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A method for preparing tranexamic acid by catalytic hydrogenation of p-aminomethylbenzoic acid

A technology of aminomethylbenzoic acid and tranexamic acid, which is applied to the preparation of cyanide reaction, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of harsh reaction conditions, increased production costs, and unsuitability for industrial production, and achieves The preparation method is simple, the utilization rate is improved, and the effect of reducing the amount of use

Active Publication Date: 2011-12-14
CHANGZHOU YINSHENG PHARMA
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0009] Ru catalyst is used in the catalytic hydrogenation process, the reaction conditions are relatively harsh, high temperature and high pressure require high equipment, and it is not suitable for industrial production; the use of Rh catalyst, due to the high price of Rh, increases the production cost; the use of Pt catalyst, the reaction conditions are mild, but the reaction longer time

Method used

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  • A method for preparing tranexamic acid by catalytic hydrogenation of p-aminomethylbenzoic acid

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Effect test

Embodiment 1

[0024] Take the preparation of 1 gram of catalyst as an example: 0.135g H 2 PtCl 6 and 0.05g La(NO 3 ) 3 Dissolve in 30ml of water, impregnate 1g of activated carbon in this solution for 12 hours, heat to 100°C, add hydrazine hydrate dropwise for reduction, cool after reduction, filter, and wash with water to obtain Pt-La / C catalyst.

[0025] Catalytic hydrogenation: 0.3 g Pt-La / C catalyst, 1 g p-aminomethylbenzoic acid, 30 ml deionized water, 0.6 g H 2 SO 4 , airtight, vacuumed to -0.08 Mpa, and then replace the air with nitrogen twice, nitrogen twice with hydrogen, heat the reaction temperature to 60°C, hydrogen pressure 0.5 MPa, reaction time 4 h, the conversion of p-aminomethylbenzoic acid is 99.3%; the prepared p-aminomethylcyclohexanecarboxylic acid undergoes conformational conversion under alkaline earth metal catalysis at 220°C and 2.0MPa to obtain tranexamic acid.

Embodiment 2

[0027] Catalyst preparation: 0.135g H 2 PtCl 6 and 0.4g Ni(NO 3 ) 2 Dissolve in 30ml of water, soak 1g of activated carbon in this solution for 12 hours, heat to 100°C, add KBH dropwise 4 The solution is reduced, and after the reduction is completed, it is cooled, filtered, and washed with water to obtain a Pt-Ni / C catalyst.

[0028] Catalytic hydrogenation: Add 0.3 g of the above catalyst, 1 g p-aminomethylbenzoic acid, 30 ml deionized water, 0.6 g H 2 SO 4 , sealed, vacuumed to -0.06 Mpa, and then replaced the air with nitrogen twice, replaced nitrogen twice with hydrogen, heated the reaction temperature to 50 ° C, hydrogen pressure 0.6 MPa, reaction time 3 h, the conversion of p-aminomethylbenzoic acid was 98.6%; the prepared p-aminomethylcyclohexanecarboxylic acid undergoes conformational conversion under alkaline earth metal catalysis at 220°C and 2.5MPa to obtain tranexamic acid.

Embodiment 3

[0030] Catalyst preparation: 0.135g H 2 PtCl 6 and 0.4g Co(NO 3 ) 2 Dissolve in 30ml of water, impregnate 1g of activated carbon in this solution for 12 h, heat to 100°C, add CH 3 COONa solution, cooled after reduction, filtered and washed with water to prepare Pt-Co / C catalyst.

[0031] Catalytic hydrogenation: Add 0.3 g of the above catalyst, 1 g p-aminomethylbenzoic acid, 30 ml deionized water, 0.6 g H 2 SO 4, airtight, vacuum to -0.07 Mpa, and then replace the air with nitrogen twice, nitrogen twice with hydrogen, heat the reaction temperature to 40 ° C, hydrogen pressure 0.5 MPa, reaction time 4 h, the conversion of p-aminomethylbenzoic acid is 97.6%; the prepared p-aminomethylcyclohexanecarboxylic acid undergoes conformational transformation under the catalysis of alkaline earth metals at 220°C and 2.2MPa to obtain tranexamic acid.

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Abstract

The invention relates to a method for preparing tranexamic acid from para-aminomethylbenzoic acid by catalytic hydrogenation. A Pt-M / C catalyst (M is selected from Ru, La, Ce, Co and Ni) is used for carrying out catalytic hydrogenation on the para-aminomethylbenzoic acid, and has the advantages of mild reaction conditions, reaction temperature of 30-60 DEG C, hydrogen pressure of 0.3-0.5MPa, high activity, reaction time of 2-4 hours, para-aminomethylbenzoic acid conversion rate up to 99 percent, tranexamic acid yield up to 95 percent, shortened reaction time, improvement of unit yield and high industrial application value.

Description

technical field [0001] The invention belongs to the application technical field of catalytic hydrogenation, in particular to a method for preparing tranexamic acid by catalytic hydrogenation of p-aminomethylbenzoic acid under mild conditions. Background technique [0002] Tranexamic acid is a trans-aminomethylcyclohexylcarboxylate, which can reversibly block the lysine bound to the plasminogen molecule, thereby producing an anti-fibrinogen effect, and is effective for bleeding In a wide range of situations, it is usually used for respiratory tract, gastrointestinal bleeding, bleeding, surgical bleeding, etc. [0003] The synthetic method of tranexamic acid mainly contains two kinds, and a kind of is methyl acrylate method, generates tranexamic acid through a series of reactions by methyl acrylate and chlorobutadiene; Another kind is p-aminomethylbenzoic acid method, Tranexamic acid is produced by catalytic hydrogenation and conversion of p-aminomethylbenzoic acid. Due to t...

Claims

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Application Information

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IPC IPC(8): C07C229/46C07C227/16B01J23/63B01J23/89B01J23/46
Inventor 陶鑫王争吴荆刚董杜平
Owner CHANGZHOU YINSHENG PHARMA
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