Perfluoromethyldecalin

Perfluoromethyldecalin is a fluorocarbon liquid—a perfluorinated derivative of the hydrocarbon methyldecalin. It is chemically and biologically inert. It is mainly of interest as a blood substitute, exploiting the high solubility of air in this solvent.[1]

Perfluoromethyldecalin
Names
Other names
Flutec PP9
Identifiers
ChemSpider
ECHA InfoCard 100.005.630
EC Number
  • 206-191-9
UNII
Properties
C11F20
Molar mass 512.089 g·mol−1
Appearance Clear, colorless liquid
Density 1.972 g/mL
Melting point −70 °C (−94 °F; 203 K)
Boiling point 160 °C (320 °F; 433 K)
10 ppm
Hazards
Main hazards None
Flash point None
None
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Structural Isomers

Most commercially available perfluoromethyldecalin consists of both perfluoro-1-methyldecalin and perfluoro-2-methyldecalin. Each structural isomer has its own CAS registry number (RN). The mixture also has a unique RN.

Name Perfluoro-1-methyldecalin Perfluoro-2-methyldecalin
CAS registry number 306-92-3 306-95-6
IUPAC Name 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluorodecahydro-8-(trifluoromethyl)naphthalene 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,8,8,8a-heptadecafluorodecahydro-7-(trifluoromethyl)naphthalene
Structure
SMILES FC(F)(F)C1(F)C(F)(F)C2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(F)(F)C1(F)F FC(F)(F)C1(F)C(F)(F)C2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(F)(F)C1(F)F

The two isomers are chemically and physically very similar.

Manufacture

Perfluoromethyldecalin can be manufactured by the Fowler process, which involves moderating the action of elemental fluorine with cobalt fluoride in the gas phase from methylnaphthalene. Methylnaphthalene is preferred as the starting material vs methyldecalin as is consumes less fluorine.[2]

Properties

Perfluoromethyldecalin is chemically inert and thermally stable (to over 400 °C). It is non-toxic,[3] so much so that it has been widely evaluated as a blood substitute.

It is a colorless liquid, with a relatively high density, low viscosity, and low surface tension that evaporates rapidly for a compounds with its high molecular weight. It is a relatively good solvent for gases, but a poor solvent for solids and liquids.[4]

In common with other cyclic perfluorocarbons, perfluorodecalin can be detected at extremely low concentrations; it has therefore been proposed for use as a perfluorocarbon tracer.[5] Its higher boiling makes it suitable for use in water flow.[6]

Other applications include use as a heat transfer agent and a dielectric fluid.

References
  1. Siegemund, G.; Schwertfeger, W.; Feiring, A.; Smart, B.; Behr, F.; Vogel, H.; McKusick, B. "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349.
  2. Sandford G (2003). "Perfluoroalkanes". Tetrahedron. 59 (4): 437–454. doi:10.1016/s0040-4020(02)01568-5.
  3. "FLUTEC PP9". F2 Chemicals.
  4. "Solubility in Liquids" (PDF). F2 Chemicals.
  5. Begley P.; Foulger B.; Simmonds P. (1988). "Femtogram detection of perfluorocarbon tracers using capillary gas chromatography-electron-capture negative ion chemical ionisation mass spectrometry". J. Chromatogr. 445 (1): 119–128. doi:10.1016/s0021-9673(01)84513-1. PMID 3215967.
  6. Fogelqvist E, Krysell M, Öhman P (1989). "Evaluation of perfluoromethyldecalin as a deliberate tracer for the study of water mixing processes". Marine Chemistry. 26 (4): 339–349. doi:10.1016/0304-4203(89)90039-x.
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