IP Library Granted Patent US 11,591,218
Granted Patent B2
US 11,591,218 · App. 17/117,284 · Granted Feb 28, 2023

Integrated processes for producing bis(fluorosulfonyl) imide

Inventors: Matthew H. Luly (Hamburg, NY); Bernard E. Pointner (Buffalo, NY); Brian Leone (Morris Plains, NJ)
Assignee: Honeywell International Inc.
C01B21/093B01D3/14B01J19/0013B01D2202/00B01J2219/00031B01J2219/00033
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Quick Facts
Patent No.
US 11,591,218
App. No.
17/117,284
Granted
Feb 28, 2023
Kind
B2
Abstract

A process for producing bis(fluorosulfonyl) imide includes providing a solution comprising fluorosulfonic acid and urea, the solution maintained at a solution temperature from about 0° C. to about 70° C.; reacting the solution in the presence of a reaction medium at a reaction temperature from 80° C. to about 170° C. to produce a product stream including bis(fluorosulfonyl) imide, ammonium fluorosulfate and the reaction medium; separating the ammonium fluorosulfate from the product stream to produce an intermediate product stream; and separating the intermediate product stream into a concentrated product stream and a first recycle stream, the concentrated product stream including a higher concentration of bis(fluorosulfonyl) imide than the first recycle stream.

Claims (35)

1. A process for producing bis(fluorosulfonyl) imide, the process comprising:

providing a solution comprising fluorosulfonic acid and urea, the solution maintained at a solution temperature from about 0° C. to about 70° C.;

reacting the solution in the presence of a reaction medium at a reaction temperature from 80° C. to about 170° C. to produce a product stream including bis(fluorosulfonyl) imide, ammonium fluorosulfate and the reaction medium;

separating the ammonium fluorosulfate from the product stream to produce an intermediate product stream; and

separating the intermediate product stream into a concentrated product stream and a first recycle stream, the concentrated product stream including a higher concentration of bis(fluorosulfonyl) imide than the first recycle stream.

2. The process of claim 1 , further comprising recycling the first recycle stream back to the reacting step.

3. The process of claim 2 , wherein the process is a continuous process.

4. The process of claim 1 , further comprising recycling the first recycle stream to a storage tank.

5. The process of claim 4 , wherein the process is a semi-batch process.

6. The process of claim 1 , wherein the reaction medium includes fluorosulfonic acid.

7. The process of claim 1 , wherein a concentration of bis(fluorosulfonyl) imide in the first recycle stream is less than 50 wt. % of the first recycle stream.

8. The process of claim 7 , wherein a concentration of bis(fluorosulfonyl) imide in the first recycle stream is less than 20 wt.% of the first recycle stream.

9. The process of claim 8 , wherein a concentration of bis(fluorosulfonyl) imide in the first recycle stream is less than 10 wt.% of the first recycle stream.

10. The process of claim 9 , wherein a concentration of bis(fluorosulfonyl) imide in the first recycle stream is less than 5 wt.% of the first recycle stream.

11. The process of claim 1 , wherein in the providing step, the solution comprising fluorosulfonic acid and urea is formed by mixing the urea and the fluorosulfonic acid together at the solution temperature.

12. The process of claim 11 , wherein in the providing step, the solution comprising fluorosulfonic acid and urea is formed by mixing the fluorosulfonic acid and the urea together at a mole ratio of from about 2.0:1 to about 3.0:1.

13. The process of claim 1 , wherein separating the intermediate product stream into the concentrated product stream and the first recycle stream includes distilling the product stream.

14. The process of claim 1 , wherein separating the ammonium fluorosulfate from the product stream includes evaporating the product stream to form the intermediate product stream.

15. The process of claim 1 , further comprising:

separating the concentrated product stream into a further concentrated product stream and a second recycle stream, the further concentrated product stream including a higher concentration of bis(fluorosulfonyl) imide than the second recycle stream.

16. An integrated system for the production of bis(fluorosulfonyl) imide, the system comprising:

a vessel configured to connect to a urea input stream and a first fluorosulfonic acid input stream, the vessel configured to produce a solution comprising fluorosulfonic acid and urea, the vessel configured to maintain the solution at a solution temperature from about 0° C. to about 70° C.;

a reactor fluidly coupled to the vessel to receive the solution comprising fluorosulfonic acid and urea, the reactor including a second fluorosulfonic acid input stream, the reactor configured to produce a product stream including bis(fluorosulfonyl) imide, ammonium fluorosulfate and fluorosulfonic acid; the reactor configured to maintain a reactor temperature from 80° C. to about 170° C.;

a first separator fluidly coupled to the product stream, the first separator configured to separate the ammonium fluorosulfate from the product stream to produce an intermediate product stream; and

a second separator fluidly coupled to the intermediate product stream, the second separator configured to produce a concentrated product stream and a first recycle stream, the concentrated product stream including a concentration of bis(fluorosulfonyl) imide that is greater than a concentration of bis(fluorosulfonyl) imide in the first recycle stream.

17. The system of claim 16 , wherein the first recycle stream is recycled back to the reactor.

18. The system of claim 16 , wherein the first recycle stream is directed to a storage tank.

19. The system of claim 16 , further comprising:

a third separator fluidly coupled to the concentrated product stream, the third separator configured to produce a further concentrated product stream and a second recycle stream, the further concentrated product stream including a concentration of bis(fluorosulfonyl) imide that is greater than a concentration of bis(fluorosulfonyl) imide in the second recycle stream.

20. The system of claim 16 , wherein a concentration of bis(fluorosulfonyl) imide in the first recycle stream is less than 50 wt. % of the first recycle stream.

21. The system of claim 20 , wherein a concentration of bis(fluorosulfonyl) imide in the first recycle stream is less than 20 wt.% of the first recycle stream.

22. The system of claim 21 , wherein a concentration of bis(fluorosulfonyl) imide in the first recycle stream is less than 10 wt.% of the first recycle stream.

23. The system of claim 16 , wherein the solution comprising the fluorosulfonic acid and the urea comprises the fluorosulfonic acid and the urea in a mole ratio of from about 2.0:1 to about 3.0:1.

24. The system of claim 16 , wherein the system is configured for continuous operation.

25. The system of claim 16 , wherein the system is configured for semi-batch operation.

Assignments (4)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 13, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074350/0505 →
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2021
From: LULY, MATTHEW H.; POINTNER, BERNARD E.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 056047/0717 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2021
From: LEONE, BRIAN
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 056047/0831 →
Continuity (2)
Provisional Application 62949105 · Dec 17, 2019
Related Publication 20210179428A1 · Jun 17, 2021