Method for producing fluorinated organic compounds
View Patent ↗Disclosed are methods for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF 3 CHXCH 2 X (I) to at least one compound of formula (II) CF 3 CZCHZ (II). where X is independently Cl, Br, I or F, and Z independently is H or F. In certain preferred embodiments, each Z is different.
1. A method of preparing fluorinated organic compounds comprising convening at least one compound of formula (I):
CF 3 CHXCH 2 X (I)
to at least one compound of formula (II)
CF 3 CZCHZ (II)
where X is independently Cl or F, and Z is independently is H or F,
wherein at least a portion of said converting step is conducted in the gas phase and in the presence of a catalyst comprising at least one material selected from the group consisting of nickel, chromium oxide, activated carbon, palladium, and ferric chloride;
wherein said method further comprises forming said compound of formula 1by halogen addition comprising contacting a fluorinated C3 olefin with a halogen addition agent comprising ClF under conditions effective to produce a compound of formula (I).
2. A method for preparing fluorinated organic compounds comprising convening at least one compound of formula (I):
CF 3 CHXCH 2 X (I)
to at least one compound of formula (II)
CF 3 CZCHZ (II)
where X is independently Cl or F, and Z is independently is H or F,
wherein at least a portion of said converting step is conducted in the gas phase and in the presence of a catalyst comprising at least one material selected from the group consisting of nickel, chromium oxide, activated carbon, palladium, and ferric chloride, and wherein said compound of formula (I) comprises 1,1,1,3-tetrafluoro-2-chloropropane and said compound of formula (II) comprises HFO-1234ze.
3. The method of claim 2 wherein said converting step is carried out under conditions effective to convert at least about 50% of said 1,1,1,3-tetrafluoro-2-chloropropane and to provide a selectivity to HFO-1234ze of at least about 70%.
4. A method for preparing fluorinated organic compounds comprising converting at least one compound of formula (I):
CF 3 CHXCH 2 X (I)
to at least one compound of formula (II)
CF 3 CZCHZ (II)
where X is independently Cl or F, and Z is independently is H or F, wherein at least a portion of said converting step is conducted in the gas phase and in the presence of a catalyst comprising nickel.
5. The method of claim 4 wherein the compound of formula (I) comprises 1,1,1,2,3 pentafluoropropane and the compound of formula (II) comprises HFO-1234yf.
6. The method of claim 5 wherein said catalyst comprises nickel mesh.
7. The method of claim 5 wherein said catalyst comprises nickel on a carbon support.
8. The method of claim 4 wherein the compound of formula (I) comprises 1,1,1,3-tetrafluoro-2-chloropropane and the compound of formula (II) comprises HFO-1234ze.
9. The method of claim 8 wherein said catalyst comprises nickel mesh.
10. The method of claim 8 wherein said catalyst comprises nickel on a carbon support.
11. The method of claim 10 wherein at least a portion of said converting step is conducted at a temperature of from about 400° C. to about 550° C.
12. The method of claim 4 wherein said catalyst comprises activated carbon.
13. The method of claim 12 wherein at least a portion of said converting step is conducted at a temperature of from about 450° C. to about 500° C.