4,4'-Difluorobenzophenone

4,4’-Difluorobenzophenone is an organic compound with the formula of (FC6H4)2CO. This 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.

4,4'-Difluorobenzophenone
Names
Preferred IUPAC name
Bis(4-fluorophenyl)methanone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.879
EC Number
  • 206-466-3
UNII
  • InChI=1S/C13H8F2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H checkY
    Key: LSQARZALBDFYQZ-UHFFFAOYSA-N checkY
  • InChI=1/C13H8F2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H
    Key: LSQARZALBDFYQZ-UHFFFAOYAZ
  • O=C(c1ccc(F)cc1)c2ccc(F)cc2
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)
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H315, H319, H335, H411
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
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

Synthesis

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]

FC6H4C(O)Cl + C6H5F → (FC6H4)2CO + HCl

Uses

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

  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.
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