IP Library Granted Patent US 7,683,209
Granted Patent B2
US 7,683,209 · App. 11/447,713 · Granted Mar 23, 2010

Manufacture of hydrofluoroalkanesulfonic acids

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Quick Facts
Patent No.
US 7,683,209
App. No.
11/447,713
Granted
Mar 23, 2010
Kind
B2
Abstract

A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.

Claims (18)

1. Process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to a carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising:

a) contacting fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12;

b) removing water from said solution to form a solid;

c) directly treating said solid with oleum to form a mixture that includes hydrofluoroalkanesulfonic acid; and

d) distilling said hydrofluoroalkanesulfonic acid from said mixture.

2. Process of claim 1 wherein no free radical initiator is added to said solution.

3. Process of claim 1 wherein said fluoroolefin is a perfluoroolefin.

4. Process of claim 1 wherein said fluoroolefin is an alpha-olefin.

5. Process of claim 1 wherein said fluoroolefin is tetrafluoroethylene.

6. Process of claim 1 wherein said fluoroolefin is hexafluoropropylene.

7. Process of claim 1 wherein the source of said sulfite in aqueous solution is sulfur dioxide.

8. Process of claim 1 wherein said pH of said aqueous solution is adjusted without use of extraneous reagents.

9. Process of claim 1 wherein said pH of said aqueous solution is adjusted by addition of at least one reagent selected from the group consisting of sulfurous acid, sulfuric acid, bisulfite, bisulfate, metabisulfite, bicarbonate, sulfur dioxide, and carbon dioxide.

10. Process of claim 1 wherein said removing water from said solution to form a dry solid is done by freeze drying said solution.

11. Process of claim 1 wherein said solid is a freeze dried solid.

12. Process of claim 1 wherein said removing water from said solution to form a dry solid is done by spray-drying said solution.

13. Process of claim 1 wherein said solid is a spray dried solid.

14. Process of claim 1 wherein said hydrofluoroalkanesulfonic acid is 1,1,2,2-tetrafluoroethanesulfonic acid.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →