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Iron Catalyzed Synthesis and Chemical Recycling of Telechelic, 1,3-Enchained Oligocyclobutanes

preprint
submitted on 17.03.2020 and posted on 18.03.2020 by Megan Mohadjer Beromi, C. Rose Kennedy, Jarod M. Younker, Alex E. Carpenter, Sarah J. Mattler, Joseph A. Throckmorton, Paul J. Chirik
Closed-loop recycling offers the opportunity to help mitigate plastic waste through reversible polymer construction and deconstruction. While examples of the chemical recycling polymers are known, few have been applied to materials derived from abundant commodity olefinic monomers that are the building blocks of ubiquitous plastic resins. Here we describe a [2+2] cycloaddition oligomerization of 1,3-butadiene to yield a previously unrealized telechelic microstructure of (1,n’-divinyl)oligocyclobutane. This material is thermally stable, has stereoregular segments arising from chain-end control, and exhibits high crystallinity even at low molecular weight. Exposure of the oligocyclobutane to vacuum in the presence of the pyridine(diimine) iron precatalyst used to synthesize it resulted in deoligomerization to generate pristine butadiene, demonstrating a rare example of closed-loop chemical recycling of an oligomeric material derived from a commodity hydrocarbon feedstock.

Funding

Firmenich

F32 GM126640

History

Email Address of Submitting Author

mberomi@princeton.edu

Institution

Princeton University

Country

United States

ORCID For Submitting Author

0000-0002-9140-9148

Declaration of Conflict of Interest

C. R. K. and P. J. C. are inventors on the patent application US 2019/0211142 A1 titled “Oligomeric and Polymeric Species Comprising Cyclobutane Units”. J. M. Y., A. E. C., S. J. M. and J. A. T. are employees of ExxonMobil Chemical Company.

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