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Phenolic amine antioxidant and preparation method and application thereof

An antioxidant and phenolamine technology, applied in the field of antioxidants, can solve the problems of cumbersome preparation process operation, harsh process conditions, limited improvement range, etc., and achieve the effects of simple post-processing, simple and easy operation process, and short reaction time.

Active Publication Date: 2016-04-20
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although the thermal stability and antioxidant performance of these existing composite antioxidants have been improved compared with traditional hindered phenolic antioxidants and alkylated diphenylamine antioxidants, the improvement range is limited, and The preparation process is cumbersome, the process conditions are harsh, and the cost is high

Method used

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  • Phenolic amine antioxidant and preparation method and application thereof
  • Phenolic amine antioxidant and preparation method and application thereof
  • Phenolic amine antioxidant and preparation method and application thereof

Examples

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preparation example Construction

[0064] In some embodiments, the preparation method specifically includes: taking hindered phenol halides, diphenylamine and / or diphenylamine derivatives and / or phenothiazines and / or phenothiazine derivatives and N-alkylated catalysts in Mixing and reacting in a liquid phase reaction medium to obtain the phenolic amine antioxidant.

[0065] For example, in a more specific embodiment, the preparation method may include: reacting the reactants (A) and (B) in the presence of a catalyst (C) and optionally in a liquid phase reaction medium (D), thereby forming a suitable It is especially suitable for reaction products of phenolic amines as antioxidants.

[0066] For example, the following components can be used as reactants to form the products of the invention:

[0067] Reactant (A): hindered phenol halide, which can be selected from non-limiting sterically hindered 3,5-disubstituted-4-hydroxybenzyl chloride, 3,5-disubstituted-4-hydroxybenzyl bromide, 3,5-Disubstituent-4-hydroxyb...

Embodiment 1

[0087]Embodiment 1: After fully drying the three-necked reaction flask of 250ml, add reaction product diphenylamine (3.57g), reaction solvent toluene (80ml) successively, after diphenylamine is completely dissolved, add sodium hydroxide (1.77g), at room temperature After stirring for 40 minutes, 3,5-di-tert-butyl-4-hydroxybenzyl iodide (5.40 g) was added, the temperature was raised to 100° C., and the mixture was reacted for 5 hours. Then dilute with 80ml of water and 80ml of ethyl acetate, after phase separation, the organic phase is washed with water (2×80ml), washed with anhydrous MgSO 4 dry. The solvent was removed under reduced pressure to obtain 5.0 g of light yellow solid product 2,6-di-tert-butyl-4((dianilino)methyl)phenol. of the product 1 HNMR spectrum (DMSO, 400MHz) and 13 CNMR spectrum (DMSO, 100MHz) can be found in Figure 2-Figure 3 .

Embodiment 2

[0088] Example 2: After fully drying the 250ml three-necked reaction flask, add the reaction product diisooctyldiphenylamine (12.22g) and the reaction solvent xylene (100ml) in sequence, and after the diisooctyldiphenylamine is completely dissolved, add the hydrogenation Calcium (2.50g), stirred at room temperature for 40 minutes, added 3,5-di-tert-butyl-4-hydroxybenzyl bromide (5.40g), heated to 90°C, and reacted for 3 hours. Then diluted with 100ml of water and 100ml of ethyl acetate, after phase separation, the organic phase was washed with water (2×10ml), washed with anhydrous MgSO 4 dry. The solvent was removed under reduced pressure to obtain the light yellow solid product 2,6-di-tert-butyl-4-((bis-(4-(2,4,4-trimethylpentyl-2 base) diphenylamino ) methyl) phenol 11.07g. The product 1 HNMR spectrum (CDCl 3 , 400MHz) and 13 CNMR spectrum (CDCl 3 , 100MHz) can refer to Figure 4-Figure 5 .

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Abstract

The present invention discloses a phenolic amine antioxidant which comprises a compound having the structure as shown in the specification, wherein R1, R2 and R3 are respectively independently selected from H, alkyl, cycloalkyl, aryl, alkaryl and aralkyl groups; at least one of R4 and R5 is selected from the structure as shown in a formula in the specification, R6 is at least selected from-S-,-O-and-NH-, m is 0 or 1; R8 and R7 are respectively independently selected from H, alkyl, cycloalkyl, aryl, alkaryl and aralkyl groups; n is selected from any integer of 1 to 12. The present invention also discloses a preparation method of the phenolic amine antioxidant. The phenolic amine antioxidant has excellent thermal stability and good oxidation resistance, the preparation process is simple and practical, rapid, mild in reaction conditions and simple in post-treatment, the phenolic amine antioxidant is suitable for being widely used in the field of lubrication oil, fuels (especially fuel oil), plastic or rubber, and the like.

Description

technical field [0001] The invention relates to an antioxidant, in particular to a phenolamine antioxidant, its preparation method and application. Wherein, the phenolic amine antioxidant refers to a compound antioxidant having double units of hindered phenol and diphenylamine in the same antioxidant molecule. Background technique [0002] Many organic materials are prone to oxidative degradation during storage and use, especially in air or oxygen atmosphere and high temperature conditions. At present, the most effective way to inhibit and delay the degradation and deterioration of organic materials is to add antioxidants to these organic materials. Alkylated diphenylamines and hindered phenolic antioxidants are two types of primary antioxidants that are widely used. These two types of primary antioxidants contain active hydrogen atoms in their molecules, so they can interact with organic materials in the process of oxidative degradation. The free radicals produced in the ...

Claims

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Application Information

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IPC IPC(8): C10M133/14C10M135/36C10M177/00C10L1/223C10L1/24C08K5/18C08K5/46C10N30/10C10N30/06C10N30/08
Inventor 刘升高王立敏俞莎莎王声培贺军令刘丹
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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