Method for producing trans-1-chloro-3,3,3-trifluoropropene

1. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising:

reacting a starting material containing a plurality of halogenated hydrocarbon compounds, each having 3 carbon atoms of Formula (1):

C 3 H X Cl Y F Z   (1)

in a gas phase with hydrogen fluoride in the presence of chlorine as a catalyst,

wherein X is 2 or 3; and when X=2, Y is an integer from 1 to 4, Z is an integer from 0 to 3, and Y+Z=4; and when X=3, Y is an integer from 1 to 5, Z is an integer from 0 to 4, and Y+Z=5; provided that Formula (1) shown above represents a halogenated hydrocarbon compound having 3 carbon atoms excluding trans-1-chloro-3,3,3-trifluoropropene.

2. The production method according to claim 1 wherein a hydrocarbon compound having 3 carbon atoms of Formula (2):

C 3 H V F W   (2)

is further added and reacted in a gas phase with hydrogen fluoride in the presence of chlorine,

wherein when V+W=8, then V is an integer from 0 to 8; when V+W=6, then V is an integer from 0 to 6; and when V+W=4, then V is an integer from 0 to 4.

3. The production method according to claim 1 wherein each of the plurality of halogenated hydrocarbon compounds having 3 carbon atoms is selected from the group consisting of 1,1,3,3-tetrachloro-1-fluoropropane (241fa), 1,1,1,3-tetrachloro-3-fluoropropane (241fb), 1,3,3-trichloro-3-fluoropropene (1231zd), 1,3,3-trichloro-1-fluoropropene (1231zb), 3,3,3-trichloro-1-fluoropropene (1231ze), 1,1,3-trichloro-3-fluoropropene (1231za), 1,3,3-trichloro-1,1-difluoropropane (242fa), 1,1,3-trichloro-1,3-difluoropropane (242fb), 1,3-dichloro-3,3-difluoropropene (1232zd), 3,3-dichloro-1,3-difluoropropene (1232ze), 3,3-dichloro-1,1-difluoropropene (1232zc), 1,3-dichloro-1,3-difluoropropene (1232zb), cis-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), 3,3-dichloro-1,1,1-trifluoropropane (243fa) and 3-chloro-1,1,1,3-tetrafluoropropane (244fa).

4. The production method according to claim 1 wherein the reaction temperature is from 150° C. to 600° C.

5. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising reacting a starting material containing a plurality of halogenated hydrocarbon compounds, each selected from the group consisting of 1,1,3,3-tetrachloro-1-fluoropropane (241fa), 1,1,1,3,3-pentachloropropane (240fa), 1,3,3-trichloro-1,1-difluoropropane (242fa) in a gas phase with hydrogen fluoride as a catalyst at a temperature from 150° C. to 600° C. in the presence of chlorine as a catalyst.

6. The production method according to claim 5 wherein a hydrocarbon compound having 3 carbon atoms of Formula (3):

C 3 H V F W   (3)

is further added and reacted in a gas phase with hydrogen fluoride in the presence of chlorine,

wherein when V+W=8, then V is an integer from 0 to 8; when V+W=6, then V is an integer from 0 to 6; and when V+W=4, then V is an integer from 0 to 4.

7. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising:

Step (A) for reacting 1,1,1,3,3-pentachloropropane (240fa) with hydrogen fluoride, and

Step (B) for reacting a plurality of intermediate products, each obtained in the Step (A) in a gas phase with hydrogen fluoride at a temperature from 150° C. to 600° C. in the presence of chlorine as a catalyst to obtain trans-1-chloro-3,3,3-trifluoropropene.

8. The production method according to claim 7 wherein a hydrocarbon compound having 3 carbon atoms of Formula (4):

C 3 H V F W   (4)

is further added and reacted in a gas phase with hydrogen fluoride in the presence of chlorine,

wherein when V+W=8, then V is an integer from 0 to 8; when V+W=6, then V is an integer from 0 to 6; and when V+W=4, then V is an integer from 0 to 4.

9. The production method according to claim 7 wherein

the Step (A) is conducted under a catalyst-free condition in a liquid phase to recover a reaction product gas containing trans-1-chloro-3,3,3-trifluoropropene, and

the reaction fluid of the Step (A) is recovered and the intermediate products contained in said reaction fluid are employed in the Step (B).

10. The production method according to claim 9 wherein

the 1,1,1,3,3-pentachloropropane and the hydrogen fluoride are introduced continuously or intermittently to the Step (A), and

the reaction product gas and the reaction fluid are recovered continuously or intermittently.

11. The production method according to claim 7 wherein each of the plurality of intermediate products is selected from the group consisting of 1,1,3,3-tetrachloro-1-fluoropropane (241fa), 1,1,1,3-tetrachloro-3-fluoropropane (241fb), 1,3,3-trichloro-3-fluoropropene (1231zd), 1,3,3-trichloro-1-fluoropropene (1231zb), 3,3,3-trichloro-1-fluoropropene (1231ze), 1,1,3-trichloro-3-fluoropropene (1231za), 1,3,3-trichloro-1,1-difluoropropane (242fa), 1,1,3-trichloro-1,3-difluoropropane (242fb), 1,3-dichloro-3,3-difluoropropene (1232zd), 3,3-dichloro-1,3-difluoropropene (1232ze), 3,3-dichloro-1,1-difluoropropene (1232zc), 1,3-dichloro-1,3-difluoropropene (1232zb), cis-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), 3,3-dichloro-1,1,1-trifluoropropane (243fa), 1,3-dichloro-1,1,3-trifluoropropane (243fb), 1,1-dichloro-1,3,3-trifluoropropane (243fc), 1-chloro-1,1,3,3-tetrafluoropropane (244fb) and 3-chloro-1,1,1,3-tetrafluoropropane (244fa).

12. The production method according to claim 7 wherein at least one of the plurality of intermediate products comprises 1,3,3-trichloro-1,1-difluoropropane (242fa).

13. The production method according to claim 7 wherein the reaction temperature of the Step (B) is from 150° C. to 500° C.

14. The production method according to claim 7 wherein unreacted intermediate products are recovered and employed in the Step (B).

15. The production method according to claim 7 wherein cis-1-chloro-3,3,3-trifluoropropene is obtained in the Step (B) together with trans-1-chloro-3,3,3-trifluoropropene.

16. The production method according to claim 15 wherein cis-1-chloro-3,3,3-trifluoropropene obtained is subjected as intermediate products to the Step (B).

17. The production method according to claim 15 wherein cis-1-chloro-3,3,3-trifluoropropene obtained is heated at a temperature from 150° C. to 600° C. to obtain trans-1-chloro-3,3,3-trifluoropropene.

18. The production method according to claim 2 wherein the hydrocarbon compound having 3 carbon atoms is at least one selected from the group consisting of 1,1,1,3,3-pentafluoropropane (245fa), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), cis-1,3,3,3-tetrafluoropropene (1234ze(Z)), 1,1,3,3-tetrafluoropropene (1234zc), and 3 ,3,3-trifluoropropine.

19. The production method according to claim 6 wherein the hydrocarbon compound having 3 carbon atoms is at least one selected from the group consisting of 1,1,1,3,3-pentafluoropropane (245fa), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), cis-1,3,3,3-tetrafluoropropene (1234ze(Z)), 1,1,3,3-tetrafluoropropene (1234zc), and 3,3,3-trifluoropropine.

20. The production method according to claim 8 wherein the hydrocarbon compound having 3 carbon atoms is at least one selected from the group consisting of 1,1,1,3,3-pentafluoropropane (245fa), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), cis-1,3,3,3-tetrafluoropropene (1234ze(Z)), 1,1,3,3-tetrafluoropropene (1234zc), and 3,3,3-trifluoropropine.