Organic amine collection method

Patent metadata

Field	Value
Publication number	US-12180136-B2
Application number	US-202218091697-A
Country	US
Kind code	B2
Filing date	Dec 30, 2022
Priority date	Dec 27, 2017
Publication date	Dec 31, 2024
Grant date	Dec 31, 2024

Abstract

A method is provided for collecting a compound of formula (III) (in which R31 is a monovalent to trivalent organic group and n31 is an integer of 1 to 3) from a liquid phase component that is formed as a by-product in a method for producing a compound of general formula (I) (in which R11 is a monovalent to trivalent organic group and n11 is an integer of 1 to 3), wherein the collection method contains steps (1) to (3) or steps (A) and (B), and step (4). Step (1): a step for reacting the liquid phase component with at least one active hydrogen-containing compound in a reactor. Step (2): a step for returning a condensed liquid obtained by cooling gas phase components in the reactor to the reactor. Step (3): a step for discharging gas phase components that are not condensed in the step (2) to the outside of the reactor. Step (A): a step for mixing the liquid phase component, water, and a compound of general formula (III). Step (B): a step for reacting the liquid phase component with water inside the reactor. Step (4): a step for discharging, as a liquid phase component inside the reactor, the reaction liquid containing the compound of general formula (III) to the outside of the reactor.

First claim

The invention claimed is:

1. A method for collecting a compound of general formula (III) from a liquid phase component that is formed as a by-product in a method for producing a compound of general formula (I), comprising:
step (A): a step for mixing the liquid phase component, water, and the compound of general formula (III);
step (B): a step for reacting the liquid phase component with water in a reactor; and
step (4): a step for discharging, as a liquid phase component inside the reactor, the reaction liquid containing the compound of general formula (III) to an outside of the reactor,

in the general formula (I), R 11 represents a monovalent to trivalent organic group, and n11 represents an integer of 1 to 3, and

in the general formula (III), R 31 represents a monovalent to trivalent organic group, and n31 represents an integer of 1 to 3, wherein the liquid phase component that is formed as a by-product in the method for producing the compound of general formula (I) is a liquid phase component extracted from a thermal decomposition reactor when a gas phase component comprising the compound of general formula (I) generated by supplying a liquid containing a carbamate produced from a carbonic acid derivative, a hydroxy compound and the compound of general formula (III) to the thermal decomposition reactor and then subjecting the carbamate to thermal decomposition reaction is collected.

2. The collection method according to claim 1 , wherein the method for producing a compound of general formula (I) is a method in which the compound of general formula (I) is produced from a carbonic acid derivative, a hydroxy compound and the compound of general formula (III).

3. The collection method according to claim 1 , wherein the thermal decomposition reactor comprises: a tubular reactor; and a separation tank in which the liquid phase component and the gas phase component comprising the compound of general formula (I) are separated,
wherein a flow rate per wetted perimeter of the tubular reactor is 10 kg/hour·m to 1000 kg/hour·m.

4. The collection method according to claim 1 , wherein a linear velocity of the gas phase component in a separation tank in which the liquid phase component and the gas phase component comprising the compound of general formula (I) are separated is 10 m/second or less.

5. The collection method according to claim 1 , wherein the liquid phase component comprises a hydroxy compound.

6. The collection method according to claim 1 , wherein the liquid phase component comprises a compound having at least one group selected from the group consisting of a group of formula (II-1) and a group of formula (II-2):

7. The collection method according to claim 6 , wherein the liquid phase component comprising a high-boiling point compound comprises a hydroxy compound in an amount of 20% by mass to 70% by mass, relative to a total mass of the liquid phase component.

8. The collection method according to claim 1 , wherein the liquid phase component has a viscosity at 150° C. of 100 mPa·s or less.

9. The collection method according to claim 1 , wherein the reactor is at least one reactor selected from the group consisting of a tank-type reactor, an extruder and a thin-film evaporator.

10. The collection method according to claim 1 , further comprising:
step (5): a step for separating the compound of the general formula (III) from the reaction liquid obtained in the step (4); and
step (6): a step for purifying the compound of the general formula (III).

11. The collection method according to claim 10 , wherein the compound of the general formula (III) is collected by distillation in the step (6), such that, relative to a total mass of the compound of the general formula (III), an amount of metallic components becomes 1000 ppm by mass or less and an amount of halogen atoms becomes 1000 ppm by mass or less.

12. The collection method according to claim 10 , wherein the compound of the general formula (III) collected in the step (6) is recycled to produce the compound of general formula (I).

13. The collection method according to claim 10 , wherein the liquid phase component comprises a compound having a group of general formula (IV),
a compound of general formula (V) is separated in the step (5) together with the compound of the general formula (III) from the reaction liquid obtained in the step (4), and
further comprising:
step (7): a step for purifying the compound of the general formula (V),
wherein the step (7) is conducted after the step (6),

in the general formulae (IV) and (V), X 41 represents a C6-12 unsubstituted or substituted aromatic hydrocarbon ring or heteroaromatic ring, R 41 represents a C1-20 alkyl group, which may be substituted with at least one group selected from the group consisting of a phenyl group and a hydroxy phenyl group, an amino group, or a hydroxy group, and n41 represents an integer of 0 to 4, and R 41 is identical to or different from each other when n41 is 2 or more.

14. The collection method according to claim 13 , wherein the compound of the general formula (V) is collected by distillation in the step (7), such that, relative to a total mass of the compound of the general formula (V), an amount of metallic components becomes 1000 ppm by mass or less and an amount of halogen atoms becomes 1000 ppm by mass or less.

15. The collection method according to claim 13 , wherein the compound of the general formula (V) collected in the step (7) is recycled to produce the compound of general formula (I).

16. The collection method according to claim 1 , wherein the compound of general formula (III) is diaminohexane, diaminotoluene, diaminomethyltrimethylcyclohexane, dicyclohexylmethane diamine, diphenylmethane diamine, isophorone diamine, hexamethylene diamine, pentamethylene diamine, xylylene diamine, bis(aminopropyl)benzene, bis(aminopropyl)cyclohexane, or aminomethyloctane diamine.

17. The collection method according to claim 2 , wherein the carbonic acid derivative is urea or a carbonic acid ester.

Assignees

• Asahi Chemical Ind
• Asahi Kasel Kk

Inventors

• Miyake Nobuhisa
• Shinohata Masaaki
• Sakurai Yusuke
• Ishii Yusuke
• Sasaki Takeharu

Classifications

• C07C209/86

  Separation · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C269/04

  from amines with formation of carbamate groups · CPC title

• C07C209/84 Primary

  Purification · CPC title

• C07C263/04 Primary

  from or via carbamates or carbamoyl halides · CPC title