IP Library Granted Patent US 7,722,781
Granted Patent B2
US 7,722,781 · App. 12/301,070 · Granted May 25, 2010

Tetrafluoropropene production processes

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Quick Facts
Patent No.
US 7,722,781
App. No.
12/301,070
Granted
May 25, 2010
Kind
B2
Abstract

A process is disclosed for the manufacture of CF 3 CF═CH 2 and CF 3 CH═CHF. The process involves dehydrofluorinating CF 3 CHFCH 2 F in the presence of a dehydrofluorination catalyst to produce a product mixture comprising CF 3 CF═CH 2 and CF 3 CH═CHF, and recovering said CF 3 CF═CH 2 and CF 3 CH═CHF from the product mixture. The present invention also provides a composition comprising (a) the Z-isomer of CF 3 CH═CHF and (b) HF; wherein the HF is present in an effective amount to form an azeotropic combination with the Z—CF 3 CH═CHF.

Claims (15)

1. A process for the manufacture of 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene comprising; (a) dehydrofluorinating pentafluoropropane consisting essentially of 1,1,1,2,3-pentafluoropropane in the presence of a dehydrofluorination catalyst to produce a product mixture comprising 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene; and (b) recovering said 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene from the product mixture produced in (a); wherein said 1,3,3,3-tetrafluoropropene is recovered from the product mixture as a HF/1,3,3,3-tetrafluoropropene azeotrope.

2. A process for the manufacture of 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene comprising; (a) dehydrofluorinating 1,1,1,2,3-pentafluoropropane in the presence of a dehydrofluorination catalyst to produce a product mixture comprising 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene; and (b) recovering said 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene from the product mixture produced in (a); wherein said 2,3,3,3-tetrafluoropropene is recovered from the product mixture as a HF/2,3,3,3-tetrafluoropropene azeotrope.

3. The process of claim 1 wherein unconverted 1,1,1,2,3-pentafluoropropane is recovered as an HF/1,1,1,2,3-pentafluoropropane azeotrope and recycled back to the dehydrofluorination as said azeotrope.

4. The process of claim 2 wherein the catalyst is selected from the group consisting of fluorided alumina, aluminum fluoride and mixtures thereof.

5. The process of claim 2 wherein pure 2,3,3,3-tetrafluoropropene is further recovered from said HF/2,3,3,3-tetrafluoropropene azeotrope.

6. A process for the manufacture of 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene comprising; (a) dehydrofluorinating pentafluoropropane consisting essentially of 1,1,1,2,3-pentafluoropropane in the presence of a dehydrofluorination catalyst to produce a product mixture comprising 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene; and (b) recovering said 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene from the product mixture produced in (a); wherein said dehydrofluorination is run under a pressure of less than one atmosphere.

7. The process of claim 1 wherein pure 1,3,3,3-tetrafluoropropene is further recovered from said HF/1,3,3,3-tetrafluoropropene azeotrope.

8. The process of claim 1 wherein said dehydrofluorination reaction is conducted at a temperature of from about 200° C. to about 500° C.

9. The process of claim 1 wherein said dehydrofluorination reaction is conducted at a temperature of from about 300° C. to about 450° C.

10. The process of claim 1 wherein said dehydrofluorination reaction is conducted at near atmospheric pressure.

11. The process of claim 1 wherein said dehydrofluorination reaction is carried out in the presence of an inert gas.

12. The process of claim 11 wherein said inert gas is selected from the group consisting of nitrogen, helium and argon

13. The process of claim 11 wherein the mole ratio of said inert gas to said HFC-245eb is from about 5:1 to about 0.5:1.

14. The process of claim 6 wherein the catalyst is selected from the group consisting of fluorided alumina, aluminum fluoride and mixtures thereof.

15. The process of claim 6 wherein the catalyst is selected from the group consisting of lanthanum oxide and fluorided lanthanum oxide.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →