Synthesis of three partially fluorinated alkanesulfonic acids as potential fuel-cell electrolytes

Bunyagidj, Chaiyun; Piotrowska, H.; Aldridge, Mary H.

doi:10.1021/je00025a039

Cited by 22 publications

(3 citation statements)

References 5 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Trifluoroethanesulfonic acid ( 464 ) was prepared in very low yield by the reaction of sodium sulfite with 1-bromo-2,2,2-trifluoroethane. Even at elevated temperature the nucleophilic substitution proceeds without significant success . 1,1,1-Trifluoroethyl chloride as well as bromide and iodide can be easily converted into the corresponding sulfinate 463a′ using Na 2 S 2 O 4 –NaHCO 3 in DMSO at 75 °C.…”

Section: Chemical Properties Of Polyfluorinated Ethanesmentioning

confidence: 99%

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

2015

View full text Add to dashboard Cite

Section: Chemical Properties Of Polyfluorinated Ethanesmentioning

confidence: 99%

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

2015

View full text Add to dashboard Cite

“…Mass spectral data showed a molecular fragment. - [11] No product was isolated. Instead a thick brown oily residue was formed.…”

Section: Ch30cf2cf2sq2f With Clcf2(o)cf3mentioning

confidence: 99%

Monomeric and Polymeric Fluoroalkyl Sulfonyl Fluorides, Sulfonate Salts and Sulfonic Acids for Use as Electrolytes and Coatings

Hamel¹

2000

View full text Add to dashboard Cite

show abstract

“…However, the acid hydrate is too volatile for extended use at the operating temperature of fuel cells (> 100°C), and in addition it tends to wet the Teflon surface of the electrodes used (1). A variety of other partially fluorinated or perfluoroalkylsulfonic and disulfonic acids (1)(2)(3)(4)(5) as well as phosphonic acids ( 6 4 , mixed sulfonic or phosphonic/carboxylic acids (9), and a mixed sulfonic/phosphonic acid (10) have been synthesized for evaluation as potential fuel cell electrolytes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of fluorinated phosphonic, sulfonic, and mixed phosphonic/sulfonic acids

Su¹,

Cen²,

Kirchmeier³

et al. 1989

Can. J. Chem.

View full text Add to dashboard Cite

. 67, 1795 (1989). The acids (H0)2P(0)CFHS03H, (H0)2P(0)(CF2)40(CF2)2S03H, H(CF2)20(CF2)2P(0)(OH)2, H(CF2)20(CF2)4P(0)-(OH)2, (H0)2P(0)(CF2)20(CF2)4H, and the acid precursor (C2H50)2P(0)CF(S03Na)2 have been synthesized. Elemental analysis, 1 9~, 'H, and 3 '~ NMR, and mass spectroscopy were used for characterization of these materials. They are very strong acids, and exhibit a high degree of stability in aqueous solution at elevated temperature, which makes them attractive candidates for use as electrolytes in fuel cells. Introduction Many fluorinated sulfonic and phosphonic acids exhibit properties that make them potentially useful as electrolytes in fuel cells. They are much stronger acids than their nonfluorinated analogues, and are generally more stable. In addition, oxygen solubility is greatly enhanced, and volatility at elevated temperatures may be lower. In fuel cell applications, these factors combine to provide increased conductivity, enhanced oxygen reduction kinetics, and longer term system stability when compared to phosphoric acid as the electrolyte.The primary acid used in fuel cells today is H3PO4. However, it has many drawbacks, including low oxygen solubility and anion adsorption on the catalyst surface. There is a need to develop new compounds that have the desirable properties of H3PO4 but fewer of the less desirable ones, in order to enhance the usefulness of fuel cells as alternative energy sources.Fluorocarbon electrolytes have the ability to lower the surface tension of water. This effect is in part due to several structural factors: (1) terminal grouping; (2) chain-length; and (3) the presence of heteroatoms in the chain. For example, a CF3 terminal group attached to a CF2 chain will have a greater surface tension lowering effect than a HCF2 terminal group attached to a similar chain. The solubility of oxygen in fluorocarbon systems is dependent on the boiling point, density, molecular weight, and viscosity of the fluorocarbon. These properties in turn are dependent in part on the structural factors and composition mentioned above.At low temperature trifluoromethanesulfonic acid has been found to be superior to H3P04 with respect to electrode kinetics. However, the acid hydrate is too volatile for extended use at the operating temperature of fuel cells (> 100°C), and in addition it tends to wet the Teflon surface of the electrodes used (1). A variety of other partially fluorinated or perfluoroalkylsulfonic and disulfonic acids (1-5) as well as phosphonic acids ( 6 4 , mixed sulfonic or phosphonic/carboxylic acids (9), and a mixed sulfonic/phosphonic acid (10) have been synthesized for evaluation as potential fuel cell electrolytes.

show abstract

Synthesis of three partially fluorinated alkanesulfonic acids as potential fuel-cell electrolytes

Cited by 22 publications

References 5 publications

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

Monomeric and Polymeric Fluoroalkyl Sulfonyl Fluorides, Sulfonate Salts and Sulfonic Acids for Use as Electrolytes and Coatings

Synthesis of fluorinated phosphonic, sulfonic, and mixed phosphonic/sulfonic acids

Contact Info

Product

Resources

About