Method for producing fluorinated organic compounds
View Patent ↗Disclosed is a process for the preparation of fluorinated olefins. In preferred embodiments C3 olefins are produced by methods comprising contacting a compound of the Formula (I) C(R 1 a R 2 b R 3 c ) (I) with a compound of Formula (II) C(R 1 a R 2 b R 3 c )C n (R 1 a R 2 b R 3 c ) II wherein R 1 a , R 2 b , and R 3 c are independently a hydrogen atom or a halogen selected from the group consisting of fluorine; chlorine, bromine and iodine, provided that the compound of formula I has at least three halogen substituents and that said at three halogen substituents comprise at least one fluorine; a, b and c are independently=0, 1, 2 or 3 and (a+b+c)=2 or 3; and n is 0 or 1, under conditions effective to produce at least one C3 fluoroolefin.
1. A process for the preparation of fluorinated olefins having three carbon atoms comprising:
contacting a compound of Formula (I)
C(R 1 a R 2 b R 3 c ) (I)
with a compound of Formula (II)
C(R 1 a R 2 b R 3 c )C(R 1 a R 2 b R 3 c ) (II)
wherein R 1 , R 2 , and R 3 are each independently H or a halogen selected from the group consisting of fluorine; chlorine, bromine and iodine, provided that the compound of Formula (I) has at least three halogen substituents and that said at least three halogen substituents comprise at least one fluorine; a, b and c are each independently 0, 1, 2 or 3; said contacting step being carried out in the presence of a metal-based catalyst wherein said metal is selected from the group consisting of Ni, Pd, Sb, Al, and Fe to produce at least one tetrafluoropropene.
2. The process of claim 1 wherein said contacting step is effective to convert at least about 50% of said compound of Formula (II).
3. The process of claim 1 wherein said contacting step is effective to convert at least about 70% of said compound of Formula (II).
4. The process of claim 1 wherein said contacting step is effective to convert at least about 90% of said compound of Formula (II).
5. The process of claim 1 wherein said contacting step comprises a reacting step where at least one Formula (I) compound is reacted with at least one Formula (II) compound in the presence of a catalyst wherein said reacting step is effective to produce a reaction product having at least about 20% selectivity to one or more tetrafluoropropenes.
6. The process of claim 5 wherein said reacting step is effective to produce a reaction product having at least about 40% selectivity to one or more tetrafluoropropenes.
7. The process of claim 5 wherein said reacting step is effective to produce a reaction product having at least about 70% selectivity to one or more tetrafluoropropenes.
8. The process of claim 1 wherein said contacting step comprises a reacting step where at least one Formula (I) compound is reacted with at least one Formula (II) compound in the presence of a catalyst; wherein said reacting step is effective to produce a reaction product comprising HFO-1234yf.
9. The process of claim 8 wherein said reacting step is effective to produce a reaction product having at least about 20% selectivity to one or more HFO-1234yf.
10. The process of claim 8 wherein said reacting step is effective to produce a reaction product having at least about 70% selectivity to one or more HFO-1234yf.
11. The process of claim 8 wherein said reacting step comprises a gas phase reaction.
12. The process of claim 1 wherein said contacting step comprises introducing into a reactor one or more compounds of Formula (I) and one or more compounds of Formula (II) in a Formula (II):Formula (I) mole ratio of from about 0.5:1 to about 10:1.
13. The process of claim 12 wherein said Formula (II) in a Formula (II):Formula (I) mole ratio is form about 1:1 to about 3:1.
14. The process of claim 1 wherein said Formula (I) compound comprises CF 3 Cl.
15. The process of claim 1 wherein said Formula (II) compound comprises CH 3 CF 2 Cl.
16. The process of claim 15 wherein said CH 3 CF 2 Cl and CF 3 Cl are present in a CH 3 CF 2 Cl:CF 3 Cl mole ratio of about 1:1 to about 4:1.
17. The process of claim 16 wherein said CH 3 CF 2 Cl:CF 3 Cl mole ratio is from about 1.5:1 to about 2.5:1.
18. The process of claim 1 wherein said contacting step consists essentially of a reaction taking place in substantially one reaction vessel.
19. The process of claim 1 wherein said contacting step further comprises contacting said compounds of Formula (I) and Formula (II) in the presence of an oxygen-containing composition.
20. The process of claim 19 wherein said oxygen-containing composition comprises air.
21. A process for the preparation of fluorinated olefins having three carbon atoms comprising:
contacting a first compound selected from the group consisting of CH 4 and CH 3 Cl,
with a second compound of Formula (II):
C(R 1 a R 2 b R 3 c )C(R 1 a R 2 b R 3 c ) (II)
wherein R 1 , R 2 , and R 3 are each independently H or a halogen selected from the group consisting of fluorine; chlorine, bromine and iodine, provided that the compound of Formula (II) has at least three fluorine; a, b and c are each independently 0, 1, 2, or 3, said contacting step being carried out in the presence of a metal-based catalyst wherein said metal is selected from the group consisting of Ni, Pd, Sb, Al, and Fe to produce at least one tetrafluoropropene.
22. The process of claim 21 wherein Formula (II) is a compound selected from the group consisting of CF 3 CFHCl, CF 3 CFCl 2 , and CF 3 CF 2 H.
23. The process of claim 22 wherein said tetrafluoropropene is HFO-1234yf.
24. The process of claim 20 wherein said metal-based catalyst is a nickel-based catalyst.
25. The process of claim 24 wherein said metal-based catalyst is selected from the group consisting of nickel mesh, Ni/C, La 2 NiO 4 , Ni/BaO, Ni/CaO, and Ni/MgO.