Perfluorinated compound
A perfluorinated compound (PFC) or perfluoro compound is an
Applications
One class of perfluorinated compounds, the fluorosurfactants, are widely used in the production of
Production
A common industrial method for synthesizing perflurocompounds is
Examples by functional group
Perfluorinated alkyl halides
- alkylatingagent.
- Pentafluoroethyl iodide, an alkylating agent.
- sonography; fluid used in liquid breathing.
- Dichlorodifluoromethane, a refrigerant.
Perfluoroalkenes
- Tetrafluoroethylene, precursor to polytetrafluoroethylene (PTFE).
- Chlorotrifluoroethylene, refrigerant and precursor to polychlorotrifluoroethylene (PCTFE).
- Dichlorodifluoroethylene (three isomers).
Perfluoroethers and epoxides
- Hexafluoropropylene oxide, precursor to perfluoromethyl vinyl ether (CF2=CFOCF3), the monomer precursor to Krytox, perfluorinated polyether used in special oils and greases.
Perfluoroalcohols
- Nonafluoro-tert-butyl alcohol
- Perfluorotriethylcarbinol
- Pentafluorophenol, a moderately strong acid.
Primary and secondary perfluorinated alcohols are unstable with respect to dehydrofluorination.
Perfluoroamines
- Perfluorotripentylamine (and related derivatives) are found in Fluorinert, electronic coolants.
Perfluoroketones
- Hexafluoroacetone, a 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.
- Teflon.
- Perfluorononanoic acid (PFNA), a surfactant in the emulsion polymerization of fluoropolymers, like PFOA.
Perfluoronitriles and isonitriles
- Trifluoromethylisocyanide, the simplest perfluorinated isonitrile.
- Trifluoromethylacetonitrile, the simplest perfluorinated nitrile.
- Triflic acid, a useful strong acid
- perfluorobutanesulfonic acid (PFBS) used as a replacement for PFOS in 3M's reformulated Scotchgard.
- perfluorobutane sulfonamide (FBSA), sulfonamide derivative of PFBS.
- 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
- weakly coordinating anion.
Environmental and health concerns
Several environmental and health concerns surround the industrial production and use of perfluoroalkane compounds. The exceptional stability of perfluorinated compounds is desirable from the applications perspective is also a cause for environmental and health concerns.
Perfluoroalkanes
Low-boiling perfluoroalkanes are potent
Fluorosurfactants
The fluorocarbons
Fluorosurfactants tend to
As of 2015, the U.S. Air Force had been testing 82 former and active US military installations for fluorosurfactants contained in fire fighting foam.
A 2018 report to Congress indicated that "at least 126 drinking water systems on or near military bases" were contaminated with PFAS compounds.[7][8]
A 2016 study found unsafe[9] levels of fluorosurfactants in 194 out of 4,864 water supplies in 33 U.S. states. Covering two-thirds of drinking water supplies in the United States, the study found thirteen states accounted for 75% of the detections. In order of frequency, these were: California, New Jersey, North Carolina, Alabama, Florida, Pennsylvania, Ohio, New York, Georgia, Minnesota, Arizona, Massachusetts, and Illinois. Firefighting foam was singled out as a major contributor.[10]
See also
- Per- and polyfluoroalkyl substances
- Fluorocarbons
References
- ^ Sedlak, Meg (October 2016). "Profile - Perfluorooctane Sulfonate (PFOS)" (PDF). sfei.org. San Francisco Estuary Institute. Retrieved 2 November 2016.
- ^ a b US Environmental Protection Agency. "FAQ". Perfluorooctanoic Acid (PFOA) and Fluorinated Telomers. Retrieved 11 May 2011.
- ^ Auer, Charles, Frank Kover, James Aidala, Marks Greenwood. “Toxic Substances: A Half Century of Progress.” EPA Alumni Association. March 2016.
- PMID 20423814.
- ^ "Grissom officials: Well tests show no chemical pollution". LIN Television Corporation. Associated Press. 19 September 2015. Retrieved 19 September 2015.
- ^ Strategic Environmental Research and Development Program (SERDP), Environmental Security Technology Certification Program (ESTCP) Per- and Polyfluoroalkyl Substances (PFASs): Analytical and Characterization Frontiers webinarslides, January 28, 2016
- ^ Lustgarten, Abrahm (2018-06-20). "Suppressed Study: The EPA Underestimated Dangers of Widespread Chemicals". ProPublica. Lisa Song, Talia Buford. Retrieved 2018-06-23.
- ^ Associated Press (2017-07-31). "Air Force won't pay for towns' water contamination costs". Air Force Times. Retrieved 2018-06-23.
- ^ Above the minimum reporting levels required by the EPA − 70 parts per trillion (ng/L) for PFOS and PFOA
- ^ Unsafe levels of toxic chemicals found in drinking water for 6 million Americans Science X network, phys.org, August 9, 2016
External links
- Media related to Perfluorinated compounds at Wikimedia Commons