Perfluorodecalin

Perfluorodecalin
Names
	Preferred IUPAC name Octadecafluorodecahydronaphthalene
	Other names Flutec PP6; F-decalin; Perflunafene
Identifiers
CAS Number	306-94-5 ;
3D model (JSmol)	trans-isomer: Interactive image; cis-isomer: Interactive image;
Abbreviations	PFD
ChEBI	CHEBI:38848 ;
ChemSpider	13888074 ;
ECHA InfoCard	100.005.631
EC Number	206-192-4;
KEGG	D08338 ;
PubChem CID	9386;
UNII	54A06VV62N ;
CompTox Dashboard (EPA)	DTXSID0046511 ;
	InChI 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 Key: UWEYRJFJVCLAGH-UHFFFAOYSA-N ;
	SMILES 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
Chemical formula	C10F18
Molar mass	462
Appearance	Clear, colorless liquid
Density	1.917
Boiling point	142 °C (288 °F; 415 K)
Solubility in water	10 ppm
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	None
Flash point	None
Autoignition; temperature	None
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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
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 Fluosol, an artificial blood product developed by Green Cross Corporation in the 1980s. It is also being studied for use in liquid breathing. 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.^[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.^[5] 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.^[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 Teflon AF^[9] (not to be confused with other Teflons, as PTFE, PFA and FEP).

References

^ "Flutec PP Fluorocarbon Liquids", ISC Chemicals Ltd, table E5-2/4
^ "Perfluorodecalin" (PDF). F2 Chemicals Ltd.
^ For instance, Witkowski, P.; Liu, Z.; Guo, Q.; Poumian-Ruiz, E.; Cernea, S.; Herold, K.; Hardy, M.A. (2005). "Two-Layer Method in Short-Term Pancreas Preservation for Successful Islet Isolation". Transplantation Proceedings. 37 (8): 3398–401. doi:10.1016/j.transproceed.2005.09.050. PMID 16298606.
^ Maevsky, E; Ivanitsky, G; Bogdanova, L; Axenova, O; Karmen, N; Zhiburt, E; Senina, R; Pushkin, S; Maslennikov, I; Orlov, A; Marinicheva, I (2005). "Clinical results of Perftoran application: present and future". Artificial Cells, Blood Substitutes, and Biotechnology. 33 (1): 37–46. doi:10.1081/BIO-200046654. PMID 15768564. S2CID 39902507.
^ King, A. T.; Mulligan, B. J.; Lowe, K. C. (1989). "Perfluorochemicals and Cell Culture". Nature Biotechnology. 7 (10): 1037–1042. doi:10.1038/nbt1089-1037. S2CID 25329991.
^ Littlejohn, George R.; Gouveia, João D.; Edner, Christoph; Smirnoff, Nicholas; Love, John (2010). "Perfluorodecalin enhances in vivo confocal microscopy resolution of Arabidopsis thaliana mesophyll" (PDF). New Phytologist. 186 (4): 1018–25. doi:10.1111/j.1469-8137.2010.03244.x. hdl:10026.1/9344. PMID 20374500.
^ Bernardo-Gil, Gabriela S.; Soares, Luis J. S. (July 1, 1987). "Mutual binary solubilities: perfluorodecalin/hydrocarbons". Journal of Chemical & Engineering Data. 32 (3): 327–329. doi:10.1021/je00049a014. hdl:1822/16619. ISSN 0021-9568.
^ Baranov, Dmitry; Toso, Stefano; Imran, Muhammad; Manna, Liberato (2019-02-07). "Investigation into the Photoluminescence Red Shift in Cesium Lead Bromide Nanocrystal Superlattices". The Journal of Physical Chemistry Letters. 10 (3): 655–660. doi:10.1021/acs.jpclett.9b00178. ISSN 1948-7185. PMC 6477804. PMID 30676762.
^ "Teflon AF". Sigma Aldrich.

External links

Safety Data Sheet Archived 2016-06-16 at the Wayback Machine

[1] "Flutec PP Fluorocarbon Liquids", ISC Chemicals Ltd, table E5-2/4

[2] "Perfluorodecalin" (PDF). F2 Chemicals Ltd.

[3] For instance, Witkowski, P.; Liu, Z.; Guo, Q.; Poumian-Ruiz, E.; Cernea, S.; Herold, K.; Hardy, M.A. (2005). "Two-Layer Method in Short-Term Pancreas Preservation for Successful Islet Isolation". Transplantation Proceedings. 37 (8): 3398–401. doi:10.1016/j.transproceed.2005.09.050. PMID 16298606.

[4] Maevsky, E; Ivanitsky, G; Bogdanova, L; Axenova, O; Karmen, N; Zhiburt, E; Senina, R; Pushkin, S; Maslennikov, I; Orlov, A; Marinicheva, I (2005). "Clinical results of Perftoran application: present and future". Artificial Cells, Blood Substitutes, and Biotechnology. 33 (1): 37–46. doi:10.1081/BIO-200046654. PMID 15768564. S2CID 39902507.

[5] King, A. T.; Mulligan, B. J.; Lowe, K. C. (1989). "Perfluorochemicals and Cell Culture". Nature Biotechnology. 7 (10): 1037–1042. doi:10.1038/nbt1089-1037. S2CID 25329991.

[6] Littlejohn, George R.; Gouveia, João D.; Edner, Christoph; Smirnoff, Nicholas; Love, John (2010). "Perfluorodecalin enhances in vivo confocal microscopy resolution of Arabidopsis thaliana mesophyll" (PDF). New Phytologist. 186 (4): 1018–25. doi:10.1111/j.1469-8137.2010.03244.x. hdl:10026.1/9344. PMID 20374500.

[7] Bernardo-Gil, Gabriela S.; Soares, Luis J. S. (July 1, 1987). "Mutual binary solubilities: perfluorodecalin/hydrocarbons". Journal of Chemical & Engineering Data. 32 (3): 327–329. doi:10.1021/je00049a014. hdl:1822/16619. ISSN 0021-9568.

[8] Baranov, Dmitry; Toso, Stefano; Imran, Muhammad; Manna, Liberato (2019-02-07). "Investigation into the Photoluminescence Red Shift in Cesium Lead Bromide Nanocrystal Superlattices". The Journal of Physical Chemistry Letters. 10 (3): 655–660. doi:10.1021/acs.jpclett.9b00178. ISSN 1948-7185. PMC 6477804. PMID 30676762.

[9] "Teflon AF". Sigma Aldrich.

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