Perfluorodecalin

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.

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 at STP).

Perfluorodecalin was an ingredient in Fluosol, an artificial blood product developed by Green Cross Corporation in the 1980s. It is also being studied for use in liquid breathing, and alternative methods for emergency treatment of respiratory failure. Perfluorodecalin can be applied topically, 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 to preserve tissue for pancreas transplants.

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.

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. 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 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).

This compound is sometimes used to dissolve Teflon AF (not to be confused with other Teflons, as PTFE, PFA and FEP).

References

References

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2. "Perfluorodecalin". F2 Chemicals Ltd.
3. Okabe R, Chen-Yoshikawa TF, Yoneyama Y, Yokoyama Y, Tanaka S, Yoshizawa A, Thompson WL, Kannan G, Kobayashi E, Date H, Takebe T. Mammalian enteral ventilation ameliorates respiratory failure. ''Med''. 2021 Jun 11;2(6):773-783.e5. {{doi. 10.1016/j.medj.2021.04.004 {{pmid. 35590139
4. (2005). "Two-Layer Method in Short-Term Pancreas Preservation for Successful Islet Isolation". Transplantation Proceedings.
5. (2005). "Clinical results of Perftoran application: present and future.". Artificial Cells, Blood Substitutes, and Biotechnology.
6. (1989). "Perfluorochemicals and Cell Culture". Nature Biotechnology.
7. (November 2025). "Perfluorodecalin enhances in vivo confocal microscopy resolution of Arabidopsis thaliana mesophyll". New Phytologist.
8. (July 1, 1987). "Mutual binary solubilities: perfluorodecalin/hydrocarbons". Journal of Chemical & Engineering Data.
9. (2019-02-07). "Investigation into the Photoluminescence Red Shift in Cesium Lead Bromide Nanocrystal Superlattices". The Journal of Physical Chemistry Letters.
10. "Teflon AF". Sigma Aldrich.