Process for producing 1,3-bis(3-aminophenoxy) benzene

A technology of aminophenoxy and difluorobenzene, applied in the field of preparation of polyether-polyamine compounds, can solve problems such as not found

Inactive Publication Date: 2003-11-19
三井化学FINE株式会社
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No reaction between 1,3-difluorobenzene and other phenols was found

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 71.5g (0.655mol) of 3-aminophenol, 53.5g (0.655mol) of 49 mass% hydrogen in a 500mL four-necked flask with a stirrer, reflux condenser and Dean-Stark water trap Aqueous sodium oxide solution, 250 g DMI and 50 g toluene. Toluene and water were removed azeotropically by heating the contents of the flask to 180°C with stirring while bubbling nitrogen. Subsequently, the contents of the flask were cooled to room temperature and transferred to a 600 mL autoclave with a stirrer.

[0030] Subsequently, 34 g (0.298 mol) of 1,3-difluorobenzene was added; the reactor was sealed; nitrogen gas was blown thereinto; thereafter, the autoclave was heated to 200° C.; and the reaction was allowed to proceed at 200° C. for 53 hours. Thereafter, the autoclave was cooled, and a part of the reaction mixture was analyzed by high performance liquid chromatography (hereinafter abbreviated as HPLC). As a result, the yield of 1,3-bis(3-aminophenoxy)benzene was 82% (relative to 1,3-difluorobe...

Embodiment 2

[0032] Examples of combined use of sodium salt and potassium salt

[0033] Add 71.5g (0.655mol) of 3-aminophenol, 26.7g (0.327mol) of 49 mass% hydrogen in a 500mL four-necked flask with a stirrer, reflux condenser and Dean-Stark water trap Sodium oxide aqueous solution, 19.3 g (0.327 mol) of 95 mass % potassium hydroxide aqueous solution, 250 g of DMI, and 50 g of toluene. Toluene and water were removed azeotropically by heating the contents of the flask to 180°C with stirring while bubbling nitrogen. Subsequently, the contents of the flask were cooled to room temperature and transferred to a 600 mL autoclave with a stirrer.

[0034] Subsequently, 34 g (0.298 mol) of 1,3-difluorobenzene was added; the reactor was sealed; nitrogen gas was blown thereinto; thereafter, the autoclave was heated to 200° C.; and the reaction was allowed to proceed at 200° C. for 19 hours. Thereafter, the autoclave was cooled and a portion of the reaction mixture was analyzed by high performance ...

Embodiment 3

[0037] 1-(3-Aminophenoxy)-3-fluorobenzene

[0038] Add 71.5g (0.655mol) of 3-aminophenol, 53.5g (0.655mol) of 49 mass% hydrogen in a 500mL four-necked flask with a stirrer, reflux condenser and Dean-Stark water trap Aqueous sodium oxide solution, 250 g DMI and 50 g toluene. Toluene and water were removed azeotropically by heating the contents of the flask to 180°C with stirring while bubbling nitrogen. Subsequently, the contents of the flask were cooled to room temperature and transferred to a 600 mL autoclave with a stirrer.

[0039] Subsequently, 34 g (0.298 mol) of 1,3-difluorobenzene was added; the reactor was sealed; nitrogen was blown thereinto; thereafter, the autoclave was heated to 200° C.; and the reaction was allowed to proceed at 200° C. for 2 hours, followed by abort. After this time, the reaction mixture was cooled and a portion of the reaction mixture was analyzed by HPLC. As a result, the yield of 1-(3-aminophenoxy)-3-fluorobenzene was 85.8% (relative to ...

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PUM

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Abstract

A process for industrially producing in a high yield 1,3-bis(3-aminophenoxy)benzene, which is effective as, e.g., a material for polyimides having high heat resistance, which comprises reacting 1,3-difluorobenzene with an alkali metal salt of 3-aminophenol.

Description

technical field [0001] The present invention relates to a process for the preparation of 1,3-bis(3-aminophenoxy)benzene, which is useful as a raw material for, inter alia, adhesive polyimide resins, and as a heat-resistant polymer, especially It is a polyether-polyamine compound of a polyimide raw material; and relates to an intermediate for preparing 1,3-bis(3-aminophenoxy)benzene. Background technique [0002] As a method for producing 1,3-bis(3-aminophenoxy)benzene, US Patent No. 4222962 describes the reaction between 1,3-dibromobenzene and an alkali metal salt of 3-aminophenol. However, in this method, the reactivity of the second step was poor and the yield was as low as 65%. [0003] Also described in JP-A-03-255058 is a process involving the reaction of 1,3,5-trichlorobenzene with an alkali metal salt of 3-aminophenol to form two ether linkages followed by hydrogenolytic elimination using a noble metal catalyst residual chlorine. However, in the method described in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/06C07C217/90
CPCC07C217/90C07C213/06
Inventor 朝重直树抜井康浩和田勝冈崎光树林秀俊
Owner 三井化学FINE株式会社
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