Chemical Properties
Nonafluorobutane-1-sulfonic acid is a colorless liquid. Perfluoro butyl sulfonate has the ability to react violently with water, so preventing exposure tomoisture should be a priority. It may also be incompatible with strong oxidizers. Upon decomposition, PFBS can form carbon oxides, sulfur oxides, and hydrogen fluoride.
Uses
Perfluoro butyl sulfonate (PFBS, nonafluoro-1-butanesulfonic acid, perfluorobutane sulfonic acid, 1-perfluorobutane sulfonic acid) is a four-carbon compound in the perfluoroalkyl family of chemicals. It can be found in stain repellents used for carpets and furniture. A specific form of the chemical, potassium perfluorobutane sulfonate, is being used as a flame retardant in place of brominated retardants. Perfluoro butyl sulfonate is being used as a substitute for other perfluoroalkyl compounds because it is not believed to bioaccumulate in the environment.
Nonafluorobutane-1-sulfonic acid can be considered as a superacid, which can be synthesized by reacting 1-iodononafluorobutane with sodium dithionite in the presence of sodium bicarbonate in acetonitrile/water.
Nonafluorobutane-1-sulfonic acid may be used as catalyst in the synthesis of 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorin and N-benzylpyridin-2-amine.
Definition
ChEBI: A perfluoroalkanesulfonic acid that is butane-1-sulfonic acid in which all of the hydrogens of the butyl group have been replaced by fluorines.
General Description
Nonafluorobutane-1-sulfonic acid can be considered as a superacid, which can be synthesized by reacting 1-iodononafluorobutane with sodium dithionite in the presence of sodium bicarbonate in acetonitrile/water.
Safety Profile
A poison by ingestion.When heated to decomposition it emits toxic vapors of SOx and Clí.
Synthesis
Anhydrous sulfuric acid (37 g, 360 moles) was placed in a glass round-bottomed flask equipped with a magnetic stir bar, a reflux condenser, a thermometer, and a solid dispenser. Perfluorobutane sulfonate sodium salt (C4F9SO3Na, 35 g, 109 mmol) was placed in the dispenser and added to the acid for 10 minutes. No exothermic reaction was observed. The mixture was stirred at 120°C for 30 minutes at 1,000 rpm. 19F-NMR followed the progress of the reaction. Once the complete conversion of acid was observed, the internal temperature was raised to 140°C, and a vacuum (0.8 mbar residual pressure) was applied to the reaction mixture to distill Nonafluorobutane-1-sulfonic acid as a clear liquid.
Environmental Fate
Perfluoro butyl sulfonate is embedded into the carpet and furniture to offer protection against stains and spills. It is also applied to various household products as it may play a role in the retarding of flames during a fire. Over time as furniture, carpet, and other household products begin to degrade, the chemical may be introduced into the indoor environment in house dust. Perfluoro butyl sulfonate, along with other perfluoroalkyl compounds, has been detected in house dust samples indicating a potential route for exposure for occupants (Strynar and Lindstrom, 2008). Frequent vacuuming and dust removal can prevent buildup of the contaminant in household dust and the indoor environment. Perfluoro butyl sulfonate can also be found in water systems as a result of human waste streams. Samples of tap water collected in China, Japan, India, the United States, and Canada, all contained detectable levels of PFBS (Mak et al., 2009). While the chemical has been detected in both the indoor environment and drinking water, the lack of toxicological data related to PFBS makes it hard to determine what levels of exposure are acceptable.
