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Title Selective Lanthanide-Organic Catalyzed Depolymerization of Nylon-6 to ε-Caprolactam
ID_Doc 17524
Authors Wursthorn, L; Beckett, K; Rothbaum, JO; Cywar, RM; Lincoln, C; Kratish, Y; Marks, TJ
Title Selective Lanthanide-Organic Catalyzed Depolymerization of Nylon-6 to ε-Caprolactam
Year 2023
Published Angewandte Chemie-International Edition, 62, 4
DOI 10.1002/anie.202212543
Abstract Nylon-6 is selectively depolymerized to the parent monomer epsilon-caprolactam by the readily accessible and commercially available lanthanide trisamido catalysts Ln(N(TMS)(2))(3) (Ln=lanthanide). The depolymerization process is solvent-free, near quantitative, highly selective, and operates at the lowest Nylon-6 to epsilon-caprolactam depolymerization temperature reported to date. The catalytic activity of the different lanthanide trisamides scales with the Ln(3+) ionic radius, and this process is effective with post-consumer Nylon-6 as well as with Nylon-6+polyethylene, polypropylene or polyethylene terephthalate mixtures. Experimental kinetic data and theoretical (DFT) mechanistic analyses suggest initial deprotonation of a Nylon terminal amido N-H bond, which covalently binds the catalyst to the polymer, followed by a chain-end back-biting process in which epsilon-caprolactam units are sequentially extruded from the chain end.
Author Keywords Chemical Recycling; Green Chemistry; Lanthanides; Nylon; Plastic
Index Keywords Index Keywords
Document Type Other
Open Access Open Access
Source Science Citation Index Expanded (SCI-EXPANDED); Current Chemical Reactions (CCR-EXPANDED)
EID WOS:000899133100001
WoS Category Chemistry, Multidisciplinary
Research Area Chemistry
PDF https://rss.onlinelibrary.wiley.com/doi/am-pdf/10.1002/anie.202212543
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