Perfluorodecalin

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Perfluorodecalin
Names
Preferred IUPAC name
Octadecafluorodecahydronaphthalene
Other names
Flutec PP6
F-decalin
Perflunafene
Identifiers
3D model (
JSmol
)
Abbreviations PFD
ChEBI
ChemSpider
ECHA InfoCard
 100.005.631 Edit this at Wikidata
EC Number
  • 206-192-4
KEGG
UNII
  • InChI=1S/C10F18/c11-1-2(12,5(17,18)9(25,26)7(21,22)3(1,13)14)6(19,20)10(27,28)8(23,24)4(1,15)16 ☒N
    Key: UWEYRJFJVCLAGH-UHFFFAOYSA-N ☒N
  • trans-isomer: FC1(F)C(F)(F)C(F)(F)[C@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C1(F)F
  • cis-isomer: FC1(F)C(F)(F)C(F)(F)[C@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@]2(F)C1(F)F
Properties
C10F18
Molar mass 462
Appearance Clear, colorless liquid
Density 1.917
Boiling point 142 °C (288 °F; 415 K)
10 ppm
Hazards
Occupational safety and health (OHS/OSH):
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).
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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.

Manufacture

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.

Isomers

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.[1]

  • cis
    cis
  • trans
    trans

Medical applications

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[2]).

Perfluorodecalin was an ingredient in

pancreas transplants.[3]

It is an ingredient of Perftoran, a blood substitute that also contains perfluoro-N-(4-methylcyclohexyl)-piperidine along with a surfactant, proxanol-268. It was developed in Russia and as of 2005 was marketed there.[4]

Other applications

Due to its gas-carrying capacity, perfluorodecalin has been used to enhance oxygen delivery during cell culture.

mesophyll. Mounting leaves in perfluorodecalin significantly improves the optical qualities of the leaf, thereby enabling high-resolution imaging over twofold deeper into the mesophyll, compared with using water. The physiological impact of mounting the specimen in perfluorodecalin is also minimal compared to water.[6]

Perfluorodecalin is partially miscible with hydrocarbons[7] which makes it an attractive inert anti-solvent for some specialized applications, such as self-organization of perovskite nanocrystals into supercrystals (also known as superlattices).[8]

This compound is sometimes used to dissolve

PFA and FEP
).

References

  1. ^ "Flutec PP Fluorocarbon Liquids", ISC Chemicals Ltd, table E5-2/4
  2. ^ "Perfluorodecalin" (PDF). F2 Chemicals Ltd.
  3. PMID 16298606
    .
  4. S2CID 39902507
    .
  5. S2CID 25329991
    .
  6. PMID 20374500
    .
  7. ISSN 0021-9568
    .
  8. PMID 30676762
    .
  9. ^ "Teflon AF". Sigma Aldrich.

External links

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