Perfluorodecalin
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| Names | |||
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IUPAC name
octadecafluorodecalin
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| Other names
Flutec PP6
F-Decalin Perfluanfene |
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| Identifiers | |||
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3D model (Jmol)
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| Abbreviations | PFD | ||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.005.631 | ||
| EC Number | 206-192-4 | ||
| KEGG | |||
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PubChem CID
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| Properties | |||
| C10F18 | |||
| Molar mass | 462 | ||
| Appearance | Clear, colorless liquid | ||
| Density | 1.917 | ||
| Boiling point | 142 °C (288 °F; 415 K) | ||
| 10 ppm | |||
| Hazards | |||
| Main hazards | None | ||
| Flash point | None | ||
| None | |||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| 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.
It is manufactured by the fluorination of tetralin or decalin with cobalt(III) fluoride in the Fowler process. For most applications, several steps of purification are required after reaction.
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.
cis
trans
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 can dissolve 49 mL of oxygen at STP).
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.
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Wikipedia