Synthesis method of polysubstituted hindered phenol antioxygen

A technology of hindered phenol antioxidant and synthesis method, which is applied in the direction of chemical instruments and methods, preparation of organic compounds, production of bulk chemicals, etc., and can solve problems such as high yield, small amount of acid used, and impossibility

Inactive Publication Date: 2010-08-18
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses a small amount of acid and has a high yield, but there is a need to maintain a low pressure during the reaction, a large amount of molecular sieves are needed to absorb the by-product methanol, and 2,6-di-tert-butyl-4-methoxymethyl is still required to be added dropwise. Phenol, long reaction time and other disadvantages
[0015] The above invention generally realizes that the continuous process is complex or impossible, and the yield of the intermediate 3,5-dialkyl-4-hydroxybenzyl methyl ether is relatively low

Method used

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  • Synthesis method of polysubstituted hindered phenol antioxygen
  • Synthesis method of polysubstituted hindered phenol antioxygen
  • Synthesis method of polysubstituted hindered phenol antioxygen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Add 49.6g 2,6-di-tert-butylphenol, 200mL methanol, 12.1g paraformaldehyde, 1.5ml diethylamine, 3.0mL tetramethylethylenediamine into a 500mL autoclave, under the protection of nitrogen, at 70℃ , The reaction is 5h, and the reaction adopts a batch reactor;

[0066] After the reaction, the solvent and the catalyst diethylamine and tetramethylethylenediamine were directly distilled off under reduced pressure, and then cooled to room temperature to obtain 58.2g crude product of 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether. , The content is 93.8%, the recovered solvent methanol, formaldehyde and catalyst are directly used in the next batch of reactions;

[0067] In a 250mL three-necked flask, at a temperature of 25℃, add 25mL dichloromethane, 2.8ml ether, 3ml 95% sulfuric acid, 1.2g mesitylene and 6.4g 3,5-di-tert-butyl-4-hydroxy under stirring. Benzyl methyl ether crude product, reaction temperature is 10℃, time is 0.5h, and then slowly flowed into 3.2g 3,5-di-tert-butyl-4-hy...

Embodiment 2

[0070] Add 49.6g 2,6-di-tert-butylphenol, 13.6g paraformaldehyde, 200mL methanol, 1.5ml dipropylamine, 3.0mL tetramethylethylenediamine into a 500mL autoclave, under the protection of nitrogen, at a temperature of 100℃ , The reaction is 4h, and the reaction adopts a continuous reactor;

[0071] After the reaction, part of the solvent methanol, formaldehyde, catalyst diethylamine and tetramethylethylenediamine were evaporated, then cooled to room temperature, crystallized and filtered to obtain crude 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether It is 58.4g and the content is 93.2%. The recovered solvent methanol, formaldehyde and catalyst are directly used in the next batch of reactions;

[0072] In a 250mL three-necked flask at 15℃, add 25mL dichloromethane, 3.2ml tetrahydrofuran, 3ml 90% sulfuric acid, 1.2g mesitylene and 6.4g 3,5-di-tert-butyl-4-hydroxyl group under stirring. Benzyl methyl ether crude product, reaction temperature is 20℃, time is 1.5h, and then slowly flowed i...

Embodiment 3

[0075] Add 49.6g 2,6-di-tert-butylphenol, 14.4g paraformaldehyde, 200mL 5% aqueous methanol solution, 1.5ml dipropylamine, 3.0mL tetramethylethylenediamine in a 500mL autoclave, under nitrogen protection, React at 110°C for 3h, using batch reactor for reaction;

[0076] After the reaction, under reduced pressure, the solvent and the catalyst diethylamine and tetramethylethylenediamine were directly distilled off, and then cooled to room temperature to obtain the crude product of 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether 58.4 g, the content is 93.8%, the recovered solvent methanol, formaldehyde and catalyst are directly used in the next batch of reactions;

[0077] In a 250mL three-necked flask at a temperature of 40°C, add 25mL of dichloromethane, 1.7ml of dioxane, 3ml of 80% sulfuric acid, 1.2g of mesitylene and 6.4g of 3,5-di-tert-butyl under stirring. The crude product of 4-hydroxybenzyl methyl ether, the reaction temperature is 25℃, the time is 2h, and then 3.2g of crude ...

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Abstract

The invention relates to a synthesis method of polysubstituted hindered phenol antioxygen. In the method, the composition of tertiary amine and secondary amine serves as catalyst to synthetize an intermediate product; after the reaction ends, solvent and the catalyst are distilled to obtain an intermediate crude product; the intermediate is added into halogenated hydrocarbon solution containing organic ether, sulfuric acid and mesitylene reactant once or in batches at room temperature to synthetize polysubstituted hindered phenol antioxygen. The method of the invention avoids the phenomenon that the traditional method utilizes acid to inactivate catalyst and crystallize to produce intermediate 3,5-dialkyl group-4-hydroxy benzyl methyl ether at low temperature; at normal temperature, catalyst is added once, and quick feeding is carried out to synthetize the polysubstituted hindered phenol antioxygen. The method simplifies operation steps, shortens reaction time, reduces material loss, lowers production cost, realizes catalyst recycle and obtains higher yield.

Description

Technical field [0001] The invention relates to a method for synthesizing a multi-substituted hindered phenol antioxidant with relatively mild two-step conditions. Background technique [0002] Multi-substituted hindered phenol antioxidant is a hindered phenol antioxidant with odorless, odorless, low volatility and high molecular weight. The most representative is antioxidant-330, chemical name: 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, and Antioxidant with certain asymmetry 1,3,5-trimethyl-2-(3-methyl-5-tert-butyl-4-hydroxybenzyl)-4,6-bis(3,5- Di-tert-butyl-4-hydroxybenzyl)benzene. It has excellent dielectric properties and is suitable for polyolefin electrical films, PET and PBT and other thermoplastic polyesters, polyamides, styrene resins, polyurethane, natural rubber and other elastomer materials. It has good compatibility with resins and is resistant to extraction. , Low volatility, high anti-oxidant efficiency and good electrical insulation, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/15C07C37/16
CPCY02P20/52Y02P20/584
Inventor 赵文军王华王旭高林王强杨丹红文彬向迎梅
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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