Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins

Parke, Sarah M.; Lopez, Jaqueline C.; Cui, Shilin; LaPointe, Anne M.; Coates, Geoffrey W.

doi:10.1002/ange.202301927

Title: Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins

Journal Article · 15 June 2023 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.202301927 · OSTI ID:1985168

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Department of Chemistry and Chemical Biology Cornell University Ithaca NY 14853–1301 USA

Abstract 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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Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1985168

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 30 Vol. 135; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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