Method for producing bio-based homoserine lactone and bio-based organic acid from O-acyl homoserine produced by microorganisms

Patent metadata

Field	Value
Publication number	US-9834491-B2
Application number	US-201414219307-A
Country	US
Kind code	B2
Filing date	Mar 19, 2014
Priority date	Mar 20, 2013
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.

First claim

What is claimed is:

1. A method for producing bio-based homoserine lactone and bio-based organic acid, comprising hydrolysis of O-acyl homoserine produced by a microorganism in the presence of a hydrochloric acid catalyst.

2. The method according to claim 1 , wherein the O-acyl homoserine includes O-acetyl-L-homoserine or O-succinyl-L-homoserine.

3. The method according to claim 1 , wherein the bio-based organic acid includes acetic acid or succinic acid.

4. The method according to claim 1 , wherein the O-acyl homoserine is produced by the microorganism whose cystathionine gamma synthase, O-succinylhomoserine sulfhydrylase or O-acetylhomoserine sulfhydrylase activity was removed or weakened as compared to the endogenous form thereof.

5. The method according to claim 2 , wherein the O-acetyl-L-homoserine is produced by the microorganism whose homoserine O-acetyl transferase activity was enhanced as compared to the endogenous form thereof.

6. The method according to claim 2 , wherein the O-succinyl-L-homoserine is produced by the microorganism whose O-succinyl transferase activity was enhanced as compared to the endogenous form thereof.

7. A method for producing gamma-butyrolactone, comprising the steps of:
hydrolyzing O-acyl homoserine produced by a microorganism in the presence of a hydrochloric acid catalyst to produce bio-based homoserine lactone and bio-based organic acid; and
deaminating the homoserine lactone by hydrodenitrification in the presence of a metal catalyst and hydrogen gas to produce gamma-butyrolactone.

8. The method according to claim 7 , wherein the method further comprises the steps of:
etherifying the gamma-butyrolactone in the presence of an indium bromide catalyst and a silane compound to produce tetrahydrofuran.

9. The method according to claim 7 , wherein the method further comprises the steps of:
producing 2-pyrrolidone from the gamma-butyrolactone in the presence of an aqueous ammonia solution.

10. The method according to claim 7 , wherein the method further comprises the steps of:
producing N-methyl-2-pyrrolidone from the gamma-butyrolactone in the presence of liquid methylamine.

11. The method according to claim 7 , wherein the method further comprises the steps of:
dehydrating the gamma-butyrolactone in the presence of liquid ethyl alcohol amine to produce N-(2-hydroxyethyl)-2-pyrrolidone (first-stage reaction); and
dehydrating the N-(2-hydroxyethyl)-2-pyrrolidone in the presence of an oxide catalyst containing an alkali metal or an alkaline earth metal and silicon to produce N-vinyl-2-pyrrolidone (second-stage reaction).

12. The method according to claim 7 , wherein the method further comprises the steps of:
hydrogenating the gamma-butyrolactone with an imidazole ligand in the presence of a ruthenium catalyst to produce 1,4-butanediol.

13. A method for producing ethanol, comprising the steps of:
hydrolyzing O-acetyl-L-homoserine produced by a microorganism in the presence of a hydrochloric acid catalyst to produce bio-based homoserine lactone and bio-based acetic acid; and
hydrogenating the acetic acid in the presence of a catalyst comprising a first metal, a siliceous support and at least one support modifier to produce ethanol.

14. The method according to claim 13 , wherein the method further comprises the steps of:
dehydrating the ethanol in the presence of a zeolite (ZSM-5) catalyst to produce ethylene.

15. The method according to claim 13 , wherein the method further comprises the steps of:
dehydrating the ethanol in the presence of a catalyst to produce ethylene; and
polymerizing the ethylene in the presence of a Ziegler-Natta catalyst to produce polyethylene.

16. The method according to claim 13 , wherein the method further comprises the steps of:
hydrolyzing the ethanol in the presence of a platinum-based catalyst to produce monoethylene glycol.

17. A method for producing 1,4-butanediol, comprising the steps of:
hydrolyzing O-succinyl-L-homoserine produced by a microorganism in the presence of a hydrochloric acid catalyst to produce bio-based homoserine lactone and bio-based succinic acid; and
hydrogenating the succinic acid in the presence of a metal catalyst on a carbon support to produce 1,4-butanediol and tetrahydrofuran.

18. The method according to claim 17 , wherein the method further comprises the step of:
dehydrogenating the 1,4-butanediol in the presence of a copper-zinc-based catalyst to produce gamma-butyrolactone.

19. A method for producing gamma-butyrolactone and tetrahydrofuran, comprising the steps of:
hydrolyzing O-succinyl-L-homoserine produced by a microorganism in the presence of a hydrochloric acid catalyst to produce bio-based homoserine lactone and bio-based succinic acid;
treating the succinic acid with MCM-41; and
hydrogenating the treated succinic acid in the presence of a noble metal catalyst selected from platinum, palladium and ruthenium to produce gamma-butyrolactone and tetrahydrofuran.

20. The method according to claim 17 , wherein the method further comprises the steps of:
dehydrating the 1,4-butanediol in the presence of a catalyst selected from inorganic acid, tungstic oxide and iron phosphate to produce tetrahydrofuran.

Assignees

• Cj Cheiljedang Corp

Inventors

• Lee Han Won
• Yang Young Lyeol
• Kim So Young
• Shin Yong Uk
• Chang Jin Sook
• Um Hye Won
• Goh Young Hyoung
• Jhon Sung Hoo

Classifications

• C07C29/09

  by hydrolysis · CPC title

• C07C1/24 Primary

  by elimination of water · CPC title

• C07C31/12

  containing four carbon atoms · CPC title

• C07C2529/40

  of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11 · CPC title

• C07C11/04

  Ethene · CPC title