Perfluoropropionic acid

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]

Perfluoropropionic acid
Names
Other names
pentafluoropropionic acid
perfluoropropanoic acid
PFPrA
C3 PFCA[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.384 Edit this at Wikidata
EC Number
  • 207-021-6
  • InChI=1S/C3HF5O2/c4-2(5,1(9)10)3(6,7)8/h(H,9,10)
    Key: LRMSQVBRUNSOJL-UHFFFAOYSA-N
  • C(=O)(C(C(F)(F)F)(F)F)O
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
Occupational safety and health (OHS/OSH):
Main hazards
corrosive
GHS labelling:[2]
GHS05: CorrosiveGHS07: Exclamation mark
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).

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

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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

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  1. ^ 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.
  2. ^ "Pentafluoropropionic acid, 97% – Perfluoropropionic acid – A12791". Alfa Aesar. Retrieved 2022-03-23.
  3. ^ 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.
  4. ^ "Perfluoropropionic acid | 422-64-0". ChemicalBook. Retrieved 2024-02-03.
  5. ^ 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.
  6. ^ 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.