Perfluoropropionic acid

Perfluoropropionic acid (PFPrA^[2]) or pentafluoropropionic acid is the perfluoroalkyl carboxylic acid with the formula CF₃CF₂CO₂H. It is a colorless liquid that is strongly acidic and soluble in water and polar organic solvents.

Perfluoropropionic acid

Names
Other names pentafluoropropionic acid perfluoropropanoic acid PFPrA C3 PFCA
Identifiers
CAS Number	422-64-0
3D model (JSmol)	Interactive image
ChemSpider	56147
ECHA InfoCard	100.006.384
EC Number	207-021-6
PubChem CID	62356
CompTox Dashboard (EPA)	DTXSID8059970
InChI InChI=1S/C3HF5O2/c4-2(5,1(9)10)3(6,7)8/h(H,9,10) Key: LRMSQVBRUNSOJL-UHFFFAOYSA-N
SMILES C(=O)(C(C(F)(F)F)(F)F)O
Properties
Chemical formula	C3HF5O2
Molar mass	164.031 g·mol^−1
Appearance	colorless liquid
Density	1.561 g/mL
Boiling point	96–97 °C (205–207 °F; 369–370 K)
Acidity (pKa)	0.38±0.10
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	corrosive
GHS labelling:^[1]
Pictograms
Signal word	Danger
Hazard statements	H314, H332
Precautionary statements	P280, P301+P330+P331, P305+P351+P338, P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It has a predicted pK_a of 0.38, with an uncertainty of 0.10. ^[3]

A convenient, safe method for generating tetrafluoroethylene is the pyrolysis of the sodium salt of pentafluoropropionic acid:^[4]

C₂F₅CO₂Na → C₂F₄ + CO₂ + NaF

References

1. "Pentafluoropropionic acid, 97% – Perfluoropropionic acid – A12791". Alfa Aesar. Retrieved 2022-03-23.
2. Buck, Robert C; Franklin, James; Berger, Urs; Conder, Jason M; Cousins, Ian T; de Voogt, Pim; Jensen, Allan Astrup; Kannan, Kurunthachalam; Mabury, Scott A; van Leeuwen, Stefan PJ (2011). "Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology, classification, and origins". Integrated Environmental Assessment and Management. 7 (4): 513–541. doi:10.1002/ieam.258. PMC 3214619. PMID 21793199.
3. "Perfluoropropionic acid | 422-64-0". ChemicalBook. Retrieved 2024-02-03.
4. Hercules, Daniel A.; Parrish, Cameron A.; Sayler, Todd S.; Tice, Kevin T.; Williams, Shane M.; Lowery, Lauren E.; Brady, Michael E.; Coward, Robert B.; Murphy, Justin A.; Hey, Trevyn A.; Scavuzzo, Anthony R.; Rummler, Lucy M.; Burns, Emory G.; Matsnev, Andrej V.; Fernandez, Richard E.; McMillen, Colin D.; Thrasher, Joseph S. (2017). "Preparation of tetrafluoroethylene from the pyrolysis of pentafluoropropionate salts". Journal of Fluorine Chemistry. 196: 107–116. doi:10.1016/j.jfluchem.2016.10.004.