Method for producing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf)
View Patent ↗The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
1. A reaction mixture for preparing fluorinated organic compounds comprising a C3 chlorocarbon; a halogenating agent; at least one catalyst and at least one stabilizer, wherein the stabilizer is selected from the group consisting of an amine stabilizer, a hydroquinone stabilizer, a methoxy-hydroquinone, a triethylamine, a di-isopropyl amine, a butylated hydroxyl anisole (BHA), and combinations thereof, and wherein said reaction mixture produces a C3 haloolefin.
2. The reaction mixture of claim 1 wherein said C3 haloolefin is 2-chloro-3,3,3,-trifluoropropene.
3. The reaction mixture of claim 2 wherein said C3 chlorocarbon comprises at least one compound selected from the group consisting of 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, and 1,1,1,2,3-pentachloropropane.
4. The reaction mixture of claim 1 wherein said halogenating agent is a fluorinating agent.
5. The reaction mixture of claim 4 wherein said fluorinating agent comprises hydrogen fluoride.
6. The reaction mixture of claim 1 wherein at least a portion of said mixture is in a gas phase.
7. The reaction mixture of claim 1 wherein said catalyst comprises at least one fluorination catalyst.
8. The reaction mixture of claim 7 where the at least one fluorination catalyst is selected from the group consisting of Cr 2 O 3 , FeCl 3 /C, Cr 2 O 3 , Cr 2 O 3 /Al 2 O 3 , Cr 2 O 3 /AlF 3 , Cr 2 O 3 /carbon, CoCl 2 /Cr 2 O 3 /Al 2 O 3 , NiCl 2 /Cr 2 O 3 /Al 2 O 3 , CoCl 2 /AlF 3 , NiCl 2 /AlF 3 and combinations thereof.
9. The reaction mixture of claim 7 wherein at least one fluorination catalyst comprises Cr 2 O 3 .
10. The reaction mixture of claim 1 wherein said stabilizer comprises an amine stabilizer.
11. The reaction mixture of claim 1 wherein said stabilizer comprises a hydroquinone stabilizer.
12. The reaction mixture of claim 1 wherein said stabilizer is selected from the group consisting of methoxy-hydroquinone, triethylamine, di-isopropyl amine, butylated hydroxy anisole (BHA), and combinations thereof.
13. The reaction mixture of claim 1 wherein said stabilizer comprises triethylamine.
14. The reaction mixture of claim 1 wherein said stabilizer comprises di-isopropyl amine.
15. The reaction mixture of claim 1 wherein said stabilizer comprises methoxy-hydroquinone.
16. The reaction mixture of claim 1 wherein said stabilizer comprises butylated hydroxy anisole (BHA).
17. The reaction mixture of claim 1 wherein a concentration of said stabilizer is less than about 300 ppm.
18. The reaction mixture of claim 1 wherein a concentration of said stabilizer is less than about 100 ppm.
19. The reaction mixture of claim 1 wherein a concentration of said stabilizer is about 10 ppm or less.
20. The reaction mixture of claim 3 wherein said chlorocarbon is 1,1,2,3-tetrachloropropene.
21. The reaction mixture of claim 3 wherein said chlorocarbon is 2,3,3,3-tetrachloropropene.
22. The reaction mixture of claim 3 wherein said chlorocarbon is 1,1,1,2,3-pentachloropropane.