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]
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.006.384 |
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PubChem CID
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CompTox Dashboard (EPA)
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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 |
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Main hazards
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corrosive |
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| Danger | |
| H314, H332 | |
| 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).
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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
editThe 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
edit- ^ 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. Bibcode:2011IEAM....7..513B. doi:10.1002/ieam.258. PMC 3214619. PMID 21793199.
- ^ "Pentafluoropropionic acid, 97% – Perfluoropropionic acid – A12791". Alfa Aesar. Retrieved 2022-03-23.
- ^ 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". ChemicalBook. Retrieved 2024-02-03.
- ^ Neuwald, Isabelle J.; Hübner, Daniel; Wiegand, Hanna L.; Valkov, Vassil; Borchers, Ulrich; Nödler, Karsten; Scheurer, Marco; Hale, Sarah E.; Arp, Hans Peter H.; Zahn, Daniel (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. Bibcode:2022EnST...56.6380N. doi:10.1021/acs.est.1c07949. hdl:11250/3069800.
- ^ 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.