Process for the preparation of 3,5-difluoroaniline

• US 5,965,775 A
• Filed: 05/13/1998
• Issued: 10/12/1999
• Est. Priority Date: 05/15/1997
• Status: Expired due to Fees

• Current Assignee: Clariant GmbH (Clariant AG)
• Original Assignee: Clariant GmbH (Clariant AG)
• Inventors: Krause, Stefan, Pfirmann, Ralf
• Primary Examiner(s): Burn, Brian M.
• Application Number:
  US09/078,012
• Time in Patent Office: 517 Days
• Field of Search: 564/407, 564/405
• US Class Current: 564/407
• CPC Class Codes: C07C 209/18 with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 211/45 Monoamines

Abstract

The present invention relates to a process for the preparation of 3,5-difluoroaniline by reacting 3,5-difluorochlorobenzene with ammonia in the presence of a solvent in the presence of a copper compound and at least one metal selected from the group consisting of copper, iron, cobalt, nickel, chromium, molybdenum and zinc, at 100 to 250° C.

Claims

1. A process for the preparation of 3,5-difluoroaniline, which comprises:

reacting 3,5-difluorochlorobenzene with ammonia in the presence of a solvent and a catalyst at 100 to 250°

C.;

said catalyst comprising a copper compound and at least one metal, said metal being selected from the group consisting of copper, iron, cobalt, nickel, chromium, molybdenum and zinc.

2. The process as claimed in claim 1, wherein ammonia and 3,5-difluorochlorobenzene are employed in the molar ratio (1 to 100):

1.

3. The process as claimed in claim 1, wherein ammonia and 3,5-difluorochlorobenzene are employed in the molar ratio (5 to 30):

1.

4. The process as claimed in claim 1, wherein ammonia and 3,5-difluorochlorobenzene are employed in the molar ratio (10 to 20):

1.

5. The process as claimed in claim 1, wherein the solvent employed is water or a mixture containing water and a water-soluble solvent.

6. The process as claimed in claim 1, wherein the solvent employed is water.

7. The process as claimed in claim 1, wherein ammonia is employed in the form of a 10 to 35% by weight ammonia-containing aqueous solution.

8. The process as claimed in claim 1, wherein ammonia is employed in the form of a 15 to 30% by weight ammonia-containing aqueous solution.

9. The process as claimed in claim 1, wherein the copper compound employed is a copper(I) compound, a copper(II) compound or a mixture thereof.

10. The process as claimed in claim 1, wherein the copper compound employed is a copper(I) salt or copper(I) oxide.

11. The process as claimed in claim 1, wherein the copper compound employed is copper(I) chloride, copper(I) bromide or copper(I) iodide.

12. The process as claimed in claim 1, wherein the reaction is carried out in the presence of at least one metal selected from the group consisting of copper, iron, cobalt and nickel.

13. The process as claimed in claim 1, wherein the reaction is carried out in the presence of at least one metal selected from the group consisting of copper, iron and cobalt.

14. The process as claimed in claim 1, wherein the metal employed is copper or iron.

15. The process as claimed in claim 1, wherein the metal employed is copper.

16. The process as claimed in claim 1, wherein the copper compound and 3,5-difluorochlorobenzene are employed in the molar ratio (0.05 to 1.5):

1.

17. The process as claimed in claim 1, wherein the copper compound and 3,5-difluorochlorobenzene are employed in the molar ratio (0.1 to 0.6):

1, in particular (0.15 to 0.4);

1.

18. The process as claimed in claim 1, wherein (0.05 to 1.5) g atom of metal are employed per mole of 3,5-difluorochlorobenzene.

19. The process as claimed in claim 1, wherein (0.1 to 0.6), in particular (0.15 to 0.4) g atom of metal are employed per mole of 3,5-difluorochlorobenzene.

20. The process as claimed in claim 1, wherein the reaction is carried out at 130 to 200°

C.

21. The process as claimed claim 1, wherein the reaction is carried out at 140 to 190°

C.

22. The process as claimed in claim 1, wherein a 3,5-difluorochlorobenzene prepared from 1,3,5-trichlorobenzene by fluorine-chlorine exchange is employed.