IP Library Granted Patent US 10,875,819
Granted Patent B2
US 10,875,819 · App. 16/797,677 · Granted Dec 29, 2020

Processes for producing trifluoroiodomethane using metal trifluoroacetates

Inventors: Christian Jungong (Depew, NY); Haiyou Wang (Amherst, NY); Terris Yang (East Amherst, NY)
Assignee: Honeywell International Inc.
C07C17/363C07C17/093C07C19/16
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Quick Facts
Patent No.
US 10,875,819
App. No.
16/797,677
Granted
Dec 29, 2020
Kind
B2
Abstract

The present disclosure provides a process for producing trifluoroiodomethane. The process includes providing a metal trifluoroacetate, iodine, a phase transfer catalyst, and an organic solvent, and reacting the metal trifluoroacetate and iodine in the presence of the phase transfer catalyst and the organic solvent to produce trifluoroiodomethane.

Claims (24)

1. A process for producing trifluoroiodomethane (CF 3 I), the process comprising:

providing a metal trifluoroacetate, iodine, a phase transfer catalyst, and an organic solvent; and

reacting the metal trifluoroacetate and iodine in the presence of the phase transfer catalyst and the organic solvent to produce trifluoroiodomethane.

2. The process of claim 1 , wherein in the providing step, the phase transfer catalyst is provided for the reaction at a mole percent of the metal trifluoroacetate from about 0.5% to about 50%.

3. The process of claim 1 , wherein in the providing step, the metal trifluoroacetate is at least one selected from the group of lithium trifluoroacetate, potassium trifluoroacetate, sodium trifluoroacetate, rubidium trifluoroacetate, cesium trifluoroacetate, calcium trifluoroacetate, magnesium trifluoroacetate, iron trifluoroacetate, zinc trifluoroacetate, and copper trifluoroacetate.

4. The process of claim 1 , wherein in the providing step, the organic solvent comprises less than about 500 ppm by volume of water.

5. The process of claim 1 , wherein in the providing step, the organic solvent is at least one selected from the group of an ionic liquid and a polar aprotic solvent.

6. The process of claim 5 , wherein the organic solvent is at least one selected from the group of imidazolium salts, caprolactamium hydrogen sulfate, sulfolane, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, benzonitrile, N-methyl-2-pyrrolidone, and dimethyl sulfone.

7. The process of claim 6 , wherein the organic solvent consists of sulfolane.

8. The process of claim 1 , wherein in the providing step, the phase transfer catalyst is at least one selected from the group of quaternary ammonium salts and quaternary phosphonium salts.

9. The process of claim 8 , wherein the phase transfer catalyst comprises tetraphenylphosphonium bromide.

10. The process of claim 1 , wherein in the reacting step, the metal trifluoroacetate, the iodine, the phase transfer catalyst, and the organic solvent are at a temperature from about 100° C. to about 250° C.

11. A process for producing trifluoroiodomethane (CF 3 I), the process comprising:

mixing a metal trifluoroacetate, iodine, a phase transfer catalyst, and an organic solvent; and

heating the metal trifluoroacetate, iodine, the phase transfer catalyst, and the organic solvent to react the metal trifluoroacetate and iodine to produce trifluoroiodomethane and a metal iodide.

12. The process of claim 11 , further including separating the trifluoroiodomethane from the metal iodide.

13. The process of claim 11 , wherein the process is a continuous process.

14. The process of claim 11 , wherein the process is a batch process.

15. The process of claim 11 , wherein the metal trifluoroacetate is at least one selected from the group of lithium trifluoroacetate, potassium trifluoroacetate, sodium trifluoroacetate, rubidium trifluoroacetate, cesium trifluoroacetate, calcium trifluoroacetate, magnesium trifluoroacetate, iron trifluoroacetate, zinc trifluoroacetate, and copper trifluoroacetate.

16. The process of claim 11 , wherein the organic solvent is at least one selected from the group of an ionic liquid and a polar aprotic solvent.

17. The process of claim 16 , wherein the organic solvent is at least one selected from the group of imidazolium salts, caprolactamium hydrogen sulfate, sulfolane, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, benzonitrile, N-methyl-2-pyrrolidone, and dimethyl sulfone.

18. The process of claim 11 , wherein the phase transfer catalyst is at least one selected from the group of quaternary ammonium salts and quaternary phosphonium salts.

19. The process of claim 11 , wherein the phase transfer catalyst comprises tetraphenylphosphonium bromide.

20. The process of claim 11 , wherein the metal trifluoroacetate, the iodine, phase transfer catalyst, and the organic solvent are heated to a temperature from about 100° C. to about 250° C.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074344/0212 →
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 Nov 3, 2020
From: JUNGONG, CHRISTIAN; WANG, HAIYOU; YANG, TERRIS
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 054258/0391 →
Continuity (2)
Provisional Application 62813499 · Mar 4, 2019
Related Publication 20200283360A1 · Sep 10, 2020