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A '''perfluorinated compound''' ('''PFC''') is an ] with containing only ]s (no C-H bonds) but also other heteroatomes. PFCs have properties that represent a blend of ]s (containing only C-F and C-C bonds) and the parent organic species.<ref>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}}</ref> A '''perfluorinated compound''' ('''PFC''') is an ] containing only ]s no C-H bonds) and C-C bonds but also other heteroatomes. PFCs have properties that represent a blend of ]s (containing only C-F and C-C bonds) and the parent organic species.<ref>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}}</ref>


==Applications== ==Applications==
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==Classes of PFCs by functional group== ==Classes of PFCs by functional group==
Representative members of this large family of compounds are listed below. Perfluorinated alcohols are not represented as they are unstable with respect to dehydrofluorination, so they are not represented. Also numerous are compounds that contain many fluoride centers but also some hydrogen, e.g., ]. 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., ].


===Perfluorinated alkyl and aryl halides=== ===Perfluorinated alkyl and aryl halides===
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:*] , precursor to perfluoro(methyl vinyl ether (CF<sub>2</sub>=CFOCF<sub>3</sub>), a useful ] :*] , precursor to perfluoro(methyl vinyl ether (CF<sub>2</sub>=CFOCF<sub>3</sub>), a useful ]
:*], perfluorinated polyether used in special greases :*], perfluorinated polyether used in special greases

===Perfluoroalcohols===
Perfluorinated alcohols are unstable with respect to dehydrofluorination.
:*Pentafluorophenol, a moderately strong acid


===Perfluoroamines=== ===Perfluoroamines===
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===Perfluoroketones=== ===Perfluoroketones===
:*], reagent in organofluorine chemistry. :*], building block in organofluorine chemistry.


===Perfluorocarboxylic acids=== ===Perfluorocarboxylic acids===
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:*], a moderately strong acid that is useful in organic and analytical chemistry :*], a moderately strong acid that is useful in organic and analytical chemistry
:*], a moderately strong acid of interest in research community :*], a moderately strong acid of interest in research community
:*PFOA or ], used to make ]s such as ], among other applications. :*] (PFOA), surfactant used to make ]s such as ]
:*PFNA or ], used as ] in the ] of fluoropolymers, like PFOA. :*] (PFNA), ] in the ] of fluoropolymers, like PFOA.

===Perfluoronitriles and isonitriles===
:*], the simplest perfluorinated isonitrile.
:*Trifluoromethylacetonitrile, the simplest perfluorinated nitrile


===Perfluorosulfonic acids and related derivatives=== ===Perfluorosulfonic acids and related derivatives===
:*], a useful strong acid :*], a useful strong acid
:*PFBS or ], used as a replacement for PFOS in 3M's reformulated Scotchgard. :*] (PFBS) used as a replacement for PFOS in 3M's reformulated Scotchgard.
:*POSF or ], used to make PFOS-based compounds. :*] (POSF), precursor to PFOS-based compounds.
:*PFOSA or ], formerly used in 3M's Scotchgard formulation. :*] (PFOSA), used in 3M's Scotchgard formulation.
:*PFOS or ], used in the semiconductor industry, ]'s former ] formulation, and 3M's former fire-fighting foam mixture. :*] (PFOS,) used in the semiconductor industry, ]'s former ] formulation, and 3M's former fire-fighting foam mixture.


===Perfluorinated aryl borates=== ===Perfluorinated aryl borates===

Revision as of 15:06, 4 February 2014

A perfluorinated compound (PFC) is an organofluorine compound containing only carbon-fluorine bonds no C-H bonds) and C-C bonds but also other heteroatomes. PFCs have properties that represent a blend of fluorocarbons (containing only C-F and C-C bonds) and the parent organic species.

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

Fluorochloroalkenes

Perfluoroethers and epoxides

Main article: Fluoroether

Perfluoroalcohols

Perfluorinated alcohols are unstable with respect to dehydrofluorination.

  • Pentafluorophenol, a moderately strong acid

Perfluoroamines

Perfluoroketones

Perfluorocarboxylic acids

Perfluoronitriles and isonitriles

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

Perfluorosulfonic acids and related derivatives

Perfluorinated aryl borates


Environmental and health concerns

Despite the presence of some natural fluorocarbons such as tetrafluoromethane, which has been reported in rocks, 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. 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.

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.

See also

References

  1. 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
  2. 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.
  3. ^ US Environmental Protection Agency. "FAQ". Perfluorooctanoic Acid (PFOA) and Fluorinated Telomers. Retrieved 11 May 2011.
  4. 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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