Azeotrope-like compositions of pentafluoropropane, chlorotrifluoropropene, and hyrdrogen fluoride

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

a. reacting a starting material comprising at least one hydrochlorocarbon and/or hydrochlorofluorocarbon with a fluorinating agent to produce a reaction product comprising 1-chloro-3,3,3-trifluoropropene, hydrogen fluoride, and 1,1,1,3,3-pentafluoropropane;

b. distilling said reaction product to produce a distillate comprising a ternary azeotrope-like composition comprising an effective amount of 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene, and hydrogen fluoride; and

c. contacting said distillate with one or more substances to separate at least a portion of said 1-chloro-3,3,3-trifluoropropene, hydrogen fluoride, and/or 1,1,1,3,3-pentafluoropropane from said distillate, wherein said 1-chloro-3,3,3-trifluoropropene, hydrogen fluoride, and/or 1,1,1,3,3-pentafluoropropane are separated in an amount sufficient to break said ternary azeotrope-like composition.

2. The method of claim 1 wherein said contacting involves contacting said distillate with sulfuric acid or a caustic solution and subsequently removing at least a portion of said hydrogen fluoride from said distillate to produce a purified distillate comprising said 1-chloro-3,3,3-trifluoropropene and 1,1,1,3,3-pentafluoropropane.

3. The method of claim 2 further comprising contacting said purified distillate with an extraction media having a selective affinity for 1-chloro-3,3,3-trifluoropropene relative to 1,1,1,3,3-pentafluoropropane and subsequently separating said 1-chloro-3,3,3-trifluoropropene from said 1,1,1,3,3-pentafluoropropane.

4. The method of claim 1 wherein said starting material comprises 1,1,1,3,3-pentachloropropane.

5. The method of claim 1 wherein said ternary azeotrope-like composition comprises 1,1,1,3,3-pentafluoropropane in an amount of about 24 to about 45 weight percent based upon the total weight of the azeotrope-like mixture; 1-chloro-3,3,3-trifluoropropene in an amount of about 42 to about 65 weight percent based upon the total weight of the azeotrope-like mixture; and hydrogen fluoride in an amount of about 0.5 to about 22 weight percent based upon the total weight of the azeotrope-like mixture.

6. The method of claim 1 wherein said ternary azeotrope-like composition comprises 1,1,1,3,3-pentafluoropropane in an amount of about 32.3 to about 40.8 weight percent based upon the total weight of the azeotrope-like mixture; 1-chloro-3,3,3-trifluoropropene in an amount of about 52.8 to about 58.3 weight percent based upon the total weight of the azeotrope-like mixture; and hydrogen fluoride in an amount of about 6.4 to about 9.4 weight percent based upon the total weight of the azeotrope-like mixture, provided that said azeotrope-like mixture has a temperature of about 23±2° C. and a pressure of about 23±2 psia.

7. The method of claim 1 wherein said ternary azeotrope-like composition comprises 1,1,1,3,3-pentafluoropropane in an amount of about 33.0 to about 37.1 weight percent based upon the total weight of the azeotrope-like mixture; 1-chloro-3,3,3-trifluoropropene in an amount of about 50.4 to about 56.0 weight percent based upon the total weight of the azeotrope-like mixture; and hydrogen fluoride in an amount of about 6.9 to about 16.6 weight percent based upon the total weight of the azeotrope-like mixture, provided that said azeotrope-like mixture has a temperature of about 70±2° C. and a pressure of about 120±2 psia.

8. The method of claim 1 wherein said ternary azeotrope-like composition comprises 1,1,1,3,3-pentafluoropropane in an amount of about 29.8 to about 30.3 weight percent based upon the total weight of the azeotrope-like mixture; 1-chloro-3,3,3-trifluoropropene is present in an amount of about 50.6 to about 54.6 weight percent based upon the total weight of the azeotrope-like mixture; and hydrogen fluoride in an amount of about 15.6 to about 19.1 weight percent based upon the total weight of the azeotrope-like mixture, provided that said azeotrope-like mixture has a temperature of about 42±2° C. and a pressure of about 46±2 psia.

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

a. reacting a starting material comprising at least one hydrochlorocarbon and/or hydrochlorofluorocarbon with a fluorinating agent to produce a reaction product comprising 1-chloro-3,3,3-trifluoropropene, hydrogen fluoride, and 1,1,1,3,3-pentafluoropropane;

b. distilling said reaction product to produce a distillate comprising a ternary azeotrope-like composition comprising an effective amount of 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene, and hydrogen fluoride;

c. contacting said distillate with sulfuric acid or a caustic solution to remove at least a portion of said hydrogen fluoride and produce a second distillate comprising 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene; and

d. contacting said second distillate with an extraction media having a selective affinity for one of 1-chloro-3,3,3-trifluoropropene or 1,1,1,3,3-pentafluoropropane and separating 1-chloro-3,3,3-trifluoropropene from 1,1,1,3,3-pentafluoropropane.

10. The method of claim 9 , wherein the distillate is contacted with sulfuric acid.

11. The method of claim 9 , wherein the extraction media has selective affinity to 1-chloro-3,3,3-trifluoropropene.

12. The method of claim 11 , wherein the extraction media comprises mineral oil.

13. The method of claim 11 , wherein the extraction media comprises silicone oil.