N2O deconstruction of polycyclooctene to generate carbonyl-functionalized macromonomers

Ogbu, Ikechukwu Martin; Tu, Chien-Hua; Fastow, Eli; Hinton, Zachary R.; Winey, Karen I.; Kozlowski, Marisa C.

doi:10.1016/j.polymdegradstab.2024.110987

N₂O deconstruction of polycyclooctene to generate carbonyl-functionalized macromonomers

Journal Article · Tue Sep 03 00:00:00 EDT 2024 · Polymer Degradation and Stability

DOI:https://doi.org/10.1016/j.polymdegradstab.2024.110987· OSTI ID:2440731

^[1]; Tu, Chien-Hua ^[1]; ^[1]; Hinton, Zachary R. ^[2]; ^[1]; ^[1]

University of Pennsylvania, Philadelphia, PA (United States)
University of Delaware, Newark, DE (United States)

Deconstruction of polyolefins into functionalized macromonomers presents a compelling strategy for polyolefin upcycling by creating macromonomers through dehydrogenation/depolymerization. We show that nitrous oxide (N₂O), a greenhouse gas waste product from the production of nylon, mediates the deconstruction of polycyclooctene (PCOE) and generates carbonyl-functionalized macromonomers. Carbonyl incorporation and macromonomer molar mass were well controlled by reaction time, and subsequent hydrogenation readily removed residual carbon-carbon double bonds. Here, we also demonstrated that the reaction could progress efficiently with substrates of moderate levels of unsaturation, closely mimicking partially dehydrogenated polyethylene. Such carbonyl-functionalized macromonomers could serve as feedstock for preparing vitrimers and other functional polymers.

View Accepted Manuscript (DOE)

Research Organization:: University of Pennsylvania, Philadelphia, PA (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0022238

OSTI ID:: 2440731

Alternate ID(s):: OSTI ID: 2475903

Journal Information:: Polymer Degradation and Stability, Journal Name: Polymer Degradation and Stability Vol. 229; ISSN 0141-3910

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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N₂O deconstruction of polycyclooctene to generate carbonyl-functionalized macromonomers