Rapid Synthesis of Chemically Recyclable Polycarbonates from Renewable Feedstocks

Derek J. Saxon; Ethan A Gormong; Vijay M Shah; Theresa M. Reineke

doi:10.1021/acsmacrolett.0c00747

Rapid Synthesis of Chemically Recyclable Polycarbonates from Renewable Feedstocks

Derek J. Saxon, Ethan A Gormong, Vijay M Shah, Theresa M. Reineke

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

44 Scopus citations

Abstract

We report the rapid, one-pot synthesis of functional polycarbonates derived from renewable alcohols (i.e., glucose tetraacetate, acetyl isosorbide, lauryl alcohol, and ethanol) and a cyclic carbonate bearing an imidazolecarboxylate. This tandem functionalization/ring-opening polymerization strategy can be performed on multigram scale and eliminates the need for rigorous purification and specialized equipment. A wide range of glass transition temperatures (Tg) was accessible from these renewable pendant groups (>75 °C Tg window). We also synthesized several statistical copolycarbonates to show the thermal properties can be tailored with this tandem method. Additionally, we demonstrate a circular polymer economy via chemical recycling to a cyclic carbonate precursor. This work may facilitate development of sustainable polycarbonates with tailored properties that work toward eliminating plastic waste streams.

Original language	English (US)
Pages (from-to)	98-103
Number of pages	6
Journal	ACS Macro Letters
Volume	10
Issue number	1
DOIs	https://doi.org/10.1021/acsmacrolett.0c00747
State	Published - Jan 19 2021

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation Center for Sustainable Polymers (CHE-1901635), an NSF-funded Center for Chemical Innovation. Mass spectrometry analysis was performed at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota, as well as The National Science Foundation (NSF, Award CHE-1336940). The authors acknowledge Dr. Anne LaPointe for assistance with high-throughput experimentation and helpful discussions. The authors also acknowledge John Beumer for help in preparing the TOC graphic.

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abstract = "We report the rapid, one-pot synthesis of functional polycarbonates derived from renewable alcohols (i.e., glucose tetraacetate, acetyl isosorbide, lauryl alcohol, and ethanol) and a cyclic carbonate bearing an imidazolecarboxylate. This tandem functionalization/ring-opening polymerization strategy can be performed on multigram scale and eliminates the need for rigorous purification and specialized equipment. A wide range of glass transition temperatures (Tg) was accessible from these renewable pendant groups (>75 °C Tg window). We also synthesized several statistical copolycarbonates to show the thermal properties can be tailored with this tandem method. Additionally, we demonstrate a circular polymer economy via chemical recycling to a cyclic carbonate precursor. This work may facilitate development of sustainable polycarbonates with tailored properties that work toward eliminating plastic waste streams. ",

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note = "Funding Information: This work was supported by the National Science Foundation Center for Sustainable Polymers (CHE-1901635), an NSF-funded Center for Chemical Innovation. Mass spectrometry analysis was performed at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota, as well as The National Science Foundation (NSF, Award CHE-1336940). The authors acknowledge Dr. Anne LaPointe for assistance with high-throughput experimentation and helpful discussions. The authors also acknowledge John Beumer for help in preparing the TOC graphic. Publisher Copyright: {\textcopyright} ",

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N1 - Funding Information: This work was supported by the National Science Foundation Center for Sustainable Polymers (CHE-1901635), an NSF-funded Center for Chemical Innovation. Mass spectrometry analysis was performed at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota, as well as The National Science Foundation (NSF, Award CHE-1336940). The authors acknowledge Dr. Anne LaPointe for assistance with high-throughput experimentation and helpful discussions. The authors also acknowledge John Beumer for help in preparing the TOC graphic. Publisher Copyright: ©

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N2 - We report the rapid, one-pot synthesis of functional polycarbonates derived from renewable alcohols (i.e., glucose tetraacetate, acetyl isosorbide, lauryl alcohol, and ethanol) and a cyclic carbonate bearing an imidazolecarboxylate. This tandem functionalization/ring-opening polymerization strategy can be performed on multigram scale and eliminates the need for rigorous purification and specialized equipment. A wide range of glass transition temperatures (Tg) was accessible from these renewable pendant groups (>75 °C Tg window). We also synthesized several statistical copolycarbonates to show the thermal properties can be tailored with this tandem method. Additionally, we demonstrate a circular polymer economy via chemical recycling to a cyclic carbonate precursor. This work may facilitate development of sustainable polycarbonates with tailored properties that work toward eliminating plastic waste streams.

AB - We report the rapid, one-pot synthesis of functional polycarbonates derived from renewable alcohols (i.e., glucose tetraacetate, acetyl isosorbide, lauryl alcohol, and ethanol) and a cyclic carbonate bearing an imidazolecarboxylate. This tandem functionalization/ring-opening polymerization strategy can be performed on multigram scale and eliminates the need for rigorous purification and specialized equipment. A wide range of glass transition temperatures (Tg) was accessible from these renewable pendant groups (>75 °C Tg window). We also synthesized several statistical copolycarbonates to show the thermal properties can be tailored with this tandem method. Additionally, we demonstrate a circular polymer economy via chemical recycling to a cyclic carbonate precursor. This work may facilitate development of sustainable polycarbonates with tailored properties that work toward eliminating plastic waste streams.

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Rapid Synthesis of Chemically Recyclable Polycarbonates from Renewable Feedstocks

Abstract

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