Preparation method of 4-aminobenzoyl-N-(4-aminobenzoyl) amine

A technology of aminobenzoyl and nitrobenzamide, which is applied in the field of compound preparation and can solve problems such as increased cost, high manufacturing cost of intermediates, and complicated process

Inactive Publication Date: 2006-11-29
SHENYANG RES INST OF CHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the investigation of relevant enterprises, it was found that the difficulty in producing organic pigment yellow C.I 181# mainly focused on the synthesis of its intermediate 4-aminobenzoyl-N-(4-aminobenzamide)amine. The problem is, first: the synthetic intermediate is difficult to meet the quality requirements required for the synthesis of the final product; second: the manufacturing cost of the intermediate is too high, making it difficult for the final product to meet the needs of market competition
There are few reports on the synthesis of 4-aminobenzoyl-N-(4-aminobenzamide) amide in relevant literature, and only a synthetic literature about organic pigment yellow 181# in DE2.845.947 is included in American Chemical Abstracts, while There is also only one related report (Synth.Commun; EN32, 8 2002) in Beil., although the synthetic method adopted in it has achieved satisfactory results in yield and product quality, but the catalyst loading he adopted Hydrogenation complicates the process and increases the cost accordingly

Method used

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Examples

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Embodiment Construction

[0015] The following specific examples are provided to further illustrate the present invention.

[0016] 1) Ammonolysis reaction of p-nitrobenzoyl chloride to prepare p-nitrobenzamide

[0017] In a 1000ml four-neck flask equipped with stirring, reflux condenser, thermometer, and water bath heating, add 218g, 25% ammonia water (3.20mol), and 135g water in sequence, start stirring, and then add 1.0g (70% ) phase transfer catalyst—hexadecyltrimethylammonium chloride, cover the bottle stopper, and heat the system slowly to 55-60°C by means of external heating in a water bath. At this time, the catalyst is completely dissolved and the system is homogeneous , keep warm and stir for later use;

[0018] In addition, a 500ml three-necked bottle is installed with stirring, a thermometer, and a heating water bath, and then 265g of toluene is added thereto, and the stirring is started. Under stirring conditions, 200g, 99% (1.07mol) of p-nitrobenzoyl chloride are slowly added thereto Af...

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PUM

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Abstract

A process for preparing 4-aminobenzoyl-N-(4-aminobenzoyl) amine includes such steps as dissolving nitrobenzoyl chloride in organic solvent, adding it to ammonia water, ammonolysis reaction to obtain p-nitrobenzoylamine, iron powder reducing reaction or hydrocatalytic nitro reducing reaction in alcohol-water solution to obtain p-amino benzoylamine, condensating reaction on p-nitrobenzoyl chloride in organic solvent under existence of acid binding agent to obtain 4-nitrobenzoyl-N-(4-aminobenzoyl) amine, and iron powder reducing reaction of hydrocatalytic nitro reducing reaction in solvent.

Description

technical field [0001] The invention belongs to the technical field of compound preparation methods, in particular to a preparation method of 4-aminobenzoyl-N-(4-aminobenzoyl)amine. Background technique [0002] 4-Aminobenzoyl-N-(4-aminobenzamide) amine is an organic pigment intermediate, the main purpose is to synthesize organic pigment yellow C.I 181#. Organic Pigment Yellow C.I 181# is a high-grade organic pigment with very good properties. The most important raw material in its synthesis is 4-aminophenoyl-N-(4-aminophenoyl)amine. So far, only a few countries such as Germany and the United States have industrialized production of this product in the world, while my country has not yet had a production enterprise of this product, and the use of this product in our country still relies on foreign imports. In the investigation of relevant enterprises, it was found that the difficulty in producing organic pigment yellow C.I 181# mainly focused on ...

Claims

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Application Information

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IPC IPC(8): C07C237/52C07C231/02
Inventor 谭立哲孟明扬沈德堂康列克储消和
Owner SHENYANG RES INST OF CHEM IND
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