Methods of making chlorinated hydrocarbons
Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.
1. A process for producing 1,1,2,3- tetrachloropropene, the process comprising:
i. preparing 1,1,1,2,3-pentachloropropane by combining 1,1,1,3-tetrachloropropane and chlorine within a reaction vessel in the presence of carbon tetrachloride and a catalyst that catalyzes the dehydrochlorination of 1,1,1,3-tetrachloropropane to one or more trichloropropenes and promotes the addition of chlorine to the one or more trichloropropenes;
ii. removing the 1,1,1,2,3-pentachloropropane from the reaction vessel;
iii. optionally combining the 1,1,1,2,3-pentachloropropane with ferric chloride to form a mixture of 1,1,1,2,3-pentachloropropane and ferric chloride; and
iv. heating the mixture of 1,1,1,2,3-pentachloropropane and ferric chloride to produce 1,1,2,3-tetrachloropropene.
2. The process of claim 1 , wherein said step of heating takes place within a reaction zone of a reactive distillation system.
3. The process of claim 2 , wherein the reactive distillation system includes a separation zone above the reaction zone.
4. The process of claim 3 , wherein the separation zone is maintained at about 100 to about 600 torr.
5. The process of claim 4 , wherein said mixture is agitated during said step of heating.
6. The process of claim 1 , wherein said mixture does not include more than 1000 ppm of water, trialkylphosphate, and alcohol.
7. The process of claim 1 , wherein said 1,1,1,2,3-pentachloropropane is removed from the reaction vessel within a crude product stream, and where the crude product stream is combined with ferric chloride.
8. The process of claim 1 , wherein said 1,1,1,2,3-pentachloropropane is removed from the reaction vessel within a crude product stream, and where the 1,1,1,2,3-pentachloropropane is isolated from the crude product stream prior to said step of combining the 1,1,1,2,3-pentachloropropane with ferric chloride.
9. The process of claim 1 , wherein said step of heating takes place at about 120° C. to about 180° C.
10. The process of claim 1 , wherein the process includes the step of combining the 1,1,1,2,3-pentachloropropane with ferric chloride.
11. A process for producing 1,1,2,3- tetrachloropropene, the process comprising:
i. preparing 1,1,1,2,3-pentachloropropane by combining 1,1,1,3-tetrachloropropane and chlorine within a reaction vessel in the presence of carbon tetrachloride and a catalyst that catalyzes the dehydrochlorination of 1,1,1,3-tetrachloropropane to one or more trichloropropenes and promotes the addition of chlorine to the one or more trichloropropenes;
ii. removing the 1,1,1,2,3-pentachloropropane from the reaction vessel;
iii. combining the 1,1,1,2,3-pentachloropropane with a catalyst that catalyzes the dehydrochlorination of the 1,1,1,2,3-pentachloropropane to form a mixture of the 1,1,1,2,3-pentachloropropane and the catalyst, where said mixture includes less than 1000 ppm of water, trialkylphosphate, alcohol, or other materials that may deactivate the catalyst; and
iv. heating the mixture of 1,1,1,2,3-pentachloropropane and the catalyst to produce 1,1,2,3-tetrachloropropene.
12. The process of claim 11 , wherein said step of heating takes place within a reaction zone of a reactive distillation system.
13. The process of claim 12 , wherein the reactive distillation system includes a separation zone above the reaction zone.
14. The process of claim 13 , wherein the separation zone is maintained at about 100 to about 600 torr.
15. The process of claim 14 , wherein said mixture is agitated during said step of heating.
16. The process of claim 15 , wherein said agitation is provided by a pumped circulation loop.
17. The process of claim 11 , wherein said 1,1,1,2,3-pentachloropropane is removed from the reaction vessel within a crude product stream, and where the catalyst is ferric chloride.
18. The process of claim 11 , wherein said 1,1,1,2,3-pentachloropropane is removed from the reaction vessel within a crude product stream, and where the 1,1,1,2,3-pentachloropropane is isolated from the crude product stream prior to said step of combining the 1,1,1,2,3-pentachloropropane with the catalyst.
19. The process of claim 11 , wherein said step of heating takes place at about 120° C. to about 180° C.