Process for producing fluorine-containing olefin
In the production of fluorine-containing olefins using a chlorine-containing alkane or a chlorine-containing alkene as a starting material, a process for producing a plurality of useful fluorine-containing olefins with high selectivity using the same raw material, the same equipment, and the same conditions is provided. The present invention provides a process for producing fluorine-containing olefins, the process comprising reacting a chlorine-containing compound represented by a specific formula and anhydrous hydrogen fluoride in the presence of oxidative gas and a fluorination catalyst, wherein the fluorination catalyst is a catalyst in which at least one metal element M selected from the group consisting of Group VIII and Group IX is present together with chromium. This production process can simultaneously produce two or more fluorine-containing olefin compounds, including HFO-1234yf and HFO-1234ze, with high selectivity.
1. A process for producing two or more fluorine-containing olefins of Formula (7): CF 3 CA=CHB, wherein one of A and B is F or Cl, and the other is H,
the process comprising reacting a chlorine-containing compound and anhydrous hydrogen fluoride in the presence of oxidative gas and a fluorination catalyst to produce two or more fluorine-containing olefins,
the chlorine-containing compound being at least one compound selected from the group consisting of:
a chlorine-containing alkane of Formula (1): CX 3 CClYCH 2 Z, wherein X is independently F or Cl, Y is H or F, when Y is H, Z is Cl or F, and when Y is F, Z is H;
a chlorine-containing alkane of Formula (2): CX 3 CH 2 CHX 2 , wherein X is independently F or Cl, with the proviso that at least one of X is Cl;
a chlorine-containing alkene of Formula (3): CX 3 CCl═CH 2 , wherein X is independently F or Cl;
a chlorine-containing alkene of Formula (4): CX 3 CH═CHX, wherein X is independently F or Cl, with the proviso that at least one of X is Cl;
a chlorine-containing alkene of Formula (5): CH 2 XCCl═CX 2 , wherein X is independently F or Cl; and
a chlorine-containing alkene of Formula (6): CHX 2 CH═CX 2 , wherein X is independently F or Cl;
wherein the fluorination catalyst is a catalyst in which at least one metal element M is present together with chromium,
wherein said at least one metal element M is an element selected from the group consisting of Group VIII and Group IX, and said at least one metal element M is an element of Period 5 or 6 of the periodic table.
2. The production process according to claim 1 , wherein the chlorine-containing compound is at least one member selected from the group consisting of 1,1,1,2,3-pentachloropropane (HCC-240db), 1,1,2,3-tetrachloropropene (HCO-1230xa), 2,3,3,3-tetrachloropropene (HCO-1230xf), 2,3-dichloro-1,1,1-trifluoropropane (HCFC-243db), 1,2,3-trichloro-1,1-difluoropropane (HCFC-242dc), 2,3,3-trichloro-3-fluoropropene (HCFO-1231xf), 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf), and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf).
3. The production process according to claim 1 , wherein the fluorine-containing olefins include at least one member selected from the group consisting of 2,3,3,3-tetrafluoropropene (HFO-1234yf) and 1,3,3,3-tetrafluoropropene (HFO-1234ze).
4. The production process according to claim 1 , wherein the fluorine-containing olefins include 2,3,3,3-tetrafluoropropene (HFO-1234yf) and 1,3,3,3-tetrafluoropropene (HFO-1234ze).
5. The production process according to claim 1 , wherein the metal element M is ruthenium.
6. The production process according to claim 1 , wherein the molar ratio of the metal element M and chromium is 0.05:99.95 to 15:85.