Method for producing fluorinated organic compounds
Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF 3 CF═CH 2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl 2 ═CClCH 2 Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF 3 CCl═CH 2 , preferably in a 80-96% selectivity. The CF 3 CCl═CH 2 is preferably converted to CF 3 CFClCH 3 (244-isomer) using a SbCl 5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr 2 O 3 and FeCl 3 /C is preferably used as the catalyst to achieve high selectivity to CF 3 CCl═CH 2 (96%). In the second step, SbCl 5 /C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF 3 CFClCH 3 . The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.
1. A method for producing fluorinated organic compounds comprising converting at least one compound of Formula (I)
C(X) m CCl(Y) n C(X) m (I)
to at least one compound of Formula (II)
CF 3 CF═CHZ (II)
where each X, Y and Z is independently H, F, Cl, I or Br, and each m is independently 1, 2 or 3, and n is 0 or 1.
2. The method of claim 1 wherein said converting step is a direct converting step.
3. The method of claim 1 wherein said converting step is an indirect converting step.
4. The method of claim 1 wherein said at least one compound of Formula (I) comprises a compound wherein n is 0, each X is independently H or Cl, and wherein Z in said compound of Formula (II) is H.
5. The method of claim 1 wherein said at least one compound of Formula (I) comprises a compound Formula (IA):
C(X) 2 ═CClC(X) 3 (IA)
wherein X is as identified in claim 1 .
6. The method of claim 5 wherein Z in said compound of Formula (II) is H.
7. The method of claim 5 wherein X is independently H or Cl.
8. The method of claim 1 wherein said at least one compound of Formula (I) comprises at least one tetrachloropropene.
9. The method of claim 5 wherein said at least one compound of Formula (IA) comprises at least one tetrachloropropene.
10. The method of claim 1 wherein said at least one compound of Formula (I) comprises CH 2 ═CClCCl 3 .
11. The method of claim 1 wherein said at least one compound of Formula (I) comprises CCl 2 ═CClCH 2 Cl.
12. The method of claim 1 wherein said at least one compound of Formula (I) comprises CHCl═CClCCl 2 H.
13. The method of claim 1 wherein said at least one compound of Formula (I) is selected from the group consisting of CH 2 ═CClCCl 3 , CCl2═CClCH 2 Cl, CHCl═CClCCl 2 H, and combinations of these.
14. The method of claim 1 wherein said at least one compound of Formula (I) comprises a compound wherein n is 0 and the terminal saturated carbon has three (3) F substituents.
15. The method of claim 1 wherein said at least one compound of Formula (I) comprises a compound Formula (IAA):
C(X) 2 ═CClCF 3 (IAA)
wherein X is as identified in claim 1 .
16. The method of claim 1 wherein each X in said compound of Formula (IAA) is independently H or Cl.
17. The method of claim 1 wherein said at least one compound of Formula (I) comprises at least one trifluoropropene.
18. The method of claim 17 wherein said at least one trifluoropropene comprises CH 2 ═CClCF 3 (HCFC-1223xf).
19. The method of claim 1 wherein said at least one compound of Formula (I) comprises a compound of Formula (IB):
C(X) 3 CClYC(X) 3 (IB)
wherein X and Y are as identified in claim 1 .
20. The method of claim 19 wherein each X in said compound of Formula (IB) is independently H or Cl.