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A perfluorinated compound (PFC) is an organofluorine compound containing only carbon-fluorine bonds (no C-H bonds) and C-C bonds but also other heteroatoms. PFCs have properties that represent a blend of fluorocarbons (containing only C-F and C-C bonds) and the parent functionalized organic species. For example, perfluorooctanoic acid functions as a carboxylic acid but with strongly altered surfactant and hydrophobic characteristics.^[1]

1 Applications
2 Classes of PFCs by functional group
- 2.1 Perfluorinated alkyl and aryl halides
- 2.2 Fluorochloroalkenes
- 2.3 Perfluoroethers and epoxides
- 2.4 Perfluoroalcohols
- 2.5 Perfluoroamines
- 2.6 Perfluoroketones
- 2.7 Perfluorocarboxylic acids
- 2.8 Perfluoronitriles and isonitriles
- 2.9 Perfluorosulfonic acids and related derivatives
- 2.10 Perfluorinated aryl borates
3 Environmental and health concerns
4 See also
5 References

Applications

Many perfluorinated compounds are useful. For example, fluorosurfactants powerfully reduce surface tension by concentrating at the liquid-air interface due to the lipophobicity of fluorocarbons, due to the polar functional group added to the fluorocarbon chain. Other groups or atoms for fluorocarbon based compounds the oxygen atom incorporated into an ether group for anesthetics, and the chlorine atom for chlorofluorocarbons (CFCs). In a sharp contrast to true fluorocarbons, the chlorine atom produces a chlorine radical which degrades ozone. Fluorosurfactants are widely used in the production of teflon and related fluorinated polymers. They have also been used to confer hydrophobic, stain-resisting properties to fabrics.

Classes of PFCs by functional group

Representative members of this large family of compounds are listed below. Also numerous are compounds that contain many fluoride centers but also some hydrogen, e.g., trifluoroethanol.

Perfluorinated alkyl and aryl halides

Trifluoroiodomethane, an alkylating agent
Pentafluoroethyl iodide, an alkylating agent
Perfluorooctyl bromide (perflubron) is a contrast medium for magnetic resonance imaging, computer tomography and sonography. It has also been used in liquid breathing.
Dichlorodifluoromethane, refrigerant

Fluorochloroalkenes

Chlorotrifluoroethylene, monomer
Dichlorodifluoroethylene (three isomers), monomers

Perfluoroethers and epoxides

hexafluoropropylene oxide , precursor to perfluoromethyl vinyl ether (CF₂=CFOCF₃), a useful monomer
Krytox, perfluorinated polyether used in special greases

Perfluoroalcohols

Pentafluorophenol, a moderately strong acid

Perfluorinated alcohols are unstable with respect to dehydrofluorination.

Perfluoroamines

Perfluorotripentylamine (and related derivatives) are found in Fluorinert, electronic coolants.

Perfluoroketones

Hexafluoroacetone, building block in organofluorine chemistry.

Perfluorocarboxylic acids

Trifluoroacetic acid, a moderately strong acid useful in organic chemistry
Heptafluorobutyric acid, a moderately strong acid that is useful in organic and analytical chemistry
Pentafluorobenzoic acid, a moderately strong acid of interest in research community
perfluorooctanoic acid (PFOA), surfactant used to make fluoropolymers such as Teflon
perfluorononanoic acid (PFNA), surfactant in the emulsion polymerization of fluoropolymers, like PFOA.

Perfluoronitriles and isonitriles

Trifluoromethylisocyanide, the simplest perfluorinated isonitrile.
Trifluoromethylacetonitrile, the simplest perfluorinated nitrile

Perfluorosulfonic acids and related derivatives

Triflic acid, a useful strong acid
perfluorobutanesulfonic acid (PFBS) used as a replacement for PFOS in 3M's reformulated Scotchgard.
perfluorooctanesulfonyl fluoride (POSF), precursor to PFOS-based compounds.
perfluorooctanesulfonamide (PFOSA), used in 3M's Scotchgard formulation.
perfluorooctanesulfonic acid (PFOS,) used in the semiconductor industry, 3M's former Scotchgard formulation, and 3M's former fire-fighting foam mixture.

Perfluorinated aryl borates

Na[B(C₆F₅)₄], salt of a weakly coordinating anion.

Environmental and health concerns

Despite the presence of some natural fluorocarbons such as tetrafluoromethane, which has been reported in rocks,^[2] man-made fluorocarbons are potent greenhouse gases.

Certain fluorocarbons tend to bioaccumulate, since they are extremely stable and can be stored in the bodies of both humans and animals. Examples of fluorocarbons include PFOA (perfluorooctanoic acid) and PFOS (perfluorooctane sulfonate), frequently present in water resistant textiles and sprays conferring water resistant properties to textiles.^[3] Data from animal studies of PFOA indicate that it can cause several types of tumors and neonatal death and may have toxic effects on the immune, liver, and endocrine systems. Data on the human health effects of PFOA are however sparse.^[4]

The fluorocarbon, PFOA and PFOS have both been subject for numerous investigations by the EU and the United States Environmental Protection Agency (EPA) regarding them being harmful to the environment.^[3]

References

^ Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick "Fluorine Compounds, Organic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a11_349
^ Murphy CD, Schaffrath C, O'Hagan D.: "Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya" Chemosphere. 2003 Jul;52(2):455-61.
^ ^a ^b US Environmental Protection Agency. "FAQ". Perfluorooctanoic Acid (PFOA) and Fluorinated Telomers. Retrieved 11 May 2011.
^ Steenland, Kyle; Fletcher, Tony; Savitz, David A. (2010). "Epidemiologic Evidence on the Health Effects of Perfluorooctanoic Acid (PFOA)". Environmental Health Perspectives 118 (8): 1100–8. doi:10.1289/ehp.0901827. PMC 2920088. PMID 20423814. Retrieved 2011-05-11.

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English Journal

Liposome encapsulated perfluorohexane enhances radiotherapy in mice without additional oxygen supply.

Xu L1,2,3, Qiu X1,2,3, Zhang Y2, Cao K1,2,3, Zhao X1,3, Wu J4, Hu Y5, Guo H6,7.
Journal of translational medicine.J Transl Med.2016 Sep 20;14:268. doi: 10.1186/s12967-016-1033-3.
BACKGROUND: To investigate the effect of perfluorochemical preparations in enhancing radiotherapy, perfluocarbon nanoparticles were by encapsulating perfluorohexane into liposome [lip(PFH)].METHODS: After intravenous injection, lip(PFH) could accumulate in the tumor site over time, with a prominent
PMID 27646172

Screening of Toxic Chemicals in a Single Drop of Human Whole Blood Using Ordered Mesoporous Carbon as a Mass Spectrometry Probe.

Huang X1,2, Liu Q1,3,4, Fu J1, Nie Z2, Gao K1, Jiang G1,4.
Analytical chemistry.Anal Chem.2016 Apr 5;88(7):4107-13. doi: 10.1021/acs.analchem.6b00444. Epub 2016 Mar 24.
Surface-enhanced laser desorption/ionization (SELDI) is a versatile and high-throughput mass spectrometry (MS) technique that uses a probe for extraction, enrichment, desorption, and ionization of target analytes. Here we report ordered mesoporous carbon as a new SELDI probe for rapid screening and
PMID 26985970

Liquid perfluorochemical-supported hybrid cell culture system for proliferation of chondrocytes on fibrous polylactide scaffolds.

Pilarek M1, Grabowska I, Senderek I, Wojasiński M, Janicka J, Janczyk-Ilach K, Ciach T.
Bioprocess and biosystems engineering.Bioprocess Biosyst Eng.2014 Sep;37(9):1707-15. doi: 10.1007/s00449-014-1143-3. Epub 2014 Feb 16.
CP5 bovine chondrocytes were cultured on biodegradable electrospun fibrous polylactide (PLA) scaffolds placed on a flexible interface formed between two immiscible liquid phases: (1) hydrophobic perfluorochemical (PFC) and (2) aqueous culture medium, as a new way of cartilage implant development. Ro
PMID 24532258

Japanese Journal

膵臓・膵島移植における臓器保存法

膵臓 26(2), 142-152, 2011
NAID 130004495951

Liquid Perfluorochemical Inhibits Inducible Nitric Oxide Synthase Expression and Nitric Oxide Formation in Lipopolysaccharide-Treated RAW 264.7 Macrophages