IP Library Granted Patent US 9,024,092
Granted Patent B2
US 9,024,092 · App. 12/631,728 · Granted May 5, 2015

Method for producing fluorinated organic compounds

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Quick Facts
Patent No.
US 9,024,092
App. No.
12/631,728
Granted
May 5, 2015
Kind
B2
Abstract

Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl 3 , SbCl 5 , SbF 5 , TiCl 4 , SnCl 4 , Cr 2 O 3 , and fluorinated Cr 2 O 3 .

Claims (17)

1. A process for making 2-chloro-1,1,1,2-tetrafluoropropane, comprising hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl 3 , SbCl 5 , SbF 5 , TiCl 4 , and SnCl 4 to produce a product composition comprising 2-chloro-1,1,1,2-tetrafluoropropane, wherein the product composition exhibits a 2-chloro-3,3,3-trifluoropropene conversion of about 90% or more and a 2-chloro-1,1,1,2-tetrafluoropropane selectivity of about 80% or more.

2. The process of claim 1 , wherein the catalyst is in bulk form.

3. The process of claim 1 , wherein the catalyst is supported.

4. The process of claim 3 , wherein the support is selected from the group consisting of carbon, alumina, fluorinated alumina, or aluminum fluoride.

5. The process of claim 1 where the catalyst is activated using anhydrous hydrogen fluoride.

6. The process of claim 1 where the catalyst is activated using anhydrous chlorine.

7. The process of claim 1 , wherein the hydrofluorination is vapor-phase fluorination.

8. The process of claim 7 , wherein the catalyst for vapor-phase fluorination reaction is SbCl 5 supported on activated carbon.

9. The process of claim 7 , wherein the vapor-phase fluorination reaction is carried out at a temperature of about 50° C. to about 120° C. and at a pressure of about 30 psia to about 175 psia.

10. The process of claim 7 , wherein the mole ratio of hydrogen fluoride to 2-chloro-3,3,3-trifluoropropene is from about 2:1 to about 15:1.

11. The process of claim 7 , wherein the hydrofluorination of 2-chloro-3,3,3-trifluoropropene is under conditions effective to obtain a conversion of about 90% or more and a 2-chloro-1,1,1,2-tetrafluoropropane selectivity of about 90% or more.

12. The process of claim 1 , wherein the hydrofluorination is liquid-phase fluorination.

13. The process of claim 12 , wherein the catalyst for liquid-phase fluorination reaction is SbCl 5 .

14. The process of claim 12 , wherein the liquid-phase fluorination reaction is carried out at a temperature of about 50° C. to about 120° C. and at a pressure of about 50 psia to about 175 psia.

15. The process of claim 12 , wherein the mole ratio of hydrogen fluoride to 2-chloro-3,3,3-trifluoropropene is from about 2:1 to about 15:1.

16. The process of claim 12 , wherein the hydrofluorination of 2-chloro-3,3,3-trifluoropropene is under conditions effective to obtain a conversion of about 93% or more and a 2-chloro-1,1,1,2-tetrafluoropropane selectivity of about 80% or more.

17. The process of claim 1 , wherein the hydrofluorination of 2-chloro-3,3,3-trifluoropropene is under conditions effective to obtain a conversion of about 93% or more.

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2010
From: MERKEL, DANIEL C.; JOHNSON, ROBERT C.; TUNG, HSUEH SUNG
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 023914/0624 →