2,3,3,3-tetrafluoro-2-(heptafluoropropoxy)propanoic Acid
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FRD-903 (also known as hexafluoropropylene oxide dimer acid, HFPO-DA, and 2,3,3,3-tetrafluoro-2-(heptafluoropropoxy)propanoic acid) is a
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
that is among the class of
per- and polyfluoroalkyl substances Per- and polyfluoroalkyl substances (also PFAS, PFASs, and informally referred to as "forever chemicals") are a group of synthetic organofluorine chemical compounds that have multiple fluorine atoms attached to an alkyl chain; there are 7 milli ...
(PFASs). More specifically, this synthetic
petrochemical Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable s ...
is also described as a perfluoroalkyl
ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R†...
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
(PFECA) and a Fluorointermediate. It is not biodegradable and is not
hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
by water.


Production

The production process involves 2 molecules of
hexafluoropropylene oxide Hexafluoropropylene oxide (HFPO) is an intermediate used in industrial organofluorine chemistry; specifically it is a monomer for fluoropolymers. This colourless gas is the epoxide of hexafluoropropylene, which is a fluorinated analog of propylen ...
(HFPO) to produce hexafluoropropylene oxide dimer acid fluoride (FRD-903). The
ammonium Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) polyatomic ion, molecular ion with the chemical formula or . It is formed by the protonation, addition of a proton (a hydrogen nucleu ...
salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
of FRD-903 is FRD-902 (ammonium (2,3,3,3-tetrafluoro-2-(heptafluoropropoxy)propanoate)), which is the specific chemical which
Chemours The Chemours Company (, ) is an American chemical industry, chemical company that was founded in July 2015 as a Corporate spin-off, spin-off from DuPont. It has its corporate headquarters in Wilmington, Delaware, United States. Chemours is the m ...
has trademarked as part of
GenX 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 fluoroche ...
process. FRD-903 is used as an aid within the manufacturing process for fluoropolymers by reducing the surface tension in the process, allowing polymer particles to increase in size. The process is completed with chemical treatment or heating to remove the FRD-903 from the final polymer product. It can then be recovered for re-use within the process.


Drinking water

In 2020, Michigan adopted drinking water standards for five previously unregulated PFAS compounds including HFPO-DA which has a
maximum contaminant level Maximum contaminant levels (MCLs) are standards that are set by the United States Environmental Protection Agency (EPA) for drinking water quality.Joseph Cotruvo, Victor Kimm, Arden Calvert“Drinking Water: A Half Century of Progress.”EPA Alumn ...
(MCL) of 370 parts per trillion (ppt). In March 2023, the EPA announced drinking water standards for several PFAS chemicals, which included FRD-903.


References

{{Reflist Perfluorocarboxylic acids Ethers