Amide-based compounds, production, recovery, purification and uses thereof

1. A method of producing at least one amide, comprising:

providing an organic liquid comprising at least one ketoxime;

providing at least one acid catalyst;

adding the at least one catalyst to the organic liquid to form a rearrangement mass, wherein the rearrangement mass comprises at least one amide, at least one impurity, and the at least one catalyst; and

heating the rearrangement mass to a temperature of at least about 115° C. for a period of time in order to sulfonate some of the at least one impurity in the rearrangement mass.

2. The method of claim 1 , further comprising purifying the at least one amide.

3. The method of claim 2 , wherein purifying the at least one amide comprises:

adding water, a base and a solvent to the rearrangement mass to form a dual phase liquid;

separating the dual phase liquid into an aqueous phase and an organic phase;

distilling the organic phase to produce a solvent distillate and an amide product;

crystallizing the at least one amide in the amide product; and

distilling and drying the at least one amide.

4. The method of claim 1 , wherein the acid catalyst comprises oleum.

5. The method of claim 1 , wherein the at least one impurity comprises an octahydrophenazine (OHP) precursor.

6. The method of claim 1 , wherein the at least one amide comprises a cyclic amide.

7. The method of claim 6 , wherein the cyclic amide is ε-caprolactam.

8. The method of claim 1 , wherein heating the rearrangement mass comprises heating the rearrangement mass to a temperature from about 115° C. to about 140° C.

9. The method of claim 8 , wherein the temperature is from about 120° C. to about 140° C.

10. The method of claim 9 , wherein the temperature is from about 120° C. to about 135° C.

11. The method of claim 10 , wherein the temperature is from about 120° C. to about 125° C.

12. The method of claim 3 , wherein distilling comprises vacuum distillation.

13. The method of claim 8 , wherein heating further comprises heating from about 1 minute to about 30 minutes.

14. The method of claim 13 , wherein heating comprises heating from about 4 minutes to about 16 minutes.

15. A method of producing at least one amide, comprising:

providing an organic liquid comprising at least one ketoxime;

providing at least one acid catalyst;

adding the at least one catalyst to the organic liquid to form a rearrangement mass, wherein the rearrangement mass comprises at least one amide, at least one impurity, and the at least one catalyst; and heating the rearrangement mass to a temperature above about 115° C. for a period of time in order to break down some of the at least one impurity in the rearrangement mass.

16. The method of claim 15 , further comprising purifying the at least one amide.

17. The method of claim 16 , wherein purifying the at least one amide comprises:

adding water, a base and an organic solvent to the rearrangement mass to form a dual phase liquid;

separating the dual phase liquid into an aqueous phase and an organic phase;

distilling the organic phase to produce a solvent distillate and an amide product;

crystallizing the at least one amide in the amide product; and

distilling and drying the at least one amide.

18. The method of claim 15 , wherein the acid catalyst comprises oleum.

19. The method of claim 15 , wherein the at least one impurity comprises an octahydrophenazine precursor.

20. The method of claim 15 , wherein the at least one amide comprises a cyclic amide.

21. The method of claim 20 , wherein the cyclic amide is ε-caprolactam.

22. The method of claim 15 , wherein heating the rearrangement mass comprises heating the rearrangement mass to a temperature from about 115° C. to about 140° C.

23. The method of claim 22 , wherein the temperature is from about 120° C. to about 140° C.

24. The method of claim 23 , wherein the temperature is from about 120° C. to about 135° C.

25. The method of claim 24 , wherein the temperature is from about 120° C. to about 125° C.

26. The method of claim 17 , wherein distilling comprises vacuum distillation.

27. The method of claim 22 , wherein heating further comprises heating from about 1 minute to about 30 minutes.

28. The method of claim 27 , wherein heating comprises heating from about 4 minutes to 16 minutes.

29. The method of claim 3 or 17 , wherein the base comprises ammonia.

30. The method of claim 3 or 17 , wherein the organic solvent comprises toluene or benzene.

31. A method of producing caprolactam, comprising:

providing an organic liquid comprising at least one ketoxime;

providing at least one acid catalyst;

adding the at least one catalyst to the organic liquid to form a rearrangement mass, wherein the rearrangement mass comprises caprolactam, at least one impurity, and the at least one catalyst; and

heating the rearrangement mass to a temperature of at least about 115° C. for a period of time in order to sulfonate some of the at least one impurity in the rearrangement mass.

32. The method of claim 31 , further comprising purifying the caprolactam.

33. The method of claim 32 , wherein purifying caprolactam comprises:

adding water, a base and a solvent to the rearrangement mass to form a dual phase liquid;

separating the dual phase liquid into an aqueous phase and an organic phase;

distilling the organic phase to produce a solvent distillate and a caprolactam product;

crystallizing the caprolactam in the caprolactam product; and

distilling and drying the caprolactam.

34. A method of producing caprolactam, comprising:

providing an organic liquid comprising at least one ketoxime;

providing at least one acid catalyst;

adding the at least one catalyst to the organic liquid to form a rearrangement mass, wherein the rearrangement mass comprises caprolactam, at least one impurity, and the at least one catalyst; and

heating the rearrangement mass to a temperature above about 115° C. for a period of time in order to break down some of the at least one impurity in the rearrangement mass.

35. The method of claim 34 , further comprising purifying the caprolactam.

36. The method of claim 35 , wherein purifying the caprolactam comprises:

adding water, a base and an organic solvent to the rearrangement mass to form a dual phase liquid;

separating the dual phase liquid into an aqueous phase and an organic phase;

distilling the organic phase to produce a solvent distillate and a caprolactam product;

crystallizing the caprolactam in the caprolactam produce; and

distilling and drying the caprolactam.