Process for the manufacture of 2-chloro-1,1,1,2-tetrafluoropropane by liquid phase fluorination of 2-chloro-3,3,3-trifluoropropene

Patent metadata

Field	Value
Publication number	US-9255044-B2
Application number	US-201013880755-A
Country	US
Kind code	B2
Filing date	Oct 25, 2010
Priority date	Oct 25, 2010
Publication date	Feb 9, 2016
Grant date	Feb 9, 2016

Abstract

Process of catalytic fluorination in liquid phase of product 2-chloro-3,3,3-trifluoropropene into product 2-chloro-1,1,1,2-tetrafluoropropane, with an ionic liquid based catalyst. Process for manufacturing 2,3,3,3-tetrafluoropropene.

First claim

The invention claimed is:

1. A process comprising reacting, in the liquid phase, 2-chloro-3,3,3-trifluoropropene with HF in the presence of the fluorinated complex catalyst ethyl-methyl-imidazolium + Sb 2 F 11 − to produce 2-chloro-1,1,1,2-tetrafluoropropane, wherein an inert gas selected from the group consisting of nitrogen, helium, and combinations thereof is injected during the reaction.

2. Process according to claim 1 , carried out in a catalyst-rich phase.

3. Process according to claim 2 , with a molar ratio of catalyst to organics higher than 50 mol %.

4. Process according to claim 1 in which chlorine is added during the reaction.

5. Process according to claim 4 in which chlorine is added according to a molar ratio from 0.05 to 20 mole % of chlorine per mole of starting compound.

6. Process according to claim 4 in which chlorine is added according to a molar ratio from 1 to 17 mole % of chlorine per mole of starting compound.

7. Process according to claim 1 , in which the flow of inert gas, compared to the flow of the 2-chloro-3,3,3-trifluoropropene lies between 0.5:1 and 5:1.

8. Process according to claim 7 , in which the flow of inert gas, compared to the flow of the starting product lies between 1:1 and 3:1.

9. Process according to claim 1 , in which the 2-chloro-1,1,1,2-tetrafluoropropane is withdrawn in the gaseous state.

10. Process according to claim 1 , in which the temperature of the reaction ranges between 30° C. and 200° C.

11. Process according to claim 1 , in which the pressure of the reaction is higher than 2 bar.

12. Process according to claim 1 , in which the molar ratio of HF:2-chloro-3,3,3-trifluoropropene lies between 0.5:1 and 50:1.

13. The process according to claim 1 which is continuous.

14. Process according to claim 1 , wherein said inert gas is nitrogen or helium.

15. Process according to claim 1 , in which the temperature of the reaction ranges between 40° C. and 170° C.

16. Process according to claim 1 , in which the temperature of the reaction ranges between 50° C. and 150° C.

17. Process according to claim 1 , in which the pressure of the reaction is between 4 and 50 bar.

18. Process according to claim 1 , in which the pressure of the reaction is 5 and 15 bar.

19. Process according to claim 1 , in which the molar ratio of HF:2-chloro-3,3,3-trifluoropropene lies between 3:1 with 20:1.

20. Process according to claim 1 , in which the molar ratio of HF:2-chloro-3,3,3-trifluoropropene lies between 5:1 and 15:1.

21. Process according to claim 1 , comprising:
(i) contacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in a liquid phase in the presence of an ionic liquid based catalyst under conditions sufficient to form a reaction mixture comprising 2-chloro-1,1,1,2-tetrafluoropropane;
(ii) separating HCl and HF by a separation process from the reaction mixture to form an organic mixture;
(iii) separating said organic mixture into a first stream comprising 2-chloro-1,1,1,2-tetrafluoropropane, and a second stream comprising unreacted 2-chloro-3,3,3-trifluoropropene; and
(iv) recycling the unreacted 2-chloro-3,3,3-trifluoropropene to step (i).

22. Process for preparing 2,3,3,3-tetrafluoropropene, comprising the steps of:
(i) preparing 2-chloro-1,1,1,2-tetrafluoro propane by the process according to claim 1 ; and
(ii) dehydrochlorinating said 2-chloro-1,1,1,2-tetrafluoropropane into 2,3,3,3-tetra fluoropropene.

23. Process according to claim 22 , wherein the dehydrochlorination is performed in a gas phase.

Assignees

• Pigamo Anne
• Wendlinger Laurent
• Bonnet Philippe
• Arkema France

Inventors

• Pigamo Anne
• Wendlinger Laurent
• Bonnet Philippe

Classifications

• C07C17/087 Primary

  to unsaturated halogenated hydrocarbons · CPC title

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · 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

• C07C17/38

  Separation; Purification; Stabilisation; Use of additives · CPC title

• B01J31/0222

  comprising sulfonyl groups · CPC title