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Perfluorodecalin
Perfluorodecaline.jpg
IUPAC name
Other names Flutec PP6
F-Decalin
Perfluanfene
Abbreviations PFD
Identifiers
CAS number 306-94-5
PubChem 9386
SMILES
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

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.

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]

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].

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.

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

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