Production method for dicyanocyclohexane

Patent metadata

Field	Value
Publication number	US-11352318-B2
Application number	US-201816636182-A
Country	US
Kind code	B2
Filing date	Aug 6, 2018
Priority date	Aug 18, 2017
Publication date	Jun 7, 2022
Grant date	Jun 7, 2022

Abstract

The present invention provides a production method for dicyanocyclohexane, including a step of obtaining dicyanocyclohexane by reacting cyclohexanedicarboxylic acid and/or a salt thereof, or a heated concentrate of an aqueous ammonia solution of cyclohexanedicarboxylic acid with ammonia in a solvent having a boiling point equal to or higher than a reaction temperature.

First claim

The invention claimed is:

1. A method for producing dicyanocyclohexane, the method comprising:
reacting cyclohexanedicarboxylic acid and/or a salt thereof, or a heated concentrate of an aqueous ammonia solution of cyclohexanedicarboxylic acid with ammonia in a solvent having a boiling point equal to or higher than a reaction temperature, thereby producing dicyanocyclohexane,
wherein the boiling point of the solvent having the boiling point equal to or higher than the reaction temperature is 350° C. or higher.

2. The method according to claim 1 , further comprising: conducting a hydrogenation reaction of phthalic acid in an aqueous ammonia solution, thereby producing the cyclohexanedicarboxylic acid and/or the salt thereof, or the aqueous ammonia solution of cyclohexanedicarboxylic acid.

3. The method according to claim 2 ,
wherein a part of an aqueous ammonia solution included in a reaction solution after the conducting is used as an ammonia source for the reacting.

4. The method according to claim 1 , further comprising:
heating the aqueous ammonia solution of cyclohexanedicarboxylic acid to 100 to 200° C. to remove at least a part of water, thereby forming the heated concentrate.

5. A method for producing dicyanocyclohexane, the method comprising:
reacting cyclohexanedicarboxylic acid and/or a salt thereof, or a heated concentrate of an aqueous ammonia solution of cyclohexanedicarboxylic acid with ammonia in a solvent having a boiling point equal to or higher than a reaction temperature, thereby producing dicyanocyclohexane,
wherein the solvent having the boiling point equal to or higher than the reaction temperature is one or more selected from the group consisting of alkylnaphthalene, stearic acid amide, stearonitrile and triphenylmethane.

6. A method for producing bis(aminomethyl)cyclohexane, the method comprising:
obtaining dicyanocyclohexane by the method according to claim 1 , and
obtaining bis(aminomethyl)cyclohexane by subjecting the dicyanocyclohexane to a hydrogenation reaction.

7. The method according to claim 2 , further comprising:
heating the aqueous ammonia solution of cyclohexanedicarboxylic acid to 100 to 200° C. to remove at least a part of water, thereby forming the heated concentrate.

8. The method according to claim 3 , further comprising:
heating the aqueous ammonia solution of cyclohexanedicarboxylic acid to 100 to 200° C. to remove at least a part of water, thereby forming the heated concentrate.

9. A method for producing bis(aminomethyl)cyclohexane, the method comprising:
obtaining dicyanocyclohexane by the method according to claim 2 , and
obtaining bis(aminomethyl)cyclohexane by subjecting the dicyanocyclohexane to a hydrogenation reaction.

10. A method for producing bis(aminomethyl)cyclohexane, the method comprising:
obtaining dicyanocyclohexane by the method according to claim 3 , and
obtaining bis(aminomethyl)cyclohexane by subjecting the dicyanocyclohexane to a hydrogenation reaction.

11. A method for producing bis(aminomethyl)cyclohexane, the method comprising:
obtaining dicyanocyclohexane by the method according to claim 4 , and
obtaining bis(aminomethyl)cyclohexane by subjecting the dicyanocyclohexane to a hydrogenation reaction.

12. A method for producing bis(aminomethyl)cyclohexane, the method comprising:
obtaining dicyanocyclohexane by the method according to claim 5 , and
obtaining bis(aminomethyl)cyclohexane by subjecting the dicyanocyclohexane to a hydrogenation reaction.

13. A method for producing bis(aminomethyl)cyclohexane, the method comprising:
obtaining dicyanocyclohexane by the method according to claim 7 , and
obtaining bis(aminomethyl)cyclohexane by subjecting the dicyanocyclohexane to a hydrogenation reaction.

14. A method for producing bis(aminomethyl)cyclohexane, the method comprising:
obtaining dicyanocyclohexane by the method according to claim 8 , and
obtaining bis(aminomethyl)cyclohexane by subjecting the dicyanocyclohexane to a hydrogenation reaction.

15. The method according to claim 1 , wherein the boiling point of the solvent having the boiling point equal to or higher than the reaction temperature is higher than 350° C.

16. The method according to claim 1 , wherein the boiling point of the solvent having the boiling point equal to or higher than the reaction temperature is higher than 350° C. to 600° C. or lower.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Iida Akifumi
• Nakano Emi
• Kanbara Yutaka

Classifications

• C07C209/48 Primary

  by reduction of nitriles · CPC title

• C07C255/46

  to carbon atoms of non-condensed rings · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C253/22 Primary

  by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups · CPC title

• C07B61/00

  Other general methods · CPC title