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Phenol amine antioxidant as well as preparation method and application thereof

A technology of antioxidants and phenolic amines, applied in the field of antioxidants and their preparation, can solve the problems of few types of antioxidants and cannot meet diversified needs, and achieve low dyeing pollution, easy industrialization, and not easy to deteriorate Effect

Active Publication Date: 2021-12-24
GUIZHOU MATERIAL IND TECH INSTITUE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been reports of hindered phenol and hindered amine intramolecular compounding to form composite antioxidants in existing reports, such as patent CN102516157B, which discloses a synthetic method of hindered phenol / hindered amine intramolecular composite antioxidants, but , the types of such antioxidants are still relatively small, and cannot meet the diverse needs of the market

Method used

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  • Phenol amine antioxidant as well as preparation method and application thereof
  • Phenol amine antioxidant as well as preparation method and application thereof
  • Phenol amine antioxidant as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The synthetic route is as follows:

[0048]

[0049] The synthesis steps are as follows:

[0050] (1) Dissolve compound I (1mol) and compound II (1mol) in toluene, then add 2.5mol of Na 2 CO 3 The prepared 2mol / L aqueous solution and 0.06mol of Pd(PPh 3 ) 4 , after replacing the nitrogen three times, under the protection of nitrogen, react at 85°C for 6 hours;

[0051] (2) After the reaction is completed, cool to room temperature, add water to wash, take the upper organic phase, dry it with anhydrous magnesium sulfate, and remove the solvent by rotary evaporation, then pass through 200-300 mesh silica gel column chromatography, and the eluent composition is volume ratio 2 Chloromethane pure: petroleum ether = 3: 1, to obtain compound III;

[0052] (3) Compound III (1mol), Pd / C catalyst (50g) and N 2 h 4 -H 2 O (hydrazine hydrate, 200ml) was dissolved in EtOH, and reacted at 60°C for 2 hours. After the reaction, the Pd / C catalyst was removed by suction filtrat...

Embodiment 2

[0056] Synthetic route is with embodiment 1, and synthetic steps are as follows:

[0057] (1) Dissolve compound I (1mol) and compound II (1mol) in dioxane, then add 2.5mol of K 2 CO 3 Prepared 2mol / L aqueous solution and 0.06mol PdCl 2 , after replacing the nitrogen three times, under the protection of nitrogen, react at 85°C for 6 hours;

[0058] (2) After the reaction is completed, cool to room temperature, add water 3-5 times the volume of the reaction solution, and precipitate a large amount of crude product. After filtering, dissolve in dichloromethane, dry with anhydrous magnesium sulfate, and pass through 200-300 mesh silica gel Column chromatography, the eluent composition is pure by volume ratio of dichloromethane:petroleum ether=3:1, to obtain compound III;

[0059] (3) Compound III (1mol), Pd / C catalyst (50g) and N 2 h 4 -H 2 O (hydrazine hydrate, 200ml) was dissolved in EtOH, and reacted at 60°C for 2 hours. After the reaction, the Pd / C catalyst was removed b...

Embodiment 3

[0063] The synthetic route is as follows:

[0064]

[0065] The synthesis steps are as follows:

[0066] (1) Dissolve compound I (1mol) and compound II (1mol) in toluene or dioxane, then add 2mol of Cs 2 CO 3 Prepared 2mol / L aqueous solution and 0.03mol Pd(dppf)Cl 2 , after replacing the nitrogen three times, under the protection of nitrogen, react at 70°C for 8 hours;

[0067] (2) After the reaction is completed, cool to room temperature, add water to wash, take the upper organic phase, dry with anhydrous sodium sulfate, and remove the solvent by rotary evaporation, then pass through 200-300 mesh silica gel column chromatography, and the eluent composition is volume ratio 2 Chloromethane pure: petroleum ether = 3: 1, to obtain compound III;

[0068] (3) Compound III (1mol), Pd / C catalyst (30g) and N 2 h 4 -H 2 O (hydrazine hydrate, 150ml) was dissolved in EtOH, and reacted at 55°C for 3h. After the reaction, the Pd / C catalyst was removed by suction filtration, dried...

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Abstract

The invention discloses a phenol amine antioxidant as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving a compound I and a compound II in an organic solvent, then adding a Na2CO3 aqueous solution and a Pd catalyst, carrying out a heating reaction, cooling the reaction product to room temperature, and carrying out post-treatment and chromatographic separation to obtain a compound III; dissolving the compound III in EtOH, then adding a Pd / C catalyst and N2H4-H2O, heating to react, filtering and drying after the reaction, and spin-drying to obtain a compound IV; mixing a compound IV, dry toluene, Pd (dba) 2, t-Bu3P and NaOBu-t, slowly adding a toluene solution of a compound V, and carrying out a heating reaction to obtain a product C; and cooling the product C to room temperature, washing, standing, taking an upper organic phase, drying, carrying out rotary evaporation, and carrying out chromatographic separation to obtain a compound VI. The phenol amine antioxidant disclosed by the invention belongs to a novel composite antioxidant, has the characteristics of good oxidation resistance and small dyeing pollution, and can be widely applied to synthetic resin; preparation conditions are mild, raw materials are easy to obtain, and industrial popularization is easy.

Description

technical field [0001] The invention relates to an antioxidant and its preparation method and application, in particular to a phenolamine antioxidant and its preparation method and application. Background technique [0002] Antioxidant is a kind of chemical substance, when it only exists in a small amount in the polymer system, it can delay or inhibit the oxidation process of the polymer, thereby preventing the aging of the polymer and prolonging its service life, also known as " anti-aging agent". There are many types of antioxidants currently on the market, and hindered phenol antioxidants and hindered amine antioxidants are two common types. [0003] Among them, hindered phenolic antioxidants are mostly used in plastic products, and show synergistic effects with auxiliary antioxidants such as phosphite and thioether. Representative varieties include 2,8-di-tert-butyl-4-methylphenol, antioxidant 1010, etc. Hindered amine is a relatively new type of anti-ultraviolet / anti...

Claims

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Application Information

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IPC IPC(8): C08K5/3417C08K5/18C07D209/86C07C225/22C07C221/00C08L67/02C08J5/18
CPCC08K5/3417C08K5/18C07D209/86C07C225/22C07C221/00C07C201/12C08J5/18C08J2367/02C07C205/45Y02P20/52
Inventor 黄绍文庞会霞李娟高成涛罗珊珊王彦文张黎
Owner GUIZHOU MATERIAL IND TECH INSTITUE
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