IP Library Granted Patent US 9,102,579
Granted Patent B2
US 9,102,579 · App. 11/619,589 · Granted Aug 11, 2015

Method for producing fluorinated organic compounds

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Quick Facts
Patent No.
US 9,102,579
App. No.
11/619,589
Granted
Aug 11, 2015
Kind
B2
Abstract

Disclosed is a process for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of Formula (I): C(X) 3 CF 2 C(X) 3   (I) to at least one compound of Formula (II) CF 3 CF═CHZ  (II) where each X and Z is independently H, F, Cl, I or Br, said process preferably not including any substantial amount of oxygen-containing catalyst in certain embodiments. Preferably Z is H.

Claims (30)

1. A method for producing fluorinated organic compounds comprising converting at least one compound of Formula (IA)

C(X) 3 CF 2 CH 3   (IA)

to 1,1,1,2,2-pentafluoropropane (HFC-245cb), wherein each X in Formula IA is independently H, F, Cl, I, or Br and at least one X is a chlorine wherein said converting step occurs in the presence of at least one catalyst selected from the group consisting of an Sb-based catalyst, an Fe-based catalyst, TiCl 4 SnCl 4 , AlCl 3 , AlF 3 , and combinations thereof;

dehydrofluorinating 1,1,1,2,2-pentafluoropropane (HFC-245cb) to form 2,3,3,3-tetrafluoropropene (HFO-1234yf), wherein said dehydrofluorinating step is carried out in the absence of a catalyst or in the presence of an optionally supported catalyst selected from the group consisting of a carbon-based catalyst, a nickel-based catalyst, palladium-based catalyst, and combinations thereof.

2. The method of claim 1 wherein said at least one compound of Formula (IA) comprises at least one trichlorinated, difluorinated propane.

3. The method of claim 1 wherein said at least one compound of Formula (IA) comprises 1,1,1-trichloro-2,2-difluoropropane (HCFC-242bb).

4. The method of claim 1 wherein said converting step comprises at least one gas phase catalytic reaction.

5. The method of claim 1 further comprising the step of providing said compound of Formula (IA) by converting at least one compound of Formula (III):

C(X) 2 ═CClC(X) 3   (III)

to at least one compound of Formula (IA), where each X in Formula III is independently H, F, Cl, I or Br, provided at least one X is Cl, I or Br.

6. The method of claim 5 wherein at least one X on the unsaturated carbon of Formula (III) is Cl, I or Br.

7. The method of claim 5 wherein at least one X on the unsaturated carbon of Formula (III) is Cl.

8. The method of claim 5 wherein converting step comprises converting said compound of Formula (III) in the presence of a catalyst.

9. A method for producing fluorinated organic compounds comprising converting at least one compound of Formula (I)

C(X) 3 CF 2 C(X) 3   (I)

to at least one compound of Formula (II)

CF 3 CF═CHZ  (II)

where each X and Z is independently H, F, Cl, I or Br, wherein said at least one compound of Formula (I) comprises at least a first compound of Formula (IA)

C(X) 3 CF 2 CH 3   (IA)

wherein X is independently H, F, Cl, I or Br, wherein said first compound of Formula (IA) is not pentafluorinated, and wherein said converting step comprises a first reaction stage of converting said first compound of Formula (IA) to a second compound of Formula (IA) wherein said second compound is pentafluorinated and a second reaction stage where the second compound of Formula (IA) is converted to form at least one compound of Formula II.

10. The method of claim 9 wherein said first reaction stage comprises a gas phase catalytic reaction.

11. The method of claim 9 wherein said second compound of Formula (IA) comprises HFC-245cb.

12. The method of claim 9 wherein said first reaction stage includes at least a first catalyst and said second reaction stage includes at least a second catalyst.

13. The method of claim 9 wherein said first reaction stage comprises a fluorination reaction stage containing at least a first fluorination catalyst.

14. The method of claim 13 wherein said first fluorination catalyst comprises a Sb-based catalyst.

15. The method of claim 13 wherein said first fluorination catalyst comprises a Fe-based catalyst.

16. The method of claim 12 wherein said second catalyst comprises a metal-based catalyst.

17. The method of claim 12 wherein said second catalyst comprises a nickel-based catalyst.

18. The method of claim 12 wherein said second catalyst comprises a carbon-based catalyst.

19. The method of claim 9 wherein said compound of Formula (II) comprises HFO-1234yf.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2008
From: MUKHOPADHYAY, SUDIP; TUNG, HSUEH S.; VAN DER PUY, MICHAEL; MERKEL, DANIEL C.; PHILLIPS, STEVEN D.; FLEMING, KIM M.; FERGUSON, SUSAN A.; MA, JING JI; BORTZ, CHERYL L.; LIGHT, BARBARA A.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 021344/0239 →