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Synthesis method of chloroanthraquinone

A synthetic method, the technology of chloroanthracene, applied in the field of preparation of fine chemicals, can solve the problems of lowering the export price of products, difficult and troublesome metal mercury treatment, and achieve the effect of improving quality

Inactive Publication Date: 2010-06-02
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the preparation method of 1-chloroanthraquinone mainly uses anthraquinone as a raw material, through sulfonation under the effect of metal mercury as a positioning agent, to generate 1-sulfonic acid anthraquinone, and then obtain 1-chloroanthraquinone in chlorination, this The biggest defect of the method is that the participation of metallic mercury brings a lot of trouble to the post-processing. It is difficult to clean the metallic mercury, which seriously affects the quality of the product and greatly reduces the export price of the product.

Method used

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  • Synthesis method of chloroanthraquinone

Examples

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Effect test

example 1

[0016] Preparation of 1-chloroanthraquinone

[0017] Pass 3.0g (42.3mM) of chlorine gas into the mixture of 4mL of dichlorophenylphosphine and 50mL of phenylphosphonic dichloride at room temperature, heat the reaction slightly, but do not exceed 30°C, previously colorless The transparent solution turned into a light yellow transparent solution, and 7.1 g (28.1 mM) of 1-nitroanthraquinone was added to the mixed solution, and then heated to 170° C. for 5 h. After cooling the reaction solution, the reaction solution was poured into 500 mL of water, then neutralized to pH 7 with 50% sodium hydroxide solution, and the neutralized solution was extracted with 500 mL (5×100 mL) of ethyl acetate, and the organic phase was mixed after extraction. , then use 200mL (2 × 100mL) saturated saline solution to elute the organic phase, dry with 5% anhydrous magnesium sulfate after the elution, then suction filter to obtain the filtrate, and obtain the concentrated solution after the filtrate is...

example 2

[0019] Preparation of 2-chloroanthraquinone

[0020] Pass 3.0g (42.3mM) of chlorine gas into the mixture of 4mL of dichlorophenylphosphine and 50mL of phenylphosphonic dichloride at room temperature, heat the reaction slightly, but do not exceed 30°C, previously colorless The transparent solution turned into a light yellow transparent solution, and 7.2 g (28.3 mM) of 2-nitroanthraquinone was added to the mixed solution, and then heated to 170° C. for 5 h. After cooling the reaction solution, the reaction solution was poured into 500 mL of water, then neutralized to pH 7 with 50% sodium hydroxide solution, and the neutralized solution was extracted with 500 mL (5×100 mL) of ethyl acetate, and the organic phase was mixed after extraction. , then use 200mL (2 × 100mL) saturated saline solution to elute the organic phase, dry with 5% anhydrous magnesium sulfate after the elution, then suction filter to obtain the filtrate, and obtain the concentrated solution after the filtrate is...

example 3

[0022] Preparation of 1,5-dichloroanthraquinone

[0023] Pass 12.2g (171.0mM) of chlorine gas into the mixture of 16mL of dichlorophenylphosphine and 200mL of phenylphosphonic dichloride at room temperature, heat the reaction slightly, but do not exceed 30°C, colorless before The transparent solution turned into a light yellow transparent solution, and 17.0 g (57.0 mM) of 1,5-dinitroanthraquinone was added to the mixed solution, and then heated to 170° C. for 5 h. After the reaction solution was cooled, the reaction solution was poured into 1000 mL of water, then neutralized to pH 7 with 50% sodium hydroxide solution, and the neutralized solution was extracted with 1000 mL (5×200 mL) of ethyl acetate, and the organic phase was mixed after extraction. , then elute the organic phase with 400mL (2×200mL) saturated saline solution, dry with 5% anhydrous magnesium sulfate after the elution, and then filter with suction to obtain the filtrate, and vacuum rotary distillation of the f...

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Abstract

The invention relates to a synthesis method of chloroanthraquinone. Firstly, chlorine is introduced into the mixed liquid of benzene phosphorus dichloride and phenyl phosphonyl chloride at the temperature lower than or equal to 30 DEG C to prepare chlorinating reagent 4-chlorophenyl phosphine, then raw material nitroanthraquinone is added to react for 4 to 6 hours at 160 to 180 DEG C, after the reaction is accomplished, cooling is performed and water is added for dilution, and NaOH solution is used for neutralization, and pH is neutralized to 6.5 to 7.5, then ethyl acetate is used for extraction separation, after extract phase is washed and dried, exsolution and concentration are performed, and finally freezing crystallization is separated, and the separated crystal is the chloroanthraquinone. The method has the advantages that the use of heavy metal is avoided, and the method is beneficial to improving the quality of products and protecting the environment.

Description

1. Technical field [0001] The invention relates to a method for preparing fine chemicals, in particular to a method for preparing a dye intermediate, specifically a method for synthesizing chlorinated anthraquinone. 2. Technical background [0002] Anthraquinone dyes occupy a very important position in the dye industry. Chloroanthraquinone is one of the important intermediates for the synthesis of anthraquinone dyes. The chlorine at the 1-position of anthraquinone is relatively active, and can be easily condensed with aminoanthraquinone to dehydrochloride to form a vat dye with bright colors and excellent firmness. The corresponding dyes can be obtained by reacting 1-chloroanthraquinone, 1,5-dichloroanthraquinone, 1,6-dichloroanthraquinone and 1-aminoanthraquinone. At present, the preparation method of 1-chloroanthraquinone mainly uses anthraquinone as a raw material, through sulfonation under the action of metal mercury as a positioning agent, to generate 1-sulfonic acid ...

Claims

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Application Information

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IPC IPC(8): C07C50/24C07C46/00
Inventor 许华建张博冯乙巳陈四清
Owner HEFEI UNIV OF TECH
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