Process for producing 2,3,3,3-tetrafluoropropene
View Patent ↗The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, particularly, 1,1,2,3-tetrachloropropene (1230xa), oligomerization/polymerization of such starting reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that providing one or more organic co-feed to the fluoroolefin starting stream reduces such oligomerization/polymerization and improves catalystic stability.
1. A process for preparing 2-chloro-3,3,3-trifluoropropene comprising:
providing a starting composition comprising at least one compound of formula I
CX 2 ═CCl—CH 2 X (I)
wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; and
contacting said starting composition with a fluorinating agent and an effective amount of one or more organic co-feed compounds, other than the compound of formula I, to produce a final composition comprising 2-chloro-3,3,3trifluoropropene.
2. The process of claim 1 , wherein the organic co-feed compound has a boiling point that is lower than the compound of Formula I.
3. The process of claim 2 , wherein the organic co-feed compound is a halocarbon or haloolefin.
4. The process of claim 1 , wherein the organic co-feed compound is selected from the group consisting of trichlorofluoropropene (1231), dichlorodifluoropropene (1232), 1,2-dichloro-3,3,3-trifluoropropene (1223xd), 2-chloro-3,3,3-trifluoropropene (1233xf), 3,3,3,2-tetrafluoropropylene (1234yf), 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane (HFC-245cb), 1,1,1,2,3-pentafluoropropane (245eb), tetrachlorofluoropropane (241), trichlorodifluoropropane (242), dichlorotrifluoropropane (243) and combinations thereof.
5. The process of claim 1 , wherein the effective amount of organic co-feed compound is between about 0.1 to about 99.9 wt %.
6. The process of claim 1 , wherein the effective amount of organic co-feed compound is between about 1 to about 50 wt %.
7. The process of claim 1 , wherein the effective amount of organic co-feed compound is between about 5 to about 15 wt %.
8. The process of claim 1 , wherein at least one compound of formula I is a compound comprising at least one X is a chlorine.
9. The process of claim 1 , wherein at least one compound of formula I is a compound where all Xs are chlorine.
10. The process of claim 1 , wherein the at least one compound of formula I comprises 1,1,2,3-tetrachloropropene.
11. The process of claim 1 , wherein the contacting of said starting composition with a fluorinating agent occurs in a vapor phase.
12. The process of claim 1 , wherein the contacting step occurs in the presence of a catalyst.
13. The process of claim 12 wherein the catalyst is a vapor phase catalyst selected from the group consisting of a chromium oxide, a chromium hydroxide, a chromium halide, a chromium oxyhalide, an aluminum oxide, an aluminum hydroxide, an aluminum halide, an aluminum oxyhalide, a cobalt oxide, a cobalt hydroxide, a cobalt halide, a cobalt oxyhalide, a manganese oxide, a manganese hydroxide, a manganese halide, a manganese oxyhalide, a nickel oxide, a nickel hydroxide, a nickel halide, a nickel oxyhalide, an iron oxide, an iron hydroxide, an iron halide, an iron oxyhalide, inorganic salts thereof, fluorinated derivatives thereof and combinations thereof.
14. The process of claim 13 wherein the catalyst comprises a chromium oxide.
15. The process of claim 1 , wherein the contacting step occurs in the presence of at least one stabilizer.
16. The process of claim 15 , wherein the at least one stabilizer is an amine-based stabilizer.
17. The process of claim 15 , wherein the at least one stabilizer is selected from the group consisting of p-tap(4-tert-Amylphenol), methoxy-hydroquinone, 4-methoxyphenol(HQMME), triethylamine, di-isopropyl amine, butylated hydroxy anisole (BHA), thymol and combinations thereof.