Method for producing epsilon-caprolactam

Patent metadata

Field	Value
Publication number	US-10196352-B2
Application number	US-201515523120-A
Country	US
Kind code	B2
Filing date	Oct 27, 2015
Priority date	Oct 30, 2014
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

A method for selective production of ε-caprolactam, wherein a substance inducible from a biomass resource is used as a material; the reaction process is short; ammonium sulfate is not produced as a by-product; and production of by-products is suppressed; is disclosed. The method for producing ε-caprolactam comprises the step of reacting a particular compound inducible from a biomass resource, such as α-hydromuconic acid, 3-hydroxyadipic acid, or 3-hydroxyadipic acid-3,6-lactone, or a salt thereof with hydrogen or ammonia.

First claim

The invention claimed is:

1. A method for producing ε-caprolactam, comprising the step of reacting a compound represented by General Formula (I) or (II):

wherein R 1 , R 2 , and R 3 each independently represent OR 4 or NR 5 R 6 ; each R 4 independently represents H or C 1 -C 5 alkyl; each R 5 independently represents H or C 1 -C 5 alkyl; and X represents —CH(OH)CH 2 CH 2 —, CH 2 CH(OH)CH 2 —, —CH═CHCH 2 —, or —CH 2 CH═CH—,
or a salt thereof with hydrogen and ammonia.

2. The method according to claim 1 , wherein the compound represented by General Formula (I) or (II) is α-hydromuconic acid, 3-hydroxyadipic acid, or 3-hydroxyadipic acid-3,6-lactone, or an ester thereof.

3. The method according to claim 2 , wherein the compound represented by General Formula (I) or (II) is α-hydromuconic acid or an ester thereof.

4. The method according to claim 2 , wherein the compound represented by General Formula (I) or (II) is 3-hydroxyadipic acid or an ester thereof.

5. The method according to claim 2 , wherein the compound represented by General Formula (I) or (II) is 3-hydroxyadipic acid-3,6-lactone or an ester thereof.

6. The method according to claim 1 , wherein said step is carried out in the presence of a catalyst.

7. The method according to claim 6 , wherein said catalyst is at least one selected from the group consisting of palladium, platinum, gold, copper, ruthenium, rhodium, cobalt, rhenium, and nickel.

8. The method according to claim 7 , wherein said catalyst is at least one selected from the group consisting of palladium, platinum, gold, ruthenium, rhodium, cobalt, rhenium, and nickel.

9. The method according to claim 8 , wherein said catalyst is palladium.

10. The method according to claim 1 , wherein the hydrogen pressure at the beginning of the reaction in said step is 0.5 MPa to 10 MPa at normal temperature in terms of the gauge pressure.

11. The method according to claim 2 , wherein said step is carried out in the presence of a catalyst.

12. The method according to claim 3 , wherein said step is carried out in the presence of a catalyst.

13. The method according to claim 4 , wherein said step is carried out in the presence of a catalyst.

14. The method according to claim 5 , wherein said step is carried out in the presence of a catalyst.

Assignees

• Toray Industries

Inventors

• Ito Masateru
• Tsukamoto Daijiro
• Kawamura Kenji
• Yamashita Kohei
• Akahira Masato
• Yamada Katsushige
• Yamauchi Koji

Classifications

• C08G69/14

  Lactams · CPC title

• C07D223/10

  attached in position 2 · CPC title

• C07D201/08 Primary

  from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles · CPC title

• Y02P20/52

  using catalysts, e.g. selective catalysts · CPC title

• C07B61/00

  Other general methods · CPC title