PFOA is considered a surfactant, or fluorosurfactant, due to its chemical structure, which consists of a perfluorinated, n-octyl "tail group" and a carboxylate "head group".
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PFOA is considered a surfactant, or fluorosurfactant, due to its chemical structure, which consists of a perfluorinated, n-octyl "tail group" and a carboxylate "head group".
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PFOA is one of many synthetic organofluorine compounds collectively known as per- and polyfluoroalkyl substances .
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PFOA is used in several industrial applications, including carpeting, upholstery, apparel, floor wax, textiles, fire fighting foam and sealants.
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PFOA serves as a surfactant in the emulsion polymerization of fluoropolymers and as a building block for the synthesis of perfluoroalkyl-substituted compounds, polymers, and polymeric materials.
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PFOA has been manufactured since the 1940s in industrial quantities.
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PFOA is used as a surfactant because it can lower the surface tension of water more than hydrocarbon surfactants while having exceptional stability due to having perfluoroalkyl tail group.
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The stability of PFOA is desired industrially but is a cause of concern environmentally.
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PFOA has been detected in industrial waste, stain-resistant carpets, carpet-cleaning liquids, house dust, microwave popcorn bags, water, food, and Teflon products.
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The toxicity, mobility and bioaccumulation potential of PFOS and PFOA pose potential adverse effects for the environment and human health.
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The chemical has received attention due to litigation from the PFOA-contaminated community around DuPont's Washington Works facility in Washington, West Virginia, along with EPA focus.
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Research on PFOA has demonstrated ubiquity, animal-based toxicity, and some associations with human health parameters and potential health effects.
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However, because products manufactured with PFOA were such an integral part of DuPont's earnings, $1 billion in annual profit, they chose to continue using PFOA.
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Later research eventually found that PFOA had an outsized effect based on gender on several negative health outcomes in mice that had been exposed to the chemical.
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PFOA has two main synthesis routes, electrochemical fluorination and telomerization.
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PFOA is synthesized by the telomerization represented below, where the telogen is the organoiodine compound and the taxogen is the tetrafluoroethylene.
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The telomerization synthesis of PFOA was pioneered by DuPont, and is not well suited to the laboratory.
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PFOA formed by telomerization is completely linear, in contrast to the mixture of structures formed by ECF.
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In 1976, PFOA was reported as a water and oil repellent "in fabrics and leather and in the production of floor waxes and waxed papers"; however, it is believed that paper is no longer treated with perfluorinated compounds, but with fluorotelomers with less than 0.
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In PTFE processing, PFOA is in aqueous solution and forms micelles that contain tetrafluoroethylene and the growing polymer.
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PFOA can be used to stabilize fluoropolymer and fluoroelastomer suspensions before further industrial processing and in ion-pair reversed-phase liquid chromatography it can act as an extraction agent.
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PFOA finds uses in electronic products and as an industrial fluorosurfactant.
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PFOA has been detected in the central Pacific Ocean at low parts per quadrillion ranges, and at low parts per trillion levels in coastal waters.
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PFOA is detected widely in surface waters, and is present in numerous mammals, fish, and bird species.
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PFOA is in the blood or vital organs of Atlantic salmon, swordfish, striped mullet, gray seals, common cormorants, Alaskan polar bears, brown pelicans, sea turtles, sea eagles, Midwestern bald eagles, California sea lions and Laysan albatrosses on Sand Island, a wildlife refuge on Midway Atoll, in the middle of the North Pacific Ocean, about halfway between North America and Asia.
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PFOA can be measured in water from industrial sites other than fluorochemical plants.
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PFOA has been detected in emissions from the carpet industry, paper and electronics industries.
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The majority of waste water treatment plants that have been tested output more PFOA than is input, and this increased output has been attributed to the biodegradation of fluorotelomer alcohols.
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People who lived in the PFOA-contaminated area around DuPont's Washington Works facility were found to have higher levels of PFOA in their blood from drinking water.
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PFOA is formed as an unintended byproduct in the production of fluorotelomers and is present in finished goods treated with fluorotelomers, including those intended for food contact.
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PFOA was detected in fodder grass grown in these soils and the blood of the cattle feeding on this grass.
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PFOA is frequently found in household dust, making it an important exposure route for adults, but more substantially, children.
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PFOA is a possible carcinogen, a possible liver toxicant, a possible developmental toxicant, and a possible immune system toxicant, and exerts hormonal effects including alteration of thyroid hormone levels at very high concentrations Animal studies show developmental toxicity from reduced birth size, physical developmental delays, endocrine disruption, and neonatal mortality.
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PFOA has been described as a member of a group of "classic non-genotoxic carcinogens".
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However, a provisional German assessment notes that a 2005 study found PFOA to be genotoxic via a peroxisome proliferation pathway that produced oxygen radicals in HepG2 cells, and a 2006 study demonstrated the induction and suppression of a broad range of genes; therefore, it states that the indirect genotoxic potential of PFOA cannot be dismissed.
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An additional study has shown PFOA to be developmentally toxic, hepatotoxic, immunotoxic, and to have negative effects of thyroid hormone production.
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PFOA is resistant to degradation by natural processes such as metabolism, hydrolysis, photolysis, or biodegradation and has been found to persist in the environment.
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PFOA is found in environmental and biological fluids as the anion perfluorooctanoate.
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PFOA can be absorbed from ingestion and can penetrate skin.
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The acid headgroup of PFOA enables binding to proteins with fatty acid or hormone substrates such as serum albumin, liver fatty acid-binding protein, and the nuclear receptors PPARa and possibly CAR.
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In humans, PFOA has an average elimination half-life of about three years.
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Blood serum levels of PFOA were associated with an increased time to pregnancy—or "infertility"—in a 2009 study.
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PFOA exposure was associated with decreased semen quality, increased serum alanine aminotransferase levels, and increased occurrence of thyroid disease.
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Kidney and testicular cancer are of interest given that animal studies have found that PFOA is distributed mainly in the kidneys and because PFOA has been found to induce testicular tumors in rats.
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One study that followed a Danish pregnancy cohort suggests that in utero exposure to PFOA could be associated with lower levels of sperm concentration and total sperm count in adult males, reduced testicular size, and higher adjusted levels of luteinizing hormone and follicle-stimulating hormone.
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In utero PFOA exposure is demonstrated to impact female development.
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PFOA is shown to have obesogenic effects, and an experimental study found a positive correlation to low-dose prenatal exposure of PFOA and prevalence of overweight and high waist circumference in females at age 20.
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PFOA has been associated with signs of reduced fetal growth including lower birth weight.
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Maternal PFOA levels were not associated with an offspring's increased risk of hospitalization due to infectious diseases, behavioral and motor coordination problems, or delays in reaching developmental milestones.
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In 2002, a panel of toxicologists, including several from EPA, proposed a level of 150 ppb for drinking water in the PFOA contaminated area around DuPont's Washington Works plant.
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In 2007 the New Jersey Department of Environmental Protection announced that it found PFOA at "elevated levels in the system's drinking water near DuPont's massive Chambers Works chemical plant".
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PFOA contaminated waste was incorporated into soil improver and spread on agricultural land in Germany, leading to PFOA drinking water contamination of up to 0.
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PFOA was identified as a PBT substance in the EU in 2013.
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