Catalytic chlorination of 3,3,3-trifluoropropene to 2,3-dichloro-1,1,1-trifluoropropane

Patent metadata

Field	Value
Publication number	US-9938208-B2
Application number	US-201415106418-A
Country	US
Kind code	B2
Filing date	Dec 18, 2014
Priority date	Dec 18, 2013
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The present invention relates to a process for preparing 1,1,1-trifluoro-2,3-dichloropropane which comprises contacting chlorine with 3,3,3-trifluoropropene in the presence of a catalyst to form 1,1,1-trifluoro-2,3-dichloropropane, wherein the catalyst comprises at least one metal halide, where the metal is a metal from Group 13, 14 or 15 of the periodic table or a transition metal or combination thereof.

First claim

What is claimed is:

1. A process for preparing 1,1,1-trifluoro-2,3-dichloropropane which comprises contacting chlorine with 3,3,3-trifluoropropene in the presence of a catalyst to form 1,1,1-trifluoro-2,3-dichloropropane, wherein the catalyst comprises at least one metal halide, where the metal is a metal from Group 13, 14 or 15 of the periodic table or a transition metal or combination thereof, said reaction being conducted in the liquid phase or vapor phase, such that when conducted in the vapor phase, the metal halide is supported on activated carbon; and when conducted in the liquid phase, the catalyst is present in an amount ranging from about 0.02 to about 10 wt % of the total weight of chlorine and 3,3,3-trifloropropene.

2. The process according to claim 1 where the reaction is conducted in the vapor phase wherein the activated carbon may optionally be acid washed or caustic washed.

3. The process according to claim 1 wherein the metal is nickel, chromium, iron, scandium, yttrium, lanthanum, titanium, zirconium, hafnium, vanadium, molybdenum, tungsten, manganese, rhenium, ruthenium, osmium, cobalt, palladium, copper, zinc, tantalum, aluminum, tin, or lead.

4. The process according to claim 1 wherein the metal halide is nickel halide, iron halide or chromium halide.

5. The process according to claim 1 wherein the halide is a chloride.

6. The process according to claim 1 wherein the metal halide is nickel chloride, iron halide or chromium halide.

7. The process according to claim 1 wherein the chlorination occurs in the vapor phase at a temperature ranging from about 80° C. to about 200° C. and a pressure ranging from about 10 psig to about 100 psig, with the mole ratio of 3,3,3-trifluoropropene to chlorine gas ranging from about 1:0.02 to about 1:1.

8. The process according to claim 7 wherein the mole ratio of 3,3,3-trifluoropropene to chlorine gas ranges from about 1:0.1 to about 1:0.8.

9. The process according to claim 7 wherein the temperature ranges from about 80° C. to about 160° C.

10. The process according to claim 7 wherein the pressure ranges from about 1 atmosphere to about 50 psig.

11. The process according to claim 7 wherein the contact time ranges from about 0.1 seconds to about 2 minutes.

12. The process according to claim 11 wherein the contact time ranges from about 5 seconds to about 1 minute.

13. The process according to claim 1 wherein chlorine is contacted with 3,3,3-trifluoropropene in the presence of a catalyst to form 1,1,1-trifluoro-2,3-dichloropropane in the liquid phase, wherein the temperature ranges from about 20° C. to about 200° C., the pressure is autogenous and the mole ratio of 3,3,3-trifluoropropene to chlorine gas ranges from about 1:0.02 to about 1:1.

14. The process according to claim 13 wherein the temperature ranges from about 30° C. to about 110° C.

15. The process according to claim 13 wherein the mole ratio of 3,3,3-trifluoropropene to chlorine gas ranges from about 1:0.1 to about 1:0.95.

16. The process according to claim 13 wherein the chlorine is contacted with 3,3,3-trifluoropropene in the presence of a metal halide in a solvent, said solvent being carbon tetrachloride, 1,1,2-trichloro-1,2,2-trifluoroethane, a C 5-8 linear perfluoroalkyl compound represented by CF 3 (CF 2 ) n CF 3 , where n is an integer from 3 to 6, inclusive, or a hexachloracetone.

17. The process according to claim 1 wherein chlorine is prepared in situ, wherein HCl is co-fed with O 2 and with 3,3,3-trifluoropropene.

18. The process according to claim 17 wherein the HCl is present in 0.5% to about 20 mol % relative to the mol % of 3,3,3-trifluorpropene present.

19. The process according to claim 13 wherein chlorine is prepared in situ, wherein HCl is co-fed with O 2 and the chlorine thus prepared is reacted with 3,3,3-trifluoropropene.

20. The process according to claim 19 when HCl is present in 0.5% to about 20 mol % relative to the mol % of 3,3,3-trifluoropropene present.

Assignees

• Chemours Co Fc Llc

Inventors

• Sun Xuehui
• Nappa Mario Joseph

Classifications

• B01J27/128

  with iron group metals or platinum group metals · CPC title

• B01J27/132

  with chromium, molybdenum, tungsten or polonium · CPC title

• B01J21/18

  Carbon · CPC title

• C07C17/04 Primary

  to unsaturated halogenated hydrocarbons · CPC title

• C07C19/10

  and chlorine · CPC title