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A kind of bifunctional compound, its synthesis method and application as antioxidant

A synthesis method and bifunctional technology, applied in the field of its synthesis and compound, can solve the problems of antioxidant precipitation, human health hazards, and health effects.

Active Publication Date: 2022-03-29
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When medical polyolefin infusion preforms are sterilized at 120°C for 30 minutes after being filled with normal saline and glucose, the hindered phenolic antioxidants described in US4716244, US5481023, US5563291, US6878843, US2003166962, WO198249 and CN200510112503.9, The phosphite antioxidants described in CN200710056079.X and CN200710176407.X have low molecular weight and are easy to migrate to medicines. The antioxidants migrating to medicines have a certain impact on the health of the human body. When food containers hold food for a long time There will also be a small amount of antioxidants precipitated into the food, affecting human health
Even if the bifunctional antioxidant as described in CN103319523A still has more antioxidants to separate out from the resin due to the small steric hindrance of the hindered phenolic group in the molecule, causing harm to human health

Method used

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  • A kind of bifunctional compound, its synthesis method and application as antioxidant
  • A kind of bifunctional compound, its synthesis method and application as antioxidant
  • A kind of bifunctional compound, its synthesis method and application as antioxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Add 293.5g of 2,6-di-tert-butylphenol, 68.4g of paraformaldehyde, 0.7L of methanol, 2.8g of piperazine and 7.1g of ethylenediamine into a 1.5L reactor, and raise the temperature of the reaction solution to 135°C. Heating was continued under stirring for 3 h and then the heating was stopped. After the reaction solution returned to room temperature, the reaction solution was filtered. The solid product was washed three times with 0.45 L of methanol each time, and the solid was dried to obtain 299.2 g of white product 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether, with a yield of 84%.

[0083] In a 2.5L three-neck round bottom flask, add 1L of dichloromethane, add 38.9g of mesitylene and 299.2g of 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether, and control the temperature of the reaction solution under an ice-salt bath At 0°C, under slow stirring, 104.7 g of concentrated sulfuric acid with a concentration of 0.84% ​​was added dropwise to the reaction solution. The dropwi...

Embodiment 2

[0090] Add 293.5g of 2,6-di-tert-butylphenol, 68.4g of paraformaldehyde, 0.7L of methanol, 2.8g of piperazine and 7.1g of ethylenediamine into a 1.5L reactor, and raise the temperature of the reaction solution to 135°C. Heating was continued under stirring for 3 h and then the heating was stopped. After the reaction solution returned to room temperature, the reaction solution was filtered. The solid product was washed three times with 0.45 L of methanol each time, and the solid was dried to obtain 299.2 g of white product 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether, with a yield of 84%.

[0091] In a 2.5L three-neck round bottom flask, add 1L of dichloromethane, add 38.9g of mesitylene and 299.2g of 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether, and control the temperature of the reaction solution under an ice-salt bath At 0°C, under slow stirring, 104.7 g of concentrated sulfuric acid with a concentration of 0.84% ​​was added dropwise to the reaction solution. The dropwi...

Embodiment 3

[0098] Add 293.5g of 2,6-di-tert-butylphenol, 68.4g of paraformaldehyde, 0.7L of methanol, 2.8g of piperazine and 7.1g of ethylenediamine into a 1.5L reactor, and raise the temperature of the reaction solution to 135°C. Heating was continued under stirring for 3 h and then the heating was stopped. After the reaction solution returned to room temperature, the reaction solution was filtered. The solid product was washed three times with 0.45 L of methanol each time, and the solid was dried to obtain 299.2 g of white product 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether, with a yield of 84%.

[0099] In a 2.5L three-neck round bottom flask, add 1L of dichloromethane, add 38.9g of mesitylene and 299.2g of 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether, and control the temperature of the reaction solution under an ice-salt bath At 0°C, under slow stirring, 104.7 g of concentrated sulfuric acid with a concentration of 0.84% ​​was added dropwise to the reaction solution. The dropwi...

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PUM

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Abstract

A bifunctional compound, its synthesis method and application as an antioxidant. The bifunctional compound is composed of hindered phenol units, phosphite units, trimethylbenzene units and linear chain segment units. By controlling the length of the linear chain unit to adjust the synergistic strength of the hindered phenol unit and the phosphite unit and the content of the effective functional group per unit mass, the trimethylbenzene structure is beneficial to prevent the antioxidant compound from the polymer. Precipitate. The compounds of the present invention are useful as antioxidants for polypropylene or polyethylene.

Description

technical field [0001] The invention relates to a compound and a synthesis method thereof, in particular to a compound containing both hindered phenol and phosphite bifunctional groups in a single molecule and a synthesis method thereof, and the compound can be used as an antioxidant of polyolefin. Background technique [0002] Hindered phenolic compounds can compete with polymers for peroxy radicals formed in auto-oxidation, and through the transfer of hydrogen atoms, form carboxylic acids and a stable antioxidant radical, which has the ability to capture active free radicals. ability to terminate the second kinetic chain of the polymer chain oxidation reaction. The phosphite compound decomposes the peroxide into a stable product through the conversion of itself to the phosphate compound to protect the polymer. Hindered phenolic compounds and phosphite compounds show a very good synergistic effect on the anti-oxidation of polymers. For example, the compounded antioxidants ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/141C08K5/524C08L23/12
CPCC07F9/1411C08K5/524C08L2201/08C08L23/12
Inventor 李广全段宏义李丽吴建杨喜棠高杜娟刘芸赵东波杨世元熊华伟杨柳李艳芹樊洁张顺强张红星
Owner PETROCHINA CO LTD
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