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Preparing method for 3,5-bis(tertiary butyl)-4-hydroxybenzoic acid hexadecane alkyl ester

A technology of n-hexadecyl hydroxybenzoate and hydroxybenzoic acid, which is applied in the field of preparation of n-hexadecyl hydroxybenzoate, can solve solvent distillation recovery energy Consumption, environmental pollution, solvent loss and other problems, to achieve the effect of saving solvent consumption and energy consumption, reducing production costs, and less environmental pollution

Inactive Publication Date: 2016-05-04
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the problems that the existing preparation method has more solvent loss and is easy to cause environmental pollution and high energy consumption for solvent distillation and recovery, the present invention provides a solvent-free preparation of hindered phenol antioxidant and light stabilizer 3,5-di-tert-butyl The method of base-4-hydroxybenzoic acid n-hexadecyl ester, the preparation method of the present invention has the advantages that no solvent is needed in the reaction process, environmental protection, simple production process, and convenient operation

Method used

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  • Preparing method for 3,5-bis(tertiary butyl)-4-hydroxybenzoic acid hexadecane alkyl ester
  • Preparing method for 3,5-bis(tertiary butyl)-4-hydroxybenzoic acid hexadecane alkyl ester

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Experimental program
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Effect test

Embodiment 1

[0024] Add 100g (0.4mol) of 3,5-di-tert-butyl-4-hydroxybenzoic acid, n-deca 290.4 g (1.2 mol) of hexaol and 10 g of p-toluenesulfonic acid as a catalyst were introduced into a nitrogen stream, the temperature was raised to 90° C., the pressure was 10 kPa and the temperature was maintained for 10 h. The end point of the reaction was monitored by TLC. After the reaction, the reaction solution was cooled to 70-75°C, and then the reaction solution was added to saturated aqueous sodium carbonate solution (50mL) (to remove the catalyst and unreacted raw material 3,5-di-tert-butyl-4-hydroxybenzoic acid ), then washed with water until the pH of the water layer was 6.5 to 7, then took the organic layer and evaporated the residual moisture under reduced pressure to obtain a crude product, which was recrystallized with anhydrous methanol, filtered, and the filter cake was dried to obtain White crystalline solid product light stabilizer 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ...

Embodiment 2

[0026] Add 100g (0.4mol) of 3,5-di-tert-butyl-4-hydroxybenzoic acid, n-deca 96.8 g (0.4 mol) of hexanol and 5.0 g of sodium bisulfate were passed through a stream of carbon dioxide, the temperature was raised to 90° C., and the pressure was kept at 6 kPa for 8 hours. The end point of the reaction was monitored by TLC. After the reaction, the reaction solution was cooled to 70-75°C, and then the reaction solution was added to a saturated sodium carbonate aqueous solution (20mL) (to remove the catalyst and unreacted raw material 3,5-di-tert-butyl-4-hydroxybenzoic acid ), then washed with water until the pH of the water layer was 6.5 to 7, then took the organic layer and evaporated the residual moisture under reduced pressure to obtain a crude product, which was recrystallized with anhydrous methanol, filtered, and the filter cake was dried to obtain White crystalline solid product light stabilizer 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester 175.4g, yield reaches 92...

Embodiment 3

[0028] Add 100g (0.4mol) of 3,5-di-tert-butyl-4-hydroxybenzoic acid, n-deca 145.2 g (0.6 mol) of hexaol and 8.0 g of polyphosphoric acid were passed through a stream of carbon dioxide, the temperature was raised to 140° C., and the pressure was kept at 10 kPa for 8 hours. The end point of the reaction was monitored by TLC. After the reaction, the reaction solution was cooled to 70-75°C, and then the reaction solution was added to saturated aqueous sodium bicarbonate solution (50mL) (to remove the catalyst and unreacted raw material 3,5-di-tert-butyl-4-hydroxybenzene formic acid), then washed with water until the pH of the water layer was 6.5-7, then the organic layer was evaporated under reduced pressure to remove the residual moisture to obtain a crude product, which was recrystallized with anhydrous methanol, filtered, and the filter cake was dried Obtain white crystalline solid product light stabilizer 3,5-di-tert-butyl-4-hydroxyl benzoic acid n-hexadecyl ester 170.3g, yiel...

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Abstract

The invention provides a preparing method for 3,5-bis(tertiary butyl)-4-hydroxybenzoic acid hexadecane alkyl ester. The preparing method comprises the steps that 3,5-bis(tertiary butyl)-4-hydroxybenzoic acid, cetyl alcohol and a catalyst are added into a reaction vessel, flow of inert gas is introduced, a heat-preserving reaction is carried out at the temperature of 80 DEG C-160 DEG C, TLC tracks and monitors the reaction till the reaction endpoint, and reaction liquid is subjected to after-treatment to obtain 3,5-bis(tertiary butyl)-4-hydroxybenzoic acid hexadecane alkyl ester. By means of the preparing method, it is unnecessary to adopt other solvent, production cost is saved, and waste gas exhaustion of organic solvent is avoided in the synthesis process; the inert gas serves as a water-carrying agent and a protective agent, operation and control are simple, production safety is good, the color of products is improved, and the method has remarkable economic benefits and has remarkable environmental protection significance.

Description

(1) Technical field [0001] The invention relates to a preparation method of hindered phenol antioxidant and light stabilizer 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester. (2) Background technology [0002] 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester, white solid powder, melting point 60°C, excellent antioxidant light stabilizer, small coloring, low volatility, acid resistance alkali. Light stabilizer suitable for polypropylene, polyethylene and polyvinyl chloride plastics. It can be used alone or in combination with benzophenone UV absorbers or phosphite antioxidants. It has a good synergistic effect. Its molecular formula for C 31 h 54 o 3 , molecular weight is 474.8, molecular structure formula: [0003] [0004] The synthetic method of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl ester has: 1) direct esterification method, for example: with 3,5-di-tert-butyl-4-hydroxybenzoic acid and n-hexadecyl Cetyl alcohol as raw material, cyc...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/84
CPCC07C67/08
Inventor 严晓阳郑绍成丁晓阳
Owner ZHEJIANG NORMAL UNIVERSITY
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