Method for producing compound, compound, epoxy curing agent, and method for producing amine composition

Patent metadata

Field	Value
Publication number	US-11186537-B2
Application number	US-201917057463-A
Country	US
Kind code	B2
Filing date	May 28, 2019
Priority date	May 31, 2018
Publication date	Nov 30, 2021
Grant date	Nov 30, 2021

Abstract

Provided are: a method for producing a compound that excels in storage stability and handleability; the compound; and an epoxy curing agent containing the compound. The method for producing a compound represented by Formula (1-1) includes subjecting the compound represented by Formula (5-1) to an addition reaction to add ethylene and/or propylene in the presence of a base. In Formula (5-1), RX to RZ each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3. In Formula (1-1), RA to RD each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3.

First claim

The invention claimed is:

1. A method for producing a compound represented by Formula (1-1), the method comprising subjecting a compound represented by Formula (5-1) to an addition reaction to add ethylene and/or propylene in the presence of a base:

where in Formula (5-1), R X to R Z each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3;

where in Formula (1-1), R A to R D each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3,
wherein at least two of R A to R D are independently an ethyl group, an n-propyl group, or an isopropyl group, and
Formula (1-1) excludes:
a case where n is 1, a —C(R C )(R D )(NH 2 ) group is at para position or at meta position, either R A or R B and either R C or R D are each an n-propyl group, and the remaining two of R A to R D are hydrogen atoms; and
a case where n is 1, a —C(R C )(R D )(NH 2 ) group is at ortho position, either R A or R B and either R C or R D are each an ethyl group, and the remaining two of R A to R D are hydrogen atoms.

2. A method for producing a compound represented by Formula (1-2), the method comprising contacting a compound represented by Formula (5-2) with ethylene-and subjecting the compound to alkylation in the presence of a base,
wherein a temperature of a reaction solution at the time of ethylene filling is from 0 to 10° C., and a filling pressure of the ethylene is from 1.5 to 2.3 MPa:

where in Formula (5-2), R X2 to R Z2 each independently represent a hydrogen atom or an ethyl group, and n is an integer of from 1 to 3;

where in Formula (1-2), R A2 to R D2 each independently represent a hydrogen atom or an ethyl group, and n is an integer of from 1 to 3,
wherein at least two of R A2 to R D2 are ethyl groups.

3. The compound production method according to claim 1 , wherein the base is a base composition comprising:
at least one alkali metal-containing compound (A) which is selected from the group consisting of rubidium carbonate, rubidium hydroxide, cesium carbonate, and cesium hydroxide; and
a metallic sodium (B).

4. The compound production method according to claim 1 , comprising dividing the base into two or more portions and introducing into a reaction system.

5. The compound production method according to claim 1 , wherein n in Formula (5-1) is 1.

6. The compound production method according to claim 1 , wherein the compound represented by Formula (5-1) comprises at least one compound selected from the group consisting of o-xylylenediamine, m-xylylenediamine, p-xylylenediamine, 1,2,3-benzene trimethanamine, 1,2,4-benzene trimethanamine and 1,2,4,5-benzene tetramethanamine.

7. The compound production method according to claim 1 , wherein the compound represented by Formula (5-1) comprises m-xylylenediamine.

8. The compound production method according to claim 1 , wherein the compound represented by Formula (1-1) is represented by Formula (2-1):

where in Formula (2-1), at least two of R A to R D are the same group selected from the group consisting of an ethyl group, an n-propyl group, and an isopropyl group, and the remainder of R A to R D is a hydrogen atom,
wherein, when two of R A to R D are n-propyl groups, Formula (2-1) excludes a case where either R A or R B , and either R C or R D are each an n-propyl group;

9. The compound production method according to claim 1 , wherein at least three of R A to R D in Formula (1-1) are ethyl groups, and the remainder of R A to R D is a hydrogen atom.

10. The compound production method according to claim 1 , wherein the compound represented by Formula (1-1) is represented by Formula (3) or Formula (4):

11. A compound represented by Formula (1-1):

where in Formula (1-1), R A to R D each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3,
wherein at least two of R A to R D are independently an ethyl group, an n-propyl group, or an isopropyl group, and
Formula (1-1) excludes:
a case where n is 1, a —C(R C )(R D )(NH 2 ) group is at para position or at meta position, either R A or R B and either R C or R D are each an n-propyl group, and the remaining two of R A to R D are hydrogen atoms; and
a case in where n is 1, a —C(R C )(R D )(NH 2 ) group is at ortho position, either R A or R B and either R C or R D are each an ethyl group, and the remaining two of R A to R D are hydrogen atoms.

12. The compound according to claim 11 , wherein n in Formula (1-1) is 1.

13. The compound according to claim 11 , represented by Formula (2-1):

where in Formula (2-1), at least two of R A to R D are the same group selected from the group consisting of an ethyl group, an n-propyl group, and an isopropyl group, and the remainder of R A to R D is a hydrogen atom,
wherein, when two of R A to R D are n-propyl groups, Formula (2-1) excludes a case where either R A or R B , and either R C or R D are each an n-propyl group.

14. The compound according to claim 11 , represented by Formula (3)

15. The compound according to claim 11 , represented by Formula (4)

16. A method for producing an amine composition containing a compound represented by Formula (1-2), the method comprising contacting a compound represented by Formula (5-2) with ethylene and subjecting the compound to alkylation in the presence of a base,
wherein a temperature of a reaction solution at the time of the ethylene filling is from 0 to 10° C., and a filling pressure of the ethylene is from 1.5 to 2.3 MPa:

where in Formula (5-2), R X2 to R Z2 each independently represent a hydrogen atom or an ethyl group, and n is an integer of from 1 to 3;

where in Formula (1-2), R A2 to R D2 each independently represent a hydrogen atom or an ethyl group, and n is an integer of from 1 to 3,

wherein at least two of R A2 to R D2 are ethyl groups.

17. The compound production method according to claim 2 , wherein the base is a base comp

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Takano Yoichi
• Uera Kazuyoshi

Classifications

• C07C211/27

  having amino groups linked to the six-membered aromatic ring by saturated carbon chains · CPC title

• C07C211/09

  Diamines · CPC title

• C07C209/68 Primary

  from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title

• C08G59/50

  Amines · CPC title

• C08G59/5033 Primary

  aromatic · CPC title