Chlorination process

• US 5,484,929 A
• Filed: 09/21/1993
• Issued: 01/16/1996
• Est. Priority Date: 09/21/1993
• Status: Expired due to Term

• Current Assignee: Vertellus Specialties Inc.
• Original Assignee: Reilly Industries, Inc. (VSI Holdings LLC)
• Inventors: Toomey, Joseph E.
• Primary Examiner(s): Rotman, Alan L.
• Application Number:
  US08/124,807
• Time in Patent Office: 847 Days
• Field of Search: 546/286, 546/345, 546/346
• US Class Current: 546/286
• CPC Class Codes: C07D 213/84 Nitriles

Abstract

A process for the selective chlorination of pyridine, a lower alkyl pyridine or 3-cyanopyridine includes passing the pyridine compound, chlorine and an inert gas through a two stage reaction. In a first reaction zone, these materials are subjected to a hot spot controlled at a temperature of about 350° to about 500° C. The materials are then subsequently passed through a second reaction zone at a relatively lower temperature, for example below about 340° C.

Claims

1. A process for selectively chlorinating 3-cyanopyridine, comprising:

passing a vaporized reed stream including 3-cyanopyridine, chlorine and an inert gas into a first reaction zone having a hot spot controlled at a temperature of at about 350°

C. to about 500°

C., and subsequently through a second reaction zone at a temperature below about 340°

C.

2. The process or claim 1 wherein the first reaction zone has a hot spot controlled at a temperature of about 360°

C. to about 470°

C.

3. The process of claim 1 wherein the first reaction zone has a hot spot controlled at a temperature of about 360°

C. to about 420°

C.

4. Thee process of claim 1 wherein the second reaction zone is at a temperature above about 100°

C.

8. The process of claim 1 wherein the inert gas is water vapor.

9. The process of claim 8 wherein the inert gas is water vapor.

10. The process of claim 9 wherein the feed stream includes 3-cyanopyridine so as to produce 2-chloro-5-cyanopyridine.

5. The process of claim I wherein the second reaction zone is at a temperature above about 200°

C.

6. The process of claim 5 wherein the second reaction zone is at a temperature above about 100°

C.

7. The process of claim 5 wherein the second reaction zone is at a temperature above about 200°

C.

11. A process for producing 2-chloro-5-cyanopyridine by chlorination of 3-cyanopyridine with chlorine, comprising:

passing a vaporized feed stream including 3-cyanopyridine, chlorine and an inert gas into a first reaction zone having a hot spot at a temperature of about 350°

C. to about 420°

C., and subsequently passing the stream through a second reaction zone having a temperature of about 200°

C. to about 340°

C., so as to produce 2-chloro-5-cyanopyridine.

12. The process of claim 11 wherein the residence time of said feed stream in said first reaction zone is about 2 seconds or less.

13. The process of claim 11 wherein said residence time is about 1 second or less.

14. The process of claim 11 wherein said inert gas is water vapor.

15. The process of claim 11 wherein the molar ratio of chlorine to 3-cyanopyridine in said feed stream is about 0.2:

1 to 2.0;

1.

16. The process of claim 15 wherein said molar ratio is about 0.5:

1 tp 1.5;

1.

17. A process for selectively chlorinating pyridine, a lower alkyl pyridine or 3-cyanopyridine, comprising:

passing a vaporized feed stream including pyridine, or lower alkyl pyridine or 3-cyanopyridine, chlorine and an inert gas into a first reaction zone having a hot spot controlled at a temperature of at about 350°

C. to about 500°

C., and subsequently through a second reaction zone at a temperature below about 340°

C.

18. The process of claim 17 wherein the vaporized feed stream includes 3 -cyanopyridine.

19. The process of claim 17 wherein the first reaction zone has a hot spot controlled at a temperature of about 360°

C. to about 470°

C.

20. The process of claim 17 wherein the first reaction zone has a hot spot controlled at a temperature of about 360°

C. to about 420°

C.

21. The process of claim 17 wherein the second reaction zone is at a temperature above about 100°

C.

22. The process of claim 17 wherein the second reaction zone is at a temperature above about 200°

C.

23. The process of claim 22 wherein the second reaction zone is at a temperature above about 100°

C.

24. The process of claim 22 wherein the second reaction zone is at a temperature above about 200°

C.

25. The process of claim 18 wherein the inert gas is water vapor.

26. The process of claim 25 wherein the inert gas is water vapor.

27. The process of claim 26 wherein the feed stream includes 3-cyanopyridine so as to produce 2-chloro-5-cyanopyridine.