Method for producing 1,2-dichloro-3,3,3-Trifluoropropene

Patent metadata

Field	Value
Publication number	US-10611708-B2
Application number	US-201716094228-A
Country	US
Kind code	B2
Filing date	Apr 10, 2017
Priority date	Apr 19, 2016
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

A method for producing 1,2-dichloro-3,3,3-trifluoropropene according to the present invention includes the step of reacting 1,1,2,3,3-pentachloropropene with a fluorinating agent where hydrogen fluoride is used as the fluorinating agent.

First claim

The invention claimed is:

1. A method for producing 1,2-dichloro-3,3,3-trifluoropropene by fluorinating 1,1,2,3,3-pentachloropropene by a reaction with a fluorinating agent, wherein hydrogen fluoride is used as the fluorinating agent, and the reaction is conducted in a liquid phase.

2. The method according to claim 1 , wherein usage of the hydrogen fluoride is 3 to 40 mol relative to 1 mol of 1,1,2,3,3-pentachloropropene.

3. The method according to claim 1 , wherein the reaction is conducted at 100 to 200° C.

4. The method according to claim 1 , wherein the reaction is conducted at 140 to 180° C.

5. The method according to claim 1 , wherein the reaction is conducted in the absence or presence of catalyst.

6. The method according to claim 1 , wherein the reaction is conducted in the absence of solvent.

7. The method according to claim 1 , wherein 1,2,3-trichloro-3,3-difluoropropene, together with 1,2-dichloro-3,3,3-trifluoropropene, is formed by the reaction.

8. The method according to claim 7 , wherein 1,2,3-trichloro-3,3-difluoropropene is separated and then is used in the reaction as a raw material for producing 1,2-dichloro-3,3,3-trifluoropropene.

9. The method according to claim 1 , further comprising the step of purifying 1,2-dichloro-3,3,3-trifluoropropene.

10. The method according to claim 1 , further comprising the step of dehydrochlorinating 1,1,1,2,3,3-hexachloropropane in a liquid phase in the presence of a Lewis acid catalyst to obtain the 1,1,2,3,3-pentachloropropene.

11. The method according to claim 10 , wherein the Lewis acid catalyst to be used in the dehydrochlorination of 1,1,1,2,3,3-hexachloropropane comprises a halide of a metal that is at least one selected from the group consisting of aluminum, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zirconium, niobium, molybdenum, ruthenium, rhodium, palladium, silver, tin, antimony, tantalum, and tungsten.

12. The method according to claim 10 , further comprising the step of chlorinating 1,1,3,3-tetrachloropropene in a liquid phase in the presence of a Lewis acid catalyst to obtain the 1,1,1,2,3,3-hexachloropropane.

13. The method according to claim 12 , further comprising the step of dehydrochlorinating 1,1,1,3,3-pentachloropropane in a liquid phase in the presence of a Lewis acid catalyst to obtain the 1,1,3,3-tetrachloropropene.

14. The method according to claim 13 , wherein, when conducting the dehydrochlorination of 1,1,1,3,3-pentachloropropane as a first step, the chlorination of 1,1,3,3-tetrachloropropene as a second step and the dehydrochlorination of 1,1,1,2,3,3-hexachloropropane as a third step in this order, the Lewis acid catalyst used in the first step is reused in the second and third steps as the Lewis acids of the second and third steps.

15. A method for producing both 1,2-dichloro-3,3,3-trifluoropropene and 1,2,3-trichloro-3,3-difluoropropene by reacting 1,1,2,3,3-pentachloropropene with hydrogen fluoride, and the reaction is conducted in a liquid phase.

16. The method according to claim 15 , wherein the reaction is conducted in the presence or absence of a catalyst.

17. The method according to claim 15 , further comprising the step of separating 1,2-dichloro-3,3,3-trifluoropropene and 1,2,3-trichloro-3,3-difluoropropene.

18. A method for producing 1,2-dichloro-3,3,3-trifluoropropene by fluorinating 1,1,2,3,3-pentachloropropene by a reaction with a fluorinating agent, wherein hydrogen fluoride is used as the fluorinating agent, and the reaction is conducted in a gas phase and in the absence of catalyst.

19. The method according to claim 18 , wherein the reaction is conducted at 160 to 600° C.

20. The method according to claim 18 , wherein the reaction is conducted in the presence of at least one selected from the group consisting of chlorine, oxygen and air.

21. The method according to claim 18 , wherein 1,2,3-trichloro-3,3-difluoropropene is further produced and wherein 1,2,3-trichloro-3,3-difluoropropene is separated and then is used in the reaction as a raw material for producing 1,2-dichloro-3,3,3-trifluoropropene.

22. A method for producing both 1,2-dichloro-3,3,3-trifluoropropene and 1,2,3-trichloro-3,3-difluoropropene by fluorinating 1,1,2,3,3-pentachloropropene by a reaction with a fluorinating agent, wherein hydrogen fluoride is used as the fluorinating agent, the reaction is conducted in a gas phase, and 1,2,3-trichloro-3,3-difluoropropene is separated and then is used in the reaction as a raw material for producing 1,2-dichloro-3,3,3-trifluoropropene.

23. The method according to claim 22 , wherein the reaction is conducted at 160 to 600° C.

24. The method according to claim 22 , wherein the reaction is conducted in the absence or presence of catalyst.

25. The method according to claim 22 , wherein the reaction is conducted by using a catalyst that is a metal oxide, a metal fluoride or a metal compound-supported catalyst, and wherein the catalyst is optionally subjected to a fluorination treatment to be used in the reaction.

26. The method according to claim 22 , wherein the reaction is conducted in the presence of at least one selected from the group consisting of chlorine, oxygen and air.

Assignees

• Central Glass Co Ltd

Inventors

• Matsunaga Kei
• Imura Hideaki
• Kanai Masatomi
• Tani Masahiko
• Takada Naoto
• Sumida Kohei
• Okamoto Satoru

Classifications

• C07C17/206 Primary

  the other compound being HX · CPC title

• B01J27/125

  with scandium, yttrium, aluminium, gallium, indium or thallium · CPC title

• C07C17/38

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C17/35

  by reactions not affecting the number of carbon or of halogen atoms in the reaction · CPC title

• C07C17/25

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