Hydrogenative Depolymerization of Nylons

Amit Kumar, Niklas von Wolff, Michael Rauch, You Quan Zou, Guy Shmul, Yehoshoa Ben-David, Gregory Leitus, Liat Avram, David Milstein

Research output: Contribution to journalArticle

Abstract

The widespread crisis of plastic pollution demands discovery of new and sustainable approaches to degrade robust plastics such as nylons. Using a green and sustainable approach based on hydrogenation, in the presence of a ruthenium pincer catalyst at 150 °C and 70 bar H2, we report here the first example of hydrogenative depolymerization of conventional, widely used nylons and polyamides, in general. Under the same catalytic conditions, we also demonstrate the hydrogenation of a polyurethane to produce diol, diamine, and methanol. Additionally, we demonstrate an example where monomers (and oligomers) obtained from the hydrogenation process can be dehydrogenated back to a poly(oligo)amide of approximately similar molecular weight, thus completing a closed loop cycle for recycling of polyamides. Based on the experimental and density functional theory studies, we propose a catalytic cycle for the process that is facilitated by metal-ligand cooperativity. Overall, this unprecedented transformation, albeit at the proof of concept level, offers a new approach toward a cleaner route to recycling nylons.

Original languageEnglish
Pages (from-to)14267-14275
Number of pages9
JournalJournal of the American Chemical Society
Volume142
Issue number33
DOIs
Publication statusPublished - Aug 19 2020

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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  • Cite this

    Kumar, A., von Wolff, N., Rauch, M., Zou, Y. Q., Shmul, G., Ben-David, Y., Leitus, G., Avram, L., & Milstein, D. (2020). Hydrogenative Depolymerization of Nylons. Journal of the American Chemical Society, 142(33), 14267-14275. https://doi.org/10.1021/jacs.0c05675