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Preparation method of hindered phenol antioxidant 2-methyl-4-hydroxymethyl-6-tert-butyl phenol

A technology of tert-butylphenol and methylol, applied in the field of polymer material preparation, can solve the problems of reduced dosage, high volatility, low molecular weight, etc., and achieve the effects of low volatility, mild reaction conditions and good heat resistance

Inactive Publication Date: 2013-09-04
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 2,6-Di-tert-butylphenol, as the basic variety of phenolic antioxidants, still occupies a dominant position, but due to its relatively low molecular weight, high volatility, and shortcomings such as yellowing and discoloration, the amount is decreasing year by year

Method used

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  • Preparation method of hindered phenol antioxidant 2-methyl-4-hydroxymethyl-6-tert-butyl phenol
  • Preparation method of hindered phenol antioxidant 2-methyl-4-hydroxymethyl-6-tert-butyl phenol
  • Preparation method of hindered phenol antioxidant 2-methyl-4-hydroxymethyl-6-tert-butyl phenol

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Experimental program
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Embodiment 1

[0027] This embodiment provides a kind of 2-methyl-4-hydroxymethyl-6-tert-butylphenol, which is prepared through the following steps:

[0028] Add 80mL of tert-butanol, 2.4g of paraformaldehyde, 6.56g of 2-methyl-6-tert-butylphenol and 0.3g of catalyst potassium hydroxide into a 250mL three-necked flask equipped with a stirrer, a nitrogen conduit and a thermometer, get the mixture;

[0029] Purging with nitrogen, stirring, heating to 82°C for 2.5 hours at a constant temperature, after the reaction, add 80mL of distilled water into the three-necked flask for vacuum distillation;

[0030] Then separate out the solid to obtain the crude product;

[0031] The crude product was recrystallized twice with 60mL isopentane to obtain pure 2-methyl-4-hydroxymethyl-6-tert-butylphenol with a melting point of 125.2°C. For the reaction principle, see figure 1 , see the infrared spectrum figure 2 .

Embodiment 2

[0033] This embodiment provides a kind of 2-methyl-4-hydroxymethyl-6-tert-butylphenol, which is prepared through the following steps:

[0034] 270mL of tert-butanol, 6.2g of paraformaldehyde, 16.4g of 2-methyl-6-tert-butylphenol and 0.45g of catalyst potassium hydroxide were sequentially added to a 1000mL three-necked flask equipped with a stirrer, a nitrogen conduit and a thermometer, get the mixture;

[0035] Purging with nitrogen, stirring, heating to 82°C for 3 hours at a constant temperature, after the reaction, add 150mL of distilled water into the three-necked flask for vacuum distillation;

[0036] Then separate out the solid to obtain the crude product;

[0037] The crude product was recrystallized twice with 260mL isopentane to obtain pure 2-methyl-4-hydroxymethyl-6-tert-butylphenol with a melting point of 125.2°C. For the reaction principle, see figure 1 , see the infrared spectrum image 3 .

Embodiment 3

[0039] This embodiment provides a kind of 2-methyl-4-hydroxymethyl-6-tert-butylphenol, which is prepared through the following steps:

[0040] 590mL of tert-butanol, 13.5g of paraformaldehyde, 32.8g of 2-methyl-6-tert-butylphenol and 1.0g of catalyst potassium hydroxide were sequentially added to a 1000mL three-necked flask equipped with a stirrer, a nitrogen conduit and a thermometer, get the mixture;

[0041] Purging with nitrogen, stirring, heating to 82°C for 3.5 hours at a constant temperature, after the reaction, add 300mL of distilled water into the three-necked flask for vacuum distillation;

[0042] Then separate out the solid to obtain the crude product;

[0043] The crude product was recrystallized twice with 500mL isopentane to obtain pure 2-methyl-4-hydroxymethyl-6-tert-butylphenol with a melting point of 124.6°C and an infrared spectrum shown in Figure 4 .

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Abstract

The invention discloses a preparation method of hindered phenol antioxidant 2-methyl-4-hydroxymethyl-6-tert-butyl phenol. The preparation method comprises the following steps of: mixing raw materials, a solvent and a catalyst so as to obtain a mixture, introducing nitrogen and blowing, subsequently heating and stirring the mixture to be reacted, adding distilled water after the reaction is accomplished, carrying out pressure reduction and distillation so as to obtain a rough product; and recrystallizing the rough product by using isopentane so as to obtain the 2-methyl-4-hydroxymethyl-6-tert-butyl phenol, wherein the raw materials are multi-polyformaldehyde and 2-methyl-6-tert-butyl phenol; the solvent is tert-butyl alcohol; and the catalyst is potassium hydroxide. By utilizing the method, novel hindered phenol antioxidant 2-methyl-4-hydroxymethyl-6-tert-butyl phenol is prepared by utilizing active groups of end groups through simple chemical modification; the antioxidant comprises a methyl and a substituent tert-butyl which is large in size, so that the phenolic hydroxyl group is prevented from oxidation consumption, the complexation in charge transfer is reduced, and the oxidation resistance efficiency of the antioxidant is improved.

Description

technical field [0001] The invention relates to a preparation method of hindered phenolic antioxidant 2-methyl-4-hydroxymethyl-6-tert-butylphenol, which belongs to the technical field of polymer material preparation. Background technique [0002] Antioxidants are additives that inhibit or delay the degradation of polymers due to the action of oxygen or ozone in the atmosphere, and their applications involve almost all polymer products. [0003] Phenolic antioxidants are the main antioxidants of polymer materials. At present, the amount of phenolic antioxidants in my country accounts for about 50% of the consumption of antioxidants. oxygenated. In the chain auto-oxidative growth reaction, the alkyl peroxy ROO in the polymer makes the reaction chain grow through the reaction of abstracting hydrogen. Therefore, the phenolic antioxidant has more active hydrogen than the hydrogen in the polymer, and Compounds that generate stable free radicals after reaction can be used as chain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/11C07C37/11C08K5/13
Inventor 柳荣伟孙倩茹王浩龙华王鉴刘建山李德胜杨晓莉于俊梅李润富
Owner PETROCHINA CO LTD
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