4,4'-Difluorobenzophenone

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4,4'-Difluorobenzophenone
4,4'-Difluorobenzophenone.svg
Identifiers
345-92-6
ChemSpider 9206 YesY
Jmol-3D images Image
Properties
C13H8OF2
Molar mass 218.20 g/mol
Appearance Colorless Solid
Melting point 107.5 to 108.5 °C (225.5 to 227.3 °F; 380.6 to 381.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4,4’-Difluorobenzophenone is an organic compound with the formula of (FC6H4)2CO. This a colorless solid is commonly used as a precursor to PEEK, or polyetherether ketone, a so-called high performance polymer. Because PEEK is resistant to attack, it is commonly used in carbon fiber coatings and cable insulation.

Synthesis[edit]

4,4’-Difluorobenzophenone is prepared by the acylation of fluorobenzene with p-fluorobenzoyl chloride. The conversion is typically conducted in the presence of an aluminium chloride catalyst in a petroleum ether solvent.[1]

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

Uses[edit]

The polymer PEEK is generated from the reaction of 4,4'-difluorobenzophenone with the salts of 1,4-benzenediol.[2]

C6H4(ONa)2 + (FC6H4)2CO → 1/n[(C6H4O2)(C13H8O)]n + 2 NaF

References[edit]

  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. ^ David Parker, Jan Bussink, Hendrik T. van de Grampe, Gary W. Wheatley, Ernst-Ulrich Dorf, Edgar Ostlinning, Klaus Reinking "Polymers, High-Temperature" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.