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A New Route to Perfluoro(Propyl Vinyl Ether) Monomer: Synthesis of Perfluoro(2‐propoxypropionyl) Fluoride from Non‐Fluorinated Compounds
Authors:Takashi Okazoe  Kunio Watanabe  Masahiro Itoh  Daisuke Shirakawa  Hidenobu Murofushi  Hidekazu Okamoto  Shin Tatematsu
Abstract:Perfluoro(2‐propoxypropionyl) fluoride ( 1a ), which is the precursor of the perfluorinated propyl vinyl ether (PPVE) monomer of an industrially important perfluoroalkoxy copolymer (PFA), was synthesized by utilizing direct fluorination of the non‐fluorinated counterpart for the first time. The partially‐fluorinated ester 7 synthesized from the desired perfluorinated acid fluoride 1a itself and the non‐fluorinated alcohol 5 , which has a carbon skeleton corresponding to the desired compound 1a , was perfluorinated by liquid‐phase direct fluorination with elemental fluorine. Degradation of the resulting perfluorinated ester 8 gave 2 mols of the desired acid fluoride 1a . In a sense, this process can be called self‐multiplication of a perfluorinated acid fluoride from a non‐fluorinated alcohol.
Keywords:acyl fluorides  direct fluorination  fluorine  perfluoropolymers  perfluoro(propyl vinyl ether)  synthesis design
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