Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf)

Patent metadata

Field	Value
Publication number	US-9902671-B2
Application number	US-201715402327-A
Country	US
Kind code	B2
Filing date	Jan 10, 2017
Priority date	Jul 25, 2007
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.

First claim

What is claimed is:

1. A method of preparing fluorinated organic compounds comprising contacting at least one chlorocarbon selected from the group consisting of tetrachloropropene and pentachloropropane with a halogenating agent in the presence of at least one catalyst and at least one stabilizer under conditions effective to produce a C3 haloolefin.

2. The method of claim 1 wherein said C3 haloolefin comprises 2-chloro-3,3,3,-trifluoropropene.

3. The method of claim 2 wherein said chlorocarbon is at least one compound selected from the group consisting of 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane.

4. The method of claim 1 wherein said halogenating agent is a fluorinating agent.

5. The method of claim 4 wherein said fluorinating agent comprises hydrogen fluoride.

6. The method of claim 1 wherein at least a portion of said contacting step is conducted at a temperature of from about 80° C. to about 400° C.

7. The method of claim 1 wherein at least a portion of said contacting step is conducted at a pressure of from about 5 torr to about 150 psig.

8. The method of claim 1 wherein said contacting step comprises conducting at least a portion of said contacting step in the gas phase.

9. The method of claim 1 wherein said catalyst comprises at least one fluorination catalyst.

10. The method of claim 9 where the at least one fluorination catalyst is selected from the group consisting of Cr 2 O 3 , FeCl 3 /C, Cr 2 O 3 , Cr 2 O 3 /Al 2 O 3 , Cr 2 O 3 /AlF 3 , Cr 2 O 3 /carbon, CoCl 2 /Cr 2 O 3 /Al 2 O 3 , NiCl 2 /Cr 2 O 3 /Al 2 O 3 , CoCl 2 /AlF 3 , NiCl 2 /AlF 3 and combinations thereof.

11. The method of claim 9 wherein at least one fluorination catalyst comprises Cr 2 O 3 .

12. The method of claim 1 wherein said stabilizer comprises an amine stabilizer.

13. The method of claim 1 wherein said stabilizer comprises a hydroquinone stabilizer.

14. The method of claim 1 wherein said stabilizer is selected from the group consisting of p-tap(4-tert-Amylphenol), methoxy-hydroquinone, 4-methoxyphenol(HQMME), triethylamine, di-isopropyl amine, butylated hydroxy anisole (BHA), thymol and combinations thereof.

15. The method of claim 12 wherein said stabilizer comprises triethylamine.

16. The method of claim 12 wherein said stabilizer comprises di-isopropyl amine.

17. The method of claim 13 wherein said stabilizer comprises methoxy-hydroquinone.

18. The method of claim 13 wherein said stabilizer comprises 4-methoxyphenol (HQMME).

19. The method of claim 14 wherein said stabilizer comprises p-tap.

20. The method of claim 1 wherein the concentration of said stabilizer is less than about 300 ppm.

21. The method of claim 20 wherein the concentration of said stabilizer is less than about 100 ppm.

22. The method of claim 21 wherein the concentration of said stabilizer is about 10 ppm or less.

23. The method of claim 1 wherein said catalyst in the presence of said stabilizer is substantially operable for a greater period of time than said catalyst wherein said stabilizer is not present.

24. The method of claim 23 wherein said catalyst in the presence of said stabilizer is substantially operable at least about 40% longer than said catalyst wherein said stabilizer is not present.

25. The method of claim 23 wherein said catalyst in the presence of said stabilizer is substantially operable at least about 50% longer than said catalyst wherein said stabilizer is not present.

26. The method of claim 3 wherein said chlorocarbon comprises 1,1,2,3-tetrachloropropene.

27. The method of claim 3 wherein said chlorocarbon comprises 2,3,3,3-tetrachloropropene.

28. The method of claim 3 wherein said chlorocarbon comprises 1,1,1,2,3-pentachloropropane.

Assignees

• Honeywell Int Inc

Inventors

• Merkel Daniel C
• Tung Hsueh S

Classifications

• C07C17/42

  Use of additives, e.g. for stabilisation · CPC title

• C07C17/20

  of halogen atoms by other halogen atoms · CPC title

• C07C17/206 Primary

  the other compound being HX · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title