# US 10,501,415 B2 · Method for producing bisimide dicarboxylic acid

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- Number: US 10,501,415 B2
- Document ID: US10501415B2
- Status: Granted
- Kind: B2
- Application number: 15/564,667
- Filed: 2016-04-06
- Published: 2018-03-29
- Granted: 2019-12-10
- Earliest claimed: 2015-04-07
- Assignees: Unitika Ltd.
- Applicants: Unitaka Ltd.
- Inventors: Yumeto Fukubayashi; Makoto Nakai; Akira Shigeta; Munenori Yamada
- Web page: https://patentgrep.com/patent/US10501415B2

## CPC

- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- B01J 19/0013: {Controlling the temperature of the process}
- C07B 43/06: of amide groups
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

An object of the present invention is to provide an industrially advantageous method for producing a bisimide dicarboxylic acid, which uses substantially no solvent and requires no granulation after completion of the reaction. The above object can be achieved by a method for producing a bisimide dicarboxylic acid with a tricarboxylic acid anhydride and a diamine, including the following processes (i) and (ii): a process (i) in which, provided that a compound having a higher melting point is a high melting compound and a compound having a lower melting point is a low melting compound, when a melting point is compared between the tricarboxylic acid anhydride and the diamine, the high melting compound is heated at a temperature between less than the melting point of the high melting compound and not lower than the melting point of the low melting compound, and the low melting compound is added to the high melting compound while the high melting compound maintains its solid states, to give a mixture; and a process (ii) in which the resultant mixture in the process (i) is heated while its solid states are kept, to give bisimide dicarboxylic acid.

## Claims

### Claim 1

A method for producing a bisimide dicarboxylic acid with a tricarboxylic acid anhydride and a diamine, where said tricarboxylic acid anhydride is an aromatic tricarboxylic acid anhydride, an alicyclic tricarboxylic acid anhydride, or a mixture thereof and wherein said diamine is an aliphatic diamine, an alicyclic diamine, an aromatic diamine, or a mixture thereof, the method comprising the following processes (i) and (ii):
a process (i) in which, provided that a compound having a higher melting point is a high melting compound and a compound having a lower melting point is a low melting compound, when a melting point is compared between the tricarboxylic acid anhydride and the diamine, the high melting compound is heated at a temperature between less than the melting point of the high melting compound and not lower than the melting point of the low melting compound, and the low melting compound is added, in a melted state, at a temperature in a range lower by 5 to 10° C. or more than the ng point of the high melting compound and at a temperature in a range higher by 5 to 10° C. or more than the melting point of the low melting compound and at an addition rate from 0.005 to 2.00% by mass/minute to the high melting compound, while the high melting compound maintains its solid state, to give a mixture; and
a process (ii) in which the resultant mixture in the process (i) is heated while the solid state of the high melting compound is kept, and the melted state of the low melting compound is kept; to give bisimide dicarboxylic acid.

### Claim 2 (depends on 1)

A method of claim 1, wherein the solid state is particulate.

### Claim 3 (depends on 1)

A method of claim 1, wherein the low melting compound is added in a powdery state or a particulate state in the process (i), and
wherein the resultant mixture in the process (i) is heated at a temperature between less than the melting point of the high melting compound and not lower than the melting point of the low melting compound while the solid state of the high melting compound is kept, and the low melting compound is kept in a melted state, to give bisimide dicarboxylic acid.