Preparation method of diphenylamine or ring-substituted derivative thereof

A ring-substituted, diphenylamine technology is applied in the field of preparing diphenylamine or its ring-substituted derivatives, and can solve the problems of not achieving energy saving, consumption reduction, pollution reduction, efficiency enhancement and clean production process, shortening reaction time, etc. , to achieve the effect of improving equipment utilization, shortening the reaction cycle and simplifying the production process

Active Publication Date: 2013-05-08
SHANDONG DOCRIS CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the inventor's patent, although the utilization rate of atoms in the deacylation reaction is improved, the waste is reduced, the reaction time is shortened, the energy consumption is reduced, and the production cost is reduced, but the problem of the condensation reaction stage still exists
From the point of view of the entire production process (including condensation reaction process and deacylation reaction process) from conventional raw materials to target products, the ideal goal of a clean production process of "energy saving, consumption reduction, pollution reduction, and efficiency enhancement" has not yet been achieved.

Method used

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  • Preparation method of diphenylamine or ring-substituted derivative thereof
  • Preparation method of diphenylamine or ring-substituted derivative thereof
  • Preparation method of diphenylamine or ring-substituted derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Add 201.5g (1.0mol) of 4-bromo-3-methylanisole, 141.8g (1.05mol) of acetanilide, and 3.8g (0.038mol) of cuprous chloride into the reactor, and start heating while stirring , when the temperature of the material in the reactor reaches 200°C, start to add 234.0g (1.3mol) of 30wt% sodium methoxide methanol solution dropwise for 8 hours, and keep the temperature of the reaction material at 200°C during the dropping process. After the dropwise addition, the insulation reaction was continued for 0.5 hour, and the reaction ended. Obtained methanol and methyl acetate mixture fraction 207.3g, methyl acetate content 26.2% (gas chromatography analysis).

[0067] Add 200g of water and 500ml of toluene to the reaction mixture containing 4-methoxy-2-methyldiphenylamine to dissolve the soluble substances in the system, filter to remove the insoluble substances, separate the toluene layer, and then extract the water layer with 300ml of toluene 2 times, the toluene layer was combined w...

Embodiment 2

[0069] As described in Example 1, the difference is that 10% of the total amount of 4-bromo-3-methylanisole, that is, 20.2g (0.1mol), is added to the reactor simultaneously with acetanilide, and the remaining 90%, that is, 181.3 g (0.9mol) and 234.0g (1.3mol) of 30wt% methanol solution of sodium methoxide were added dropwise at the same time, and the rate of addition was controlled. The time for adding 4-bromo-3-methylanisole was 6 hours, and the sodium methoxide solution The dropwise addition time was 6.5 hours.

[0070] 188.0 g of the target product 4-methoxy-2-methyldiphenylamine was obtained, with a purity of 99.3% (gas chromatography analysis), and a reaction yield of 87.6%. Methanol and methyl acetate mixture distillate 195.5g, methyl acetate content 28.2% (gas chromatography analysis).

Embodiment 3

[0072] As described in Example 1, the difference is that the methanol solution of 30 wt% sodium methoxide is 198.0 g (1.1 mol). 175.4 g of the target product 4-methoxy-2-methyldiphenylamine was obtained, with a purity of 99.2% (gas chromatography analysis), and a reaction yield of 81.7%. Methanol and methyl acetate mixture distillate 184.7g, methyl acetate content 24.2% (gas chromatography analysis).

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Abstract

The invention relates to a preparation method of diphenylamine or a ring-substituted derivative thereof. The method comprises the following steps: utilizing an alkali metal alkoxide as an alkaline reagent, and performing reaction on halogenobenzene or the ring-substituted derivative thereof and N-acylated aniline or the ring-substituted derivative thereof in the presence of a catalyst to prepare the diphenylamine or the ring-substituted derivative thereof and simultaneously produce a second product, namely carboxylic acid ester. The molar ratio of the halogenobenzene or the ring-substituted derivative thereof, the N-acylated aniline or the ring-substituted derivative thereof and the alkali metal alkoxide is generally selected at 1.0:(1.0-1.1):(1.1-1.3). The method is utilized for producing the diphenylamine or the ring-substituted derivative thereof, and the method has the advantages of simple production process, short reaction period, high utilization rate of equipment, low energy consumption and a small quantity of three wastes.

Description

[0001] technical field [0002] The invention relates to an improved method for preparing diphenylamine or derivatives substituted on its ring, which belongs to the technical field of chemical industry. Background technique [0003] Diphenylamine or derivatives substituted on its ring are widely used organic intermediates for the preparation of dyes, pesticides, rubber additives and the like. For example, 4-alkoxy-2-methyldiphenylamine is a class of extremely valuable diphenylamine derivatives used as raw materials for the preparation of fluoran dyes for pressure-sensitive or heat-sensitive recording paper. [0004] The preparation method of diphenylamine or derivatives substituted on its ring comprises: deamination of aniline or derivatives substituted on its ring; reaction of aniline or derivatives substituted on its ring with bromobenzene or its derivatives to remove bromine Hydrogen; condensation and intramolecular Methods such as hydrogen transfer reaction; aniline or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/92C07C213/02
Inventor 李明晶杨树仁卢凤阳闫雪李艳杰丁瑞林李建业
Owner SHANDONG DOCRIS CHEM
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