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Method for synthesizing hindered phenol antioxidants

A synthesis method and technology of hindered phenols are applied in the synthesis field of oxidants, which can solve the problems of affecting the color and luster of antioxidants, low activity and the like, and achieve the effects of high production efficiency, high activity and excellent product performance.

Active Publication Date: 2011-01-26
圣莱科特精细化工(上海)有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These catalysts are all heterogeneous solid catalysts, so there are shortcomings such as low activity and the need to separate the steps of the catalyst after the end of the reaction. In addition, these catalysts also have weak alkalinity. After the end of the reaction, they need to be neutralized with an acid, otherwise Will affect the color of antioxidants
[0004] In the ninth issue of "Chemical World" in 2003, the paper "3-(3,5-di-tert-butyl-4-hydroxyphenyl) octadecyl propionate synthesis process improvement" proposed the use of dioctyl tin oxide As a catalyst, although this type of catalyst has high activity, organotin compounds are gradually being eliminated due to their toxicity to the human body

Method used

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  • Method for synthesizing hindered phenol antioxidants
  • Method for synthesizing hindered phenol antioxidants
  • Method for synthesizing hindered phenol antioxidants

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Synthetic method of β-(3,5-di-tert-butyl-4-hydroxyphenyl) octadecyl propionate (antioxidant 1076)

[0038] 220.0 grams of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid methyl ester (abbreviated as 35 methyl ester) and 180.0 grams of carbon octadecyl alcohol are joined in a 1000ml four-necked flask with a stirring bar and a thermometer, and the temperature is raised to Melt the material at 70°C, then vacuumize, keep the vacuum at 20mmHg for 0.5 hours, pass N 2 , remove the vacuum, then under the protection of nitrogen, add 0.73 grams of zinc isooctanoate, turn off the nitrogen, vacuumize, and start to heat up to 185 ° C at the same time, at the initial stage of the reaction, because there is more methanol produced, the vacuum degree is 10 ~ 20mmHg, reaction 2 After one hour, the vacuum was controlled at 3 to 5 mmHg, and the reaction was continued for 4 hours.

[0039] After the reaction was completed, the temperature was raised to 195° C., and 27.1 g of unreacted 35 m...

Embodiment 2

[0042] Synthetic method of β-(3,5-di-tert-butyl-4-hydroxyphenyl) octadecyl propionate (antioxidant 1076)

[0043] 200.0 grams of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid methyl ester (abbreviated as 35 methyl ester) and 220.0 grams of carbon octadecyl alcohol are added in a 1000ml four-necked flask with a stirring bar and a thermometer, and the temperature is raised to Melt the material at 70°C, then vacuumize, keep the vacuum at 20mmHg for 0.5 hours, pass N 2 , remove the vacuum, then under the protection of nitrogen, add 0.73 grams of zinc isooctanoate, turn off the nitrogen, vacuumize, and start to heat up to 185 ° C at the same time, at the initial stage of the reaction, because there is more methanol produced, the vacuum degree is 10 ~ 20mmHg, reaction 2 After one hour, the vacuum was controlled at 3 to 5 mmHg, and the reaction was continued for 4 hours.

[0044] After the reaction was completed, the temperature was raised to 195° C., and 35.3 grams of unreacted i...

Embodiment 3

[0047] Synthetic method of bis[β-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate] hexanediol ester (antioxidant 259)

[0048] Add 358.2 grams of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid methyl ester (referred to as 35 methyl ester) and 60.0 grams of hexanediol into a 1000ml four-necked flask with a stirring bar and a thermometer, and heat up to 90°C , then, vacuumize, keep the vacuum at 10mmHg for 0.5 hours, pass N2, remove the vacuum, then add 1.10 g of zinc isooctanoate under nitrogen protection, turn off the nitrogen, vacuumize, and start to heat up to 165 ° C at the same time, the initial stage of the reaction , because more methanol is produced, the vacuum degree is 10-20 mmHg, after 2 hours of reaction, the vacuum degree is controlled at 3-5 mmHg, and the reaction is continued for 3 hours.

[0049] After the reaction was completed, the temperature was raised to 195° C., and 58.2 grams of unreacted 35 methyl esters were distilled off. The temperature was lowered to...

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Abstract

The invention relates to a synthesis process of hindered phenol anti-oxidant, which comprises evenly mixing compound II and compound III, adding in catalyst whose molar percent content is 0.05-5% of compound II, pumping vacuum, conducting ester exchange reaction for 1-20 hours under the conditions that the vacuum degree is 1-100 mmHg, the temperature is 120-200 DEG C, thereby generating hindered phenol anti-oxidant with structural formula I. Compared with the prior art, the invention has the characteristics of simple process, high production efficiency and excellent product property and the like.

Description

technical field [0001] The invention relates to the synthesis of an oxidizing agent, in particular to a synthesis method of a hindered phenolic antioxidant. Background technique [0002] Hindered phenolic compounds are the most widely used antioxidants in the polymer industry because they can capture peroxyl radicals. They can inhibit the oxidative and thermal degradation of many organic compounds and polymers. They have been widely used in polyolefins, ABS resins, Synthetic rubber, polyester, ester amide, grease, paint, lubricating oil, etc., also suitable for some food packaging materials, with good compatibility, high anti-oxidation performance, no coloring, no pollution, resistance to washing, extraction, heat resistance , low volatility, and other characteristics, it has a synergistic effect when used in combination with ultraviolet absorbers. [0003] Hindered phenolic antioxidants are usually produced by transesterification under the action of a basic catalyst. US47...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/03C07C69/73C09K15/08
Inventor 严光明
Owner 圣莱科特精细化工(上海)有限公司
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