High purity E-1-chloro-3,3,3-trifluoropropene and methods of making the same
View Patent ↗The present invention discloses high purity E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and methods to produce the same. More specifically, the present invention discloses the methods of making 1233zd(E) essentially free of toxic impurities (e.g. 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoro-propene (1224), and 3,3,3-trifluoropropyne). The present invention further provides methods for making high purity 1233zd(E) with concentration of 1233xf and 1224 at or below 200 parts per million (ppm) and 3,3,3-trifluoropropyne impurities at or below 20 ppm. Formation of 1233xf impurity can be avoided if pure 1,1,1,3,3-pentachloropropane is used as a starting material. It was also found that formation of 1233xf is avoided if a liquid phase manufacturing process is used.
1. An impure product consisting essentially of a mixture of E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and 2-chloro-3,3,3-trifluoropropene (1233xf);
wherein the impure product contains greater than zero and less than about 400 parts per million of 2-chloro-3,3,3-trifluoropropene (1233xf) and has a 1233zd(E) purity of greater than about 99.6 percent by weight.
2. The impure product of claim 1 , which contains greater than zero and less than about 300 parts per million of 2-chloro-3,3,3-trifluoropropene (1233xf).
3. The impure product of claim 1 , which contains greater than zero and less than about 200 parts per million of 2-chloro-3,3,3-trifluoropropene (1233xf).
4. An impure product consisting essentially of a mixture of E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and 3,3,3-trifluoropropyne;
wherein the impure product contains greater than zero and less than about 50 parts per million of 3,3,3-trifluoropropyne; and
wherein the impure product has a 1233zd(E) purity of greater than about 99.6 percent by weight.
5. The impure product of claim 4 , which contains greater than zero and less than about 20 parts per million of 3,3,3-trifluoropropyne.
6. An impure product consisting essentially of a mixture of E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and chlorotetrafluoropropene (1224);
wherein the impure product contains greater than zero and less than about 400 parts per million of chlorotetrafluoropropene (1224) and
wherein the impure product has a 1233zd(E) purity of greater than about 99.6 percent by weight.
7. The impure product of claim 6 , which contains greater than zero and less than about 300 parts per million of chlorotetrafluoropropene (1224).
8. The impure product of claim 6 , which contains greater than zero and less than about 200 parts per million of chlorotetrafluoropropene (1224).
9. An impure product consisting essentially of a mixture of E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and 2-chloro-2,1,1,1-tetrafluoropropane (244bb);
wherein the impure product contains greater than zero and less than about 400 parts per million of 2-chloro-2,1,1,1-tetrafluoropropane (244bb), and
wherein the impure product has a 1233zd(E) purity of greater than about 99.6 percent by weight.
10. The impure product of claim 9 , which contains greater than zero and less than about 300 parts per million of 2-chloro-2,1,1,1-tetrafluoropropane (244bb).
11. The impure product of claim 10 , which contains greater than zero and less than about 200 parts per million of 2-chloro-2,1,1,1-tetrafluoropropane (244bb).
12. An impure product consisting essentially of a mixture of E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and 3-chloro-3,1,1,1-tetrafluoropropane (244fa);
wherein the impure product contains greater than zero and less than about 400 parts per million of 3-chloro-3,1,1,1-tetrafluoropropane (244fa); and
wherein the impure product has a 1233zd(E) purity of greater than about 99.6 percent by weight.
13. The impure product of claim 12 , which contains greater than zero and less than about 300 parts per million of 3-chloro-3,1,1,1-tetrafluoropropane (244fa).
14. The impure product of claim 12 , which contains greater than zero and less than about 200 parts per million of 3-chloro-3,1,1,1-tetrafluoropropane (244fa).
15. The impure product composition of claim 12 , further containing 2-chloro-3,3,3-trifluoropropene (1233xf), at an amount greater than zero and less than 400 parts per million.
16. The impure product of claim 15 , which contains greater than zero and less than about 300 parts per million of 2-chloro-3,3,3-trifluoropropene (1233xf).
17. The impure product of claim 15 , which contains greater than zero and less than about 200 parts per million of 2-chloro-3,3,3-trifluoropropene (1233xf).
18. An impure composition consisting of a mixture of at least 99.6 percent by weight E-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and 3,3,3-trifluoropropyne;
wherein the amount of 3,3,3-trifluoropropyne in the impure composition is greater than zero and less than 50 parts per million.
19. The impure composition of claim 18 , which contains greater than zero and less than about 20 parts per million of 3,3,3-trifluoropropyne.
20. An impure composition consisting of a mixture of at least 99.6 percent by weight E-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and chlorotetrafluoropropene (1224), wherein the amount of 1224 in the impure composition is greater than zero and less than 400 parts per million.
21. The impure composition of claim 20 , which contains greater than zero and less than about 300 parts per million of chlorotetrafluoropropene (1224).
22. The impure composition of claim 20 , which contains greater than zero and less than about 200 parts per million of chlorotetrafluoro-propene (1224).
23. An impure composition consisting of a mixture of at least 99.6 percent by weight E-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and 2-chloro-2,1,1,1-tetrafluoro-propane (244bb);
wherein the amount of 244bb in the impure composition is greater than zero and less than 400 parts per million.
24. The impure composition of claim 23 , which contains greater than zero and less than about 300 parts per million of 2-chloro-2,1,1,1-tetrafluoropropane (244bb).
25. The impure composition of claim 23 , which contains greater than zero and less than about 200 parts per million of 2-chloro-2,1,1,1-tetrafluoropropane (244bb).
26. A impure composition consisting of a mixture of at least 99.6 percent by weight E-1-chloro-3,3,3-trifluoropropene (1233zd(E)), and 3-chloro-3,1,1,1-tetrafluoropropane (244fa);
wherein the amount of 244fa in the impure composition is greater than zero and less than 400 parts per million.
27. The impure composition of claim 26 , which contains greater than zero and less than about 300 parts per million of 3-chloro-3,1,1,1-tetrafluoropropane (244fa).
28. The impure composition of claim 26 , which contains greater than zero and less than about 200 parts per million of 3-chloro-3,1,1,1-tetrafluoropropane (244fa).