Integrated process for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from a mixture of high-boiling fluorinated components

1. A method for producing E-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), comprising:

providing a mixture of high-boiling fluorinated components having a boiling point of greater than 39° C., the mixture further comprising heavy impurities with a boiling point of greater than 140° C.;

contacting the mixture with hydrogen fluoride (HF) to produce a combined stream;

vaporizing the combined stream to produce vaporized reactant stream;

separating the heavy impurities from the vaporized reactant stream; and

reacting the vaporized reactant stream in the presence of a catalyst to produce a product stream comprising E-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)).

2. The method of claim 1 , wherein the mixture of high-boiling fluorinated components comprises 1,1,3,3-tetrachloro-1-fluoropropane (HCFC-241fa), 1,3,3-trichloro-1,1-difluoropropane (HCFC-242fa), 1,1,3-trichloro-1,3-difluoropropane (HCFC-242fb), 3,3-dichloro-1,1,1-trifluoropropane (HCFC-243fa), 1,3-dichloro-1,1,3-trifluoropropane (HCFC-243fb), 3-chloro-1,1,1,3-tetrafluoropropane (HCFC-244fa), and combinations thereof.

3. The method of claim 1 , wherein the vaporizing step is conducted at a temperature of 220° C. or higher.

4. The method of claim 1 , wherein the reacting step is conducted at a temperature between 200° C. and 300° C.

5. The method of claim 1 , wherein the catalyst is selected from the group consisting of chromium oxides, chromium oxyfluorides, and chromium halides.

6. The method of claim 1 , wherein the catalyst is a chromium oxyfluoride catalyst.

7. The method of claim 1 , wherein the catalyst is a zinc/chromium catalyst including 0.5 to 6.0 wt. % Zn, based on the total weight of the catalyst.

8. The method of claim 1 , wherein the reacting step produces additional heavy impurities with a boiling point of greater than 140° C., the method further comprising:

condensing, and purging from the product stream, at least a portion of the additional heavy impurities; and

optionally purifying the product stream.

9. The method of claim 8 , wherein the condensing step is conducted at a temperature of 10° C. or higher.

10. The method of claim 1 , wherein:

the vaporization step is conducted at a temperature of 220° C. or higher; and

the catalyst is chromium oxide.

11. The method of claim 1 , wherein the mixture of high boiling fluorinated components comprises by-products derived from reacting HCC-240fa to form HFO-1233zd.

12. The method of claim 1 , wherein the heavy impurities comprise at least one of hexachloroethane (CC-110), tetrachloropropene (HCO-1230) isomers, dimers of 1,3,3-trichloro-3-fluoropropene, dimers of 1,2,-dichloro-3,3-difluoropropene, and combinations thereof.

13. The method of claim 1 , wherein the hydrogen fluoride includes 1000 ppm or less of water.

14. The method of claim 1 , wherein the hydrogen fluoride includes 500 ppm or less of water.

15. The method of claim 1 , wherein the vaporized reactant stream comprises a molar ratio of hydrogen fluoride (HF) to HFC-241 and HFC-242 isomers of from 0.9:1 to 5.0:1.

16. The method of claim 6 , wherein the catalyst comprises chromium (VI) in an amount of 1000 ppm or less, based on total chromium oxides in the catalyst.

17. The method of claim 6 , wherein the catalyst comprises chromium (VI) in an amount of 500 ppm or less, based on total chromium oxides in the catalyst.