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Method for preparing phenyl amino hydroxyl anthraquinone

A technology of dihydroxyanthraquinone and amino group is applied in the field of preparing 1,4-diphenylamino-5,8-dihydroxyanthraquinone, which can solve the problem that the color characteristics of products no longer meet the performance requirements.

Active Publication Date: 2019-06-04
LANXESS DEUTDCHLAND GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the color characteristics of products produced in this way no longer meet current performance requirements

Method used

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  • Method for preparing phenyl amino hydroxyl anthraquinone
  • Method for preparing phenyl amino hydroxyl anthraquinone
  • Method for preparing phenyl amino hydroxyl anthraquinone

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0085] Preparation of 1,4-bis(4-tert-butylphenylamino)-5,8-dihydroxyanthraquinone (similar to EP-A 1 074 586, not according to the invention)

[0086] First, 100 g (1010 mmol) of N-methylpyrrolidone was added to a glass reactor under nitrogen gas and heated to 70°C. Then 20 g (134 mmol) p-tert-butylaniline were added. Subsequently 17 g (44 mmol) of 5,8-dichloro-1,4-dihydroxyanthraquinone (technical grade, 80%) and 15.7 g (110.5 mmol) of disodium hydrogenphosphate were added and the reaction mixture was heated to 150°C. The reaction mixture was stirred at this temperature for 3 hours and then heated to 180° C. and stirred at this temperature for a further 10 hours. After the reaction was complete, the reaction mixture was cooled to 100°C and 30 g of methanol was added. The mixture was stirred at 80°C for one hour. After cooling to 50° C., the mixture was filtered through a Nutsche filter. The filter cake was washed first with 450 g of warm methanol and then with 1500 ml of ...

example 2

[0089] Preparation of 1,4-bis(4-tert-butylphenylamino)-5,8-dihydroxyanthraquinone (similar to EP-A 1 074 586, not according to the invention)

[0090] The reaction and work-up were carried out exactly as in Example 1, but 100 g (680 mmol) of 1,2-dichlorobenzene were used instead of 100 g of N-methylpyrrolidone.

[0091] Yield 23 g (98% of theory)

example 3

[0093] Preparation of 1,4-bis(4-tert-butylphenylamino)-5,8-dihydroxyanthraquinone (similar to EP-A 1 074 586, not according to the invention)

[0094] The reaction and work-up were carried out exactly as specified in Example 1, but 100 g (551 mmol) of 1,2,4-trichlorobenzene were used instead of 100 g of N-methylpyrrolidone.

[0095] Yield 22.6 g (96.1% of theory)

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Abstract

The invention relates to a method for preparing phenyl amino hydroxyl anthraquinone. The novel preparation method for 1,4-diphenylamino-5,8-dihydroxyanthraquinone affords these dyes having high colorstrength and excellent brilliance for coloring plastics.

Description

technical field [0001] The present invention relates to a method for preparing 1,4-diphenylamino-5,8-dihydroxyanthraquinone by reacting 1,4-dichloro-5,8-dihydroxyanthraquinone with aniline in the presence of a specific solvent new method. Background technique [0002] Phenylaminohydroxyanthraquinones represent a class of valuable dyes which are used in particular for coloring thermoplastics and are characterized by high brightness and weathering resistance. [0003] The most famous representative of this class of dyes is solvent green 28 (1,4-bis(4-tert-butylphenylamino)-5,8-dihydroxyanthraquinone (CAS No. 4851-50-7, EINECS No. 225- 443-9). [0004] From EP-A 1 074 586 a process is known for preparing phenylaminohydroxyanthraquinones by condensation of aniline with chlorohydroxyanthraquinones. Therein, the reaction of chloranthraquinone with suitable amines is carried out in the presence of specific bases from the series of alkali metal phosphates and using specific inert...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/36C09B1/514C08K5/18
CPCC07C221/00C07C225/36C08K5/00C08K5/0041C08K5/18C09B1/51C09B1/514C09B1/5145D01F1/06C08K2003/2241C08K3/22C08L25/06
Inventor 汉斯-乌尔里希·博斯特亚历克萨·马松格萨比娜·施毛泽
Owner LANXESS DEUTDCHLAND GMBH