Perfluoropropionic acid (PFPrA) or pentafluoropropionic acid is an ultra-short chain perfluoroalkyl carboxylic acid with the formula CF₃CF₂CO₂H. It is a colorless liquid that is strongly acidic. It soluble in both water and polar organic solvents. The compound is produced by

electrochemical fluorination Electrochemical fluorination (ECF), or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds.G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, ...

of the carboxylic acid or its acid fluoride derivative. It has a predicted pK_a of 0.38, with an uncertainty of 0.10. In many ways, it is comparable to

trifluoroacetic acid Trifluoroacetic acid (TFA) is a synthetic organofluorine compound with the chemical formula CF3CO2H. It belongs to the subclass of per- and polyfluoroalkyl substances (PFASs) known as ultrashort-chain perfluoroalkyl acids (PFAAs). TFA is not ...

Occurrence and use

The perfluoropropanoate form has been found in environmental samples. A convenient laboratory method for generating

tetrafluoroethylene Tetrafluoroethylene (TFE) is a fluorocarbon with the chemical formula . It is a colorless gas. Its structure is . It is used primarily in the industrial preparation of fluoropolymers. It is the simplest perfluorinated alkene. It was first repor ...

is the

pyrolysis Pyrolysis is a process involving the Bond cleavage, separation of covalent bonds in organic matter by thermal decomposition within an Chemically inert, inert environment without oxygen. Etymology The word ''pyrolysis'' is coined from the Gree ...

of the

sodium salt Sodium salts are salt (chemistry), salts composed of a sodium cation and any anion. The anion may be the conjugate base of some Inorganic compound, inorganic or organic acids, or any monatomic or polyatomic anion. They can be formed by the Neutra ...

of pentafluoropropionic acid:{{cite journal , doi = 10.1016/j.jfluchem.2016.10.004, title = Preparation of tetrafluoroethylene from the pyrolysis of pentafluoropropionate salts, year = 2017, last1 = Hercules, first1 = Daniel A., last2 = Parrish, first2 = Cameron A., last3 = Sayler, first3 = Todd S., last4 = Tice, first4 = Kevin T., last5 = Williams, first5 = Shane M., last6 = Lowery, first6 = Lauren E., last7 = Brady, first7 = Michael E., last8 = Coward, first8 = Robert B., last9 = Murphy, first9 = Justin A., last10 = Hey, first10 = Trevyn A., last11 = Scavuzzo, first11 = Anthony R., last12 = Rummler, first12 = Lucy M., last13 = Burns, first13 = Emory G., last14 = Matsnev, first14 = Andrej V., last15 = Fernandez, first15 = Richard E., last16 = McMillen, first16 = Colin D., last17 = Thrasher, first17 = Joseph S., journal = Journal of Fluorine Chemistry, volume = 196, pages = 107–116, doi-access = free :C₂F₅CO₂Na → C₂F₄ + CO₂ + NaF

References

Perfluorocarboxylic acids Propionic acids