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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

Direct Defluorination and Amination of Polytetrafluoroethylene and Other Fluoropolymers by Lithium Alkylamides

by
Guillaume Herlem
1,*,
Yaelle Roina
1,
Mathieu Fregnaux
2,
Anne-Marie Gonçalves
2,
Hélène Cattey
3,
Fabien Picaud
1 and
Frédéric Auber
1
1
Laboratoire SINERGIES, CHU Jean Minjoz, UFR Sciences & Techniques, 16 Route de Gray, 25030 Besançon CEDEX, France
2
Institut Lavoisier de Versailles, Université Paris-Saclay, UVSQ, CNRS, UMR 8180, 78035 Versailles CEDEX, France
3
Institut ICMUB—CNRS 6302, Université de Bourgogne, UFR Sciences et Techniques Mirande, 9 Avenue Alain Savary, 21000 Dijon CEDEX, France
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(13), 3045; https://doi.org/10.3390/molecules29133045
Submission received: 30 April 2024 / Revised: 29 May 2024 / Accepted: 20 June 2024 / Published: 26 June 2024
(This article belongs to the Section Macromolecular Chemistry)
Versions Notes

Abstract

Polytetrafluoroethylene (PTFE) and, by extension, fluoropolymers are ubiquitous in science, life, and the environment as perfluoroalkyl pollutants (PFAS). In all cases, it is difficult to transform these materials due to their chemical inertness. Herein, we report a direct amination process of PTFE and some fluoropolymers such as polyvinylidene fluoride (PVDF) and Nafion by lithium alkylamide salts. Synthesizing these reactants extemporaneously between lithium metal and an aliphatic primary di- or triamine that also serves as a solvent leads to the rapid nucleophilic substitution of fluoride by an alkylamide moiety when in contact with the fluoropolymer. Moreover, lithium alkylamides dissolved in suitable solvents other than amines can react with fluoropolymers. This highly efficient one-pot process opens the way for further surface or bulk modification if needed, providing an easy, inexpensive, and fast experiment protocol on large scales.
Keywords: PTFE; Nafion; PVDF; fluoropolymers; amination; defluorination PTFE; Nafion; PVDF; fluoropolymers; amination; defluorination

Share and Cite

MDPI and ACS Style

Herlem, G.; Roina, Y.; Fregnaux, M.; Gonçalves, A.-M.; Cattey, H.; Picaud, F.; Auber, F. Direct Defluorination and Amination of Polytetrafluoroethylene and Other Fluoropolymers by Lithium Alkylamides. Molecules 2024, 29, 3045. https://doi.org/10.3390/molecules29133045

AMA Style

Herlem G, Roina Y, Fregnaux M, Gonçalves A-M, Cattey H, Picaud F, Auber F. Direct Defluorination and Amination of Polytetrafluoroethylene and Other Fluoropolymers by Lithium Alkylamides. Molecules. 2024; 29(13):3045. https://doi.org/10.3390/molecules29133045

Chicago/Turabian Style

Herlem, Guillaume, Yaelle Roina, Mathieu Fregnaux, Anne-Marie Gonçalves, Hélène Cattey, Fabien Picaud, and Frédéric Auber. 2024. "Direct Defluorination and Amination of Polytetrafluoroethylene and Other Fluoropolymers by Lithium Alkylamides" Molecules 29, no. 13: 3045. https://doi.org/10.3390/molecules29133045

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