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-9567274-B2
Application number	US-201514980979-A
Country	US
Kind code	B2
Filing date	Dec 28, 2015
Priority date	Oct 25, 2010
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

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 for producing 2-chloro-1,1,1,2-tetrafluoropropane comprising:
(i) reacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride 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 and HCl as a byproduct, wherein the catalys is obtained by reacting at least one halogenated or oxyhalogenated Lewis acid based on aluminum, titanium, niobium, tantalum, tin, antimony, nickel, zinc or iron with a salt of general formula Y+A−, in which A− denotes a halide anion or hexafluoroantimonate anion and Y+ a quaternary ammonium cation, quaternary phosphonium cation or ternary sulfonium cation;
(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).

2. The process according to claim 1 , wherein the catalyst is the fluorinated complex catalyst emim + Sb 2 F 11 − .

3. The process according to claim 1 , carried out in a catalyst-rich phase.

4. The process according to claim 1 , in which chlorine is added during the reaction.

5. The process according to claim 1 , wherein a gas is injected during step (i).

6. The process according to claim 5 , in which the flow of gas, compared to the flow of the starting product lies between 0.5:1 and 5:1.

7. The process according to claim 1 , in which the product of the reaction is withdrawn in the gaseous state.

8. The process according to claim 1 , in which the temperature of the reaction ranges between 30° C. and 200° C.

9. The process according to claim 1 , in which the pressure of the reaction is higher than 2 bar.

10. The process according to claim 1 , in which the molar ratio of HF: starting compound lies between 0.5:1 and 50:1.

11. The process according to claim 1 , which is continuous.

12. A process for preparing 2,3,3,3-tetrafluoropropene, comprising:
(i) preparing 2-chloro-1,1,1,2-tetra fluoro propane by the process according to claim 1 ; and then
(ii) dehydrochlorinating said 2-chloro-1,1,1,2-tetrafluoropropane into 2,3,3,3-tetra fluoropropene.

13. The process according to claim 12 , wherein the dehydrochlorination is performed in a gas phase.

Assignees

• Arkema France

Inventors

• Pigamo Anne
• Wendlinger Laurent
• Bonnet Philippe

Classifications

• C07C17/087 Primary

  to unsaturated halogenated hydrocarbons · CPC title

• B01J2540/54

  Quaternary phosphonium groups · CPC title

• C07C17/38

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

• B01J2540/42

  Quaternary ammonium groups · CPC title

• B01J2540/34

  Sulfonyl groups · CPC title