Chemistry:Perfluoropropionic acid
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| Properties | |
| 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 | |
| Main hazards | corrosive |
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| GHS Signal word | Danger |
| H314, H332 | |
| P280, P301+330+331, P305+351+338, P310 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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 of the carboxylic acid or its acid fluoride derivative.[3]
It has a predicted pKa of 0.38, with an uncertainty of 0.10.[4] In many ways, it is comparable to trifluoroacetic acid.
Occurrence and use
The perfluoropropanoate form has been found in environmental samples.[5]
A convenient laboratory method for generating tetrafluoroethylene is the pyrolysis of the sodium salt of pentafluoropropionic acid:[6]
- C2F5CO2Na → C2F4 + CO2 + NaF
References
- ↑ Buck, Robert C; Franklin, James; Berger, Urs; Conder, Jason M; Cousins, Ian T; de Voogt, Pim; Jensen, Allan Astrup; Kannan, Kurunthachalam et al. (2011). "Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology, classification, and origins" (in en). Integrated Environmental Assessment and Management 7 (4): 513–541. doi:10.1002/ieam.258. PMID 21793199. Bibcode: 2011IEAM....7..513B.
- ↑ "Pentafluoropropionic acid, 97% – Perfluoropropionic acid – A12791". https://www.alfa.com/en/catalog/A12791/.
- ↑ Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_349. ISBN 978-3-527-30385-4.
- ↑ "Perfluoropropionic acid | 422-64-0" (in en). https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6139447.htm.
- ↑ Neuwald, Isabelle J.; Hübner, Daniel; Wiegand, Hanna L.; Valkov, Vassil; Borchers, Ulrich; Nödler, Karsten; Scheurer, Marco; Hale, Sarah E. et al. (17 May 2022). "Ultra-Short-Chain PFASs in the Sources of German Drinking Water: Prevalent, Overlooked, Difficult to Remove, and Unregulated". Environmental Science & Technology 56 (10): 6380–6390. doi:10.1021/acs.est.1c07949. Bibcode: 2022EnST...56.6380N.
- ↑ Hercules, Daniel A.; Parrish, Cameron A.; Sayler, Todd S.; Tice, Kevin T.; Williams, Shane M.; Lowery, Lauren E.; Brady, Michael E.; Coward, Robert B. et al. (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.
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