Production of 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with cyano compounds

• US 20050059829A1
• Filed: 10/15/2004
• Published: 03/17/2005
• Est. Priority Date: 03/24/2003
• Status: Active Grant

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Manzer, Leo Ernest
• Granted Patent: US 7,025,819 B2
• Time in Patent Office: Days
• US Class Current: 548/517
• CPC Class Codes: C07D 207/267 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 207/38 2-Pyrrolones

Abstract

This invention relates to a process for producing 5-methyl-N-(methyl aryl)-2-pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl cyano compounds utilizing a metal catalyst, which is optionally supported.

Claims

1. Cancel

2. Cancel

3. Cancel

4. Cancel

5. Cancel

6. Cancel

7. Cancel

8. Cancel

9. Cancel

10. Cancel

11. Cancel

12. Cancel

13. Cancel

14. Cancel

15. Cancel

16. Cancel

17. Cancel

18. Cancel

19. Cancel

20. A process for preparing an ink jet composition, the process comprising the steps of:

i) preparing 5-methyl-N-alkyl-2-pyrrolidone (VI) using a process comprising the step of contacting a levulinic acid ester (I) with an alkyl cyano compound (V) in the presence of hydrogen gas and a metal catalyst, the metal catalyst being optionally supported, and, optionally, in the presence of a solvent;

wherein R₂ is hydrocarbyl or substituted hydrocarbyl, C₁-C₁₈ unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkyl containing at least one heteroatom, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, and wherein R₄ is an alkyl group having from 1 to 30 carbons, and wherein R₄ may be C₁-C₃₀ unsubstituted or substituted alkyl, C₁-C₃₀ unsubstituted or substituted alkenyl, C₁-C₃₀ unsubstituted or substituted alkynyl, C₃-C₃₀ unsubstituted or substituted cycloalkyl, or C₃-C₃₀ unsubstituted or substituted cycloalkyl containing at least one heteroatom; and

ii) contacting 5-methyl-N-alkyl-2-pyrrolidone (VI) with at least one colorant.

21. Cancel