Perfluorononanoic acid
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| Names | |
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IUPAC name
Heptadecafluorononanoic acid
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| Other names
perfluoro-n-nonanoic acid, PFNA, perfluorononanoate
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| Identifiers | |
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.184 |
| EC Number | 206-801-3 |
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PubChem CID
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| Properties | |
| C9HF17O2 | |
| Molar mass | 464.08 g/mol |
| Appearance | white crystalline powder |
| Melting point | 59 to 62 °C (138 to 144 °F; 332 to 335 K) |
| Boiling point | 218 °C (424 °F; 491 K) |
| 9.5 g/L | |
| Solubility in other solvents | polar organic solvents |
| Acidity (pKa) | ~0 |
| Hazards | |
| Main hazards | Strong Acid, Causes Burns |
| R-phrases | R22 R34 R52/53 |
| S-phrases | S26 S36/37/39 S45 |
| Related compounds | |
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Related compounds
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Trifluoroacetic acid (TFA), Perfluorooctanoic acid (PFOA), Perfluorooctanesulfonic acid (PFOS) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
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.
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. It is produced mainly in Japan by the oxidation of a linear fluorotelomer olefin mixture containing F(CF2)8CH=CH2. It can also be synthesized by the carboxylation of F(CF2)8I. PFNA can form from the biodegradation of 8:2 fluorotelomer alcohol. Additionally, it is considered a probable degradation product of many other compounds.
PFNA is the largest perfluorinated carboxylic acid surfactant. Fluorocarbon derivatives with terminal carboxylates are only surfactants when they possess five to nine carbons. Fluorosurfactants reduce the surface tension of water down to half of what hydrocarbon surfactants can by concentrating at the liquid-air interface due to the lipophobicity of fluorocarbons. PFNA is very stable and is not known to degrade in the environment by oxidative processes because of the strength of the carbon–fluorine bond and the electronegativity of fluorine.
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Wikipedia