Synthesis of caprolactam from lysine

• US 7,977,450 B2
• Filed: 06/26/2008
• Issued: 07/12/2011
• Est. Priority Date: 06/10/2004
• Status: Active Grant

• Current Assignee: The Board of Trustees of Michigan State University (Michigan State University)
• Original Assignee: The Board of Trustees of Michigan State University (Michigan State University)
• Inventors: Frost, John W.
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): Kahn; Rachel
• Application Number:
  US12/147,256
• Publication Number:
  US 20090005532A1
• Time in Patent Office: 1,111 Days
• Field of Search: 528/323, 540/528, 540/533
• US Class Current: 528/323
• CPC Class Codes: C07D 201/08 from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
• CPC Class Codes: C07D 223/12 Nitrogen atoms not forming part of a nitro radical

Abstract

In various embodiments, the present invention can involve a method of synthesizing α-amino-ε-caprolactam. The method can comprise heating a salt of L-lysine in a solvent comprising an alcohol. In other embodiments, the present invention can involve methods for synthesizing ε-caprolactam. The methods can comprise heating a salt of L-lysine in a solvent comprising an alcohol and deaminating the reaction product. In various embodiments, the invention can include methods of converting biomass into nylon 6. The methods can comprise heating L-lysine in a solvent comprising an alcohol to produce α-amino-ε-caprolactam, deaminating to produce ε-caprolactam and polymerizing into nylon 6, wherein the L-lysine is derived from the biomass. In other embodiments, the present invention can include methods of making nylon 6. The methods can comprise synthesizing ε-caprolactam and then polymerizing, wherein the ε-caprolactam is derived from L-lysine.

Claims

1. A method for producing nylon 6, the method comprising:

(A) heating lysine in a solvent comprising an alcohol, at a temperature of about 99°

C. to about 201°

C., to produce α

-amino-ε

-caprolactam;

(B) deaminating α

-amino-ε

-caprolactam produced in (A) by a method comprising contacting it at least once with a deamination reagent or catalyst at a temperature below the freezing point of water, to produce ε

-caprolactam; and

(C) polymerizing ε

-caprolactam produced in (B) into nylon 6.

2. A method according to claim 1, wherein the lysine comprises L-lysine derived from biomass.

3. A method according to claim 2, wherein the L-lysine is derived by obtaining a sugar from the biomass and converting the sugar into L-lysine.

4. A method according to claim 3, wherein the converting comprises using a fermentation reaction to convert the sugar into L-lysine.

5. A method according to claim 4 further comprising recycling an amine, produced by deamination of α

-amino-ε

-caprolactam, into the fermentation reaction.

6. A method according to claim 2 further comprising creating lactic acid from the biomass.

7. A method according to claim 6 further comprising hydrogenating the lactic acid to produce 1,2-propanediol.

8. A method according to claim 7 further comprising using the 1,2-propanediol as the alcohol in the heating step (A).

9. A method according to claim 1, wherein the heating (A) comprises heating in the presence of a catalyst.

10. A method according to claim 1, wherein the alcohol used in the heating step (A) has from 2 to 6 carbons.

11. A method according to claim 10, wherein the alcohol comprises a diol.

12. A method according to claim 10, wherein the alcohol comprises a triol.

13. A method according to claim 10, wherein the alcohol comprises a glycol.

14. A method according to claim 10, wherein the alcohol is from the group consisting of ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1,2-propanediol, and mixtures thereof.

15. A method according to claim 14, wherein the alcohol is 1,2-propanediol.

16. A method according to claim 1, wherein the heating is below the temperature of polymerization of caprolactam.

17. A method according to claim 1, wherein the heating allows the azeotropic removal of water.

18. A method according to claim 1, wherein the heating is accomplished by reflux.