Process for making cis-1-chloro-3,3,3-trifluoropropene
View Patent ↗Disclosed is a process for making cis-1-chloro-3,3,3-trifluoropropene comprising reacting 3,3,3-trifluoropropyne with HCl in a reaction vessel at a yield of at least about 80%.
1. A process for making cis-1-chloro-3,3,3-trifluoropropene comprising reacting 3,3,3-trifluoropropyne with HCl and a Lewis acid comprising CuCl in a reaction vessel at a yield of at least about 80%.
2. The process of claim 1 , wherein a solvent is used in the reaction vessel.
3. The process of claim 2 , wherein the solvent comprises an ionic solvent.
4. The process of claim 3 , wherein the ionic solvent comprises one or more solvents with ammonium ions.
5. The process of claim 4 , wherein the ionic solvent is selected from the group consisting of salts of 1-alkyl-3-methylimidazolium, 1-alkylpyridinium, and N-methyl-N-alkylpyrrolidinium, and mixtures thereof.
6. The process of claim 4 , wherein the ionic solvent comprises 1-butyl-3-methylimidazolium chloride.
7. The process of claim 1 , wherein a catalyst is used in the reaction vessel.
8. The process of claim 7 , wherein the catalyst is on a support.
9. The process of claim 8 , wherein the catalyst support comprises activated carbon.
10. The process of claim 7 , wherein the catalyst further comprises one or more mineral acids.
11. The process of claim 10 , wherein the mineral acid comprises H 2 SO 4 .
12. The process of claim 7 , wherein the catalyst further comprises a mixture of Lewis acids.
13. The process of claim 12 , wherein the Lewis acids comprises metal salts or mixtures thereof.
14. The process of claim 13 , wherein the metal salts are selected from the group consisting of copper and antimony and mixtures thereof.
15. The process of claim 12 , wherein the Lewis acid is selected from the group consisting of CuCl 2 , SbCl 5 , ZnCl 2 , MgCl 2 , AlCl 3 , FeCl 3 , and the like (MCl x )).
16. The process of claim 1 , wherein the CuCl is supported on activated carbon.
17. The process of claim 1 , wherein the reaction temperature ranges from 100° C. to 350° C.
18. The process of claim 1 , wherein the reaction temperature is above 350° C.
19. The process of claim 1 , wherein the molar ratio of HCl to 3,3,3-trifluoro-propyne ranges from about 1:1 to about 3:1.
20. The process of claim 19 , wherein the molar ratio of HCl to 3,3,3-trifluoro-propyne ranges from about 1.1 to 2.5.
21. The process of claim 1 , wherein a carrier gas is employed in the reaction vessel.
22. The process of claim 21 , wherein the carrier gas is an inert gas.
23. The process of claim 22 , wherein the inert gas is selected from the group consisting of nitrogen, argon, and mixtures thereof.
24. The process of claim 21 , wherein the carrier gas is used at a flow rate of from about 20 mL/min. to 100 mL/min.
25. The process of claim 22 , wherein the reactants are introduced into the reaction vessel at a flow rate of from about 10 mL/min. to 50 mL/min.
26. The process of claim 1 , wherein the cis-1-chloro-3,3,3-trifluoropropene is collected from the reaction vessel in a cooling trap maintained at temperature of from −20° C. to −78° C.