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 1,1,1,2,3-pentachloropropane, the process comprising:
i. charging 1,1,1,3-tetrachloropropane to a reaction vessel, where said step of charging 1,1,1,3-tetrachloropropane may include simultaneously charging carbon tetrachloride to the reaction vessel;
ii. charging chlorine to the reaction vessel; and
iii. catalyzing within the reaction vessel at least two reactions, where a first reaction includes the dehydrochlorination of 1,1,1,3-tetrachloropropane to an intermediate trichloropropene, and where a second reaction includes an addition reaction between the intermediate trichloropropene and chlorine to produce the 1,1,1,2,3-pentachloropropane, where said process is devoid of any intermediate isolation or purification of the intermediate trichloropropene within the reaction vessel, and where said step of catalyzing dehydrochlorinates the 1,1,1,3-tetrachloropropane to intermediate trichloropropene and adds chlorine to the intermediate trichloropropene at a rate sufficient to provide a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 1.5:1.
2. The process of claim 1 , where said step of catalyzing dehydrochlorinates the 1,1,1,3-tetrachloropropane to intermediate trichloropropene and adds chlorine to the intermediate trichloropropene at a rate sufficient to provide a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 2:1.
3. The process of claim 1 , where said step of catalyzing dehydrochlorinates the 1,1,1,3-tetrachloropropane to intermediate trichloropropene and adds chlorine to the intermediate trichloropropene at a rate sufficient to provide a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 5:1.
4. The process of claim 1 , where said step of catalyzing dehydrochlorinates the 1,1,1,3-tetrachloropropane to intermediate trichloropropene and adds chlorine to the intermediate trichloropropene at a rate sufficient to provide a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 1,000:1.
5. The process of claim 1 , where said step of catalyzing dehydrochlorinates the 1,1,1,3-tetrachloropropane to intermediate trichloropropene and adds chlorine to the intermediate trichloropropene at a rate sufficient to provide a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 5,000:1.
6. The process of claim 1 , where the intermediate trichloropropene is 1,1,3-trichloropropene.
7. The process of claim 1 , where the process is a semi-batch process.
8. The process of claim 1 , where the process is a continuous process.
9. The process of claim 1 , where said step of catalyzing includes charging a Lewis acid catalyst to the reactor.
10. The process of claim 1 , where said step of charging 1,1,1,3-tetrachloropropane to the reaction vessel includes the simultaneous charging of carbon tetrachloride in amounts up to 50 weight percent of the charge.
11. A process for producing 1,1,1,2,3-pentachloropropane, the process comprising:
i. dehydrochlorinating 1,1,1,3-tetrachloropropane to form an intermediate trichloropropene, and reacting the intermediate trichloropropene with chlorine to produce 1,1,1,2,3-pentachloropropane, where said step of dehydrochlorinating the 1,1,1,3-tetrachloropropane and said step of reacting the intermediate trichloropropene with chlorine takes place within a single vessel and are catalyzed by a single catalyst, and where the process is devoid of any step of isolating or purifying the intermediate trichloropropene within the reaction vessel.
12. The process of claim 11 , where said step of dehydrochlorinating the 1,1,1,3-tetrachloropropane and said step of reacting the intermediate trichloropropene with chlorine takes place in the presence of carbon tetrachloride.
13. The process of claim 11 , where the reaction vessel includes a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 1.5:1.
14. The process of claim 11 , where the reaction vessel includes a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 5:1.
15. The process of claim 11 , where the reaction vessel includes a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 1,000:1.
16. The process of claim 11 , where the reaction vessel includes a weight ratio of 1,1,1,2,3-pentachloropropane to intermediate trichloropropene of at least 5,000:1.
17. The process of claim 11 , where said catalyst is a Lewis acid catalyst.
18. The process of claim 11 , where said step of dehydrochlorinating the 1,1,1,3-tetrachloropropane and said step of reacting the 1,1,3-trichloropropene with chlorine takes place in the presence of less than 1,000 ppm by weight of water, trialkylphosphate, alcohol, or other materials that may bind with or deactivate the catalyst.
19. The process of claim 11 , where the intermediate trichloropropene is 1,1,3-trichloropropene.