IP Library Granted Patent US 7,557,254
Granted Patent B2
US 7,557,254 · App. 12/134,629 · Granted Jul 7, 2009

Method for producing fluorinated organic compounds

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Quick Facts
Patent No.
US 7,557,254
App. No.
12/134,629
Granted
Jul 7, 2009
Kind
B2
Abstract

A method for preparing fluorinated organic compounds wherein at least one fluorinated olefin is reacted with methyl fluoride in the gas-phase and in the presence of a Lewis Acid catalyst to form at least one product having at least 3 carbon atoms.

Claims (24)

1. A method of preparing fluorinated organic compounds comprising reacting methyl fluoride with at least one fluorinated olefin having the structure:

wherein R is F, Cl, C 1 -C 2 fluorinated alkyl, or two-carbon fluorinated alkenyl,

to produce at least one hydrofluoroalkene, wherein said reaction occurs in the gas-phase and in the presence of a Lewis Acid catalyst.

2. The method of claim 1 wherein said hydrofluoroalkene is a tetrafluoropropene.

3. The method of claim 1 wherein said hydrofluoroalkene is selected from the group consisting of CH 2 ═CFCF 3 , CH 2 ═CFCF 2 CF 3 , and CH 2 ═CF CF 2 CF 2 CF 3 .

4. The method of claim 1 wherein said product further comprises at least one fluorinated alkane.

5. The method of claim 4 wherein said fluorinated alkane is selected from CH 3 CF 2 CF 3 , CH 3 CF 2 CF 2 CF 3 , and CH 3 CF 2 CF 2 CF 2 CF 3 .

6. The method of claim 4 wherein said fluorinated alkane is 1,1,1,2,2-pentafluoropropane.

7. The method of claim 6 wherein said hydrofluoroalkene is 2,3,3,3-tetrafluoro-1-propene.

8. The method of claim 1 wherein said method is performed continuously.

9. A method of preparing fluorinated organic compounds comprising reacting methyl fluoride with at least one fluorinated olefin having the structure:

wherein R is Cl, C 1 -C 2 fluorinated alkyl, or two-carbon fluorinated alkenyl,

to produce at least one product having at least 3 carbon atoms, wherein said reaction occurs in the gas-phase and in the presence of a Lewis Acid catalyst.

10. The method of claim 9 wherein R is Cl.

11. The method of claim 9 wherein said reaction product comprises at least one tetrafluoropropene and at least one pentafluoropropane.

12. The method of claim 11 wherein said tetrafluoropropene is 2,3,3,3-tetrafluoro-1-propene and said pentafluoropropane is 1,1,1,2,2-pentafluoropropane.

13. The method of claim 9 wherein said Lewis Acid catalyst is selected from the group consisting of SbF 5 , SbF 3 , and partially chlorinated compounds of such fluorides.

14. The method of claim 9 wherein said method is performed continuously.

15. A method of preparing fluorinated organic compounds comprising reacting methyl fluoride with at least one fluorinated olefin having the structure:

wherein R is F, Cl, C 1 -C 2 fluorinated alkyl, or two-carbon fluorinated alkenyl, to produce at least one product having at least 3 carbon atoms, wherein said reaction occurs in the gas-phase and in the presence of a Lewis Acid catalyst impregnated on activated carbon, wherein said catalyst comprises a metal or metalloid halide.

16. The method of claim 15 wherein said catalyst comprises at least one atom selected from the group consisting of Sb and Al.

17. The method of claim 15 wherein said Lewis Acid catalyst is selected from the group consisting of AlCl 3 , SbCl 5 and partially fluorinated compounds of such chlorides.

18. The method of claim 15 wherein said Lewis Acid catalyst is selected from the group consisting of SbF 5 , SbF 3 , and partially chlorinated compounds of such fluorides.

19. The method of claim 15 wherein said Lewis Acid catalyst is SbF 5 .

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074344/0066 →
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 May 28, 2009
From: MUKHOPADHYAY, SUDIP; TUNG, HSUEHSUNG; NAIR, HARIDASAN K; MA, JINGJI
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 022747/0993 →