Process for the preparation of fluorinated compounds

Patent metadata

Field	Value
Publication number	US-9255047-B2
Application number	US-60270709-A
Country	US
Kind code	B2
Filing date	Aug 19, 2009
Priority date	Sep 11, 2008
Publication date	Feb 9, 2016
Grant date	Feb 9, 2016

Abstract

A subject-matter of the invention is a process for the preparation of 2,3,3,3-tetrafluoro-1-propene which comprises the following stages: (i) hydrogenation of hexafluoropropylene to give 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the preceding stage to give 1,2,3,3,3-pentafluoro-1-propene; (iii) hydrogenation of the 1,2,3,3,3-pentafluoro-1-propene obtained in the preceding stage to give 1,1,1,2,3-pentafluoropropane; and (iv) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage to give 2,3,3,3-tetrafluoro-1-propene. Stages (ii) and (iv) are carried out using a water and potassium hydroxide mixture with the potassium hydroxide representing between 58 and 86% by weight of the mixture and at a temperature of between 110 and 180° C.

First claim

The invention claimed is:

1. Process for the preparation of 2,3,3,3-tetrafluoro-1-propene which comprises the following stages:
(i) hydrogenation of hexafluoropropylene to give 1,1,1,2,3,3-hexafluoropropane;
(ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the preceding stage to give 1,2,3,3,3-pentafluoro-1-propene using a water and potassium hydroxide mixture with the potassium hydroxide representing between 58 and 86% by weight of the mixture and at a temperature of between 110 and 180° C.;
(iii) hydrogenation of the 1,2,3,3,3-pentafluoro-1-propene obtained in the preceding stage to give 1,1,1,2,3-pentafluoropropane;
(iv) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage to give 2,3,3,3-tetrafluoro-1-propene using a water and potassium hydroxide mixture with the potassium hydroxide representing between 58 and 86% by weight of the mixture and at a temperature of between 155 and 170° C.

2. The process according to claim 1 , in which the potassium hydroxide represents between 60 and 75% by weight of the water-potassium hydroxide mixture of stage (ii) and/or (iv).

3. The process according to claim 1 , characterized in that the stream resulting from stage (i) and/or stage (iii) is conveyed directly to the following stage.

4. The process according to claim 1 , characterized in that the stream resulting from stage (ii) is subjected to a purification stage before being conveyed to stage (iii).

5. The process according to claim 1 , characterized in that it is carried out continuously.

6. The process according to claim 1 , characterized in that stage (ii) and/or stage (iv) is carried out in at least two reactors in series.

7. The process according to claim 1 , characterized in that stage (i) and/or stage (iii) is carried out in a multistage reactor or in at least two reactors in series.

8. The process according to claim 1 in which stage (ii) and/or stage (iv) is carried out at a temperature of between 155 and 165° C.

9. The process according to claim 1 , wherein dehydrofluorination in stage (ii) and/or stage (iv) takes place in the absence of a solvent and/or a phase transfer catalyst.

10. The process according to claim 9 , wherein conversion in stage (ii) or stage (iv) is 95% or greater.

11. The process according to claim 9 , wherein conversion in stage (ii) and stage (iv) is 95% or greater.

Assignees

• Pigamo Anne
• Devic Michel
• Wendlinger Laurent
• Arkema France

Inventors

• Pigamo Anne
• Devic Michel
• Wendlinger Laurent

Classifications

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C07C17/25 Primary

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

• C07C17/354

  by hydrogenation · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C19/08

  containing fluorine · CPC title