Perfluorodecalin () is a

fluorocarbon Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often has distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Fluorocarbons and their derivatives are commerci ...

, a derivative of

decalin Decalin (decahydronaphthalene, also known as bicyclo .4.0ecane and sometimes decaline), a bicyclic organic compound, is an industrial solvent. A colorless liquid with an aromatic odor, it is used as a solvent for many resins or fuel additives. I ...

in which all of the

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

atom Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, and ...

s are replaced by

fluorine Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reacti ...

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 Tetralin (1,2,3,4-tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12. It is a partially hydrogenated derivative of naphthalene. It is a colorless liquid that is used as a hydrogen-donor solvent. Production Tetralin is pro ...

with

cobalt(III) fluoride Cobalt(III) fluoride is the inorganic compound with the formula . Hydrates are also known. The anhydrous compound is a hygroscopic brown solid. It is used to synthesize organofluorine compounds. The related cobalt(III) chloride is also known but ...

in the

Fowler process The Fowler process is an industry and laboratory route to fluorocarbons, by fluorinating hydrocarbons or their partially fluorinated derivatives in the vapor phase over cobalt(III) fluoride. Background The Manhattan Project required the producti ...

. 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. File:Cis-Perfluordecalin.svg, ''cis'' File:Trans-Perfluordecalin.svg, ''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 Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

STP STP may refer to: Places * São Tomé and Príncipe (ISO 3166-1 alpha-3 code, IOC country code, and FIFA country code STP) * St Pancras railway station, London St Pancras (Domestic) railway station (National Rail code STP) * St. Paul Downtown Air ...

). Perfluorodecalin was an ingredient in

Fluosol A blood substitute (also called artificial blood or blood surrogate) is a substance used to mimic and fulfill some functions of biological blood. It aims to provide an alternative to blood transfusion, which is transferring blood or blood-based ...

, an

artificial blood A blood substitute (also called artificial blood or blood surrogate) is a substance used to mimic and fulfill some functions of biological blood. It aims to provide an alternative to blood transfusion, which is transferring blood or blood-based ...

product developed by Green Cross Corporation in the 1980s. It is also being studied for use in

liquid breathing Liquid breathing is a form of respiration in which a normally air-breathing organism breathes an oxygen-rich liquid (such as a perfluorocarbon), rather than breathing air. By selecting a liquid that is capable of holding large amounts of oxyg ...

. Perfluorodecalin can be applied

topical A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes ...

ly, to provide extra oxygen to a specific location, to accelerate wound healing. Organs and tissues can be stored for longer in oxygenated perfluorodecalin; the "two-layer method" uses perfluorodecalin and

UW solution Viaspan was the trademark under which the University of Wisconsin cold storage solution (also known as University of Wisconsin solution or UW solution) was sold. Currently, UW solution is sold under the Belzer UW trademark and others like Bel-Gen o ...

to preserve tissue for

pancreas transplant A pancreas transplant is an organ transplant that involves implanting a healthy pancreas (one that can produce insulin) into a person who usually has diabetes. Overview Because the pancreas is a vital organ, performing functions necessary in the ...

s. It is an ingredient of Perftoran, a blood substitute that also contains perfluoro-N-(4-methylcyclohexyl)-piperidine along with a

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

, proxanol-268. It was developed in Russia and as of 2005 was marketed there.

Other applications

Due to its gas-carrying capacity, perfluorodecalin has been used to enhance oxygen delivery during cell culture. Perfluorodecalin has also been shown to dramatically enhance '' in vivo '' microscopy resolution of airspace-containing tissues such as

mesophyll A leaf ( : leaves) is any of the principal appendages of a vascular plant stem, usually borne laterally aboveground and specialized for photosynthesis. Leaves are collectively called foliage, as in "autumn foliage", while the leaves, ste ...

. 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. Perfluorodecalin is partially miscible with

hydrocarbons In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...

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 A superlattice is a periodic structure of layers of two (or more) materials. Typically, the thickness of one layer is several nanometers. It can also refer to a lower-dimensional structure such as an array of quantum dots or quantum wells. Di ...

). This compound is sometimes used to dissolve

Teflon AF Polytetrafluoroethylene (PTFE) is a synthetic fluoropolymer of tetrafluoroethylene that has numerous applications. It is one of the best-known and widely applied PFAS. The commonly known brand name of PTFE-based composition is Teflon by Chemou ...

(not to be confused with other Teflons, as

PTFE Polytetrafluoroethylene (PTFE) is a synthetic fluoropolymer of tetrafluoroethylene that has numerous applications. It is one of the best-known and widely applied PFAS. The commonly known brand name of PTFE-based composition is Teflon by Chemour ...

, PFA and FEP).

References

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External links

Safety Data Sheet
Perfluoroalkanes Halogenated solvents Coolants