Processes for producing trifluoroiodomethane using metal trifluoroacetates

Patent metadata

Field	Value
Publication number	US-10875819-B2
Application number	US-202016797677-A
Country	US
Kind code	B2
Filing date	Feb 21, 2020
Priority date	Mar 4, 2019
Publication date	Dec 29, 2020
Grant date	Dec 29, 2020

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.

First claim

What is claimed is:

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.

Assignees

• Honeywell Int Inc

Inventors

• Jungong Christian
• Wang Haiyou
• Yang Terris

Classifications

• C07C19/16

  and iodine · CPC title

• C07C17/389 Primary

  by adsorption on solids · CPC title

• C07C17/363 Primary

  by elimination of carboxyl groups · CPC title

• C07C17/093

  by replacement by halogens · CPC title

• B01J31/0268

  Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous · CPC title