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A New Route to Perfluoro(Propyl Vinyl Ether) Monomer: Synthesis of Perfluoro(2‐propoxypropionyl) Fluoride from Non‐Fluorinated Compounds
Author(s) -
Okazoe Takashi,
Watanabe Kunio,
Itoh Masahiro,
Shirakawa Daisuke,
Murofushi Hidenobu,
Okamoto Hidekazu,
Tatematsu Shin
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(20010226)343:2<215::aid-adsc215>3.0.co;2-7
Subject(s) - chemistry , fluoride , fluorine , vinyl ether , monomer , organic chemistry , ether , alcohol , polymer chemistry , copolymer , polymer , inorganic chemistry
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.