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Method for converting 4,4'-dicarboxyl dibenzylamine into p-methylbenzoic acid and p-aminomethylbenzoic acid by debenzylation

A technology for debenzylation of dicarboxydibenzylamine and p-toluic acid, applied in the field of debenzylation of 4,4'-dicarboxydibenzylamine into p-toluic acid and p-aminomethylbenzoic acid, It can solve the problems that have not been reported, and achieve the effect of simple process and low processing cost

Inactive Publication Date: 2017-09-22
CHANGZHOU UNIV
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There is no report on the treatment method of this waste at home and abroad

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In a 500ml autoclave, add 50g of waste residue containing 28% 4,4'-dicarboxydibenzylamine and 200g of distilled water to adjust the pH. Add 1 g of 5% Pd / C and 3 drops of cocatalyst. Then hydrogenation reaction was carried out at 0.5Mpa and 30°C for 20h. The reaction solution was detected by high-pressure liquid chromatography, and 4,4'-dicarboxydibenzylamine was not detected, while the contents of p-toluic acid and p-aminomethylbenzoic acid increased by about 13% and 14%, respectively, and also did not Discovery of new substances.

Embodiment 2

[0019] In a 500ml autoclave, add 50g of waste residue containing 28% 4,4'-dicarboxydibenzylamine and 200g of distilled water to adjust the pH. Add 1.5 g of 5% Pd and 3 drops of cocatalyst. Then hydrogenation reaction was carried out at 0.3Mpa and room temperature for 15h. The reaction solution was detected by high-pressure liquid chromatography, and 4,4'-dicarboxydibenzylamine was not detected, while the contents of p-toluic acid and p-aminomethylbenzoic acid increased by about 13% and 14%, respectively, and also did not Discovery of new substances.

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PUM

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Abstract

In a hemostatic tranexamic acid production process, the chlorination single-pass conversion rate of p-methylbenzoic acid is normally controlled in a range of 65-70% in order to control impurity generation, which causes that 30-35% of p-methylbenzoic acid does not participate in reaction; further, impurities such as p-dichloromethyl benzoic acid are inevitably generated in a chlorination process; in an ammoniation process, di-substituted and tri-substituted side reactions are generated besides generation of p-aminomethylbenzoic acid, and thus a great quantity of solid wastes are generated, wherein by analysis, the solid wastes include 5% of p-aminomethylbenzoic acid, 13% of p-formylbenzoic acid, 35% of p-methylbenzoic acid, 28% of 4,4'-dicarboxyl dibenzylamine, 3% of 4,4',4''-tricarboxyl tribenzylamine, 11% of N-(p-aminomethylbenzoyl)-aminomethylbenzoic acid and 5% of others. The invention provides a method for converting 4,4'-dicarboxyl dibenzylamine into p-methylbenzoic acid and p-aminomethylbenzoic acid by hydrogenation debenzylation in presence of catalysts, and the recovery rate is not lower than 90%.

Description

technical field [0001] The invention relates to a method for debenzylation of 4,4'-dicarboxydibenzylamine contained in the production waste residue of the hemostatic drug aminocarboxylamine into p-toluic acid and p-aminomethylbenzoic acid. Background technique [0002] Tranexamic acid and its derivative product, tranexamic acid, are effective hemostatic drugs, which produce anti-lytic fibrinogen by reversibly blocking the binding of lysine on the plasminogen molecule. role. Its hemostatic mechanism is the same as the hemostatic drug aminocaproic acid, and its hemostatic effect is 5-10 times stronger than that of aminocaproic acid. It is mainly used for upper gastrointestinal bleeding, bleeding, bleeding in surgical operations and bleeding in obstetrics and gynecology. In addition, amino acid has a certain effect on the treatment of tonsil inflammation, tuberculosis and hemoptysis, acne, and chloasma. [0003] Although tranexamic acid and tranexamic acid are not new drugs, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/377C07C63/04C07C227/18C07C229/38
CPCC07C51/377C07C227/18C07C63/04C07C229/38
Inventor 吴卫忠叶青吕新宇周永生
Owner CHANGZHOU UNIV
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