Perfluoromethyldecalin

Perfluoromethyldecalin
Perfluoro-1-methyldecalin	Perfluoro-2-methyldecalin
Names
	IUPAC names 1-methyl: 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluorodecahydro-8-(trifluoromethyl)naphthalene; 2-methyl: 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,8,8,8a-heptadecafluorodecahydro-7-(trifluoromethyl)naphthalene;
	Other names Flutec PP9
Identifiers
	Compounds; Mixture; 1-methyl: Perfluoro-1-methyldecalin; 2-methyl: Perfluoro-2-methyldecalin;
CAS Number	Mixture: 51294-16-7 ; 1-methyl: 306-92-3 ; 2-methyl: 306-95-6 ;
3D model (JSmol)	1-methyl: Interactive image; 2-methyl: Interactive image;
ChemSpider	Mixture: 17340230 ;
ECHA InfoCard	100.005.630
EC Number	Mixture: 206-191-9;
PubChem CID	Mixture: 39977;
UNII	Mixture: VWJ68OB6TM;
CompTox Dashboard (EPA)	Mixture: DTXSID30897561 ;
	InChI 1-methyl: InChI=1S/C11F20/c12-1-2(13,6(19,20)10(27,28)9(25,26)4(1,15)16)5(17,18)8(23,24)7(21,22)3(1,14)11(29,30)31 Key: LWRNQOBXRHWPGE-UHFFFAOYSA-N; 2-methyl: InChI=1S/C12F22/c13-1-2(14,11(29,30)31)4(16,12(32,33)34)8(23,24)6(19,20)3(1,15)7(21,22)10(27,28)9(25,26)5(1,17)18 Key: UYXKOSTWUQXOMT-UHFFFAOYSA-N;
	SMILES 1-methyl: FC1(C(F)(C2(C(F)(C(F)(C(F)(C(F)(C2(C(F)(C1(F)F)F)F)F)F)F)F)F)C(F)(F)F)F; 2-methyl: 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;
Properties
Chemical formula	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)
Solubility in water	10 ppm
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	None
Flash point	None
Autoignition; temperature	None
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

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, as does the mixture. 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 has been evaluated as a blood substitute.[1]

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.[3]

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.[4] Its higher boiling makes it suitable for use in water flow.[5]

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

References

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.
Sandford G (2003). "Perfluoroalkanes". Tetrahedron. 59 (4): 437–454. doi:10.1016/s0040-4020(02)01568-5.
"Solubility in Liquids" (PDF). F2 Chemicals.
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.
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. Bibcode:1989MarCh..26..339F. doi:10.1016/0304-4203(89)90039-x.

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[Ullmann-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] "Solubility in Liquids" (PDF). F2 Chemicals.

[4] 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.

[5] 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. Bibcode:1989MarCh..26..339F. doi:10.1016/0304-4203(89)90039-x.