Method for producing fluorine group-containing haloolefin compound and composition

Patent metadata

Field	Value
Publication number	US-10053405-B2
Application number	US-201515514618-A
Country	US
Kind code	B2
Filing date	Oct 7, 2015
Priority date	Oct 7, 2014
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

The present invention provides a method for producing a fluorine-containing haloolefin compound, said method being able to reduce the generation of overly fluorinated compounds as by-products in the production of the fluorine-containing haloolefin compound and produce the target product of high purity at a high yield. The invention also provides a halogenated hydrocarbon composition. The method for producing a haloolefin compound through the step of fluorinating a starting material containing at least one of a pentachloropropane or a tetrachloropropene in the presence of a fluorinating agent in a reactor, according to the present invention, includes the step of adding hydrogen chloride to the reactor. The composition according to the present invention contains: at least one member selected from the group consisting of a pentachloropropane and a tetrachloropropene; and hydrogen chloride.

First claim

The invention claimed is:

1. A method for producing a fluorine-containing haloolefin compound through the step of fluorinating a starting material containing at least one of a pentachloropropane or a tetrachloropropene in the presence of a fluorinating agent in a reactor,
the method comprising the step of adding hydrogen chloride to the reactor, wherein the fluorination is performed in a gas phase, wherein the selectivity for haloolefin compounds having more than 3 fluorine atoms as substituents is 10% or less.

2. The method for producing a fluorine-containing haloolefin compound according to claim 1 , wherein the fluorinating agent is hydrogen fluoride.

3. The method according to claim 1 , wherein the pentachloropropane is at least one member selected from the group consisting of 1,1,1,2,3-pentachloropropane and 1,1,2,2,3-pentachloropropane; the tetrachloropropene is at least one member selected from the group consisting of 1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene; and the fluorine-containing haloolefin compound is 2-chloro-3,3,3-trifluoropropene.

4. The method according to claim 1 , wherein the starting material is at least one member selected from the group consisting of 1,1,1,2,3-pentachloropropane and 1,1,2,2,3-pentachloropropane; and the fluorine-containing haloolefin compound is 2-chloro-3,3,3-trifluoropropene.

5. The method according to claim 1 , wherein the starting material is at least one member selected from the group consisting of 1,1,1,3,3-pentachloropropane and 1,1,3,3-tetrachloropropene; and the fluorine-containing haloolefin compound is 1-chloro-3,3,3-trifluoropropene.

6. The method according to claim 5 , wherein the starting material is 1,1,1,3,3-pentachloropropane; and the fluorine-containing haloolefin compound is 1-chloro-3,3,3-trifluoropropene.

7. The method according to claim 1 , wherein the hydrogen chloride is added in an amount of 1×10 −4 to 2 molar equivalents based on the total amount of the pentachloropropane and the tetrachloropropene.

8. The method according to claim 1 , wherein the hydrogen chloride is added in an amount of 1×10 −2 to 1 molar equivalents based on the total amount of the pentachloropropane and the tetrachloropropene.

9. The method according to claim 1 , wherein the hydrogen chloride is added in an amount of 1×10 −1 to 1 molar equivalents based on the total amount of the pentachloropropane and the tetrachloropropene.

10. A composition comprising: at least one member selected from the group consisting of a pentachloropropane and a tetrachloropropene; and hydrogen chloride, wherein the content of the hydrogen chloride is 1×10 −4 to 2 molar equivalents based on the total amount of the pentachloropropane and the tetrachloropropene.

11. The composition according to claim 10 , wherein the content of the hydrogen chloride is 1×10 −2 to 1 molar equivalents based on the total amount of the pentachloropropane and the tetrachloropropene.

12. The composition according to claim 10 , wherein the content of the hydrogen chloride is 1×10 −1 to 1 molar equivalents based on the total amount of the pentachloropropane and the tetrachloropropene.

13. The composition according to claim 10 , wherein the pentachloropropane is at least one member selected from the group consisting of 1,1,1,2,3-pentachloropropane, 1,1,2,2,3-pentachloropropane, and 1,1,1,3,3-pentachloropropane; and the tetrachloropropene is at least one member selected from the group consisting of 1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene.

14. The composition according to claim 10 , wherein the pentachloropropane is at least one member selected from the group consisting of 1,1,1,2,3-pentachloropropane, 1,1,2,2,3-pentachloropropane, and 1,1,1,3,3-pentachloropropane.

15. The method according to claim 1 , wherein the selectivity for haloolefin compounds having more than 3 fluorine atoms as substituents is 5% or less.

16. The method according to claim 1 , wherein the selectivity for haloolefin compounds having more than 3 fluorine atoms as substituents is 3% or less.

Assignees

• Daikin Ind Ltd

Inventors

• Karube Daisuke
• Kishimoto Masayuki
• Komatsu Yuzo
• Chaki Takehiro

Classifications

• C07C17/25 Primary

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

• C07C21/18

  containing fluorine · CPC title

• C07C17/206

  the other compound being HX · CPC title

• C07C17/20

  of halogen atoms by other halogen atoms · CPC title

• C07C21/04

  Chloro-alkenes · CPC title