ChemicalBook CAS DataBase List Nonafluorobutane-1-sulfonic acid

Nonafluorobutane-1-sulfonic acid synthesis

8synthesis methods

Product Name:Nonafluorobutane-1-sulfonic acid
CAS Number:375-73-5
Molecular formula:C4HF9O3S
Molecular Weight:300.1

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.

1-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro-, sodium salt (1:1)

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Yield:375-73-5 94%

Reaction Conditions:

with sulfuric acid at 120; for 0.5 h;

Steps:

1.a Step a) Conversion of perfluorobutane sulfonate sodium salt into perfluorobutane sulfonic acid

[0091]Anhydrous sulfuric acid (37 g, 360 mmoles) 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 mmols) was placed in the dispenser and added to the acid in 10 minutes. No exothermic reaction was observed. The mixture was stirred at 120°C for 30 minutes at 1,000 rpms. The progress of the reaction was followed by ¹⁹F-NMR. Once complete conversion of acid was observed (the -CF₂-SO₃H peak shifted from -114.5 ppm to -112 ppm and the -CF₂CF₂SO₃H peak shifted from -121 ppm to -122 ppm; total shift = 3.5 ppms), the internal temperature was raised to 140°C and vacuum (0.8 mbar residual pressure) was applied to the reaction mixture to distil perfluorobutane sulfonic acid as a clear liquid. [0092]Yield: 28.1 g (94 mmols); 94 mol%.

References:

WO2017/16943,2017,A1 Location in patent:Paragraph 0090-0092

29420-49-3 Synthesis