Perfluorodecalin
IUPAC name	octadecafluoronaphthalene
Other names	Flutec PP6 F-Decalin Perfluanfene
Abbreviations	PFD
Identifiers
CAS number	306-94-5
PubChem	9386
SMILES	FC1(F)C(F)(F)C(F)(F)[C@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C1(F)F
Properties
Molecular formula	C10F18
Molar mass	462
Appearance	Clear, colorless liquid
Density	1.917
Boiling point	142 °C, 415 K, 288 °F
Solubility in water	10 ppm
Hazards
Main hazards	None
Flash point	None
Autoignition temperature	None
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Perfluorodecalin (C₁₀F₁₈) is a fluorocarbon, a derivative of decalin in which all of the hydrogen atoms are replaced by fluorine atoms. It is chemically and biologically inert, and stable up to 400°C. Several applications make use of its ability to dissolve gases.

Contents 1 Manufacture 2 Isomers 3 Medical applications 4 Other applications 5 References 6 External links

[edit] Manufacture

Commercially, perfluorodecalin is manufactured by fluorination with cobalt(III) fluoride (the Fowler process). The preferred starting material is tetralin, having fewer hydrogens than decalin itself (and so requiring less fluorine), and a liquid, unlike naphthalene (so readily handled). For most applications, several steps of purification are required after reaction.

[edit] Isomers

Perfluorodecalin exhibits cis-trans isomerism, as the tertiary fluorines atoms on the bridge carbon atoms can be either on the same side as each other (cis-isomer) or on opposite sides (trans-isomer). Both isomers are chemically and biologically inert, and are very similar in their physical properties. The most notable difference is in the melting point, which is -3.6°C for the cis-isomer, +18°C for the trans-isomer, and -6.7°C for a 50/50 mixture.^[1]

[edit] Medical applications

Of all the perfluorocarbons, perfluorodecalin has probably seen the most interest in medical applications. Most applications utilize its ability to dissolve large amounts of oxygen (100 ml of perfluorodecalin at 25°C will dissolve 49 ml of oxygen at STP [1]).

Perfluorodecalin was an ingredient in Fluosol, an artificial blood product developed by Green Cross Corporation in the 1980s. It is also being studied for use in liquid breathing. Perfluorodecalin can be applied topically, to provide extra oxygen to a specific location, to accelerate wound healing. Organs and tissues can be stored for longer in oxygenated perfluorodecalin; the "two-layer method" uses perfluorodecalin and UW solution to preserve tissue for pancreas transplants, for instance [2].

[edit] Other applications

As a development of the medical applications, perfluorodecalin is an ingredient in several cosmetic products, where its ability to dissolve oxygen is thought to revitalize skin, reducing wrinkles. The same effect has been used to grow cell cultures.^[2] Furthermore, it is sometimes used to dissolve teflon.

[edit] References

1. ^ "Flutec PP Fluorocarbon Liquids", ISC Chemicals Ltd, table E5-2/4
2. ^ King, A. T.; Mulligan, B. J.; Lowe, K. C. Biotechnology, 7, 1989, p1037-1042

[edit] External links

• Material Safety Data Sheet