IP Library Granted Patent US 8,389,779
Granted Patent B2
US 8,389,779 · App. 12/842,737 · Granted Mar 5, 2013

Process for the preparation of fluorinated compounds

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Quick Facts
Patent No.
US 8,389,779
App. No.
12/842,737
Granted
Mar 5, 2013
Kind
B2
Abstract

A subject-matter of the invention is a process for the preparation of 2,3,3,3-tetrafluoro-1-propene comprising 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; (iv) purification of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage; and (v) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage to give 2,3,3,3-tetrafluoro-1-propene; and (vi) purification of the 2,3,3,3-tetrafluoro-1-propene of the preceding stage.

Claims (24)

1. A process for the preparation of 2,3,3,3-tetrafluoro- l -propene comprising the following steps:

(i) hydrogenating hexafluoropropylene in the gas phase in the presence of a super-stoichiometric amount of hydrogen and of a hydrogenation catalyst in a reactor to yield 1,1,1,2,3,3-hexafluoropropane;

(ii) dehydrofluorinating the 1,1,1,2,3,3-hexafluoropropane obtained in the preceding step in the presence of a dehydrofluorination catalyst or a water and potassium hydroxide mixture to yield 1,2,3,3,3-pentafluoro-1-propene;

(iii) hydrogenating the 1,2,3,3,3-pentafluoro-1-propene obtained in the preceding step in the gas phase in the presence of a superstoichiometric amount of hydrogen and of a catalyst in a reactor to yield 1,1,1,2,3-pentafluoropropane;

(iv) purifying the 1,1,1,2,3-pentafluoropropane obtained in the preceding step to a purity greater than 98% by weight;

(v) dehydrofluorinating the purified 1,1,1,2,3-pentafluoropropane in the presence of a dehydrofluorination catalyst or a water and potassium hydroxide mixture, to yield 2,3,3,3-tetra-fluoro-1-propene;

(vi) purifying the 2,3,3,3-tetrafluoro-1-propene obtained in the preceding step to yield the 2,3,3,3-tetrafluoro-1-propene in a purity greater than 99.5% by weight.

2. The process of claim 1 , wherein the purifying of the 1,1,1,2,3-pentafluoropropane in step (iv) comprises a distillation step at a pressure ranging from 1 to 20 bar absolute.

3. The process of claim 1 , wherein the compounds to be removed in step (iv) have a boiling point at least 20° C. lower than the boiling point of 1,1,1,2,3-penta-fluoropropane.

4. The process of claim 3 , wherein the compounds to be removed in step (iv) have a boiling point at least 10° C. lower than the boiling point of 1,1,1,2,3-penta-fluoropropane.

5. The process of claim 1 , wherein the amount of potassium hydroxide in the water/potassium hydroxide mixtures of steps (ii) and/or (v) ranges from 55 to 75% by weight of the water/potassium hydroxide mixture.

6. The process of claim 1 , wherein step (ii) and/or step (v) is or are carried out at a temperature ranging from 80 to 180° C.

7. The process of claim 6 , wherein step (ii) and/or step (v) is or are carried out at a temperature ranging from 145 to 165° C.

8. The process of claim 1 , wherein a stream resulting from step (ii) is purified before step (iii) is performed.

9. The process of claim 8 , wherein the purification comprises a double distillation.

10. The process of claim 1 , wherein said process is carried out continuously.

11. Process of claim 1 , wherein step (i) and/or step (iii) is or are carried out in an optionally multistep adiabatic reactor or in at least two adiabatic reactors in series.

12. The process of claim 1 , wherein a portion of a gaseous output stream resulting from step (i) and/or (iii) is recycled.

13. The process of claim 1 , further comprising partially condensing a gaseous output stream resulting from step (i) and/or (iii).

14. The process of claim 1 , further comprising treating potassium fluoride coproduced in the dehydrofluorination steps (ii) and (v) with calcium hydroxide.

15. The process of claim 1 , wherein the catalyst of step (i) and/or step (iii) comprises from 5 to 10% by weight of palladium supported on alumina or carbon.

16. The process of claim 15 , wherein the catalyst of step (i) and/or step (iii) comprises from 0.1 to 5% by weight of palladium supported on alumina or carbon.

17. The process of claim 1 , wherein the reactor of step (i) has a temperature at the inlet of the reactor ranging from 30 to 100° C.

18. The process of claim 1 , wherein the reactor of step (iii) has a temperature at the inlet of the reactor ranging from 80 to 140° C.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2010
From: AVRIL, KARINE; COLLIER, BERTRAND
To: ARKEMA FRANCE
Reel/Frame 024854/0582 →