Perfluorooctane

Perfluorooctane^[1]
Names
	Preferred IUPAC name Octadecafluorooctane
	Other names PF5080
Identifiers
CAS Number	307-34-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:38826 ;
ChemSpider	9018 ;
ECHA InfoCard	100.005.637
EC Number	206-199-2;
PubChem CID	9387;
UNII	6P60ZBK0QL ;
CompTox Dashboard (EPA)	DTXSID0059794 ;
	InChI 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 Key: YVBBRRALBYAZBM-UHFFFAOYSA-N ; 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;
	SMILES 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
Chemical formula	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)
Solubility in water	10 ppm
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	None
Flash point	None
Autoignition; temperature	None
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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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]

Production

Perfluorooctane can be produced 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

^ Perfluorooctane at Sigma-Aldrich
^ 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.
^ "3M Performance Fluid PF-5080". 3M.
^ "Tradeline Medical - Buy Medical Grade Perfluorooctane". tradelinemedical.net. Archived from the original on 2014-05-20.
^ 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.

[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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