Selective catalytical dehydrochlorination of hydrochlorofluorocarbons

• US 8,884,083 B2
• Filed: 02/10/2012
• Issued: 11/11/2014
• Est. Priority Date: 02/21/2011
• Status: Active Grant

• Current Assignee: The Chemours Company FC, LLC (The Chemours Company)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Sun, Xuehui, Nappa, Mario Joseph
• Primary Examiner(s): Parsa, Jafar
• Assistant Examiner(s): BAHTA, MEDHANIT W
• Application Number:
  US13/370,397
• Publication Number:
  US 20120215038A1
• Time in Patent Office: 1,005 Days
• Field of Search: 570/155, 570/156, 570/226, 570/227
• US Class Current: 570/157
• CPC Class Codes: C07C 17/25 by splitting-off hydrogen halides from halogenated hydrocarbons
• CPC Class Codes: C07C 19/10 and chlorine
• CPC Class Codes: C07C 21/18 containing fluorine

Abstract

A dehydrochlorination process is disclosed. The process involves contacting R_fCHClCH₂Cl with a catalyst in a reaction zone to produce a product mixture comprising R_fCCl═CH₂, wherein said catalyst comprises MY supported on carbon, and wherein R_f is a perfluorinated alkyl group, M=K, Na or Cs, and Y=F, Cl or Br.

Claims

1. A dehydrochlorination process comprising contacting R_fCHClCH₂Cl with a catalyst in a reaction zone to produce a product mixture comprising R_fCCl═

CH₂, wherein said catalyst comprises an alkali metal halide salt of the formula MY supported on carbon, and wherein R_f is a perfluorniated alkyl group, M=K, Na or Cs, and Y=F, Cl or Br and wherein the catalyst contains from about 5wt % to about 40wt % alkali metal halide salt based on the total amount of alkali metal halide salt and carbon.

2. The dehydrochlorination process of claim 1 wherein the carbon is an activated carbon.

3. The dehydrochlorination process of claim 2 wherein the carbon is an acid washed activated carbon.

4. The dehydrochlorination process of claim 1 wherein M is K and Y is F or Cl.

5. The dehydrochlorination process of claim 1 wherein the temperature in the reaction zone is from about 140°

C. to about 400°

C.

6. The dehydrochlorination process of claim 5 wherein the temperature in the reaction zone is from about 150°

C. to about 250°

C.

7. The dehydrochlorination process of claim 6 wherein the temperature in the reaction zone is from about 175°

C. to about 225°

C.

8. The dehydrochlorination process of claim 1 wherein the product selectivity to R_fCCl═

CH₂ is at least 90 mole %.

9. The dehydrochlorination process of claim 1 wherein the product selectivity to R_fCCl═

CH₂ is at least 96 mole %.

10. The dehydrochlorination process of claim 1 wherein the dehydrochlorination selectivity to R_fCCl═

CH₂ is at least 95 mole %.

11. The dehydrochlorination process of claim 1 wherein R_f is CF₃.

12. The dehydrochlorination process according to claim 1 wherein the catalyst contains from about 10 wt % to about 30 wt % alkali metal halide salt based on the total amount of alkali metal halide salt and carbon.

13. A dehydrochlorination process comprising contacting R_fCHClCH₂Cl with a catalyst in a reaction zone to produce a product mixture comprising R_fCCl═

CH₂, wherein said catalyst comprises MY supported on carbon, and wherein R_f is a perfluorniated alkyl group, M=K, Na or Cs, and Y=F, Cl or Br, wherein the product selectivity to R_fCCl═

CH₂ is at least 90 mole %.

14. The dehydrochlorination process of claim 13 wherein the carbon is an activated carbon.

15. The dehydrochlorination process of claim 14 wherein the carbon is an acid washed activated carbon.

16. The dehydrochlorination process of claim 13 wherein M is K and Y is F or Cl.

17. The dehydrochlorination process of claim 13 wherein the temperature in the reaction zone is from about 140°

C. to about 400°

C.

18. The dehydrochlorination process of claim 17 wherein the temperature in the reaction zone is from about 150°

C. to about 250°

C.

19. The dehydrochlorination process of claim 18 wherein the temperature in the reaction zone is from about 175°

C. to about 225°

C.

20. The dehydrochlorination process of claim 13 wherein the product selectivity to R_fCCl═

CH₂ is at least 96 mole %.

21. The dehydrochlorination process of claim 13 wherein the dehydrochlorination selectivity to R_fCCl═

CH₂ is at least 95 mole %.

22. The dehydrochlorination process of claim 13 wherein R_f is CF₃.