関: perfluorochemical、PFC

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create by mixing or combining
(chemistry) a substance formed by chemical union of two or more elements or ingredients in definite proportion by weight (同)chemical_compound
put or add together; "combine resources" (同)combine
an enclosure of residences and other building (especially in the Orient)
a whole formed by a union of two or more elements or parts
combine so as to form a whole; mix; "compound the ingredients" (同)combine
calculate principal and interest
composed of more than one part; "compound leaves are composed of several lobes; "compound flower heads"
consisting of two or more substances or ingredients or elements or parts; "soap is a compound substance"; "housetop is a compound word"; "a blackberry is a compound fruit"
combined into or constituting a chemical compound

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Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/21 01:29:17」(JST)

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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

Fate of a broad spectrum of perfluorinated compounds in soils and biota from Tierra del Fuego and Antarctica.

Llorca M, Farré M, Tavano MS, Alonso B, Koremblit G, Barceló D.SourceDepartment of Environmental Chemistry, IDAEA-CSIC, Barcelona, Spain.
Environmental pollution (Barking, Essex : 1987).Environ Pollut.2012 Apr;163:158-66. Epub 2012 Jan 12.
In this study, the presence of 18 perfluorinated compounds was investigated in biota and environmental samples from the Antarctica and Tierra de Fuego, which were collected during a sampling campaign carried out along February and March 2010. 61 samples were analysed including fish, superficial soil
PMID 22325444

Distribution of perfluorinated compounds in Yellow-legged gull eggs (Larus michahellis) from the Iberian Peninsula.

Vicente J, Bertolero A, Meyer J, Viana P, Lacorte S.SourceDepartment of Environmental Chemistry, Insitute of Environmental Diagnostics and Water Studies, CSIC, Jordi Girona 18-26, 08034 Barcelona, Catalonia, Spain.
The Science of the total environment.Sci Total Environ.2012 Feb 1;416:468-75. Epub 2011 Dec 29.
This study is aimed to evaluate the presence and distribution of Perfluorinated Compounds (PFCs) in Yellow-legged gull eggs (Larus michahellis) collected from 8 National or Natural Parks from the Iberian Peninsula. In each colony, 12 eggs were randomly collected and pooled from 3 areas of the colony
PMID 22209369

Japanese Journal

北海道内の冬季中の有機フッ素化合物の沈着量調査

田原るり子,山口高志
環境化学 24(1), 11-17, 2014
… A survey of perfluorinated chemicals (PFCs) deposition during winter was performed at rural areas and hinterlands in Hokkaido (9 points). … PFBA was the dominant compound, and PFOA and PFNA were also detected. …
NAID 130004691312

Levels and profiles of long-chain perfluorinated carboxylic acids in human breast milk and infant formulas in East Asia.

Fujii Yukiko,Yan Junxia,Harada Kouji H,Hitomi Toshiaki,Yang Hyeran,Wang Peiyu,Koizumi Akio
Chemosphere 86(3), 315-321, 2012-01
… PFOA was the predominant compound and was detected in more than 60% of samples in all three countries. … The median PFOA concentrations were 89pgmL(-1) (48% of total perfluorinated carboxylic acids (PFCAs) (C8-C13)) in Japan, 62pgmL(-1) (54%) in Korea, and 51pgmL(-1) (61%) in China. …
NAID 120003779162