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4,4'-Difluorobenzophenone

4,4'-Difluorobenzophenone
Identifiers
CAS number [345-92-6]
Properties
Molecular formula C13H8OF
Molar mass 218.20 g/mol
Appearance Colorless Solid
Melting point

107.5-108.5 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

4,4’-difluorobenzophenone is a compound with the chemical formula of (FC6H4)2CO. It is a colorless solid that is commonly used as a precursor to PEEK, or polyetherether ketone. PEEK is a semi-crystalline polymer that is insoluble in all materials except in harsh acidic conditions. Because PEEK is resistant to attack, it is commonly used in carbon fiber coatings and cable insulation.

Synthesis

The compound is prepared by condensation with p-fluorobenzoyl chloride and fluorobenzene with an aluminium chloride catalyst using a petroleum ether solvent.[1]

FC6H5C(O)Cl + C6H5F → (FC6H4)2CO + HCl

Uses

A derivative of 4,4’-difluorobenzophenone is used in the polymer PEEK, where 4,4'-difluorobenzophenone is used for polymerization across the fluorine-carbon bond when an oxygen anion is used to generate fluoride as the leaving group. PEEK is formed via condensation of 4,4’-difluorobenzophenone with 1,4-benzenediol.[2]

C6H4(OH)2 + (FC6H4)2CO → 1/n[(C6H4O2)(C13H8O)]n + 2HF

References

  1. ^ R.D. Dunlop and John H. Gardner (1933). "Preparation of Fluorbenzophenones". J. Am. Chem. Soc. 55 (4): 1665-1666. doi:10.1021/ja01331a058. 
  2. ^ “Polymers, High Temperature – Polyaryetherkeytones; Chapter 3”. Ullmann’s Encyclopedia of Industrial Chemistry. David Parker and Gary W. Wheatley. 2002, Wiley-VCH Verlag GmbH&Co. doi: 10.1002/14356007.a21_449
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