IP Library Granted Patent US 11,584,701
Granted Patent B2
US 11,584,701 · App. 17/888,628 · Granted Feb 21, 2023

Process for preparing 3,3,3-trifluoroprop-1-ene

Inventors: Xuehui Sun (Kennett Square, PA); Karl Robert Krause (Kennett Square, PA)
Assignee: THE CHEMOURS COMPANY FC, LLC
C07C17/25C07C21/18B01J27/10C07C17/04C07C17/07C07C19/10
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Quick Facts
Patent No.
US 11,584,701
App. No.
17/888,628
Granted
Feb 21, 2023
Kind
B2
Abstract

The present application provides a process of preparing 3,3,3-trifluoroprop-1-ene, comprising reacting 3-chloro-1,1,1-trifluoropropane with a base in an aqueous solvent component in the absence of a phase transfer catalyst.

Claims (28)

1. A process of preparing a mixture of 3,3,3-trifluoropropene (HFO-1243zf) and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), comprising reacting a mixture of 3-chloro-1,1,1-trifluoropropane (HCFC-253fb) and 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db) with a base in a liquid phase and in the absence of a phase transfer catalyst.

2. The process of claim 1 wherein the reacting is conducted in the absence of an organic solvent.

3. The process of claim 1 wherein the base is a metal hydroxide base, a metal carbonate base, a metal phosphate base, or a metal fluoride base.

4. The process of claim 1 wherein the base is NaOH, KOH, LiOH, CsOH, Ca(OH) 2 , Zn(OH) 2 , Na 2 CO 3 , K 2 CO 3 , K 3 PO 4 , Na 3 PO 4 , KF, or CSF.

5. The process of claim 1 , wherein the base is KOH or NaOH.

6. The process of claim 5 , wherein the base is NaOH.

7. The process of claim 1 , wherein about 0.01 to about 5 molar equivalents of base is used based on one molar equivalent of 3-chloro-1,1,1-trifluoropropane.

8. The process of claim 1 , wherein the reacting is conducted at a temperature of from about bout 40° C. to about 80° C.

9. The process of claim 1 , wherein the reacting is conducted at a temperature of from about bout 55° C. to about 65° C.

10. The process of claim 1 , wherein the reacting is conducted at a pressure selected from one of between 5 psig to about 150 psig, 0 psig to about 100 psig and −10 to about 100 psig.

11. A process of preparing a mixture of 3,3,3-trifluoropropene (HFO-1243zf) and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), comprising reacting a mixture of 3-chloro-1,1,1-trifluoropropane (HCFC-253fb) and 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db) with a base in a liquid phase, wherein the reacting is conducted in the absence of a phase transfer catalyst and organic solvent.

12. The process of claim 11 , wherein the 3,3,3-trifluoropropene (HFO-1243zf) is isolated by removing 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf).

13. The process of claim 12 , wherein the 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) is removed by distillation.

14. A process comprising, feeding a mixture of 3-chloro-1,1,1-trifluoropropane (HCFC-253fb) and 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db) to a reactor, dehydrochlorinating the mixture, obtaining a product mixture of 3,3,3-trifluoropropene (HFO-1243zf) and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), and isolating 3,3,3-trifluoropropene (HFO-1243zf).

15. The process of claim 14 , wherein the 3,3,3-trifluoropropene (HFO-1243zf) is isolated by removing 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf).

16. The process of claim 15 wherein 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) is removed by distillation.

17. A process comprising,

providing a first mixture of 3-chloro-1,1,1-trifluoropropane (HCFC-253fb) and 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db,

dehydrochlorinating the first mixture in the absence of a phase transfer agent and organic solvent to form a second mixture,

recovering the second mixture comprising 3,3,3-trifluoropropene (HFO-1243zf) and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), and

optionally, isolating 3,3,3-trifluoropropene (HFO-1243zf).

18. The process of claim 17 wherein 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) is removed by distillation.

19. The process of claim 17 wherein dehydrochlorination is conducted in the presence of a base.

20. The process of claim 19 , wherein the base is KOH or NaOH.

21. The process of claim 20 , wherein the base is NaOH.

22. The process of claim 19 , wherein about 0.01 to about 5 molar equivalents of base is used based on one molar equivalent of 3-chloro-1,1,1-trifluoropropane.

23. The process of claim 17 , wherein the reacting is conducted at a temperature of from about 40° C. to about 80° C.

24. The process of claim 17 , wherein the reacting is conducted at a temperature of from about 55° C. to about 65° C.

Assignments (1)
SECURITY INTEREST Recorded May 7, 2024
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 067341/0844 →