Перфтороктановая кислота

Перфтороктановая кислота (англ. Perfluorooctanoic acid, PFOA) — синтетическая кислота, широко применяемая в различных областях промышленности. Также известна под названием C8.

Анион кислоты (перфтороктансульфонат, [:en:Perfluorooctane sulfonate| PFOS]) иногда рассматривается отдельно.

Перфтороктансульфоновая кислота

Систематическое название heptadecafluorooctane-1-sulfonate
Синонимы perfluorooctane sulfonate
Формула C8F17O3S (анион)
C8HF17O3S (кислота)
Масса моля 499.12 г/моль (анион)
500.13 г/моль (кислота)
Плотность  ? г/см3
Растворимость (в воде)  ? г/л
Температура плавления  ? °C
Температура кипения 133 °C при 6 Torr
CAS [45298-90-6] (анион)
[1763-23-1] (кислота)
Disclaimer and references


Химическая структура

Химическая формула перфтороктановой кислоты C8F15O(OH).

Структурно эта формула отображается так:

  F F F F F F F   OH
  | | | | | | |  /
  | | | | | | | 
  F F F F F F F  


  • Наиболее известное применение этой кислоты — это производство тефлона, Нафиона, а также других огнеупорных, влагоустойчивых и непачкающихся материалов (в том числе применяемых для иготовления одежды).
  • Соли с этим анионом используются в качестве ПАВ.

|- | align="center" colspan="2" bgcolor="#ffffff" | Изображение:Perfluorooctanoic acid.png |- ! align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | General |- | Systematic name | pentadecafluorooctanoic acid |- | Other names | perfluorooctanoic acid
PFOA |- | Molecular formula | C8HF15O2 |- | SMILES | OC(=O)C(F)(F)C(F)(F)C(F)(F)C
|- | Molar mass | 414.07 g/mol |- | Appearance | colorless liquid |- | CAS number | [335-67-1] |- ! align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | Properties |- | Density and phase | ? g/cm3 |- | Solubility in water | soluble |- | Other solvents | polar organic
solvents |- | Melting point | 55-56 °C |- | Boiling point | 189 °C (736 mm Hg) |- | Acidity (pKa) | ? |- | Viscosity | ? cP at ? °C |- ! align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | Structure |- | Molecular shape | Carboxylic acid |- | Dipole moment | ? D |- ! align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | Hazards |- | MSDS | External MSDS |- | Main hazards | strong acid |- | R/S statement | R: 22-34-52/53
S: 26-36/37/39-45 |- | RTECS number | RH0781000 |- ! align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | Supplementary data page |- | Structure and
properties | n, εr, etc. |- | Thermodynamic
data | Phase behaviour
Solid, liquid, gas |- | Spectral data | UV, IR, NMR, MS |- ! align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | Related compounds |- | Related compounds |CF3CO2H |- | align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references
|- |}

Perfluorooctanoic acid (PFOA), also known as C8, is an artificial acid that has many industrial uses. PFOA can designate the acid itself or its principal salts (like ammonium perfluorooctanoate).

Perfluorooctane sulfonate is a related compound, used as a surfactant.


PFOA - pentadecafluorooctanoic acid is an industrial surfactant. One of the most common uses of PFOA is for processing polytetrafluoroethylene PTFE, most widely recognized under the brand name Teflon by DuPont. PFOA is also a by-product of the telomerization process taking place on industrial scale in Asia, North America, and Europe by several international chemical companies. Telomerization process produces perfluorinated alcohol most commonly for many household surface finishes, as well as many indirect contact applications in flexible food packaging. PFOA by-product is also in the fabrication of water- and stain-resistant clothes and other materials, including the products StainMaster, and Gore-Tex. (3M Scotchguard(tm) complied with a voluntary phase out of PFOS, a competing technology to the Zonyl trade name). PFOA by-product is also found in aqueous film forming foam (AFFF), a component of fire-fighting foams.

Fluorotelomer compounds (produced by several international companies) are used in food packaging to make them resistant to grease; however, these compounds may form PFOA when ingested. According to a USA Today article, these compounds have been used in "microwave popcorn bags, fast food and candy wrappers, and pizza box liners" [1]. In particular, microwave popcorn bags have the most fluorotelomers of any food wrapper, and the high cooking temperatures increase the migration of these chemicals into the popcorn oil. It is estimated that microwave popcorn may account for more than 20% of the average PFOA levels measured in American residents. Its elimination half-life is reported as being 4 years [2].

As discussed below with regard to health concerns, DuPont has agreed to eliminate the use of PFOA completely by 2015 [3].

Health concerns

The durability of PFOA prevents it from breaking down once in the environment, leading to widespread buildup and bioaccumulation in food chains. Traces of PFOA-family chemicals can now be found in the blood of nearly all Americans and in the environment worldwide. Scientists do not yet know how the chemicals are transported or exactly how dangerous they are to humans, although concerns about these issues caused its major manufacturer, 3M, to announce in May 2000 that it would cease producing the chemical. DuPont, one of the largest users of PFOA, then built its own plant in Fayetteville, North Carolina to manufacture PFOA.

DuPont has used PFOA for over 50 years at its Washington Works plant near Belpre, Ohio. Area residents sued DuPont in 2001, claiming the chemical contaminated area drinking water. As part of the settlement, DuPont is paying for blood tests and health surveys of residents believed to be affected. Up to 60,000 people are expected to take part in the study, which will be reviewed by epidemiologists to determine if there are any long-term health effects.

In 2004, DuPont came under investigation by the Environmental Protection Agency (EPA) for allegedly covering up knowledge of possible health effects of PFOA exposure in a study of pregnant employees, including evidence of PFOA in umbilical cord blood.

The EPA pursued charges against DuPont for failure to report violations filed under the Toxic Substances Control Act and the Resource Conservation and Recovery Act. On December 13, 2005 DuPont announced a settlement with the EPA in which DuPont will pay US$10.25 million in fines and an additional US$6.25 million for two supplemental environmental projects without any admission of liability.

Some public watchdog groups are raising the alarm about PFOA. The Environmental Working Group says, in an online report titled "PFCs: A Family of Chemicals that Contaminate the Planet", that "PFCs seem destined to supplant DDT, PCBs, dioxin, and other chemicals as the most notorious, global chemical contaminants ever produced." Still, as with most problematic chemicals a strict scientific proof that PFOA is toxic to human beings (and not only to rats) has not yet been accomplished. Still there are serious concerns and, as a prevention measure, a ban is being discussed.

On January 25, 2006, the EPA announced a long-term, voluntary program to reduce PFOA emissions and to eliminate PFOA use in products by the year 2015. While a New York Times article the next day claimed that companies would "stop using" PFOA, the EPA described its objective as "elimination of PFOA...from emissions and products" but not as a chemical intermediate to produce other substances.

On February 15, 2006, the EPA's Science Advisory Board voted to approve a recommendation that PFOA should be considered a likely carcinogen.

See also

  • DuPont and C-8
  • Perfluorooctane sulfonate
  • Zein

External links

  • [4] Details of PFOA chemistry
  • [5] US Environmental Protection Agency - PFOAs
  • [6] The Environmental Working Group, PFC page
  • [7] Chemical in Teflon, other goods is turning up in disturbing places, Seattle Times Oct 1, 2004
  • [8] DuPont, Now in the Frying Pan, NY Times Aug 8, 2004
  • [9] US Environmental Protection Agency, PFOA Stewardship Program, Jan 25, 2006
  • Perfluorooctanoic Acid (PFOA) by Richard Clapp, a case study at DefendingScience.org


  • Farkas, Brian (Associated Press). "Plant tests thousands for exposure to Teflon chemical". Austin American-Statesman (November 18, 2005), p A27.
  • Hekster, FM, de Voogt, P, Laane, RWPM, Peijnenburg, J, 2002, Perfluoroalkylated substances: an aquatic environmental assessment, [10]
  • "DuPont reaches $16.5M deal with EPA". CNNMoney. Retrieved Dec. 15, 2005.
  • Michael Janofsky, "E.P.A. seeks to phase out a toxic chemical," New York Times, Jan 26, 2006
  • Martin, J.W.; Smithwick, M.M.; Braune, B.M.; Hoekstra, P.F.; Muir, D.C.G.; Mabury, S.A. "Identification of Long-Chain Perfluorinated Acids in Biota from the Canadian Arctic." Environmental Science and Technology 2004, 38 (2), pp. 373-380.
  • Ellis, D.A.; Mabury, S.A.; Martin, J.W.; Muir, D.C.G. "Thermolysis of fluoropolymers as a potential source of halogenated organic acids in the environment." Nature 2001, 412 (6844), pp. 321-324.
  • Lau C, Thibodeaux JR, Hanson RG, et al. [{{{url}}} Effects of perfluorooctanoic acid exposure during pregnancy in the mouse] // Toxicology Science. — 2006. — Т. 90. — № {{{issue}}}. — С. 510-518.ru:Перфтороктановая кислота

  • PFOS was a key ingredient in Scotchgard, a fabric protector made by 3M, and numerous stain repellents. In 2000, 3M decided to reformulate Scotchgard, an effort which was finished in 2002.
  • PFOS, together with PFOA, has also been used to make aqueous film forming foam (AFFF), a component of fire-fighting foams, and alcohol-type concentrate foams.
  • PFOS compounds can be also found in some impregnation agents for textiles, paper, and leather; in wax, polishes, paints, varnishes, and cleaning products for general use; in metal surfaces, and carpets.


Биологические эффекты

Многие экологи считают PFOA / PFOS очень опасным соединением, и призывают запретить её использование и производство, но промышленные гиганты (например, DuPont), использующие её в своём технологическом процессе, всё отрицают.


Проведена оценка токсичности кислоты (называемой в тексте по её аниону, Perfluorooctane Sulphonate - PFOS). Испытания на крысах показали, что он распределяется главным образом в сыворотке и печени и не участвует в последующем метаболизме. Концентрация увеличивается с дозой. Усвоение 86% дозы (4.2 мг/кг с пищей) происходит за 24-48 часов. Из организма человека выводится крайне медленно - от 2 лет до 21 года (у крыс – за 200 дней). Накапливается в организме.

90-дневных испытания на крысах, которых кормили дозой от 2 мг/кг/день, повлекли за собой многочисленные нарушения жизненных функций, потерю веса, конвульсии и смерть. Также были произведены исследования влияния токсичности PFOS на эмбрионы крыс и кроликов. При дозах 5 мг/кг/день наблюдалось уменьшение эмбриональной массы тела и изменения скелета. В результате была определена доза отсутствия токсического воздействия - 0.1 мг/кг/день и доза малого токсического воздействия - 1.0 мг/кг/день.


Доказаны канцерогенные свойства. Их подтверждает 37-летняя статистика смертей рабочих на заводе компании 3M в Алабаме. Согласно этой статистике, вероятность заболевания раком мочевого пузыря увеличилась в 13 раз. С 2001 3M отказалась от применения PFOS в своих товарах.


Risk reduction strategy and analysis of advantages and drawbacks for Perfluorooctane Sulphonate (PFOS) — отчет группы аналитиков Risk & Policy Analyst Ltd. об исследованиях вредности PFOS произведенных по заказу Департамента среды Великобритании.


  • Martin, J.W.; Smithwick, M.M.; Braune, B.M.; Hoekstra, P.F.; Muir, D.C.G.; Mabury, S.A. "Identification of Long-Chain Perfluorinated Acids in Biota from the Canadian Arctic." Environmental Science and Technology 2004, 38 (2), pp. 373-380.
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