IP Library Granted Patent US 8,461,378
Granted Patent B2
US 8,461,378 · App. 12/879,553 · Granted Jun 11, 2013

Purification of fluoroalkanesulfonate salts

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Quick Facts
Patent No.
US 8,461,378
App. No.
12/879,553
Granted
Jun 11, 2013
Kind
B2
Abstract

A process for the purification of fluoroalkanesulfonate salt comprising (a) contacting a mixture of said salt and an inorganic salt contaminant with a solvent to selectively dissolve said fluoroalkanesulfonate salt in solution, and (b) isolating the solution, to yield a fluoroalkanesulfonate salt containing less than 500 micrograms of inorganic salt contaminant per gram of fluoroalkanesulfonate salt, or containing less than a maximum of 0.3% by weight of individual solvent.

Claims (29)

1. A process for the purification of fluoroalkanesulfonate salts comprising

(a) contacting a mixture comprising

1) at least one fluoroalkanesulfonate salt of the formula

[C(H)(F)(X)CF2SO 3 ] y M  (I)

wherein

X is H, Cl, F, CF 3 , or OR;

R is C 1 -C 6 alkyl, fluoroalkyl, or perfluoroalkyl;

M is Li, Na, K, Cs, Rb, Ca, or Ba; and

y is a positive integer equal to the valence of M; and

2) at least one inorganic salt contaminant,

with one or more solvents to selectively dissolve at least a portion of said salt in solution; and

(b) isolating the solution from the mixture to yield a fluoroalkanesulfonate salt containing less than 500 micrograms of inorganic salt contaminant per gram of fluoroalkanesulfonate salt, or containing less than a maximum of 0.3% by weight of individual solvent.

2. The process of claim 1 further comprising drying the solution of fluoroalkanesulfonate salt.

3. The process of claim 1 wherein the solvent is methyl ethyl ketone, methanol, ethanol, isopropanol, acetonitrile, ethyl acetate, tetrahydrofuran, 1,2-dimethoxyethane, and dimethyl carbonate, or mixtures thereof.

4. The process of claim 1 wherein the contaminant is one or more M-salt contaminants selected from the group consisting of chlorides, fluorides, hydroxides, carbonates, hydrogen carbonates, sulfates, sulfites, hydrogen sulfites, borates, phosphates, monohydrogen phosphates, and dihydrogen phosphates wherein M is Li, Na, K, Cs, Rb, Ca, or Ba.

5. The process of claim 1 further comprising after the contacting of step (a) and prior to the isolating of step (b), mixing said solution of fluoroalkanesulfonate salt with a diluent.

6. The process of claim 5 wherein the fluoroalkanesulfonate salt is insoluble in the diluent, and the diluent has a boiling point greater than the solvent.

7. The process of claim 5 wherein the diluent is at least one of alkanes, arenes, halogenated hydrocarbons, halogen-substituted arenes, aliphatic ethers, aliphatic esters, aliphatic carbonate esters, and aliphatic ketones, each having a boiling point greater than about 90° C. and less than about 150° C., or mixtures thereof.

8. The process of claim 5 wherein the diluent further comprises water.

9. The process of claim 5 wherein the solvent is acetone and the diluent is water, or a mixture of water and xylene.

10. The process of claim 5 further comprising after the solvent removal, isolating the fluoroalkanesulfonate salt by filtration, evaporation, or centrifuging.

11. The process of claim 1 wherein the contaminant contains sulfite and sulfate salts.

12. The process of claim 11 wherein prior to contacting the mixture with a solvent in step (a), said mixture is contacted with water and an oxidizing agent to convert the sulfite and bisulfite salts to sulfate salts, followed by removal of the water.

13. The process of claim 12 wherein the oxidizing agent is air, oxygen, hydrogen peroxide, persulfate salt, sodium hypochlorite, chlorine, or chlorine dioxide.

14. The process of claim 12 wherein removal of water is by evaporation, freeze-drying, spray-drying, azeotropic drying, or vacuum stripping.

15. The process of claim 1 wherein steps (a) and (b) are repeated in sequence two or more times.

16. The process of claim 1 further comprising after step (b) recovery of the used solvent and recycling the solvent back into step (a) of the process.

17. The process of claim 5 further comprising after step (b) recovery of the used diluent and recycling the diluent back into the process.

18. The process of claim 2 wherein after drying, the salt is ground to a particle size having a maximum diameter of about 1 mm, and heated to a temperature of a minimum of 150° C. to further reduce the level of solvent.

Assignments (5)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2010
From: SIEVERT, ALLEN CAPRON; SCHULTZ, JAMES A.; SPRAGUE, LEE GRANT; WALCK, KATELYN RAE
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 025350/0095 →