Names | |
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Preferred IUPAC name 1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonamide | |
Other names Perfluorobutylsulfonamide, FBSA | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.250.644 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C4H2F9NO2S | |
Molar mass | 299.111 g/mol |
Hazards | |
GHS labelling: | |
Warning | |
H302, H312, H315, H319, H332, H335 | |
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Perfluorobutane sulfonamide, also known as FBSA or H-FBSA, is a perfluorinated surfactant. FBSA and its N-alkylated derivatives have been patented by 3M for use in acid etch solutions with low surface tension. According to the inventors, FBSA and its derivatives are expected to have a smaller tendency to accumulate in living organisms than their perfluorooctanyl analogs such as PFOS. [1] Nevertheless, a 2015 study found FBSA in 32 out of 33 samples of Canadian fish. [2]
In April 2019, 3M admitted in a letter to the EPA that the plant in Decatur, Alabama released FBSA and FBSEE into the Tennessee River, despite a 2009 EPA order prohibiting release to water. [3] Supposedly, authorities had been aware of the contamination since 2014, but did not make it public. [4] The same facility has been responsible for release of other per- and polyfluorinated alkylated substances, namely PFOS and PFOA, into the Tennessee River, prompting 3M to pay $35 million to a local water authority in order to improve drinking water purification. [5]
Belgian journalists from VTM Nieuws / Het Laatste Nieuws reported that 3M was illegally discharging the harmful chemical FBSA into the Scheldt river. This was being investigated by the Flemish authorities. On August 24, 2021, the company confessed to the allegations. [6]
Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. Surfactants may function as emulsifiers, wetting agents, detergents, foaming agents, or dispersants. The word "surfactant" is a blend of surface-active agent, coined c. 1950.
The Cape Fear River is a 191.08-mile-long blackwater river in east-central North Carolina. It flows into the Atlantic Ocean near Cape Fear, from which it takes its name. The river is formed at the confluence of the Haw River and the Deep River in the town of Moncure, North Carolina. Its river basin is the largest in the state: 9,149 sq mi.
Perfluorooctanoic acid is a perfluorinated carboxylic acid produced and used worldwide as an industrial surfactant in chemical processes and as a material feedstock. PFOA is considered a surfactant, or fluorosurfactant, due to its chemical structure, which consists of a perfluorinated, n-heptyl "tail group" and a carboxylate "head group". The head group can be described as hydrophilic while the fluorocarbon tail is both hydrophobic and lipophobic.
Perfluorooctanesulfonic acid (PFOS) is a chemical compound having an eight-carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man-made) fluorosurfactant, now regarded as a global pollutant. PFOS was the key ingredient in Scotchgard, a fabric protector made by 3M, and related stain repellents. The acronym "PFOS" refers to the parent sulfonic acid and to various salts of perfluorooctanesulfonate. These are all colorless or white, water-soluble solids. Although of low acute toxicity, PFOS has attracted much attention for its pervasiveness and environmental impact. It was added to Annex B of the Stockholm Convention on Persistent Organic Pollutants in May 2009.
In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.
The Safe Drinking Water Act (SDWA) is the principal federal law in the United States intended to ensure safe drinking water for the public. Pursuant to the act, the Environmental Protection Agency (EPA) is required to set standards for drinking water quality and oversee all states, localities, and water suppliers that implement the standards.
Firefighting foam is a foam used for fire suppression. Its role is to cool the fire and to coat the fuel, preventing its contact with oxygen, thus achieving suppression of the combustion. Firefighting foam was invented by the Russian engineer and chemist Aleksandr Loran in 1902.
Microwave popcorn is a convenience food consisting of unpopped popcorn in an enhanced, sealed paper bag intended to be heated in a microwave oven. In addition to the dried corn, the bags typically contain cooking oil with sufficient saturated fat to solidify at room temperature, one or more seasonings, and natural or artificial flavorings or both. With the many different flavors, there are many different providers.
3M Company is an American multinational conglomerate operating in the fields of industry, worker safety, healthcare, and consumer goods. The company produces over 60,000 products under several brands, including adhesives, abrasives, laminates, passive fire protection, personal protective equipment, window films, paint protection films, dental and orthodontic products, electrical and electronic connecting and insulating materials, medical products, car-care products, electronic circuits, healthcare software, and optical films. It is based in Maplewood, a suburb of Saint Paul, Minnesota.
Scotchgard is a 3M brand of products, a stain and durable water repellent applied to fabric, furniture, and carpets to protect them from stains. Scotchgard products typically rely on organofluorine chemicals as the main active ingredient along with petroleum distillate solvents.
Drinking water quality in the United States is generally safe. In 2016, over 90 percent of the nation's community water systems were in compliance with all published U.S. Environmental Protection Agency (EPA) standards. Over 286 million Americans get their tap water from a community water system. Eight percent of the community water systems—large municipal water systems—provide water to 82 percent of the US population.
Perfluorononanoic acid, or PFNA, is a synthetic perfluorinated carboxylic acid and fluorosurfactant that is also an environmental contaminant found in people and wildlife along with PFOS and PFOA.
Per- and polyfluoroalkyl substances (PFAS or PFASs) are a group of synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain. An early definition, from 2011, required that they contain at least one perfluoroalkyl moiety, –CnF2n+1–. Beginning in 2021, the Organisation for Economic Co-operation and Development (OECD) expanded their terminology, stating that "PFASs are defined as fluorinated substances that contain at least one fully fluorinated methyl or methylene carbon atom (without any H/Cl/Br/I atom attached to it), i.e., with a few noted exceptions, any chemical with at least a perfluorinated methyl group (–CF3) or a perfluorinated methylene group (–CF2–) is a PFAS."
Perfluorobutanesulfonic acid (PFBS) is a PFAS chemical compound having a four-carbon fluorocarbon chain and a sulfonic acid functional group. It is stable and unreactive because of the strength of carbon–fluorine bonds. It can occur in the form of a colorless liquid or a corrosive solid. Its conjugate base is perfluorobutanesulfonate which functions as the hydrophobe in fluorosurfactants.
A perfluorinated compound (PFC) or perfluoro compound is an organofluorine compound lacking C-H bonds. Many perfluorinated compounds have properties that are quite different from their C-H containing analogues. Common functional groups in PFCs are OH, CO2H, chlorine, O, and SO3H. Electrofluorination is the predominant method for their production. Due to their chemical stability, some of these perfluorinated compounds bioaccumulate.
Perfluorooctanesulfonyl fluoride (POSF) is a synthetic perfluorinated compound with a sulfonyl fluoride functional group. It is used to make perfluorooctanesulfonic acid (PFOS) and PFOS-based compounds. These compounds have a variety of industrial and consumer uses, but POSF-derived substances ultimately degrade to form PFOS.
Water contamination in Lawrence and Morgan Counties, Alabama, revolves around the presence of perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) in the water supply. After the US Environmental Protection Agency (EPA) released new health advisories in March 2016, there was concern over health risks of the levels of PFOA and PFOS present. The responses of different government officials, agencies, and companies raise questions as to whether or not there was any environmental injustice involved.
GenX is a Chemours trademark name for a synthetic, short-chain organofluorine chemical compound, the ammonium salt of hexafluoropropylene oxide dimer acid (HFPO-DA). It can also be used more informally to refer to the group of related fluorochemicals that are used to produce GenX. DuPont began the commercial development of GenX in 2009 as a replacement for perfluorooctanoic acid.
This timeline of events related to per- and polyfluoroalkyl substances (PFASs) includes events related to the discovery, development, manufacture, marketing, uses, concerns, litigation, regulation, and legislation, involving the human-made PFASs. The timeline focuses on some perfluorinated compounds, particularly perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) and on the companies that manufactured and marketed them, mainly DuPont and 3M. An example of PFAS is the fluorinated polymer polytetrafluoroethylene (PTFE), which has been produced and marketed by DuPont under its trademark Teflon. GenX chemicals and perfluorobutanesulfonic acid (PFBS) are organofluorine chemicals used as a replacement for PFOA and PFOS.
Perfluorohexanesulfonic acid (PFHxS) is a synthetic chemical compound. It is one of many compounds collectively known as per- and polyfluoroalkyl substances (PFASs). It is an anionic fluorosurfactant and a persistent organic pollutant with bioaccumulative properties. Although the use of products containing PFHxS and other PFASs have been banned or are being phased out in many jurisdictions, it remains ubiquitous in many environments and within the general population, and is one of the most commonly detected PFASs.