Process for producing fluorine-containing olefin

Patent metadata

Field	Value
Publication number	US-2016355453-A1
Application number	US-201615166906-A
Country	US
Kind code	A1
Filing date	May 27, 2016
Priority date	Jun 2, 2015
Publication date	Dec 8, 2016
Grant date	—

Abstract

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.

First claim

1 . A process for producing fluorine-containing olefins represented by 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, the chlorine-containing compound being at least one compound selected from the group consisting of: a chlorine-containing alkane represented by 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 represented by 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 represented by Formula (3): CX 3 CCl═CH 2 , wherein X is independently F or Cl; a chlorine-containing alkene represented by 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 represented by Formula (5): CH 2 XCCl═CX 2 , wherein X is independently F or Cl; and a chlorine-containing alkene represented by 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 selected from the group consisting of Group VIII and Group IX is present together with chromium.

2 . The production process according to claim 1 , wherein the chlorine-containing compound is at least one member selected from the group consisting of HCC-240db, HCO-1230xa, HCO-1230xf, HCFC-243db, HCFC-242dc, HCFO-1231xf, HCFO-1232xf, and 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 HFO-1234yf and HFO-1234ze.

4 . The production process according to claim 1 , wherein the fluorine-containing olefins include HFO-1234yf and HFO-1234ze.

5 . The production process according to claim 1 , wherein the metal element M is an element of Group 5 or 6 of the periodic table.

6 . The production process according to claim 1 , wherein the metal element M is ruthenium.

7 . 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.

Assignees

• Daikin Ind Ltd

Inventors

• Ohkubo Shun
• Karube Daisuke

Classifications

• B01J23/468

  Iridium · CPC title

• B01J23/462

  Ruthenium · CPC title

• C07C17/206 Primary

  the other compound being HX · CPC title

• B01J23/466

  Osmium · CPC title

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title