4,4'-Difluorobenzophenone

4,4'-Difluorobenzophenone

Identifiers
CAS number	345-92-6
ChemSpider	9206^Y
Jmol-3D images	Image 1
SMILES O=C(c1ccc(F)cc1)c2ccc(F)cc2
InChI InChI=1S/C13H8F2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8H^Y Key: LSQARZALBDFYQZ-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₁₃H₈OF₂
Molar mass	218.20 g/mol
Appearance	Colorless Solid
Melting point	107.5–108.5 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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

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

^ R.D. Dunlop and John H. Gardner (1933). "Preparation of Fluorbenzophenones". J. Am. Chem. Soc. 55 (4): 1665–1666. doi:10.1021/ja01331a058.
^ 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.