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Preparation method of carboxyl-substituted metal phthalocyanine

The technology of metal phthalocyanine and carboxylic acid group is applied in the field of preparation of carboxylic acid group-substituted metal phthalocyanine, which can solve the problems of poor economy, long route, expensive raw materials and the like, and achieve the effects of low cost and simple process

Inactive Publication Date: 2013-08-07
SHANDONG UNIV AT WEIHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two methods have long routes, expensive raw materials, and poor economy.

Method used

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  • Preparation method of carboxyl-substituted metal phthalocyanine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1. Solid phase synthesis

[0021] (1) Weigh the medicine according to the following ratio

[0022] trimellitic anhydride Zinc acetate Ammonium molybdate ammonium chloride urea 0.0166mol 0.005mol 0.5mmol 0.0075mol 0.133mol

[0023] 3.20g 1.10g 0.0751g 0.4029g 8.0g

[0024] (2) Mix the medicine in a mortar, grind it fully and evenly, and transfer it to a beaker.

[0025] (3) Heating at 200°C for 3.5 hours.

[0026] (4) Obtain a blue-black tetraamide-substituted zinc phthalocyanine solid, which is soaked by heating with 6 mol / L concentrated hydrochloric acid.

[0027] (5) Wash and centrifuge until the supernatant is colorless.

[0028] 2. Amide hydrolysis

[0029] (1) In a polytetrafluoroplastic cup, transfer the tetraamide-substituted zinc phthalocyanine solid into it, add 100mL of distilled water, 4.0g of sodium hydroxide, and 40.0g of sodium chloride.

[0030] (2) Hydrolyze under alkaline conditions, t=...

Embodiment 2

[0045] 1. Solid phase synthesis

[0046] (1) Weigh the medicine according to the following ratio

[0047] trimellitic anhydride Cobalt chloride hexahydrate Ammonium molybdate ammonium chloride urea 0.0166mol 0.005mol 0.5mmol 0.0075mol 0.133mol 3.20g 1.19g 0.0751g 0.4029g 8.0g

[0048] (2) Mix the medicine in a mortar, grind it fully and evenly, transfer it to a beaker and seal it.

[0049] (3) Put it into a muffle furnace and heat at 200° C. for 3.5 hours.

[0050] (4) Obtain the solid crude product of blue-black tetraamide group substituted cobalt phthalocyanine, and soak it by heating with 6 mol / L concentrated hydrochloric acid.

[0051] (5) Wash and centrifuge until the supernatant is colorless.

[0052] 2. Amide hydrolysis

[0053] (1) In a polytetrafluoroplastic cup, transfer the amide group-substituted cobalt phthalocyanine solid into it, add 100mL distilled water, 4.0g sodium hydroxide, and 40.0g sodium chloride. ...

Embodiment 3

[0069] 1. Solid phase synthesis

[0070] (1) Weigh the medicine according to the following ratio

[0071] trimellitic anhydride copper sulfate Ammonium molybdate ammonium chloride urea 0.0166mol 0.005mol 0.5mmol 0.0075mol 0.133mol

[0072] 3.20g 0.80g 0.0751g 0.4029g 8.0g

[0073] (2) Mix the medicine in a mortar, grind it fully and evenly, transfer it to a beaker and seal it.

[0074] (3) Heating at 200°C for 3.5 hours.

[0075] (4) Obtain a blue-black tetraamide-substituted copper phthalocyanine solid, which is heated and soaked with 6 mol / L concentrated hydrochloric acid.

[0076] (5) Wash and centrifuge until the supernatant is colorless.

[0077] 2. Amide hydrolysis

[0078] (1) In a polytetrafluoroplastic cup, transfer tetraamide-substituted copper phthalocyanine into it, add 100ml of distilled water, 4.0g of sodium hydroxide, and 40.0g of sodium chloride.

[0079] (2) Hydrolyze under alkaline condition ...

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Abstract

The invention belongs to the technical field of organic compound preparation, and specifically relates to a method for preparing metal phthalocyanines substituted by carboxylic acid groups. The preparation mechanism is as follows: a crude carboxyl substituted metal phthalocyanine is synthesized by traditional phthalic anhydride thermal tetramerization reaction. Phthalocyanines with carboxylic acid substituents are not suitable for separation and purification by column chromatography due to the high polarity of the carboxylic acid group. By changing the carboxylic acid substituent around the phthalocyanine ring into an ester group, it can be separated and purified by column chromatography. After purification, high-purity carboxyl metal phthalocyanine can be obtained by hydrolysis. The invention improves the traditional phthalocyanine preparation method of tetramerization of phthalic anhydride, and no other solvent is used in the preparation. After the amide is hydrolyzed, the carboxylic acid group is reacted with the haloalkane under alkaline conditions to convert it into an ester group, and it is purified by column chromatography to obtain a high-purity carboxylic acid group-substituted metal phthalocyanine, which is low in cost and process Simple.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and in particular relates to a preparation method of metal phthalocyanines substituted with carboxylic acid groups. Background technique [0002] As an important organic functional material, phthalocyanine has many uses: it was originally used as a dye. In recent years, due to the special optical and electrical properties of phthalocyanine, it has been widely used in many fields, such as: material science, medicine , light storage, catalysis, etc. However, the solubility of phthalocyanine is limited, especially there are very few types of water-soluble phthalocyanines, and metal phthalocyanines substituted with carboxylic acid groups have been widely used as an important water-soluble phthalocyanine. At present, the high-temperature tetramerization of phthalic anhydride is the main method for preparing carboxylic acid phthalocyanine after obtaining the crude product through ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22
Inventor 柏铭张阳阳王素平方雅宋蕊马庆林刑翔
Owner SHANDONG UNIV AT WEIHAI