Perfluorobutane sulfonamide

Perfluorobutane sulfonamide, also known as FBSA or H-FBSA, is a perfluorinated surfactant. FBSA and its N-alkylated derivatives have been patented by 3M for use in acid etch solutions with low surface tension. According to the inventors, FBSA and its derivatives are expected to have a smaller tendency to accumulate in living organisms than their perfluorooctanyl analogs such as PFOS.^[1] Nevertheless, a 2015 study found FBSA in 32 out of 33 samples of Canadian fish.^[2]

Perfluorobutane sulfonamide

Names
Preferred IUPAC name 1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonamide
Other names Perfluorobutylsulfonamide, FBSA
Identifiers
CAS Number	30334-69-1 Y
3D model (JSmol)	Interactive image
ChemSpider	9133422
ECHA InfoCard	100.250.644
PubChem CID	10958205
UNII	G4V6K37HVR Y
CompTox Dashboard (EPA)	DTXSID30880251
InChI InChI=1S/C4H2F9NO2S/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16/h(H2,14,15,16) Key: FUVKFLJWBHVMHX-UHFFFAOYSA-N
SMILES C(C(C(F)(F)S(=O)(=O)N)(F)F)(C(F)(F)F)(F)F
Properties
Chemical formula	C4H2F9NO2S
Molar mass	299.111 g/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Spills

In April 2019, 3M admitted in a letter to the EPA that the plant in Decatur, Alabama released FBSA and FBSEE into the Tennessee River, despite a 2009 EPA order prohibiting release to water.^[3] Supposedly, authorities had been aware of the contamination since 2014, but did not make it public.^[4] The same facility has been responsible for release of other per- and polyfluorinated alkylated substances, namely PFOS and PFOA, into the Tennessee River, prompting 3M to pay $35 million to a local water authority in order to improve drinking water purification.^[5]

Belgian journalists from VTM Nieuws/Het Laatste Nieuws reported that 3M was illegally discharging the harmful chemical FBSA into the Scheldt river. This was being investigated by the Flemish authorities. On August 24, 2021, the company confessed to the allegations.^[6]

See also

• PFBS (Perfluorobutanesulfonic acid)

References

1. US 7169323, MJ Parent, PM Savu, RM Flynn, "Fluorinated surfactants for buffered acid etch solutions", published 2007-01-30, assigned to 3M Innovative Properties Company
2. Sinclair, Ewan; Mayack, David T.; Roblee, Kenneth; Yamashita, Nobuyoshi; Kannan, Kurunthachalam (2006). "Occurrence of Perfluoroalkyl Surfactants in Water, Fish, and Birds from New York State". Archives of Environmental Contamination and Toxicology. 50 (3): 398–410. doi:10.1007/s00244-005-1188-z. PMID 16435086. S2CID 709700.
3. Cheryl Hogue (2019-06-25). "3M admits to unlawful release of PFAS in Alabama". Chemical & Engineering News. 97 (26).
4. Chelsea Brentzel (2019-06-19). "State of Alabama permitted 3M to release toxic chemicals into Tennessee River for years, records show". WHNT News (whnt.com). Retrieved 2019-07-03.
5. "3M Admits to Illegal Chemical Release". Water & Wastes Digest (wwdmag.com). Scranton Gillette Communications. 2019-06-17. Retrieved 2019-07-03.
6. "3M bekent lozing FBSA: "Maar alles volledig in overeenstemming met omgevingsvergunning"". Het Laatste Nieuws (in Dutch). Retrieved 2021-08-24.