Process for the preparation of 3,3,3-trifluoropropene

Patent metadata

Field	Value
Publication number	US-11767277-B2
Application number	US-202117245459-A
Country	US
Kind code	B2
Filing date	Apr 30, 2021
Priority date	Jul 17, 2015
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

The present invention provides a process for preparing 3,3,3-trifluoropropene (1243zf), the process comprising:
(a) fluorinating CCl 3 CH 2 CH 2 Cl (250fb) to produce a reaction product comprising CF 3 CH 2 CH 2 Cl (253fb) in the liquid phase in a first reactor, using HF as the fluorinating agent; and (b) (i) dehydrohalogenating 253fb to produce 1243zf in the vapour phase in the present of a catalyst in a second reactor; or (b)(ii) dehydrohalogenating 253fb to produce 1243zf in a second reactor, wherein the reaction product comprising 253fb produced in step (a) has subjected to one or more purification steps before step (b).

The present invention also provides an azeotropic or near-azeotropic composition comprising HF and 253fb.

First claim

The invention claimed is:

1. A process for preparing 3,3,3-trifluoropropene (1243zf), the process comprising:
(a) fluorinating CCl 3 CH 2 CH 2 Cl (250fb) to produce a reaction product comprising CF 3 CH 2 CH 2 Cl (253fb) in the liquid phase in a first reactor, conducted at a temperature of from 20° C. to 100° C., using HF as a fluorinating agent; and
(b) dehydrohalogenating 253fb to produce 1243zf in the vapour phase, conducted at a temperature of from 250° C. to 350° C., in the presence of a catalyst in a second reactor;
wherein the product stream exiting the second reactor is subjected to one or more separation and/or purification steps and any unreacted 253fb is recycled back into the second reactor.

2. The process according to claim 1 , wherein the catalyst used in step (b) comprises activated carbon, alumina and/or chromia or zinc/chromia.

3. The process according to claim 2 , wherein the catalyst used in step (b) comprises an additional metal or compound thereof.

4. The process according to claim 3 , wherein the catalyst used in step (b) is Pd/carbon, Pt/carbon, Au/carbon, Pd/alumina, Ni/alumina, Pt/alumina, Cr/alumina or Zn/chromia.

5. The process according to claim 3 , wherein the catalyst used in step (b) is pre-fluorinated.

6. The process according to claim 3 , wherein the catalyst used in step (b) comprises activated carbon and the process of step (b) is conducted at a temperature of from about 250° C. to about 300° C.

7. The process according to claim 5 , wherein the catalyst used in step (b) is a prefluorinated Zn/chromia catalyst.

8. The process according to claim 1 , wherein in step (b) HF is co-fed with 253fb.

9. The process according to claim 1 , wherein the reaction product comprising 253fb produced in step (a) is subjected to one or more purification steps before step (b).

10. The process according to claim 1 , wherein the 1243zf product is stored for future use or is passed directly into a further reactor.

11. A process for preparing 3,3,3-trifluoropropene (1243zf), the process comprising:
(a) fluorinating CCl 3 CH 2 CH 2 Cl (250fb) to produce a reaction product comprising CF 3 CH 2 CH 2 Cl (253fb) in the liquid phase, conducted at a temperature of from 20° C. to 100° C., using HF as a fluorinating agent; and
(b) dehydrohalogenating 253fb to produce 1243zf in the vapour phase, conducted at a temperature of from 250° C. to 350° C., in the presence of a catalyst.

12. The process according to claim 11 , wherein the catalyst used in step (b) comprises activated carbon, alumina and/or chromia or zinc/chromia.

13. The process according to claim 12 , wherein the catalyst used in step (b) comprises an additional metal or compound thereof.

14. The process according to claim 13 , wherein the catalyst used in step (b) is Pd/carbon, Pt/carbon, Au/carbon, Pd/alumina, Ni/alumina, Pt/alumina, Cr/alumina or Zn/chromia.

15. The process according to claim 13 , wherein the catalyst used in step (b) is pre-fluorinated.

16. The process according to claim 11 , wherein step (b) is conducted at a temperature of from about 250° C. to about 300° C.

17. The process according to claim 11 , wherein the catalyst used in step (b) comprises activated carbon and the process of step (b) is conducted at a temperature from about 250° C. to about 300° C.

18. The process according to claim 15 , wherein the catalyst used in step (b) is a pre-fluorinated Zn/chromia catalyst.

19. The process according to claim 11 , wherein the process is a single-step process.

20. The process according to claim 11 , wherein the fluorinating is performed in a single reactor.

21. The process according to claim 11 , wherein the fluorinating is a single-step process.

22. The process according to claim 11 , wherein in step (b) HF is co-fed with 253fb.

23. The process according to claim 11 , wherein the reaction product comprising 253fb produced in step (a) is subjected to one or more purification steps before step (b).

24. The process according to claim 11 , wherein the 1234zf product is stored for future use or is passed directly into a further reactor.

Assignees

• Mexichem Fluor Sa De Cv

Inventors

• Hodgson Emma Jayne
• Skae Clare Mary
• Lloyd Gary
• Mcguinness Claire Elizabeth
• Giddis Clive Robert
• Murray James Henry

Classifications

• C09K2205/126

  Unsaturated fluorinated hydrocarbons · CPC title

• C09K2205/122

  Halogenated hydrocarbons · CPC title

• C09K5/045

  containing only fluorine as halogen · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C19/10

  and chlorine · CPC title