topic><topic>organocatalysts</topic><topic>Phosphazene</topic><topic>Polycarbonate resins</topic><topic>Recycling</topic><topic>Substrates</topic><topic>Sustainable materials</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fukushima, Kazuki</creatorcontrib><creatorcontrib>Watanabe, Yuya</creatorcontrib><creatorcontrib>Ueda, Tetsuya</creatorcontrib><creatorcontrib>Nakai, So</creatorcontrib><creatorcontrib>Kato, Takashi</creatorcontrib><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Online Library (Open Access Collection)</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of polymer science (2020)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fukushima, Kazuki</au><au>Watanabe, Yuya</au><au>Ueda, Tetsuya</au><au>Nakai, So</au><au>Kato, Takashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organocatalytic depolymerization of poly(trimethylene carbonate)</atitle><jtitle>Journal of polymer science (2020)</jtitle><date>2022-12-15</date><risdate>2022</risdate><volume>60</volume><issue>24</issue><spage>3489</spage><epage>3500</epage><pages>3489-3500</pages><issn>2642-4150</issn><eissn>2642-4169</eissn><abstract>Aliphatic polycarbonates have attracted attention as degradable and sustainable materials contributing to the circular plastic economy. 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The reaction rate of the TBD‐catalyzed methanolysis depends on the concentration of the nucleophile and catalyst, and the ratio of the nucleophile to the substrate affects the PD yield. These results provide a highly promising standard for chemical recycling of functionalized aliphatic polycarbonates that could potentially be applied to sustainable materials in the future.</abstract><cop>Hoboken, USA</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/pol.20220551</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-3753-7800</orcidid><orcidid>https://orcid.org/0000-0001-8250-3258</orcidid><orcidid>https://orcid.org/0000-0002-0571-0883</orcidid><orcidid>https://orcid.org/0000-0002-6980-9663</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Aliphatic compounds aliphatic polycarbonates Catalytic activity Depolymerization Hydrolysis methanolysis Nucleophiles Organic acids organocatalysts Phosphazene Polycarbonate resins Recycling Substrates Sustainable materials |
title | Organocatalytic depolymerization of poly(trimethylene carbonate) |
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