Poly(2,3-Dihydrofuran): A Strong, Biorenewable, and Degradable Thermoplastic Synthesized via Room Temperature Cationic Polymerization

Scott W. Spring; Jesse H. Hsu; Renee J. Sifri; Szu Ming Yang; Chloe S. Cerione; Tristan H. Lambert; Christopher J. Ellison; Brett P. Fors

doi:10.1021/jacs.2c06103

Poly(2,3-Dihydrofuran): A Strong, Biorenewable, and Degradable Thermoplastic Synthesized via Room Temperature Cationic Polymerization

Scott W. Spring, Jesse H. Hsu, Renee J. Sifri, Szu Ming Yang, Chloe S. Cerione, Tristan H. Lambert, Christopher J. Ellison, Brett P. Fors

Chemical Engineering and Materials Science

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

24 Scopus citations

Abstract

Creation of strong and tough plastics from sustainable and biorenewable resources is a significant challenge in polymer science. This challenge is further complicated when attempting to make these materials using an economically viable process, which is often hindered by the production and availability of chemical feedstocks and the efficiency of the monomer synthesis. Herein, we report the synthesis and characterization of a strong thermoplastic made from 2,3-dihydrofuran (DHF), a monomer made in one step from 1,4-butanediol, a bioalcohol already produced on the plant scale. We developed a green, metal-free cationic polymerization to enable the production of poly(2,3-dihydrofuran) (PDHF) with molecular weights of up to 256 kg/mol at room temperature. Characterization of these polymers showed that PDHF possesses high tensile strength and toughness (70 and 14 MPa, respectively) comparable to commercial polycarbonate, high optical clarity, and good barrier properties to oxygen, carbon dioxide, and water. These properties make this material amenable to a variety of applications, from food packaging to high strength windows. Importantly, we have also developed a facile oxidative degradation process of PDHF, providing an end-of-life solution for PDHF materials.

Original language	English (US)
Pages (from-to)	15727-15734
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	144
Issue number	34
DOIs	https://doi.org/10.1021/jacs.2c06103
State	Published - Aug 31 2022

Bibliographical note

Funding Information:
This material is based upon work supported by the National Science Foundation Graduate Research Fellowship Program under grant no. DGE-1650441. Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation. This work was supported by the National Science Foundation Center for Sustainable Polymers at the University of Minnesota, a Center for Chemical Innovation (CHE-1901635). This work made use of the Cornell Center for Materials Research Shared Facilities that are supported through the NSF MRSEC program (DMR-1719875). This work made use of the NMR Facility at Cornell University that is supported, in part, by the NSF under the award number CHE-1531632. We would like to thank Meredith Silberstein and her group for generous use of their tensile tester. a

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© 2022 American Chemical Society.

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@article{73ae7f1d52b4412d8ba10b4151c8709d,

title = "Poly(2,3-Dihydrofuran): A Strong, Biorenewable, and Degradable Thermoplastic Synthesized via Room Temperature Cationic Polymerization",

abstract = "Creation of strong and tough plastics from sustainable and biorenewable resources is a significant challenge in polymer science. This challenge is further complicated when attempting to make these materials using an economically viable process, which is often hindered by the production and availability of chemical feedstocks and the efficiency of the monomer synthesis. Herein, we report the synthesis and characterization of a strong thermoplastic made from 2,3-dihydrofuran (DHF), a monomer made in one step from 1,4-butanediol, a bioalcohol already produced on the plant scale. We developed a green, metal-free cationic polymerization to enable the production of poly(2,3-dihydrofuran) (PDHF) with molecular weights of up to 256 kg/mol at room temperature. Characterization of these polymers showed that PDHF possesses high tensile strength and toughness (70 and 14 MPa, respectively) comparable to commercial polycarbonate, high optical clarity, and good barrier properties to oxygen, carbon dioxide, and water. These properties make this material amenable to a variety of applications, from food packaging to high strength windows. Importantly, we have also developed a facile oxidative degradation process of PDHF, providing an end-of-life solution for PDHF materials.",

author = "Spring, {Scott W.} and Hsu, {Jesse H.} and Sifri, {Renee J.} and Yang, {Szu Ming} and Cerione, {Chloe S.} and Lambert, {Tristan H.} and Ellison, {Christopher J.} and Fors, {Brett P.}",

note = "Funding Information: This material is based upon work supported by the National Science Foundation Graduate Research Fellowship Program under grant no. DGE-1650441. Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation. This work was supported by the National Science Foundation Center for Sustainable Polymers at the University of Minnesota, a Center for Chemical Innovation (CHE-1901635). This work made use of the Cornell Center for Materials Research Shared Facilities that are supported through the NSF MRSEC program (DMR-1719875). This work made use of the NMR Facility at Cornell University that is supported, in part, by the NSF under the award number CHE-1531632. We would like to thank Meredith Silberstein and her group for generous use of their tensile tester. a Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

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doi = "10.1021/jacs.2c06103",

language = "English (US)",

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AU - Spring, Scott W.

AU - Hsu, Jesse H.

AU - Sifri, Renee J.

AU - Yang, Szu Ming

AU - Cerione, Chloe S.

AU - Lambert, Tristan H.

AU - Ellison, Christopher J.

AU - Fors, Brett P.

N1 - Funding Information: This material is based upon work supported by the National Science Foundation Graduate Research Fellowship Program under grant no. DGE-1650441. Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation. This work was supported by the National Science Foundation Center for Sustainable Polymers at the University of Minnesota, a Center for Chemical Innovation (CHE-1901635). This work made use of the Cornell Center for Materials Research Shared Facilities that are supported through the NSF MRSEC program (DMR-1719875). This work made use of the NMR Facility at Cornell University that is supported, in part, by the NSF under the award number CHE-1531632. We would like to thank Meredith Silberstein and her group for generous use of their tensile tester. a Publisher Copyright: © 2022 American Chemical Society.

PY - 2022/8/31

Y1 - 2022/8/31

N2 - Creation of strong and tough plastics from sustainable and biorenewable resources is a significant challenge in polymer science. This challenge is further complicated when attempting to make these materials using an economically viable process, which is often hindered by the production and availability of chemical feedstocks and the efficiency of the monomer synthesis. Herein, we report the synthesis and characterization of a strong thermoplastic made from 2,3-dihydrofuran (DHF), a monomer made in one step from 1,4-butanediol, a bioalcohol already produced on the plant scale. We developed a green, metal-free cationic polymerization to enable the production of poly(2,3-dihydrofuran) (PDHF) with molecular weights of up to 256 kg/mol at room temperature. Characterization of these polymers showed that PDHF possesses high tensile strength and toughness (70 and 14 MPa, respectively) comparable to commercial polycarbonate, high optical clarity, and good barrier properties to oxygen, carbon dioxide, and water. These properties make this material amenable to a variety of applications, from food packaging to high strength windows. Importantly, we have also developed a facile oxidative degradation process of PDHF, providing an end-of-life solution for PDHF materials.

AB - Creation of strong and tough plastics from sustainable and biorenewable resources is a significant challenge in polymer science. This challenge is further complicated when attempting to make these materials using an economically viable process, which is often hindered by the production and availability of chemical feedstocks and the efficiency of the monomer synthesis. Herein, we report the synthesis and characterization of a strong thermoplastic made from 2,3-dihydrofuran (DHF), a monomer made in one step from 1,4-butanediol, a bioalcohol already produced on the plant scale. We developed a green, metal-free cationic polymerization to enable the production of poly(2,3-dihydrofuran) (PDHF) with molecular weights of up to 256 kg/mol at room temperature. Characterization of these polymers showed that PDHF possesses high tensile strength and toughness (70 and 14 MPa, respectively) comparable to commercial polycarbonate, high optical clarity, and good barrier properties to oxygen, carbon dioxide, and water. These properties make this material amenable to a variety of applications, from food packaging to high strength windows. Importantly, we have also developed a facile oxidative degradation process of PDHF, providing an end-of-life solution for PDHF materials.

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Poly(2,3-Dihydrofuran): A Strong, Biorenewable, and Degradable Thermoplastic Synthesized via Room Temperature Cationic Polymerization

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