IP Library Granted Patent US 7,138,551
Granted Patent B2
US 7,138,551 · App. 10/983,201 · Granted Nov 21, 2006

Purification of fluorinated alcohols

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Quick Facts
Patent No.
US 7,138,551
App. No.
10/983,201
Granted
Nov 21, 2006
Kind
B2
Abstract

A process for reducing the level of perfluoroalkanoic acids, perfluoroalkanoic esters, and perfluoroalkyliodides in fluorinated alcohols comprising heating a fluorinated alcohol, or mixtures thereof, containing said acids, esters, or iodides to a temperature of at least 175° C. in the presence of water and a base additive is disclosed.

Claims (24)

1. A process for selectively reducing the level of perfluoroalkanoic acids or salts thereof, perfluroalkanoic esters, and perfluoroalkyliodides in fluorinated alcohols comprising heating a fluorinated alcohol, or mixtures thereof, containing said acids, salts, esters, or iodides to a temperature of at least about 175° C. in the presence of water and at least one base additive.

2. The process of claim 1 wherein the fluorinated alcohol is of formula R f (CH 2 ) m OH wherein R f is —C n F (2n+1) , n is 2 to about 20, or a mixture thereof, and m is 2 to 3.

3. The process of claim 1 wherein the base is a Brønsted base.

4. The process of claim 1 wherein the base additive is selected from the group consisting of ammonia, ammonia salts, primary amines, secondary amines, tertiary amine, amine salts, alkali metal hydroxides, alkali metal salts, and mixtures thereof.

5. The process of claim 4 wherein the base additive or mixture of base additives is present at a level of from about 0.1% to about 20% by weight of the fluorinated alcohol.

6. The process of claim 1 further comprising heating in the presence of at least one additional hydrogen atom donor.

7. The process of claim 6 wherein the hydrogen atom donor is an organic molecule containing electron-donating substituents.

8. The process of claim 6 wherein the hydrogen atom donor is selected from the group consisting of glycols, alkyl alcohols, ethers, acids, amines, salts thereof for each of the foregoing, and complexes with metals thereof for each of the foregoing.

9. The process of claim 6 wherein the hydrogen atom donor is present at a level of 0 to about 20% by weight of the fluorinated alcohol.

10. The process of claim 1 wherein the fluorinated alcohol and base additive are agitated during heating.

11. The process of claim 1 further comprising separation of the fluorinated alcohol.

12. The process of claim 1 or 6 wherein color formation is minimized by selection of the base additives.

13. The process of claim 1 or 6 wherein the heating is at a temperature of from about 175° C. to about 225° C.

14. A process for selectively reducing the level of perfluoroalkanoic acids and salts thereof, and perfluoroalkyliodides in the presence of 1-iodo-1H,1H,2H, 2H-perfluoroalkane comprising heating a 1-iodo-1H,1H,2H,2H-perfluoroalkane, or mixtures thereof, containing said perfluoroalkanoic acids or salts thereof to a temperature of at least 175° C. in the presence of at least one organic additive.

15. The process of claim 14 wherein the 1-iodo-1H,1H,2H,2H-perfluroalkane is of formula R f CH 2 CH 2 I wherein R f is —C n F (2n+1) wherein n is 2 to about 20.

16. The process of claim 14 wherein the organic additive is a compound having electron-donating substituents.

17. The process of claim 14 wherein the organic additive is selected from the group consisting of glycols, alkyl alcohols, alkyl ethers, amides, tertiary amines, salts thereof, saturated and unsaturated hydrocarbons.

18. The process of claim 14 wherein the organic additive has a molecular weight from about 28 to about 1000.

19. The process of claim 14 wherein the organic additive is isopropyl alcohol.

20. The process of claim 14 wherein the organic additive or mixture of organic additives is present at a level of 0.1% to about 20% by weight of the 1-iodo-1H,1H,2H,2H-perfluoroalkane.

21. The process of claim 14 wherein the heating is at a temperature of from about 175° C. to about 225° C.

22. The process of claim 14 further comprising heating in the presence of water.

23. The process of claim 14 wherein the perfluoroalkanoic acids, salts thereof, perfluoroalkyliodides, 1-iodo-1H,1H,2H,2H-perfluoroalkane, and organic additive are agitated during heating.

24. The process of claim 14 further comprising separation of the 1-iodo-1H,1H,2H,2H-perfluoroalkane.

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 →