Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Chemically recyclable thermoplastics from reversible-deactivation polymerization of cyclic acetals

Journal Article · · Science

Identifying plastics capable of chemical recycling to monomer (CRM) is the foremost challenge in creating a sustainable circular plastic economy. Polyacetals are promising candidates for CRM but lack useful tensile strengths owing to the low molecular weights produced using current uncontrolled cationic ring-opening polymerization (CROP) methods. Here, we present reversible-deactivation CROP of cyclic acetals using a commercial halomethyl ether initiator and an indium(III) bromide catalyst. Using this method, we synthesize poly(1,3-dioxolane) (PDXL), which demonstrates tensile strength comparable to some commodity polyolefins. Depolymerization of PDXL using strong acid catalysts returns monomer in near-quantitative yield and even proceeds from a commodity plastic waste mixture. Our efficient polymerization method affords a tough thermoplastic that can undergo selective depolymerization to monomer.

Sponsoring Organization:
USDOE
OSTI ID:
1812976
Journal Information:
Science, Journal Name: Science Journal Issue: 6556 Vol. 373; ISSN 0036-8075
Publisher:
American Association for the Advancement of Science (AAAS)Copyright Statement
Country of Publication:
United States
Language:
English

References (52)

Completely Recyclable Monomers and Polycarbonate: Approach to Sustainable Polymers journal March 2017
Zinc(II)-triflate as catalyst precursor for ring-closing depolymerization of end-of-life polytetrahydrofuran to produce tetrahydrofuran journal August 2013
Mechanical Recycling of Packaging Plastics: A Review journal September 2020
The role of pyridine derivatives in living carbocationic polymerization: Lewis base or nucleophile? journal July 1998
Living carbocationic polymerization. IV. Living polymerization of isobutylene journal July 1987
The polymerization of 1,3-dioxolane. I. Structure of the polymer and thermodynamics of its formation: THE POLYMERIZATION OF 1,3-DIOXOLANE. I journal January 1967
Toward Infinitely Recyclable Plastics Derived from Renewable Cyclic Esters journal February 2019
Indium Catalysts for Ring Opening Polymerization: Exploring the Importance of Catalyst Aggregation journal October 2017
Synthesis and Solution Self-Assembly of Poly(1,3-dioxolane) journal April 2019
Improved Li + Transport in Polyacetal Electrolytes: Conductivity and Current Fraction in a Series of Polymers journal April 2021
100th Anniversary of Macromolecular Science Viewpoint: Needs for Plastics Packaging Circularity journal September 2020
100th Anniversary of Macromolecular Science Viewpoint: Toward Catalytic Chemical Recycling of Waste (and Future) Plastics journal October 2020
Rapid Synthesis of Chemically Recyclable Polycarbonates from Renewable Feedstocks journal December 2020
100th Anniversary of Macromolecular Science Viewpoint: Redefining Sustainable Polymers journal December 2020
A Carbomethoxylated Polyvalerolactone from Malic Acid: Synthesis and Divergent Chemical Recycling journal January 2018
Approaches to Sustainable and Continually Recyclable Cross-Linked Polymers journal August 2018
Isotactic Poly(propylene oxide): A Photodegradable Polymer with Strain Hardening Properties journal March 2020
Hydrogenative Depolymerization of Nylons journal July 2020
Functionalized and Degradable Polyphthalaldehyde Derivatives journal September 2019
Architecture-Controlled Ring-Opening Polymerization for Dynamic Covalent Poly(disulfide)s journal October 2019
Seven-Membered Cyclic Acetals journal June 1957
Living cationic polymerization of N-vinylcarbazole initiated by hydrogen iodide journal May 1987
Mechanism of cyclic acetal polymerization. End of a controversy? journal June 1983
Poly(tetramethyl glycolide) from Renewable Carbon, a Racemization-Free and Controlled Depolymerizable Polyester journal December 2010
Closed-loop recycling of plastics enabled by dynamic covalent diketoenamine bonds journal April 2019
Chemical recycling of waste plastics for new materials production journal June 2017
Chemical recycling to monomer for an ideal, circular polymer economy journal April 2020
Closed-loop recycling of polyethylene-like materials journal February 2021
Copolymerization of CO 2 and meso epoxides using enantioselective β-diiminate catalysts: a route to highly isotactic polycarbonates journal January 2014
Chemically recyclable polymers: a circular economy approach to sustainability journal January 2017
Thermoplastic polyacetals: chemistry from the past for a sustainable future? journal January 2019
Organocatalysis for depolymerisation journal January 2019
Switchable living nickel( ii ) α-diimine catalyst for ethylene polymerisation journal January 2019
Selective or living organopolymerization of a six-five bicyclic lactone to produce fully recyclable polyesters journal January 2019
Controlled cationic copolymerization of vinyl monomers and cyclic acetals via concurrent vinyl-addition and ring-opening mechanisms: the systematic study of structural effects on the copolymerization behavior journal January 2019
Turning natural δ-lactones to thermodynamically stable polymers with triggered recyclability journal January 2020
The “solid-state” ring-opening cationic polymerization of 1,3,5-trioxane: frozen polymerization for suppression of oligomer formation and synthesis of ultrahigh molecular weight polymers journal January 2021
Improved Direct Acetalisation for (Strained) Cyclic Acetals journal January 1974
Thermodynamic Recycling—On Ring-Opening Polymerization and Ring-Closing Depolymerization journal September 1993
Production, use, and fate of all plastics ever made journal July 2017
High-performance pan-tactic polythioesters with intrinsic crystallinity and chemical recyclability journal August 2020
The United States’ contribution of plastic waste to land and ocean journal October 2020
The promise of plastics from plants journal November 2017
Beyond plastic waste journal November 2017
The future of plastics recycling journal November 2017
A synthetic polymer system with repeatable chemical recyclability journal April 2018
Plastic rain in protected areas of the United States journal June 2020
Predicted growth in plastic waste exceeds efforts to mitigate plastic pollution journal September 2020
Evaluating scenarios toward zero plastic pollution journal July 2020
Polyethylene upcycling to long-chain alkylaromatics by tandem hydrogenolysis/aromatization journal October 2020
Cationic polymerization of 1,3-dioxolane and 1,3-dioxepane. Application to graft and block copolymer synthesis journal January 1985
Possible Formation of Living Polymers of p-Methoxystyrene by Iodine journal January 1977

Similar Records

Catalytic closed-loop recycling of polyethylene-like materials produced by acceptorless dehydrogenative polymerization of bio-derived diols
Journal Article · Thu Feb 20 23:00:00 EST 2025 · Nature Chemistry · OSTI ID:2544979

Random Copolymerization of Substituted Dioxolanes: Rational Design of High-Performance Polymer Electrolytes
Journal Article · Thu Nov 07 23:00:00 EST 2024 · ACS Applied Polymer Materials · OSTI ID:2584836

Related Subjects