Preparation method of triazine anti-aging agent intermediate

A technology for intermediates and antioxidants, applied in the field of preparation of triazine antioxidant intermediates, can solve the problems of low product quality, high proportion of by-products, low reaction yield and the like, and achieves improved reaction yield and product quality. , the effect of reducing the proportion of by-products

Active Publication Date: 2021-07-23
SHANDONG YANGGU HUATAI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is only a process for synthesizing the intermediate with p-phenylenediamine, p-nitroaniline, and cyanuric chloride as raw materials. This process has problems such as high proportion of by-products, low reaction yield and low product quality.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A preparation method of a triazine anti-aging agent intermediate, using p-chloronitrobenzene and melamine as raw materials, the molar ratio of p-chloronitrobenzene and melamine is 3 to 5:1, firstly carry out stepwise heating under normal pressure A stepwise substitution reaction followed by a catalytic reduction reaction under high temperature and pressure conditions yields an intermediate. Specifically include the following steps:

[0022] Step 1, respectively dissolving p-chloronitrobenzene and melamine in an organic solvent, first performing a cooling reaction at -10°C to 0°C for 0.5 to 3 hours, and then raising the temperature to 30°C to 40°C to continue the reaction for 2 to 10 hours, Then raise the temperature to 70°C-90°C for 1-6 hours, add acid-binding agent for 0.5-2 hours to carry out substitution reaction;

[0023] Step 2: After the substitution reaction is completed, the feed liquid is filtered to remove the residue, the filtrate is transferred to the react...

Embodiment 2

[0029] A kind of preparation method of triazine antiaging agent intermediate, take p-chloronitrobenzene and melamine as raw material, the mol ratio of p-chloronitrobenzene and melamine is 3.5:1, at first carry out step-by-step under normal pressure stepwise temperature rise Substitution reaction, followed by catalytic reduction reaction under high temperature and high pressure conditions to obtain intermediates. Specifically include the following steps:

[0030] Step 1, respectively dissolving p-chloronitrobenzene and melamine in any one or more of methanol, ethanol, dimethyl sulfoxide, 1,4-dioxane, tetrahydrofuran, toluene, first in- Cool down the reaction between 5°C and 0°C for 1.5~2h, then raise the temperature to 30°C~35°C and continue the reaction for 5~8h, then raise the temperature to 80°C~85°C for 2~4h, add sodium bicarbonate, sodium carbonate, hydrogen Any one or more of sodium oxide and triethylamine reacted for 0.1 to 1.5 hours to carry out substitution reaction; ...

Embodiment 3

[0034] A preparation method of a triazine antioxidant intermediate, specifically comprising the following steps:

[0035] Step 1, take by weighing 6.3g melamine and dissolve in 40g dimethyl sulfoxide, stir to dissolve, add four-necked flask, then add p-chloronitrobenzene solution (27.56g p-chloronitrobenzene is dissolved in 110g dimethyl sulfoxide ), lower the temperature to -5°C to 0°C, maintain the temperature and continue the reaction for 1.5h, then raise the temperature to 30°C to 35°C and continue the reaction for 5h, then heat to 80°C to 85°C for 3h, then add sodium carbonate to react for 1h, proceed Substitution reaction;

[0036] Step 2, after the substitution reaction is completed, the feed liquid is filtered to remove the residue, and the filtrate is transferred to the reactor, and 3g of 5% palladium carbon catalyst is added to the reactor, after several times of nitrogen and hydrogen replacement, hydrogen is introduced to 2MPa, and the temperature is raised to 80 °...

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Abstract

The invention discloses a preparation method of a triazine anti-aging agent intermediate, and relates to the technical field of organic synthesis, in particular to the preparation method of the triazine anti-aging agent intermediate. The method is characterized in that parachloronitrobenzene and melamine are used as raw materials, step-by-step temperature rise is performed under normal pressure to perform step-by-step substitution reaction, and then catalytic reduction reaction is performed under high-temperature and high-pressure conditions to obtain an intermediate. Compared with the traditional synthesis method, the method has the positive effects of less by-product proportion, higher reaction yield and more stable product quality.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of a triazine antioxidant intermediate. Background technique [0002] In the field of rubber anti-aging agents, although p-phenylenediamine anti-aging agents have the best protective effect, they are easy to migrate out and react with ozone on the surface of the rubber compound to form discolored substances, polluting the tire sidewall surface and affecting the appearance of the tire. The new triazine anti-aging agent introduces a triazine ring into the p-phenylenediamine structure, which not only increases the molecular weight, but also increases the content of anti-aging active structural groups, and has the characteristics of anti-migration, anti-discoloration and long-term anti-aging performance. At present, there is only a process for synthesizing the intermediate with p-phenylenediamine or p-nitroaniline, and cyanuric chloride as raw materials...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/70
CPCC07D251/70
Inventor 王克军李剑波赵振伟杜孟成马德龙
Owner SHANDONG YANGGU HUATAI CHEM
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