Names | |
---|---|
Preferred IUPAC name Heptafluorobutanoic acid | |
Other names | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | HFBA |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.006.170 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C4HF7O2 | |
Molar mass | 214.039 g·mol−1 |
Appearance | colourless liquid |
Density | 1.64 g/ml |
Boiling point | 120 °C (248 °F; 393 K) |
high | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | strong acid |
GHS labelling: [2] | |
Danger | |
H314 | |
P260, P280, P303+P361+P353, P304+P340+P310, P305+P351+P338 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Perfluorobutanoic acid (PFBA) is a perfluoroalkyl carboxylic acid with the formula C3F7CO2H. As the perfluorinated derivative of butyric acid, this colourless liquid is prepared by electrofluorination of the corresponding butyryl fluoride. [3]
PFBA has a variety of niche applications in analytical and synthetic chemistry. It is an ion pair reagent for reverse-phase high-performance liquid chromatography. It is used in the sequencing, synthesis, and solubilizing of proteins and peptides.
Esters derived from PFBA readily undergo condensation, owing to their electrophilicity. Specialized ligands for metal ions are generated capitalizing on this property, such as Eufod.
PFBA was formerly used for manufacturing photographic film. The 3M Company was a major manufacturer of PFBA and products containing PFBA but production was phased out in 1998. [4]
PFBA is a breakdown product of other PFAS that have been used in stain-resistant fabrics, paper food packaging, carpets, and consumer products. [5] PFBA has been frequently found in U.S. rivers. [4] [6]
In laboratory animal studies, exposure to high levels of PFBA results in thyroid and liver effects, such as increased thyroid and liver weight, changes in thyroid hormones, decreased cholesterol, and cellular changes in both organs. Other effects of PFBA exposure included delayed development and decreased red blood cells and hemoglobin. [4]
The Minnesota Department of Health (MDH) developed a guidance value of 7 ppb (μg/L) for PFBA in drinking water. [4]
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.
A perchlorate is a chemical compound containing the perchlorate ion, ClO−4, the conjugate base of perchloric acid. As counterions, there can be metal cations, quaternary ammonium cations or other ions, for example, nitronium cation.
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. As confirmed by X-ray crystallography, nitrobenzene is a planar molecule.
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 carboxylic acid "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 it is a perfluorosulfonic acid and a perfluoroalkyl substance (PFAS). 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.
Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic and adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released.
Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.
Decabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs). It was commercialised in the 1970s and was initially thought to be safe, but is now recognised as a hazardous and persistent pollutant. It was added to Annex A of the Stockholm Convention on Persistent Organic Pollutants in 2017, which means that treaty members must take measures to eliminate its production and use. The plastics industry started switching to decabromodiphenyl ethane as an alternative in the 1990s, but this is now also coming under regulatory pressure due to concerns over human health.
Environmental toxicology is a multidisciplinary field of science concerned with the study of the harmful effects of various chemical, biological and physical agents on living organisms. Ecotoxicology is a subdiscipline of environmental toxicology concerned with studying the harmful effects of toxicants at the population and ecosystem levels.
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 are a group of synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain; there are 7 million such chemicals according to PubChem. PFAS came into use after the invention of Teflon in 1938 to make fluoropolymer coatings and products that resist heat, oil, stains, grease, and water. They are now used in products including waterproof fabric such as Nylon, yoga pants, carpets, shampoo, feminine hygiene products, mobile phone screens, wall paint, furniture, adhesives, food packaging, heat-resistant non-stick cooking surfaces such as Teflon, firefighting foam, and the insulation of electrical wire. PFAS are also used by the cosmetic industry in most cosmetics and personal care products, including lipstick, eye liner, mascara, foundation, concealer, lip balm, blush, and nail polish.
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 that lacks 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 PFC production. Due to their chemical stability, some of these perfluorinated compounds bioaccumulate.
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, in response to legal action due to the health effects and ecotoxicity of PFOA.
Perfluorodecanoic acid (PFDA) is a fluorosurfactant and has been used in industry.
The CompTox Chemicals Dashboard is a freely accessible online database created and maintained by the U.S. Environmental Protection Agency (EPA). The database provides access to multiple types of data including physicochemical properties, environmental fate and transport, exposure, usage, in vivo toxicity, and in vitro bioassay. EPA and other scientists use the data and models contained within the dashboard to help identify chemicals that require further testing and reduce the use of animals in chemical testing. The Dashboard is also used to provide public access to information from EPA Action Plans, e.g. around perfluorinated alkylated substances.
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.
Erin Shammel Baker is an American bioanalytical chemist specializing in developing ion mobility-mass spectrometry hybrid instruments for biological and environmental applications. Baker is an expert in the research of perfluoroalkyl and polyfluoroalkyl substances analysis.
Remediation of per- and polyfluoroalkyl substances refers to the destruction or removal of per- and polyfluoroalkyl substances (PFASs) from the environment. PFASs are a group of synthetic organofluorine compounds, used in diverse products such as non-stick cookware and firefighting foams, that have attracted great concern as persistent organic pollutants. Because they are pervasive and have adverse effects, much interest has focused on their removal.