Perfluorooctane

Perfluorooctane, also known as octadecafluorooctane, is a fluorocarbon liquid—a perfluorinated derivative of the hydrocarbon octane. It can be a good substitute for insulating oil in high voltage electronics. In addition to heat transfer applications, it has also been used as a breathable fluid in partial liquid ventilation.[2]

Perfluorooctane[1]
Structural formula of perfluorooctane
Space-filling model of perfluorooctane
Names
Preferred IUPAC name
Octadecafluorooctane
Other names
PF5080
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.637
EC Number
  • 206-199-2
UNII
  • InChI=1S/C8F18/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)26 checkY
    Key: YVBBRRALBYAZBM-UHFFFAOYSA-N checkY
  • InChI=1/C8F18/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)26
    Key: YVBBRRALBYAZBM-UHFFFAOYAG
  • FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
Properties
C8F18
Molar mass 438.06 g/mol
Appearance Clear, colorless liquid
Density 1.766 g/mL
Melting point −25 °C (−13 °F; 248 K)
Boiling point 103 to 104 °C (217 to 219 °F; 376 to 377 K)
10 ppm
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 None
Flash point None
None
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

Manufacture

Perfluorooctane can be manufactured by the Fowler process or by electrochemical fluorination.

Fowler Process

The Fowler process involves moderating the action of elemental fluorine with cobalt fluoride in the gas phase from octane.

Electrochemical fluorination

Electrolysis in hydrogen fluoride of nonanoic acid will produce both perfluorononanoic acid and perfluorooctane. Perfluorooctane manufactured this way is marketed under the name PF5080 (or FC77) by 3M as part of their Fluorinert range of heat transfer fluids.[3]

Applications

Perfluorooctane is chemically inert, but has useful physical properties, leading to its employment in diverse areas:

  • Heat transfer agent[4]
  • Dielectric fluid
  • Tamponade in eye surgery[5]

References
  1. Perfluorooctane at Sigma-Aldrich
  2. H. Proquitté; M. Rüdiger; R. R. Wauer & G. Schmalisch (2003). "Breathing gas perfluorocarbon measurements using an absorber filled with zeolites". British Journal of Anaesthesia. 91 (5): 736–8. doi:10.1093/bja/aeg247. PMID 14570799.
  3. "3M Performance Fluid PF-5080". 3M.
  4. "Tradeline Medical - Buy Medical Grade Perfluorooctane". tradelinemedical.net. Archived from the original on 2014-05-20.
  5. Claes C, Worst J, Zivojnovic R (1992). "Retinal detachment surgery following implantation of a keratoprosthesis. A case report". Bulletin de la Société Belge d'Ophtalmologie. 243: 167–169. PMID 1302147.
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