IP Library Granted Patent US 11,168,044
Granted Patent B2
US 11,168,044 · App. 16/959,197 · Granted Nov 9, 2021

Method for purifying 1,1,1,2,3-pentafluoropropane and use thereof for obtaining high-purity 2,3,3,3-tetrafluoropropene

Inventors: Pierre-Marie Sedat (Pierre-Benite, FR); Collier Bertrand (Colombes, FR)
Assignee: Arkema France
C07C21/18C07C17/25C07C17/354C07C17/383C07C19/08
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Quick Facts
Patent No.
US 11,168,044
App. No.
16/959,197
Granted
Nov 9, 2021
Kind
B2
Abstract

The present invention relates to a process for purifying 1,1,1,2,3-pentafluoropropane, comprising the steps of: i) providing a composition A1 comprising 1,1,1,2,3-pentafluoropropane and 1,1,1,3-tetrafluoropropane; ii) purifying, preferably distilling, said composition A1 under conditions that are sufficient to form at least two streams including a first stream comprising 1,1,1,2,3-pentafluoropropane and a second stream comprising 1,1,1,3-tetrafluoropropane. The present invention also relates to a process for producing 2,3,3,3-tetrafluoropropene and a composition comprising 2,3,3,3-tetrafluoropropene.

Claims (27)

1. A process for purifying 1,1,1,2,3-pentafluoropropane comprising the steps of:

i) providing a composition A1 comprising 1,1,1,2,3-pentafluoropropane and 1,1,1,3-tetrafluoropropane;

i′) optionally drying said composition A1;

ii) purifying said composition A1 under conditions that are sufficient to form at least two streams including a first stream comprising 1,1,1,2,3-pentafluoropropane and a second stream comprising 1,1,1,3-tetrafluoropropane.

2. The process as claimed in claim 1 , wherein the mass content of 1,1,1,2,3-pentafluoropropane in said composition A1 is greater than 90% on the basis of the total weight of said composition A1.

3. The process as claimed in claim 1 , wherein said composition A1 also comprises 1,1,1,2,3,3-hexafluoropropane, 1,1,2-trifluoroethane, 1,1,1-trifluoroethane and 1,1,1,2-tetrafluoropropane; and step ii) of said process is: ii) purification of said composition A1 under conditions that are sufficient to form a first stream comprising 1,1,1,2,3-pentafluoropropane, a second stream comprising 1,1,1,3-tetrafluoropropane and a third stream comprising 1,1,1,2,3,3-hexafluoropropane, 1,1,2-trifluoroethane, 1,1,1-trifluoroethane and 1,1,1,2-tetrafluoropropane.

4. The process as claimed in claim 1 , wherein said composition A1 also comprises 1,1,1,2,3,3-hexafluoropropane, 1,1,2-trifluoroethane, 1,1,1-trifluoroethane and 1,1,1,2-tetrafluoropropane; and step ii) of said process is:

ii-1) distilling said composition A1 under conditions that are sufficient to form a stream B1 comprising 1,1,1,2,3,3-hexafluoropropane, 1,1,2-trifluoroethane, 1,1,1-trifluoroethane and 1,1,1,2-tetrafluoropropane and a stream B1′ comprising 1,1,1,2,3-pentafluoropropane and 1,1,1,3-tetrafluoropropane;

ii-2) distilling said stream B1′ obtained in step ii-1) to form a stream B2 comprising 1,1,1,2,3-pentafluoropropane and a stream B2′ comprising 1,1,1,3-tetrafluoropropane.

5. The process as claimed in claim 1 , wherein the mass content of 1,1,1,3-tetrafluoropropane in said first stream or said stream B2 is less than 5000 ppm on the basis of the total weight of said first stream or of said stream B2.

6. The process as claimed in claim 4 , wherein the mass content of 1,1,1,2,3,3-hexafluoropropane in said stream B1′ or said stream B2 is less than 1000 ppm on the basis of the total weight of said stream B1′ or of said stream B2.

7. The process as claimed in claim 4 , wherein the mass content of 1,1,1,2-tetrafluoropropane in said stream B1′ or said stream B2 is less than 5000 ppm on the basis of the total weight of said stream B1′ or B2.

8. The process as claimed in claim 4 , wherein the mass content of 1,1,2-trifluoroethane and/or 1,1,1-trifluoroethane in said stream B1′ or said stream B2 is less than 50 ppm on the basis of the total weight of said stream B1′ or of said stream B2.

9. The process as claimed in claim 1 , wherein the first stream comprising 1,1,1,2,3-pentafluoropropane or said stream B2 is subjected to a dehydrofluorination step iii) to form a stream C1 comprising 2,3,3,3-tetrafluoropropene.

10. The process as claimed in claim 1 , wherein said stream C1 is purified under conditions that are sufficient to obtain a stream C3 comprising at least 99.5% of 2,3,3,3-tetrafluoropropene on the basis of the total weight of said stream C3.

11. The process as claimed in claim 1 , wherein the stream C3 also comprises 3,3,3-trifluoropropene and the mass content of 3,3,3-trifluoropropene in the stream C3 is less than 100 ppm on the basis of the total weight of said first stream C3.

12. The process as claimed in claim 10 , wherein the stream C3 also comprises 1,2,3,3,3-pentafluoropropene and the mass content of 1,2,3,3,3-pentafluoropropene in the stream C3 is less than 100 ppm on the basis of the total weight of said first stream C3.

13. The process as claimed in claim 10 , wherein the stream C3 also comprises 1,1,2-trifluoroethane and/or 1,1,1-trifluoroethane and the mass content of 1,1,2-trifluoroethane and/or 1,1,1-trifluoroethane in the stream C3 is less than 200 ppm on the basis of the total weight of said first stream C3.

14. The process as claimed in claim 1 , wherein said composition A1 is obtained via a process comprising the following steps:

a) gas-phase hydrogenation of hexafluoropropene in the presence of hydrogen and of a hydrogenation catalyst to form a stream comprising 1,1,1,2,3,3-hexafluoropropane;

a′) optionally, drying of said stream comprising 1,1,1,2,3,3-hexafluoropropane;

a″) optionally, purification of said stream comprising 1,1,1,2,3,3-hexafluoropropane obtained from step a) or a′);

b) dehydrofluorination of said stream comprising 1,1,1,2,3,3-hexafluoropropane obtained in step a) or a′) or a″) in the presence of a dehydrofluorination catalyst or using a mixture containing water and an alkaline hydroxide to form a stream comprising 1,2,3,3,3-pentafluoropropene;

b′) optionally, drying of said stream comprising 1,2,3,3,3-pentafluoropropene;

b″) optionally, purification of said stream comprising 1,2,3,3,3-pentafluoropropene obtained from step b) or b′);

c) gas-phase hydrogenation of the 1,2,3,3,3-pentafluoropropene obtained in step b) or b′) or b″) in the presence of hydrogen and of a hydrogenation catalyst under conditions that are sufficient to form said composition A1.

15. The process as claimed in claim 1 , wherein the hydrogenation catalyst used in steps a) and/or c) comprises between 0.001% and 1.0% by weight of palladium supported on alumina.

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 Jul 10, 2020
From: SEDAT, PIERRE-MARIE; BERTRAND, COLLIER
To: ARKEMA FRANCE
Reel/Frame 053175/0672 →