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Crystallization purification method of 3,5-di-tert-butyl-4-hydroxybenzoic acid

A technology of hydroxybenzoic acid and di-tert-butyl, which is applied in the field of crystallization and purification of 3,5-di-tert-butyl-4-hydroxybenzoic acid, and can solve problems such as increased ash content

Inactive Publication Date: 2018-05-29
GANSU RES INSTION OF CHEM IND GRICI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, during the acid analysis process, the solids will contain some phenoxides, which will increase the ash content of the product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1; 1. Add 50 g of crude 3,5-di-tert-butyl-4-hydroxybenzoic acid obtained by Kolbe-Schmitt reaction into 83 ml of tetrahydrofuran, stir and dissolve at 60°C, A clear solution was obtained with a solution concentration of 0.6 g / ml.

[0017] 2. Add 2.5 g of activated carbon to the solution, raise the temperature to 65°C for decolorization reaction for 2 hours, and cool down the reaction solution to 60°C after decolorization and filtration.

[0018] 3. Add petroleum ether at 60°C dropwise to the reaction solution until the solution becomes turbid, stop adding petroleum ether, raise the temperature to make the reaction solution from cloudy to clear, and slowly cool down at 5°C / h, and cool the reaction solution to 15°C After that, the crystal growth was continued for 10 h to crystallize 3,5-di-tert-butyl-4-hydroxybenzoic acid from the solvent. Then the crystal slurry was filtered, the filter cake was washed with 15 g of methanol, and dried to obtain 46.51 g of a whit...

Embodiment 2

[0019] Example 2; 1. Add 50 g of crude 3,5-di-tert-butyl-4-hydroxybenzoic acid obtained by Kolbe-Schmitt reaction into 166 ml of toluene, stir and dissolve at 80°C, A clear solution was obtained with a solution concentration of 0.3 g / ml.

[0020] 2. Add 5 g of activated carbon to the solution, raise the temperature to 110°C for decolorization reaction for 2 hours, and cool down the reaction solution to 80°C after decolorization and filtration.

[0021] 3. Add petroleum ether at 80°C dropwise to the reaction solution until the solution becomes turbid, stop the dropwise addition, raise the temperature to make the reaction solution from turbid to clear, slowly cool down at 5°C / h, cool the reaction solution to 15°C and continue to raise Crystal 10h to crystallize 3,5-di-tert-butyl-4-hydroxybenzoic acid from the solvent. Then the crystal slurry was filtered, the filter cake was washed with 15 g of ethanol, and dried to obtain 47.05 g of a white product, that is, 47.05 g of crystal...

Embodiment 3

[0022] Example 3; 1. Add 50 g of the crude 3,5-di-tert-butyl-4-hydroxybenzoic acid obtained by the Kolbe-Schmitt reaction into 166 ml of xylene, stir and dissolve at 80°C , to obtain a clear solution with a solution concentration of 0.3 g / ml.

[0023] 2. Add 2.5 g of activated carbon to the solution, raise the temperature to 110°C for decolorization reaction for 2 hours, and cool down the reaction solution to 80°C after decolorization and filtration.

[0024] 3. Add petroleum ether at 80°C dropwise to the reaction solution until the solution becomes turbid, stop the dropwise addition, raise the temperature to make the reaction solution from turbid to clear, and slowly cool down at 10°C / h, cool the reaction solution to 15°C and continue to raise Crystal 10h to crystallize 3,5-di-tert-butyl-4-hydroxybenzoic acid from the solvent. Then the crystal slurry was filtered, the filter cake was washed with 20 g of ethanol, and dried to obtain 45.8 g of a white product, that is, 45.8 g ...

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PUM

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Abstract

The invention provides a crystallization purification method of 3,5-di-tert-butyl-4-hydroxybenzoic acid, and belongs to the technical field of compound separation and purification. The obtained 3,5-di-tert-butyl-4-hydroxybenzoic acid crude product by the reaction of Kolbe-Schmitt is dissolved in a large polar good solvent, a settled solution is obtained, the concentration of the solution is 0.3-0.6 g / ml, the solution is decolorized, filtered and cooled to a certain temperature, then a soluble analysis agent is dripped into the solution until the solution is turbid, the solution is heated up until the turbid solution becomes clear, a method of slow cooling is used to cool the settled solution, 3,5-di-tert-butyl-4-hydroxybenzoic acid crystallizes from the solvent, and the impurities remain in the mother liquor. A white product is obtained after magma is filtered, washed and dried. The HPLC purity of the processed 3,5-di-tert-butyl-4-hydroxybenzoic acid reaches more than 98.5%, the colorscale is less than 50, the ash specification is less than 0.3%, the yield coefficient is more than 90%, and the crystallization purification method of 3,5-di-tert-butyl-4-hydroxybenzoic acid is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for crystallization and purification of 3,5-di-tert-butyl-4-hydroxybenzoic acid, which belongs to the technical field of compound separation and purification. Background technique [0002] 3,5-di-tert-butyl-4-hydroxybenzoic acid and its derivatives are widely used rubber and plastic antioxidants and ultraviolet absorbers, and are also intermediates in the synthesis of mosquito killers. They are also used in the synthesis of 3,5- Synthesis of 2',-4'-di-tert-butylphenyl di-tert-butyl-4-hydroxybenzoate, n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate and other products. [0003] The crystallization and purification method of 3,5-di-tert-butyl-4-hydroxybenzoic acid of the present invention relates to a method for purifying, removing impurities and reducing the crude product of unpurified 3,5-di-tert-butyl-4-hydroxybenzoic acid Chroma, method of reducing gray content. [0004] The unpurified 3,5-di-tert-butyl-4-hydroxyben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/15C07C51/42C07C51/43C07C51/47C07C65/03
CPCC07C51/15C07C51/42C07C51/43C07C51/47C07C65/03
Inventor 高玉清刘荣何开宇耿来红姬鹏燕
Owner GANSU RES INSTION OF CHEM IND GRICI