Perfluorooctane, also known as octadecafluorooctane, is a
fluorocarbon
Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often has distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Fluorocarbons and their derivatives are commerci ...
liquid—a perfluorinated derivative of the
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
octane
Octane is a hydrocarbon and an alkane with the chemical formula , and the condensed structural formula . Octane has many structural isomers that differ by the amount and location of branching in the carbon chain. One of these isomers, 2,2,4-Tri ...
. 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.
Manufacture
Perfluorooctane can be manufactured by the
Fowler process or by
electrochemical fluorination Electrochemical fluorination (ECF), or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds.G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, ...
.
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
Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock i ...
of
nonanoic acid
Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, ...
will produce both
perfluorononanoic acid
Perfluorononanoic acid, or PFNA, is a synthetic perfluorinated carboxylic acid and fluorosurfactant that is also an environmental contaminant found in people and wildlife along with PFOS and PFOA.
Chemistry and properties
In acidic form it is a ...
and perfluorooctane. Perfluorooctane manufactured this way is marketed under the name PF5080 (or FC77) by
3M as part of their
Fluorinert
Fluorinert is the trademarked brand name for the line of electronics coolant liquids sold commercially by 3M. As perfluorinated compounds (PFCs), all Fluorinert variants have an extremely high Global Warming Potential (GWP), so should be used wit ...
range of heat transfer fluids.
Applications
Perfluorooctane is chemically inert, but has useful physical properties, leading to its employment in diverse areas:
* Heat transfer agent
* Dielectric fluid
* Tamponade in eye surgery
References
{{reflist
Perfluoroalkanes
Halogenated solvents
Coolants