Perfluorooctane, also known as octadecafluorooctane, is a
fluorocarbon
Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often have distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Several fluorocarbons and their derivatives are ...
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 Hydrophobe, hydrophobic; their odor is usually fain ...
octane
Octane is a hydrocarbon and also an alkane with the chemical formula C8H18, and the condensed structural formula CH3(CH2)6CH3. Octane has many structural isomers that differ by the location of branching in the carbon chain. One of these isomers ...
. 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.
Production
Perfluorooctane can be produced by the
Fowler process The Fowler process is an industry and laboratory route to fluorocarbons, by fluorinating hydrocarbons or their partially fluorinated derivatives in the vapor phase over cobalt(III) fluoride.
Background
The Manhattan Project required the productio ...
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 The Fowler process is an industry and laboratory route to fluorocarbons, by fluorinating hydrocarbons or their partially fluorinated derivatives in the vapor phase over cobalt(III) fluoride.
Background
The Manhattan Project required the productio ...
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 chemistry, inorganic compound with chemical formula . It is a very poisonous, colorless gas or liquid that dissolves in water to yield hydrofluoric acid. It is the principal industrial source of fluori ...
of
nonanoic acid
Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula . 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, but very sol ...
will produce both
perfluorononanoic acid
Perfluorononanoic acid, or PFNA, is a synthetic perfluorinated carboxylic acid and fluorosurfactant that is also a persistent organic pollutant.
Chemistry and properties
In acidic form it is a highly reactive strong acid. In its conjugate base fo ...
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 with ...
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