Deconstruction of rubber via C–H amination and aza-Cope rearrangement

Sydney E. Towell, Maxim Ratushnyy, Lauren S. Cooke, Geoffrey M. Lewis and Aleksandr V. Zhukhovitskiy ()
Additional contact information
Sydney E. Towell: University of North Carolina at Chapel Hill
Maxim Ratushnyy: University of North Carolina at Chapel Hill
Lauren S. Cooke: University of North Carolina at Chapel Hill
Geoffrey M. Lewis: University of Michigan
Aleksandr V. Zhukhovitskiy: University of North Carolina at Chapel Hill

Nature, 2025, vol. 640, issue 8058, 384-389

Abstract: Abstract Limited strategies exist for chemical recycling of commodity diene polymers, like those found in tyres1–3. Here we apply C–H amination and backbone rearrangement of polymers to deconstruct these materials into precursors for epoxy resins. Specifically, we develop a sulfur diimide reagent4,5 that enables up to about 35% allylic amination of diene polymers and rubber. Then, we apply the cationic 2-aza-Cope rearrangement to deconstruct aminated diene polymers. In a model system, we see molecular weight reduction from 58,100 to approximately 400 g mol−1, and aminated post-consumer rubber is deconstructed over 6 hours into soluble amine-functionalized polymers, which can be utilized to prepare epoxy thermosets with similar stiffnesses to commercial bisphenol A-derived resins6. Altogether, this work demonstrates the power of C–H amination and backbone rearrangement to enable chemical recycling of post-consumer materials.

Date: 2025
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41586-025-08716-6 Abstract (text/html)
Access to the full text of the articles in this series is restricted.

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:nature:v:640:y:2025:i:8058:d:10.1038_s41586-025-08716-6

Ordering information: This journal article can be ordered from
https://www.nature.com/

DOI: 10.1038/s41586-025-08716-6

Access Statistics for this article

Nature is currently edited by Magdalena Skipper

More articles in Nature from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().