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Method for synthesizing benzotriazole compounds

A technology of benzotriazoles and synthetic methods, which is applied in the direction of organic chemistry, can solve the problems of uncontrollable reactions and ineffective effects, and achieve the effects of mild reaction conditions, low cost, and avoiding waste acid and a large amount of waste water

Active Publication Date: 2013-06-19
徐州博创建设发展集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large number of experiments have shown that the conditions for synthesizing nitrogen oxides are relatively mild, and the conditions for further reducing it to products are more violent. If only one reducing agent is used, it is difficult to control the reaction, and good results cannot be achieved.

Method used

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  • Method for synthesizing benzotriazole compounds
  • Method for synthesizing benzotriazole compounds
  • Method for synthesizing benzotriazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Synthesis of 4,4'-dichloroazooxybenzene

[0037] Add 9.42g (60mmol) of p-nitrochlorobenzene, 30mL of 95% ethanol, and 6g (30mmol) of 20% NaOH solution in a three-neck flask, heat to 55°C, and add dropwise 77.1g of a 21% glucose solution (90mmol), reacted for 4 hours, cooled, added water, and suction filtered to obtain 7.82g of solid, with a yield of 97.6%. The measured melting point was 154-155°C (lit.153-154°C). MS: m / z=268.

Embodiment 2

[0038] Example 2 Synthesis of 4,4'-dimethylazooxybenzene

[0039] Add 1.37g (10mmol) of p-nitrotoluene, 5mL of 95% ethanol, and 1.2g (6mmol) of a 20% NaOH solution in a three-neck flask, heat to 55°C, and add dropwise 12.8g of a 21% glucose solution (15 mmol), reacted for 4 hours, cooled, added water, and filtered with suction to obtain 1.05 g of solid, with a yield of 92.6%. The measured melting point was 61-62°C (lit. 61.1-62.0°C). MS: m / z=227.

Embodiment 3

[0040] Example 3 Synthesis of 4,4'-diacetyl azooxybenzene

[0041] Add 1.65g (10mmol) of p-nitroacetophenone, 5mL of 95% ethanol, and 1.2g (6mmol) of 20% NaOH solution in a three-necked flask, heat to 55°C, and add dropwise a glucose solution with a mass fraction of 21%. 12.8g (15mmol), reacted for 4 hours, cooled, added water, and suction filtered to obtain 2.65g of solid, with a yield of 93.7%. The measured melting point was 191-192°C (lit. 190.8-191.5°C). MS: m / z=282.

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Abstract

The invention discloses a method for synthesizing benzotriazole compounds, which comprises the following steps: subjecting o-nitroazoxy compounds of formula (III) to reduction reaction I under an alkaline condition by using water or an ethanol aqueous solution as a reaction solvent and glucose as a reducer; after full reaction, adding zinc chloride into the reaction system as a catalyst, and adding aluminum powder under an alkaline condition to perform a reduction ring-closure reaction II; and after the reaction is accomplished completely, obtaining the benzotriazole compounds of the formula (IV). The method provided by the method solves the problems of waste acid, lots of waste water and the like from a diazotization reaction, adopts mild reaction condition, is environment-friendly and low in cost and is an economic and practical environment-friendly technical route.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing benzotriazole compounds. (2) Background technology [0002] Benzotriazole compounds are high-efficiency light stabilizers, which are characterized by low toxicity and strong ability to absorb ultraviolet rays. They are widely used in polyolefins, polyester resins, coatings, cosmetics and food packaging materials. [0003] The current synthesis route of benzotriazole UV absorbers is to synthesize diazonium salt solution through diazotization reaction of aromatic amine, then couple to synthesize azo intermediate, and then ring-close to generate the final product. The diazotization reaction will produce a large amount of waste water and pollute the environment. As the diazo coupling is a two-step reaction, the conditions are harsh, the diazotization intermediate product is unstable, and the yield is low. The study uses aromatic nitro compounds as raw materials to directly synthesize azoxyl compounds ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/20
Inventor 裴文王海滨孙莉董志刚王菊华
Owner 徐州博创建设发展集团有限公司
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