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Green synthetic method of 2,5-diaminotoluene

A technology of diaminotoluene and nitroaniline, which is applied in 2 fields, can solve the problems of harsh reaction conditions, pollution of three wastes, and infrequent use, and achieve the effects of high reaction yield, low environmental pollution, and good product purity

Active Publication Date: 2010-03-03
山东兴安智慧科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for the reduction of nitro, the iron powder reduction method is often used in industry, and the cost is high and the three wastes are seriously polluted.
In addition, the use of liquid paraffin for reduction is not commonly used in industry at present.

Method used

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  • Green synthetic method of 2,5-diaminotoluene
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Examples

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preparation example Construction

[0018] (1) Preparation of magnetic sol:

[0019] FeSO 4 ·6H 2 O, Fe 2 (SO 4 ) 3 · x H 2 O is formulated into an aqueous solution at a molar ratio of 1:2, and this solution is added to a three-neck flask, and the temperature is controlled at 338±5K, and 20% (w / w) ammonia water is added dropwise, while vigorously stirring until the pH value is 10~ 11. Continue to age at this temperature for 60 minutes after dripping to obtain an oily black precipitate. Use a magnetic field to attract and pour off the supernatant, and then wash until neutral and free of SO 4 2- (Ba 2+ inspection), spare.

[0020] (2) Synthesis of magnetic magnesium aluminum hydrotalcite:

[0021] Take a certain amount of magnetic sol and add it to a three-necked bottle, add twice distilled water, stir vigorously, control the temperature at 280±5K, take a certain amount of Mg(NO 3 ) 2 ·6H 2 O, Al(NO 3 ) 3 9H 2 O is prepared into 250 mL of nitrate aqueous solution, wherein C (Mg 2+ )+C(Al 3+ )=1.5m...

Embodiment 1

[0023] In a 500mL three-necked flask, add 152g (1 mole) of 2-methyl-4-nitroaniline, 300mL of ethanol, and 7.6g (5%) of a magnetic magnesium-aluminum hydrotalcite solid base catalyst, stir, and heat to make p-chloronitrate Dissolve benzene, raise the temperature to 50°C, slowly add hydrazine hydrate 96g (3 moles) dropwise for 1 hour, keep warm (50°C) and react for 5 hours, filter while it is hot, take the filtrate and add 500mL of water to make the solution alkaline , cooled to below 0°C, left standing, white crystals were precipitated, filtered and dried to obtain 98 g of 2,5-diaminotoluene with a yield of 80%.

[0024] The melting point of the product is >300°C. The purity is 98% (HPLC analysis conditions: chromatographic column C18, Φ4.0×200mm, column temperature 30°C, mobile phase 30% methanol-70% 0.02M phosphate buffer). IR(KBr)cm -1 : 3045, 2880, 2610, 2090, 1605, 1555, 1510, 1168, 1145, 1010, 822, 850.

Embodiment 2

[0026] In a 500mL three-necked flask, add 152g (1 mole) of 2-methyl-4-nitroaniline, 300mL of ethanol, and 1.5g (1%) of a magnetic magnesium-aluminum hydrotalcite solid base catalyst, stir and heat to make p-chloronitrate Dissolve benzene, raise the temperature to 100°C, slowly add 64g (2 moles) of hydrazine hydrate dropwise for 1 hour, keep warm (100°C) and react for 10 hours, filter while it is hot, take the filtrate and add 500mL of water to make the solution alkaline , cooled to below 0° C., left standing, white crystals were precipitated, filtered and dried to obtain 85 g of 2,5-diaminotoluene with a yield of 70%.

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Abstract

The invention provides a green synthetic method of 2,5-diaminotoluene shown as the formula (II). The method comprises the following steps: taking 2-methyl-4-nitroaniline as raw material, magnetic Mg / Al-hydrotalcite solid alkali as catalyst and hydrazine hydrate as reducing agent, reacting at the temperature of 0-100 DEG C for 1-20 hours, and separating and purifying the reaction solution to prepare the 2,5-diaminotoluene. Compared with the prior art, the green synthetic method has the beneficial effects that: the magnetic Mg / Al-hydrotalcite solid alkali taken as catalyst and the hydrazine hydrate taken as reducing agent are applied in the synthesis of the 2,5-diaminotoluene, so that compared with the prior art, the preparation of the 2,5-diaminotoluene is simpler in processing, easy in operation, high in reaction yield, and good in product purity, has no pollution to environment, is suitable for industrialized production with a certain scale, is a green and clean synthetic line, and has no application report of industrialized production at present.

Description

(1) Technical field [0001] The invention relates to a synthesis method of 2,5-diaminotoluene, in particular to a method for preparing 2,5-diaminotoluene using a magnetic solid base as a catalyst, using 2-methyl-4-nitroaniline as a raw material, and utilizing hydrazine hydrate reduction method to prepare 2,5-diaminotoluene. - Green new process of diaminotoluene. (2) Background technology [0002] The development of new and efficient catalysts, the simplification of reaction steps, the reduction of pollution emissions, the development of new clean production technologies, the realization of efficient chemical reactions, and the realization of "zero emissions" have important application value in the field of green chemistry. 2,5-diaminotoluene is the main product that replaces p-phenylenediamine and is used in high-end hair cosmetics for dyeing. The demand in Europe, the United States and Japan alone exceeds 600 tons per year. At present, all kinds of hair dye products produce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/51C07C209/36B01J21/10
Inventor 裴文杨振平王海滨潘海燕余晓婷
Owner 山东兴安智慧科技有限公司
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