Perfluoropropionic acid

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)	DTXSID3097848 DTXSID8059970, DTXSID3097848 ;
	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:
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

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 pK_a 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; 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.

[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.

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