Chinese Journal of Applied Chemistry ›› 2024, Vol. 41 ›› Issue (4): 512-520.DOI: 10.19894/j.issn.1000-0518.230324

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Synthesis of Functional Perfluorophosphonate Vinyl Ether

Ying-Ying SONG1, Wei GE1, Xiang SHI2, Gang WEI2, Bing LI1, Chang-Kun LI1(), Chang-Ming DONG1(), Xue-Song JIANG1   

  1. 1.School of Chemistry and Chemical Engineering,Shanghai Jiao Tong University,Shanghai 200240,China
    2.State Key Laboratory of Fluorinated Functional Membrane Materials,Shandong Dongyue Future Hydrogen Energy Co. Ltd. ,Zibo 256401,China
  • Received:2023-10-19 Accepted:2024-02-01 Published:2024-04-01 Online:2024-04-28
  • Contact: Chang-Kun LI,Chang-Ming DONG
  • About
  • Supported by:
    the National Key R&D Program of China(2021YFB4001100)


Herein, a new synthesis method of perfluorophosphonate vinyl ether for phosphonic acid-based proton exchange membrane was reported. Perfluorinated sulfonyl vinyl ether was converted to perfluorinated sulfinic acid vinyl ether by sodium borohydride reduction and sulfuric acid acidification, and followed by iodination to obtain perfluorovinyl ether iodide with 58% yield. Based on the metal-halogen exchange reaction, perfluorovinyl ether iodide and halogenated (chlorine/bromine) phosphate ester were dissolved under nitrogen atmosphere, and then n-butyl lithium or Grignard reagent was dropwise added to the reaction at low temperature; according to the Michaelis-Becker reaction, perfluorovinyl ether iodide was mixed with diethyl phosphite, then sodium or lithium bis(trimethylsilyl)amide was slowly added, both methods could successfully produce perfluorophosphonate vinyl ether with yields of 34% and 25%, respectively. This strategy avoids the protection of unsaturated double bonds with highly toxic chlorine gas or liquid bromine, greatly simplifies the synthesis process compared to the reported ones, and provides a new way to synthesize functional perfluorinated vinyl ether monomers.

Key words: Perfluorovinyl ether iodide, Michaelis-Becker reaction, Perfluorophosphonate vinyl ether

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