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Catalytic preparation method for hindered phenol derivative antioxygen

A technology for the preparation of hindered phenols by catalysis, which is applied in the preparation of hydrazides, organic chemistry, etc., can solve the problems of unfavorable promotion and use, high product cost, and difficulty in recycling, so as to improve the utilization rate of reaction raw materials, reduce reaction costs, and shorten the reaction time. the effect of time

Inactive Publication Date: 2011-05-11
CHINA PETROLEUM & CHEM CORP +1
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0013] This method avoids the use of thionyl chloride, which reduces possible environmental pollution. However, since the ester compound with hindered phenol structure is added in excess of more than 50%, it is difficult to recycle, resulting in high product cost, which is not conducive to popularization and use.

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  • Catalytic preparation method for hindered phenol derivative antioxygen
  • Catalytic preparation method for hindered phenol derivative antioxygen
  • Catalytic preparation method for hindered phenol derivative antioxygen

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preparation example Construction

[0041] As mentioned above, the catalytic preparation method of the hindered phenolic derivative antioxidant disclosed by the present invention comprises the following steps:

[0042] The first step, acidification reaction:

[0043] in N 2Under protection, add an ester compound with a hindered phenol structure and a first solvent into a reactor, the molar ratio of the first solvent to the ester compound with a hindered phenol structure is 5-20:1; the first solvent At least one selected from the following: methanol, ethanol, aqueous methanol, aqueous ethanol; for example: the molar ratio of the first solvent to the ester compound with a hindered phenol structure can be 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1 or 20:1 1. When using any two, more than two, or all of methanol, ethanol, methanol aqueous solution, and ethanol aqueous solution, the ratio is arbitrary;

[0044] The reaction temperature of the acidification reaction is contr...

Embodiment 1

[0061] Add 1mol of methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (that is, an ester compound with a hindered phenol structure) and 500ml of methanol into a 1L four-necked flask, pass N 2 , start stirring, and heat in a water bath. When the temperature is constant at 60° C., start to add 220 ml of 30% NaOH solution dropwise. After the dropwise addition, slowly heat to 65°C to make the reaction proceed smoothly. After reacting for 4 hours, transfer it to a beaker, then add 1600mL of 2N dilute hydrochloric acid to neutralize, and a white precipitate precipitates, stir for 2 hours, filter, wash with water until neutral, and dry to obtain 290g of intermediate acid.

[0062] Add 1 mol of methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 2000ml of methanol into a 5L three-necked flask, add 350g of hydrazine hydrate, start stirring, heat to 40°C, and keep it for 30h , began to distill off the solvent methanol, then washed with water until neutral, filtered, and drie...

Embodiment 2

[0065] Add 1mol of methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (that is, an ester compound with a hindered phenol structure) and 600ml of methanol into a 1L four-necked flask, pass N 2 , start stirring, and heat in a water bath. When the temperature is constant at 50° C., start to add 200 ml of 30% NaOH solution dropwise. After the dropwise addition, slowly heat to 60°C to make the reaction proceed smoothly. After reacting for 5 hours, transfer to a beaker, then add 1400mL of 2N dilute hydrochloric acid, a white precipitate precipitates, stir for 2 hours, filter, wash and dry to obtain 290g of intermediate acid.

[0066] Add 1 mol of methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 3000ml of methanol into a 5L three-necked flask, add 254g of hydrazine hydrate, start stirring, heat to 50°C, and keep it for 22h , began to distill off the solvent methanol, then washed with water until neutral, filtered, and dried to obtain 291 g of the intermediate monohydra...

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Abstract

The invention discloses a catalytic preparation method for hindered phenol derivative antioxygen. In the invention, a catalytic dehydration process is adopted to prepare the hindered phenol derivative antioxygen, the reaction raw materials are subjected to acidification and monohydrazidation respectively to form two intermediates, and thionyl chloride is not used so as to reduce pollution; and then a solvent and two intermediates are added into a reactor and heated and refluxed to undergo dehydration in the presence of a catalyst, and water is separated out by a water segregator. In the invention, due to the adoption of the catalyst, the reaction temperature is lower, the raw material utilization rate is high, the reaction time is short, and the product yield is high; therefore, the method can contribute to the reduction of production cost and is suitable for industrial production. Evaluation on the use of the antioxygen in polyolefin wire and cables shows that the antioxygen prepared by the method disclosed by the invention has high antioxygen performance and metal passivating capacity.

Description

technical field [0001] The invention relates to the preparation of antioxidants, in particular to the catalytic preparation method of hindered phenolic derivative antioxidants. Background technique [0002] Antioxidants are important additives in the process of polymer processing and application, which can effectively inhibit and slow down the oxidative degradation of polymer materials and prolong their service life. Among all kinds of antioxidants, hindered phenolic primary antioxidants are the most widely used and most used antioxidants, and their consumption accounts for about 55% of the total. They are widely used in plastics, fibers, rubber, petroleum, Grease, cosmetics and food industry. With the rapid development of the plastic additives industry, higher requirements have been placed on the performance of hindered phenolic primary antioxidants. Judging from the development trend of their varieties, multifunctional groups are their main features, which can not only me...

Claims

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Application Information

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IPC IPC(8): C07C243/32C07C241/04
Inventor 贺黎明曾佳马京生何海龙
Owner CHINA PETROLEUM & CHEM CORP
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