Method for producing fluorine-containing olefin

Patent metadata

Field	Value
Publication number	US-9487459-B2
Application number	US-201414778631-A
Country	US
Kind code	B2
Filing date	Mar 7, 2014
Priority date	Apr 25, 2013
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

The present invention provides a method for producing a fluorine-containing olefin, the method comprising reacting a chlorine-containing compound represented by a specific formula with anhydrous hydrogen fluoride in the presence of a chromium atom-containing fluorination catalyst, the reaction being carried out at a temperature within the range of 200 to 350° C. in the presence of 0.0001 to 0.03 mol of molecular chlorine per mol of the chlorine-containing compound. The present invention is capable of achieving the effect of suppressing catalyst deterioration, maintaining the starting material conversion and the target product selectivity within excellent ranges, and reducing adverse effects caused by the use of a large amount of non-condensable gas.

First claim

The invention claimed is:

1. A method for producing a fluorine-containing olefin of Formula (7): CF 3 CA=CHB, wherein one of A or B is F, and the other is H,
the method comprising reacting anhydrous hydrogen fluoride with at least one chlorine-containing compound in the presence of a chromium atom-containing fluorination catalyst, the at least one chlorine-containing compound being 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, and at least one 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, and at least one 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, and at least one X is Cl;
the reaction being carried out at a temperature within a range of 200 to 350° C. in the presence of 0.0001 to 0.03 mol of molecular chlorine per mol of the chlorine-containing compound.

2. The method for producing a fluorine-containing olefin according to claim 1 , wherein the chlorine-containing compound is at least one compound selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,2,3-trichloro-1,1-difluoropropane, 1,1,2,3-tetrachloro-1-fluoropropane, 1,1,1,3,3-pentachloropropane, 2-chloro-3,3,3-trifluoropropene, 2,3,3,3-tetrachloropropene, 2,3-dichloro-3,3-difluoropropene, 1-chloro-3,3,3-trifluoropropene, 1,3,3,3-tetrachloropropene, 1,1,2,3-tetrachloropropene, and 1,1,3,3-tetrachloropropene.

3. The method for producing a fluorine-containing olefin according to claim 1 , wherein the chlorine-containing compound is 2-chloro-3,3,3-trifluoropropene, and the reaction temperature is 300 to 350° C.

4. The method for producing a fluorine-containing olefin according to claim 1 , wherein the molecular chlorine is used in an amount of 0.001 to 0.01 mol per mol of the chlorine-containing compound.

5. The method for producing a fluorine-containing olefin according to claim 2 , wherein the chlorine-containing compound is 2-chloro-3,3,3-trifluoropropene, and the reaction temperature is 300 to 350° C.

6. The method for producing a fluorine-containing olefin according to claim 2 , wherein the molecular chlorine is used in an amount of 0.001 to 0.01 mol per mol of the chlorine-containing compound.

7. The method for producing a fluorine-containing olefin according to claim 3 , wherein the molecular chlorine is used in an amount of 0.001 to 0.01 mol per mol of the chlorine-containing compound.

Assignees

• Daikin Ind Ltd

Inventors

• Karube Daisuke
• Takakuwa Tatsuya
• Komatsu Yuzo

Classifications

• C07C17/206 Primary

  the other compound being HX · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C17/20 Primary

  of halogen atoms by other halogen atoms · CPC title