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Perfluorooctanesulfonamide (PFOSA) is a synthetic organofluorine compound. It is a fluorocarbon derivative and a perfluorinated compound, having an eight-carbon chain and a terminal sulfonamide functional group. PFOSA, a persistent organic pollutant, was an ingredient in 3M's former Scotchgard formulation from 1956 until 2003, and the compound was used to repel grease and water in food packaging along with other consumer applications. It breaks down to form perfluorooctane sulfonate (PFOS). The perfluorooctanesulfonyl fluoride-based chemistry that was used to make sulfonamides like PFOSA was phased out by 3M in the United States (US) during 2000–2002 but it has grown in China by other producers.

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dbo:abstract
  • Perfluoroctansulfonamid (PFOSA) ist eine chemische Verbindung, die zu den per- und polyfluorierten Alkylverbindungen (PFAS) gehört. In der Umwelt kann PFOSA zu Perfluoroctansulfonat (PFOS) umgewandelt werden. (de)
  • Le perfluorooctanesulfonamide (PFOSA) est un composé chimique de formule C8F17SO2NH2. Il s'agit d'un composé organofluoré du groupe des sulfamidés, précurseur de l'acide perfluorooctanesulfonique C8F17SO3H (PFOS), visé par l'annexe B de la Convention de Stockholm sur les polluants organiques persistants. Il a notamment été utilisé jusqu'au début du siècle par la société 3M dans la formulation de son traitement Scotchgard destiné à l'imperméabilisation des tissus, du mobilier et des tapis. Il a également été utilisé pour traiter les papiers à contact alimentaire contre les taches d'eau et de graisse, ainsi que pour diverses autres applications grand public. Le perfluorooctanesulfonamide est cependant toxique, susceptible d'une bioaccumulation importante chez certains organismes. C'est un poison très efficace de la chaîne respiratoire, avec une concentration inhibitrice médiane IC50 d'à peine 1 µM (environ 500 ppm), ce qui a fait utiliser des composés semblables comme insecticides. Compte tenu des risques sanitaires induits par ce type de composés, 3M a arrêté leur production aux États-Unis dans les années 2000-2002, mais celle-ci s'est déplacée depuis vers la Chine, où elle s'est développée sous l'impulsion d'autres fabricants. (fr)
  • Perfluorooctanesulfonamide (PFOSA) is a synthetic organofluorine compound. It is a fluorocarbon derivative and a perfluorinated compound, having an eight-carbon chain and a terminal sulfonamide functional group. PFOSA, a persistent organic pollutant, was an ingredient in 3M's former Scotchgard formulation from 1956 until 2003, and the compound was used to repel grease and water in food packaging along with other consumer applications. It breaks down to form perfluorooctane sulfonate (PFOS). The perfluorooctanesulfonyl fluoride-based chemistry that was used to make sulfonamides like PFOSA was phased out by 3M in the United States (US) during 2000–2002 but it has grown in China by other producers. PFOSA can be synthesized from perfluorooctanesulfonyl halides by reaction with liquid ammonia or by a two step reaction via an azide followed by reduction with Zn and HCl. PFOSA is also a metabolic by-product of N-alkylated perfluorooctanesulfonamides. For example, N-ethyl perfluorooctanesulfonamidoethanol (N-EtFOSE), which was primarily used on paper,and N-methyl perfluorooctanesulfonamidoethanol (N-MeFOSE), which was primarily used on carpets and textiles, both metabolize via acetates to PFOSA. In addition, PFOSA is thought to be the biologically active form of the insecticide (N-ethyl perfluorooctanesulfonamide)as it is an extremely potent uncoupler of oxidative phosphorylationwith an IC50 of about 1 micromolar (≈500 nanograms per milliliter or parts per billion). PFOSA was the most toxic perfluorinated compound in a study with PC12 cells. Concentrations ranged from 10 to 250 micromolar in the study (or 5000 to 125,000 parts per billion). Wildlife biomonitoring studies have found the highest level of PFOSA in the liver of common dolphin (Mediterranean Sea, Italy) with a concentration of 878 parts per billion; the liver of mink from Illinois, US, contained 590 parts per billion. In fish, the highest levels detected were in the liver of Norway Pike (91 parts per billion) and homogenates of slimy sculpin (150 parts per billion) from Lake Ontario. Differences in biotransformation across species could explain some of its presence. In humans, PFOSA has been detected in sub- to low-parts per billion levels; for example, in 1999–2000 US serum samples, the 95th percentile (or value where only 5% of the population was higher) was 1.4 parts per billion while in 2003–2004 the 95th percentile fell to 0.2 parts per billion. However, whole-blood concentrations are about five times higher than those in blood plasma or serum. (en)
  • 全氟辛烷磺胺(英語:Perfluorooctanesulfonamide,缩写PFOSA)是一种人工合成的全氟化合物和含氟表面活性剂,带有8个碳的全氟烷基和一个磺胺官能团。在3M公司的生产的皮革保护剂(Scotchgard)的1956到2003年的配方含有该化合物。全氟辛烷磺胺可由(PFOSF)与液氨反应生成,在自然界中会降解为全氟辛烷磺酸(PFOS)。 (zh)
dbo:alternativeName
  • Perfluoroctylsulfonamide, Perfluorooctane sulfonamide, Heptadecafluorooctanesulphonamide, Perfluorooctanesulfonic acid amide, Deethylsulfluramid, FC-99 (en)
dbo:iupacName
  • 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluorooctane-1-sulfonamide (en)
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  • PFOSA molecule (en)
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  • Perfluoroctylsulfonamide, Perfluorooctane sulfonamide, Heptadecafluorooctanesulphonamide, Perfluorooctanesulfonic acid amide, Deethylsulfluramid, FC-99 (en)
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  • changed (en)
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rdfs:comment
  • Perfluoroctansulfonamid (PFOSA) ist eine chemische Verbindung, die zu den per- und polyfluorierten Alkylverbindungen (PFAS) gehört. In der Umwelt kann PFOSA zu Perfluoroctansulfonat (PFOS) umgewandelt werden. (de)
  • 全氟辛烷磺胺(英語:Perfluorooctanesulfonamide,缩写PFOSA)是一种人工合成的全氟化合物和含氟表面活性剂,带有8个碳的全氟烷基和一个磺胺官能团。在3M公司的生产的皮革保护剂(Scotchgard)的1956到2003年的配方含有该化合物。全氟辛烷磺胺可由(PFOSF)与液氨反应生成,在自然界中会降解为全氟辛烷磺酸(PFOS)。 (zh)
  • Perfluorooctanesulfonamide (PFOSA) is a synthetic organofluorine compound. It is a fluorocarbon derivative and a perfluorinated compound, having an eight-carbon chain and a terminal sulfonamide functional group. PFOSA, a persistent organic pollutant, was an ingredient in 3M's former Scotchgard formulation from 1956 until 2003, and the compound was used to repel grease and water in food packaging along with other consumer applications. It breaks down to form perfluorooctane sulfonate (PFOS). The perfluorooctanesulfonyl fluoride-based chemistry that was used to make sulfonamides like PFOSA was phased out by 3M in the United States (US) during 2000–2002 but it has grown in China by other producers. (en)
  • Le perfluorooctanesulfonamide (PFOSA) est un composé chimique de formule C8F17SO2NH2. Il s'agit d'un composé organofluoré du groupe des sulfamidés, précurseur de l'acide perfluorooctanesulfonique C8F17SO3H (PFOS), visé par l'annexe B de la Convention de Stockholm sur les polluants organiques persistants. Il a notamment été utilisé jusqu'au début du siècle par la société 3M dans la formulation de son traitement Scotchgard destiné à l'imperméabilisation des tissus, du mobilier et des tapis. Il a également été utilisé pour traiter les papiers à contact alimentaire contre les taches d'eau et de graisse, ainsi que pour diverses autres applications grand public. (fr)
rdfs:label
  • Perfluoroctansulfonamid (de)
  • Perfluorooctanesulfonamide (fr)
  • Perfluorooctanesulfonamide (en)
  • 全氟辛烷磺胺 (zh)
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