Granted Patent B2

US 12,286,386 · App. 17/800,315 · Granted Apr 29, 2025

Inventor: Sheng Peng (Hockessin, DE)

Assignee: THE CHEMOURS COMPANY FC, LLC

C07C17/354B01J23/44C07C17/206

Abstract

Claims (23)

1. A process for producing a product mixture comprising 1,1,1,3,3-pentachloro-4,4,4-trifluorobutane (CCl 3 CH 2 CCl 2 CF 3 , 333jfa), comprises contacting a halogenated alkane with an olefin in the presence of a mononitrile and a catalyst comprising copper (II) chloride, wherein the halogenated alkane is chosen from 1,1,1-trichloro-2,2,2-trifluoroethane (CF 3 CCl 3 , 113a) and carbon tetrachloride (CCl 4 ), provided that when the halogenated alkane is 1,1,1-trichloro-2,2,2-trifluoroethane, the olefin is vinylidene chloride (CH 2 ═CCl 2 , VDC) and when the halogenated alkane is carbon tetrachloride, the olefin is 2-chloro-3,3,3-trifluoropropene (CF 3 CCl═CH 2 , 1233xf).

2. The process of claim 1 wherein the mononitrile is chosen from acetonitrile, propionitrile, butyronitrile.

3. The process of claim 2 wherein the mononitrile is propionitrile.

4. The process of claim 1 wherein the halogenated alkane is 1,1,1-trichloro-2,2,2-trifluoroethane and the olefin is vinylidene chloride.

5. The process of claim 1 wherein the halogenated alkane is carbon tetrachloride and the olefin is 2-chloro-3,3,3-trifluoropropene.

6. The process of claim 1 wherein the molar ratio of mononitrile to catalyst is at least 10 and less than 25.

7. The process of claim 4 wherein the molar ratio of mononitrile to catalyst is between 10 and 20.

8. The process of claim 4 wherein the molar ratio of mononitrile to catalyst is between 15 and 20.

9. The process of claim 1 , further comprising contacting 1, 1,1,3,3-pentachloro-4,4,4-trifluorobutane with HF in the gas or liquid phase, with hydrogen fluoride in the presence of a fluorination catalyst, form a product comprising 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane.

10. The process of claim 9 wherein the process of contacting 1,1,1,3,3-pentachloro-4,4,4-trifluorobutane with HF is performed in the gas phase.

11. The process of claim 9 wherein the process of contacting 1,1,1,3,3-pentachloro-4,4,4-trifluorobutane with HF is performed in the liquid phase.

12. The process of claim 9 , further comprising contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with base to produce a product mixture comprising 1,1,1,4,4,4-hexafluoro-2-butyne (CF 3 C≡CCF 3 ).

13. The process of claim 12 wherein the process is performed in the presence of a phase transfer catalyst.

14. The process of claim 13 wherein the phase transfer catalyst includes a quaternary ammonium salt.

15. The method of claim 14 , wherein the quaternary ammonium salt includes tetrabutylammonium bromide or N-methyl-N, N, N-trioctylammonium chloride.

16. The method of claim 12 , further comprising contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen at a temperature and pressure sufficient to produce a product mixture comprising Z-1,1,1,4,4,4-hexafluoro-2-butene.

17. The method of claim 9 , wherein the hydrogenation catalyst is a palladium catalyst.

18. The method of claim 17 , wherein the palladium catalyst is a Lindlar catalyst.

19. The method of claim 17 , wherein the palladium catalyst comprises palladium dispersed on aluminum oxide or titanium silicate, doped with silver and/or a lanthanide.

20. The process of claim 2 wherein the halogenated alkane is 1,1,1-trichloro-2,2,2-trifluoroethane and the olefin is vinylidene chloride.

21. The process of claim 2 wherein the halogenated alkane is carbon tetrachloride and the olefin is 2-chloro-3,3,3-trifluoropropene.

22. The process of claim 20 , wherein the molar ratio of mononitrile to catalyst is at least 10 and less than 25.

23. The process of claim 21 , wherein the molar ratio of mononitrile to catalyst is at least 10 and less than 25.

Assignments (2)

Continuity (2)

References Cited (17)