Fluorotelomer alcohols, or FTOHs, are fluorotelomers with an alcohol functional group. They are volatile precursors to perfluorinated carboxylic acids, such as PFOA and PFNA, and other compounds.
Fluorotelomer alcohols, or FTOHs, are fluorotelomers with an alcohol functional group. They are volatile precursors to perfluorinated carboxylic acids, such as PFOA and PFNA, and other compounds.
Commonly, an individual fluorotelomer alcohol molecule is named by the number of carbons that are fluorinated versus the number that are hydrocarbon-based. For example, 8:2 fluorotelomer alcohol would represent a molecule with 8 fluorinated carbons and a 2 carbon ethyl alcohol group. The structure of a fluorotelomer alcohol is most commonly F(CF2)nCH2CH2OH, where n is an even number.
The synthesis of fluorotelomer alcohols requires a varying number of tetrafluoroethylene monomers that form an oligomer with a pentafluoroethyl iodide telogen. The fluorinated iodide then undergoes an addition with ethylene to form an organoiodine compound with increased synthesis possibilities. [1] The terminal iodine is replaced by a hydroxyl group to yield the fluorotelomer alcohol. The fluorotelomer alcohol can then be used to produce acrylate polymers with the fluorotelomer alcohols attached via ester functional groups. [2]
Fluorotelomer alcohols are volatile and widely detected in air. [3] [4]
Acrylate polymers with fluorotelomer substituents are under investigation for their potential to degrade into environmental contaminants." [2] The USEPA has carried out environmental degradation studies with two DuPont acrylate polymers in four soils and water. [5] [6] These studies reported environmental degradation half-life ranges for these commercial fluorotelomer-based polymers of 33 to 112 years. [5] [6] FTOHs can also be used as intermediates in the production of surfactants. [7]
Fluorotelomer alcohols can biodegrade to perfluorinated carboxylic acids, which persist in the environment and are found in the blood serum of populations and wildlife, such as the toxic PFOA and PFNA. [8] [9]
The fluorotelomer alcohols 6:2 FTOH and 8:2 FTOH have been found to be estrogenic. [11]
The atmospheric oxidation of fluorotelomer alcohols can also result in anthropogenic perfluorinated carboxylic acids. [12] In addition to perfluorinated carboxylic acids, fluorotelomer alcohols can degrade to form unsaturated carboxylic acids which have been detected in bottlenose dolphins. [13] Fluorotelomer alcohols such as 4:2 FTOH, 6:2 FTOH, 8:2 FTOH, and 10:2 FTOH, have been identified as residuals in consumer products such as stain repellents, Zonyl FSE, and windshield wash, among others. [14] The United States Environmental Protection Agency has asked eight chemical companies to reduce the amount of residuals, including fluorotelomer alcohols, from products. [14]
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.
Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers. They are used extensively in epoxy formulation in North America but its use has been phased out in Europe. These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity. The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain. Nonylphenol has been found to act as an agonist of the GPER (GPR30).
Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor.
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.
Ethylenediamine-N,N'-disuccinic acid (EDDS) is an aminopolycarboxylic acid. It is a colourless solid that is used as chelating agent that may offer a biodegradable alternative to EDTA, which is currently used on a large scale in numerous applications.
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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."
Telomerization is a reaction that produces a particular kind of oligomer with two distinct end groups. The oligomer is called a telomer. Some telomerizations proceed by radical pathways, many do not. A generic equation is:
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.
Fluorotelomers are fluorocarbon-based oligomers, or telomers, synthesized by telomerization. Some fluorotelomers and fluorotelomer-based compounds are a source of environmentally persistent perfluorinated carboxylic acids such as PFOA and PFNA, while others are under extended investigation.
Fluorous chemistry involves the use of perfluorinated compounds or perfluorinated substituents to facilitate recovery of a catalyst or reaction product. Perfluorinated groups impart unique physical properties including high solubility in perfluorinated solvents. This property can be useful in organic synthesis and separation methods such as solid phase extraction. In practice, a perfluorinated alkyl group is incorporated into an otherwise conventional organic reagent as an affinity tag. These reagents can then be separated from organic solvents by extraction with fluorinated solvents such as perfluorohexane.
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.
Perfluoroalkyl carboxylic acids (PFCAs), or perfluorocarboxylic acids are compounds of the formula CnF(2n+1)CO2H that belong to the class of per- and polyfluoroalkyl substances. The simplest example is trifluoroacetic acid. These compounds are organofluorine analogues of ordinary carboxylic acids, but they are stronger by several pKa units and they exhibit great hydrophobic character. Perfluoroalkyl dicarboxylic acids (PFdiCAs) are also known, e.g. C2F4(CO2H)2.
Surflon S-111 is a commercial product consisting of perfluorinated carboxylic acids (PFCAs) in ammonium salt form. It is commonly used as a polymerization aid in the production of fluoropolymers.
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.
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.
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.
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.