Perfluoromethyldecalin

Perfluoromethyldecalin

Names
Other names Flutec PP9
Identifiers
CAS Number	306-92-3
ChemSpider	17340230 Y
EC Number	206-191-9
PubChem	39977
InChI Key: LWRNQOBXRHWPGE-UHFFFAOYSA-N
Properties
Chemical formula	C11F20
Molar mass	512.09 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
Vapor pressure	{{{value}}}
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.

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	200px	220px
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 chemicals 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. Rearrangement during the fluorination process leads to a mixture of isomers, whichever methylnaphthalene isomer is used.

Properties

Perfluoromethyldecalin is chemically inert and thermally stable (to over 400 °C). It is non-toxic, 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.

In common with other cyclic perfluorocarbons, perfluorodecalin can be detected at extremely low concentrations, making it ideal as a tracer. Its higher boiling makes it suitable for use in water flow.

Applications

• Blood substitute
• Heat transfer agent
• Dielectric fluid
• Perfluorocarbon tracer