perfluoromethyldecalin
{{chembox
| IUPACNames = {{ubl
|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
}}
|ImageFileL1 = Perfluoro-1-methyldecalin.svg
|ImageCaptionL1 = Perfluoro-1-methyldecalin
|ImageFileR1 = Perfluoro-2-methyldecalin.svg
|ImageCaptionR1 = Perfluoro-2-methyldecalin
|OtherNames=Flutec PP9
|Section1={{Chembox Identifiers
| index_label = Mixture
| index1_label = 1-methyl
| index2_label = 2-methyl
| index_comment =
| index1_comment = Perfluoro-1-methyldecalin
| index2_comment = Perfluoro-2-methyldecalin
| CASNo = 51294-16-7
| CASNo1 = 306-92-3
| CASNo2 = 306-95-6
| PubChem = 39977
| PubChem1 =
| PubChem2 =
| ChemSpiderID = 17340230
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 =
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2 =
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo2_Ref = {{cascite|correct|CAS}}
| SMILES1 = 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
| SMILES2 = 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
| UNII = VWJ68OB6TM
| InChI1 = 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
| InChIKey1 = LWRNQOBXRHWPGE-UHFFFAOYSA-N
| InChI2 = 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
| InChIKey2 = UYXKOSTWUQXOMT-UHFFFAOYSA-N
| EINECS = 206-191-9
}}
|Section2={{Chembox Properties
| C=11 | F=20
| Appearance=Clear, colorless liquid
| Density=1.972 g/mL
| MeltingPtC=-70
| BoilingPtC=160
| Solubility=10 ppm
}}
|Section3= {{Chembox Hazards
| MainHazards=None
| FlashPt=None
| AutoignitionPt=None
}}
}}
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.{{ Ullmann | author = Siegemund, G. | author2 = Schwertfeger, W. | author3 = Feiring, A. | author4 = Smart, B. | author5 = Behr, F. | author6 = Vogel, H. | author7 = McKusick, B. | title = Fluorine Compounds, Organic | doi = 10.1002/14356007.a11_349 }}
Structural isomers
Commercially available perfluoromethyldecalin can consist of mixtures of both perfluoro-1-methyldecalin and perfluoro-2-methyldecalin or each isomer individually. Each structural isomer has its own CAS registry number, as does the mixture.
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.{{cite journal
|author=Sandford G
|title=Perfluoroalkanes
|journal=Tetrahedron
|volume=59 |pages=437–454 |year=2003
|issue=4
|doi=10.1016/s0040-4020(02)01568-5}}
Properties
Perfluoromethyldecalin is chemically inert and thermally stable (to over 400 °C). It has been 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.{{cite web | url = http://www.f2chemicals.com/pdf/technical/Liquid%20solubility.pdf | title = Solubility in Liquids | publisher = F2 Chemicals}}
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.{{cite journal | title = Femtogram detection of perfluorocarbon tracers using capillary gas chromatography-electron-capture negative ion chemical ionisation mass spectrometry. | year = 1988 | author= Begley P. | author2= Foulger B. | author3= Simmonds P. | journal = J. Chromatogr. | volume = 445 | issue = 1 | pages = 119–128 | doi=10.1016/s0021-9673(01)84513-1| pmid = 3215967 }} Its higher boiling makes it suitable for use in water flow.{{cite journal
|vauthors=Fogelqvist E, Krysell M, Öhman P |title=Evaluation of perfluoromethyldecalin as a deliberate tracer for the study of water mixing processes
|journal=Marine Chemistry
|volume=26 |pages=339–349 |year=1989
|issue=4
|doi=10.1016/0304-4203(89)90039-x|bibcode=1989MarCh..26..339F
}}
Other applications include use as a heat transfer agent and a dielectric fluid.