Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins
Open accessAbstract
Polyolefins with periodic unsaturation in the backbone chain are sought after for synthesizing chemically recyclable polymers or telechelic polyolefin macromonomers. Here we introduce a bottom‐up synthesis of unsaturated high‐density polyethylene (HDPE) via copolymerization of ethylene with dimethyl 7‐oxabicyclo[2.2.1]hepta‐2,5‐diene‐3,5‐dicarboxylate followed by post‐polymerization retro‐Diels–Alder to unveil hidden double bonds in the polymer backbone. The incorporation of this “Trojan Horse” comonomer was varied and a series of unsaturated HDPE polymers with block lengths of 1.2, 1.9, and 3.5 kDa between double bonds was synthesized. Cross metathesis of unsaturated HDPE samples with 2‐hydroxyethyl acrylate yielded telechelic ester terminated PE macromonomers suitable for the preparation of ester‐linked PE. These materials were depolymerized and repolymerized, making them suitable candidates for chemical recycling. The ester‐linked PE displayed thermal and mechanical properties comparable to commercial HDPE.
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- Authors
- Parke, S. M., Lopez, J. C., Cui, S., LaPointe, A. M., & Coates, G. W.
- Affiliations
- Cornell University (US)
- Corresponding author
- Coates, Geoffrey W.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2023-06-15
- Volume
- 62
- Issue
- 30
- Pages
- e202301927-e202301927
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W4376108845
- Cited by
- 88
- References
- 59
- Citations by year
- 2026: 27 · 2025: 30 · 2024: 23 · 2023: 8
- FWCI
- 6.69
- Type
- journal article
- Language
- en
- Open access
- green
- www.osti.gov
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- OSTI OAI (U.S. Department of Energy Office of Scientific and Technical Information) (submittedVersion)
- Funders
- U.S. Department of Energy (DE-AC02-07CH11358)
- Topics
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- retro-Diels-Alder reaction, ethylene copolymerization, cross-metathesis, 2-hydroxyethyl acrylate, chemical recycling, block copolymers
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