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Cited by 677biodegradable polymer synthesis and propertiesCarbon dioxide utilization in catalysisPolymer crystallization and properties

Completely recyclable biopolymers with linear and cyclic topologies via ring-opening polymerization of γ-butyrolactone

Hong, Miao, Chen, Eugene Y.-X.·2016·Nature Chemistry
DOI 10.1038/nchem.2391
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Abstract

Ring-opening polymerization (ROP) is a powerful synthetic methodology for the chemical synthesis of technologically important biodegradable aliphatic polyesters from cyclic esters or lactones. However, the bioderived five-membered γ-butyrolactone (γ-BL) is commonly referred as 'non-polymerizable' because of its low strain energy. The chemical synthesis of poly(γ-butyrolactone) (PγBL) through the ROP process has been realized only under ultrahigh pressure (20,000 atm, 160 °C) and only produces oligomers. Here we report that the ROP of γ-BL can, with a suitable catalyst, proceed smoothly to high conversions (90%) under ambient pressure to produce PγBL materials with a number-average molecular weight up to 30 kg mol(-1) and with controlled linear and/or cyclic topologies. Remarkably, both linear and cyclic PγBLs can be recycled back into the monomer in quantitative yield by simply heating the bulk materials at 220 °C (linear polymer) or 300 °C (cyclic polymer) for one hour, which thereby demonstrates the complete recyclability of PγBL.

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Crossref · 10.1038/nchem.2391

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52 of 52 references verified0 citation errors · 0 not checkable

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  • A modest ceiling temperature (315 °C in bulk monomer) can be leveraged to facilitate recycling.

    “Although a modest ceiling temperature (315 ° C in bulk monomer) may, in general, be considered a synthetic inconvenience, it is possible to leverage this characteristic to facilitate recycling. 32”

    From Aliphatic Polyester Block Polymer Design (2016) · cites this paper as [32]

  • At low temperatures (e.g. -40 °C), the ROP of γ-butyrolactone mediated by La[N(SiMe3)2]3 or tert-Bu-P4 can proceed to high conversions (60-90%).

    “However, Chen recently found that at low temperatures (e.g.-40 °C), the ROP of γ-BL mediated by La[N(SiMe3)2]3 or tert-Bu-P4 can proceed to high conversions (60 ~ 90%).278”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [278]

  • The topologies of the products can be controlled by the La[N(SiMe3)2]3/ROH ratios, with excess ROH favoring the formation of linear chains.

    “The topologies of the products can be controlled by the La[N(SiMe3)2]3/ROH ratios, with excess ROH favoring the formation of linear chains.”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [278]

  • At -40 °C and ambient pressure, the ROP of γ-BL proceeded smoothly in the presence of a catalyst (La[N(SiMe3)2]3 or tert-Bu-P4) to high conversions within 24 h, generating poly(γ-BL) with Mn up to 30 kDa and Ð ~ 2.0.

    “At -40 °C and ambient pressure, the ROP of γ-BL proceeded smoothly in the presence of a catalyst (La[N(SiMe3)2]3 or tert-Bu-P4) to high conversions within 24 h, generating poly(γ-BL) with Mn up to 30 kDa and Ð ~ 2.0.”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [278]

  • A clean and quantitative thermal recycling of these polymers was achieved by simply heating the bulk material at 220 °C (for the linear polymer) or 300 °C (for the cyclic polymer).

    “A clean and quantitative thermal recycling of these polymers was achieved by simply heating the bulk material at 220 °C (for the linear polymer) or 300 °C (for the cyclic polymer).”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [278]

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Authors
Hong, M., & Chen, E. Y.-X.
Affiliations
Colorado State University (US)
Corresponding author
Chen, Eugene Y.-X.
ORCID
Venue
Nature Chemistry
Publisher
Springer Science and Business Media LLC
Published
2015-11-23
Volume
8
Issue
1
Pages
42-49
ISSN
  • 1755-4330 (ISSN-L)
  • 1755-4349
DOI
10.1038/nchem.2391
OpenAlex
W2268050254
Cited by
677
References
52
Citations by year
2026: 55 · 2025: 85 · 2024: 88 · 2023: 89 · 2022: 94 · 2021: 57 · 2020: 47 · 2019: 48 · 2018: 59 · 2017: 35 · 2016: 19 · 2015: 1
FWCI
13.72
Type
journal article
Language
en
Open access
closed
Licence
www.springer.com/tdm (tdm)
Locations
  • Nature Chemistry (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • National Science Foundation
  • U.S. Department of Energy
Topics
  • Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
  • Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
Keywords
gamma-butyrolactone, ring-opening polymerization, biodegradable aliphatic polyesters, ring polymers, linear polymers, polymer recycling, thermal depolymerization, catalysts, high molecular weight polymers, biopolymers
MeSH terms
Biopolymers, Catalysis, Stress, Mechanical, Surface Properties, Thermodynamics, Viscosity, 4-Butyrolactone, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization, Polymerization, Biodegradable Plastics

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