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Preparation method of bisphenol monocarboxylic ester compound antioxidant

A bisphenol monocarboxylate and phenolic compound technology, which is applied in the field of preparation of bisphenol monocarboxylate compound antioxidants, can solve unfavorable large-scale industrial production, low recovery value of triethylamine, and partial color of product appearance Huang and other problems, to achieve the effect of facilitating industrial production, high product yield, and inhibiting polymerization

Inactive Publication Date: 2010-08-04
JIANGSU POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of the process introduced by the above two patents is that phosphorus oxychloride is used as raw material, and phosphorus-containing by-products are introduced into the product, which makes the appearance of the product yellowish.
The weak point of this method is that after the reaction is finished, the solid content in the reaction solution is a mixture of triethylamine hydrochloride and triethylamine p-toluenesulfonate, which also has difficulty in separation and purification, and the recovery value of triethylamine is small. Water washing method will produce a large amount of industrial wastewater, which is not conducive to large-scale industrial production

Method used

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  • Preparation method of bisphenol monocarboxylic ester compound antioxidant
  • Preparation method of bisphenol monocarboxylic ester compound antioxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] In a 5000mL five-necked flask equipped with a stirrer, thermometer, acryloyl chloride addition funnel, triethylamine addition funnel, and reflux cooler, add 2,2'-methylenebis(4-methyl-6-tert-butylphenol) ) 340.50g (1.00mol), 1800mL of n-heptane. Replace the air in the kettle with nitrogen, heat and stir, and raise the temperature to 57-60°C. Keep constant at this temperature, start dripping 99.56g (1.10mol) of acryloyl chloride, and finish adding in 40-50 minutes. While acryloyl chloride was dripped, 121.43g (1.20mol) of triethylamine raw material was dripped, and the time for dripping the triethylamine raw material was 70-80 minutes. After adding the triethylamine raw material, the reaction solution is heated to 63-65°C. At this temperature, the reaction is kept for 120 to 130 minutes.

[0037] After the completion of the reaction, the resulting reaction mixture is a solid-liquid mixture. After filtration, the filter cake triethylamine hydrochloride was washed with 20...

Embodiment 2

[0040] In a 5000mL five-necked flask equipped with a stirrer, thermometer, acryloyl chloride addition funnel, triethylamine addition funnel, and reflux cooler, add 2,2'-methylenebis(4-methyl-6-tert-butylphenol) ) 340.50g (1.00mol), 1800mL petroleum ether. Replace the air in the kettle with nitrogen, heat and stir, and raise the temperature to 63-65°C. Keep constant at this temperature, start dripping 108.61g (1.20mol) raw material of acryloyl chloride, and finish adding in 40-50 minutes. While acryloyl chloride was dripped, 131.55g (1.30mol) of triethylamine raw material was dripped, and the time for dripping the triethylamine raw material was 70-80 minutes. After adding the triethylamine raw material, the reaction solution is heated to 67-70°C. At this temperature, the reaction is kept for 150-160 minutes.

[0041] After the completion of the reaction, the resulting reaction mixture is a solid-liquid mixture. After filtering, the filter cake triethylamine hydrochloride was w...

Embodiment 3

[0044] In a 5000mL five-necked flask equipped with a stirrer, thermometer, acryloyl chloride addition funnel, triethylamine addition funnel, and reflux cooler, add 2,2'-methylenebis(4-methyl-6-tert-butylphenol) ) 340.50g (1.00mol), 1800mL petroleum ether. Replace the air in the kettle with nitrogen, heat and stir, and raise the temperature to 64-66°C. Keep constant at this temperature, start dripping 117.66g (1.30mol) of acryloyl chloride, and finish adding in 40-50 minutes. While acryloyl chloride was dripped, 141.67g (1.40mol) of triethylamine was dripped, and the time for dripping the triethylamine raw material was 70-80 minutes. After adding the triethylamine raw material, the reaction solution is heated to 72-75°C. At this temperature, the reaction is kept for 120 to 130 minutes.

[0045] After the completion of the reaction, the resulting reaction mixture is a solid-liquid mixture. After filtering, the filter cake triethylamine hydrochloride was washed with 200mL petrol...

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Abstract

The invention relates to a preparation method of a bisphenol monocarboxylic ester compound antioxidant product which mainly used for synthesizing high molecular materials of rubber, polyolefine plastics, engineering plastics and the like. The invention adopts bisphenol compound and fatty acyl chloride as raw materials, triethylamine as acid absorbent, and the aliphatic hydrocarbon as solvent to generate the bisphenol monocarboxylic ester compound antioxidant product by esterification reaction. Suitable process conditions for synthesizing the bisphenol monocarboxylic ester compound are as follows: the mol ratio of the bisphenol compound to the fatty acyl chloride is 1.1-1.3; the mol ratio of the bisphenol compound to the triethylamine is 1:1.3-1.5; the reaction temperature is 60-85 DEG C; and the reaction time is 120-240 minutes. The bisphenol monocarboxylic ester compound antioxidant product is obtained by filtering, separating, crystallizing and refining after the reaction. The invention has the characteristics of simple production process, high product yield, high quality and convenient industrialized production. The obtained white crystallized bisphenol monocarboxylic ester antioxidant product can be used for high molecular materials having high requirements for color.

Description

Technical field [0001] The invention relates to a preparation method of a bisphenol monocarboxylate compound antioxidant. The bisphenol monocarboxylate compound antioxidant specifically refers to the following formula (I): [0002] [0003] R in formula (I) 1 =C 1 ~C 5 Straight or branched alkyl groups; [0004] R 2 = H or CH 3 ; [0005] R 3 =CH 3 Or vinyl [0006] Bisphenol monocarboxylate antioxidant is an excellent antioxidant product, mainly used in synthetic rubber, polyolefin plastics, engineering plastics and other polymer materials. Background technique [0007] Traditional bisphenol antioxidants will be converted into coloring quinone compounds during use, causing oxidative discoloration of polymer materials and limiting the use of bisphenol antioxidants. With the improvement of the level of production and application of polymer materials, traditional bisphenol antioxidants can no longer meet the anti-aging requirements of polymer materials for their own mechanical propertie...

Claims

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Application Information

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IPC IPC(8): C07C69/54C07C67/14C07C69/16
Inventor 杜飞范延超耿旺刘涛民徐婷婷
Owner JIANGSU POLYTECHNIC UNIVERSITY
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