PFNA
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PFNA
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. Chemistry and properties In acidic form it is a highly reactive strong acid. In its conjugate base form as a salt it is stable and commonly ion paired with ammonium. In the commercial product Surflon S-111 (CAS 72968-3-88) it is the primary compound present by weight. PFNA is used as surfactant for the production of the fluoropolymer polyvinylidene fluoride.Supporting Information
(PDF).
It is produced mainly in Japan by the of a linear

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Fluorosurfactant
Per- and polyfluoroalkyl substances (PFASs) are 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–. More recently (2021) the Organisation for Economic Co-operation and Development (OECD) expanded the definition, 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." According to the OECD, at least 4,730 distinct PFASs are known with at least three perfluorinated carbon atoms. A United States Environmental Protection Agency (EPA) toxicity database, DSSTox, lists 14,735 PFASs, while PubChem lists approximately 6 million. A subgroup, the '' ...
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Perfluorooctanoic Acid
Perfluorooctanoic acid (PFOA; conjugate base perfluorooctanoate; also known colloquially as C8, for its 8 carbon chain structure) 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''-octyl "tail group" and a carboxylate "head group". The head group can be described as hydrophilic while the fluorocarbon tail is both hydrophobic and lipophobic. The tail group is inert and does not interact strongly with polar or non-polar chemical moieties; the head group is reactive and interacts strongly with polar groups, specifically water. The "tail" is hydrophobic due to being non-polar and lipophobic because fluorocarbons are less susceptible to the London dispersion force than hydrocarbons. PFOA is one of many synthetic organofluorine compounds collectively known as per- and po ...
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PFOA
Perfluorooctanoic acid (PFOA; conjugate base perfluorooctanoate; also known colloquially as C8, for its 8 carbon chain structure) 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''-octyl "tail group" and a carboxylate "head group". The head group can be described as hydrophilic while the fluorocarbon tail is both hydrophobic and lipophobic. The tail group is inert and does not interact strongly with polar or non-polar chemical moieties; the head group is reactive and interacts strongly with polar groups, specifically water. The "tail" is hydrophobic due to being non-polar and lipophobic because fluorocarbons are less susceptible to the London dispersion force than hydrocarbons. PFOA is one of many synthetic organofluorine compounds collectively known as per- and p ...
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Surflon S-111
Surflon S-111 (CAS 72968-3-88) 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. The dominant chemical compound is perfluorononanoic acid (PFNA) at 74% by weight, followed by the 11 carbon perfluoroundecanoic acid (20%), and the 13 carbon perfluorotridecanoic acid (5%).Supporting Information
(PDF).
Surflon S-111 is synthesized in Japan by oxidizing a mixture of olefins. Fluorotelomer olefins are synthesized using a

Perfluorooctanesulfonic Acid
Perfluorooctanesulfonic acid (PFOS) (conjugate base perfluorooctanesulfonate) 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. History In 1949, 3M began producing PFOS-based compounds by electrochemical fluorination resulting in the synthetic precursor perfluorooctanesulfonyl fluoride. In 1968, organofluorine content was detected in the ...
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Fluorotelomer Alcohol
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. Naming 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. Chemistry 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. The terminal iodine is replaced by a hydroxyl group to yield the fluorotelomer alcohol. The f ...
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PFOS
Perfluorooctanesulfonic acid (PFOS) (conjugate base perfluorooctanesulfonate) 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. History In 1949, 3M began producing PFOS-based compounds by electrochemical fluorination resulting in the synthetic precursor perfluorooctanesulfonyl fluoride. In 1968, organofluorine content was detected in ...
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Fluorotelomer
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. Types There are many broad categories of fluorotelomers: * Fluorotelomer alcohols (FTOH) * Fluorotelomer ethoxylates (FTEO) * Fluorotelomer fumarates * Fluorotelomer methacrylates (FTMAC) * Fluorotelomer sulphonates (FTS) Manufacture In the radical telomerization of fluorotelomer molecules, a variety of fluorinated alkenes can serve as unsaturated taxogens including tetrafluoroethylene, vinylidene fluoride, chlorotrifluoroethylene, and hexafluoropropene. However, many fluorotelomers, such as fluorotelomer alcohols, are fluorocarbon-based because they are synthesized from tetrafluoroethylene. In addition to alcohols, synthetic products include fluorotelomer iodides, olefins, and acrylate m ...
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Perfluorinated Carboxylic Acid
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.Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick "Fluorine Compounds, Organic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. Applications Trifluoroacetic acid is a widely employed acid, used for example in the synthesis of peptides. Its esters are useful in analytical chemistry. Longer-chain perfluoroalkyl carboxylic acids, e.g. with five to nine carbons, are useful fluorosurfactants and emulsifiers used in the production of po ...
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Organisation For Economic Co-operation And Development
The Organisation for Economic Co-operation and Development (OECD; french: Organisation de coopération et de développement économiques, ''OCDE'') is an intergovernmental organization, intergovernmental organisation with 38 member countries, founded in 1961 to stimulate economic progress and world trade. It is a Forum (legal), forum whose member countries describe themselves as committed to democracy and the market economy, providing a platform to compare policy experiences, seek answers to common problems, identify good practices, and coordinate domestic and international policies of its members. The majority of OECD members are High income economy, high-income economies with a very high Human Development Index, Human Development Index (HDI), and are regarded as Developed country, developed countries. Their collective population is 1.38 billion. , the OECD member countries collectively comprised 62.2% of List of countries by GDP (nominal), global nominal GDP (US$49.6 trill ...
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Carboxylate
In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,...; ''carboxylate esters'' have the general formula (or ). R and R′ are organic groups; R′ ≠ H. Synthesis Carboxylate ions can be formed by deprotonation of carboxylic acids. Such acids typically have p''K''a of less than 5, meaning that they can be deprotonated by many bases, such as sodium hydroxide or sodium bicarbonate. :RCOOH + NaOH -> RCOONa + H2O Resonance stabilization of the carboxylate ion Carboxylic acids easily dissociate into a carboxylate anion and a positively charged hydrogen ion (proton), much more readily than alcohols do (into an alkoxide ion and a proton), because the carboxylate ion is stabilized by resonance. The negative charge that is left after deprotonation of the carboxyl group is delocalized between ...
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Surface Tension
Surface tension is the tendency of liquid surfaces at rest to shrink into the minimum surface area possible. Surface tension is what allows objects with a higher density than water such as razor blades and insects (e.g. water striders) to float on a water surface without becoming even partly submerged. At liquid–air interfaces, surface tension results from the greater attraction of liquid molecules to each other (due to cohesion) than to the molecules in the air (due to adhesion). There are two primary mechanisms in play. One is an inward force on the surface molecules causing the liquid to contract. Second is a tangential force parallel to the surface of the liquid. This ''tangential'' force is generally referred to as the surface tension. The net effect is the liquid behaves as if its surface were covered with a stretched elastic membrane. But this analogy must not be taken too far as the tension in an elastic membrane is dependent on the amount of deformation of the m ...
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