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Preparation method of N1-n-octyl-N2-[2-(n-octylamino) ethyl]-1,2-ethidene diamine

A technology of n-octyl imine and ethylenediamine, which is applied in the preparation of amino compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of large amount of sewage, difficult industrial production, complicated post-treatment, etc., and achieve operability Strong, simple technology, to achieve the effect of mass production

Active Publication Date: 2015-01-28
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

However, after reduction with sodium borohydride, a large amount of impurities are introduced, the post-treatment of the product is complicated, the cost is relatively high, and a large amount of sewage is generated during the post-treatment process, which is not easy for industrial production

Method used

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  • Preparation method of N1-n-octyl-N2-[2-(n-octylamino) ethyl]-1,2-ethidene diamine

Examples

Experimental program
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Effect test

Embodiment 1

[0018] 1) Add 26.9g of 1-n-octanal, 10.3g of diethylenetriamine, 0.5g of sulfuric acid and 150ml of benzene into the reaction flask, stir, and reflux at 80°C. During the reaction, the water is separated from the reaction system in time, and the reaction 3h, diethylenetriamine content ≤ 1%, after the reaction, at a temperature of 60°C and a vacuum of 1200pa, distill off benzene and unreacted 1-n-octanal to obtain the intermediate N 1 -n-octylimine-N 2 30 g of -[2-(n-octylimine)ethyl]-1,2-ethylenediamine (hereinafter referred to as M1), the content reaches 98%, and the yield is 93%. 1 H NMR (500MHz, CDCl 3 ):7.50(t,2H,CH),2.60(t,4H,2×CH 2 ),1.53-1.61(m,8H,4×CH 2 ),1.29-1.31(m,16H,8×CH 2 ),0.88(t,6H,2×CH 2 ).

[0019] 2) Add M1, Pt / C and tetrabutylammonium bromide into the autoclave, seal the autoclave, replace with nitrogen twice, then replace twice with hydrogen, stir and heat to 80°C, hydrogen pressure 4MPa, the reaction is over , filtered at a temperature of 60°C to re...

Embodiment 2

[0022]1) Add 25.6g of 1-n-octanal and 10.3g of diethylenetriamine, 0.5g of sulfuric acid and 150ml of toluene into the reaction flask, stir, and reflux at 110°C. During the reaction, the water is separated from the reaction system in time, and the reaction 4h, diethylenetriamine content ≤ 1%. After the reaction is over, the temperature is 60°C, the vacuum degree is 600pa, and the toluene and unreacted raw materials are removed to obtain the intermediate N 1 -n-octylimine-N 2 -[2-(n-octylimine)ethyl]-1,2-ethylenediamine 29g, yield 90%, content 98%.

[0023] 2) put N 1 -n-octylimine-N 2 -[2-(n-octylimine)ethyl]-1,2-Ethylenediamine 32.3g, Raney Ni 0.33g and tetrabutylammonium bromide 0.33g were added to the autoclave, nitrogen replaced the air twice, Hydrogen was replaced by nitrogen twice, the temperature was 20°C, the pressure was 1MPa, and the hydrogenation was carried out for 8h. At the end of the reaction, heat filtration at a temperature of 60°C to remove the solid cat...

Embodiment 3

[0025] 1) Add 64g of 1-n-octanal, 10.3g of diethylenetriamine, 0.18g of toluenesulfonic acid and 150ml of benzene into the reaction flask, stir, and reflux at 80°C. During the reaction, divide the water from the reaction system in time. After reacting for 5 hours, the content of diethylenetriamine was less than or equal to 1%. After the reaction, at a temperature of 80° C. and a vacuum of 1200 Pa, the solvent and unreacted raw materials were removed to obtain 28.9 g of intermediate M1 with a yield of 90% and a content of 97.1%.

[0026] 2) Add 32.3M1, 3.3g of Raney Ni and 0.33g of tetrabutylammonium bromide into the autoclave, replace the air with nitrogen twice, replace the nitrogen twice with hydrogen, and hydrogenate at 100°C and 10MPa for 1 hour. After the reaction is completed, heat filtration at a temperature of 80°C to remove the solid matter, and cool to obtain a white solid, which is N 1 -n-octyl-N 2 -[2-(n-octylamino)ethyl]-1,2-ethylenediamine 29.3g, content 95.7%,...

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Abstract

The invention discloses a preparation method of N1-n-octyl-N2-[2-(n-octylamino) ethyl]-1,2-ethidene diamine. The method comprises the following steps: by using diethylenetriamine and 1-n-octanal as raw materials, carrying out condensation in the presence of a catalyst to generate N1-n-octyl amine-N2-[2-(n-octyl amine) ethyl]-1, 2-ethidene diamine; further hydrogenating N1-n-octyl amine-N2-[2-(n-octyl amine) ethyl]-1, 2-ethidene diamine to obtain N1-n-octyl-N2-[2-(n-octylamino) ethyl]-1, 2-ethidene diamine. The preparation method disclosed by the invention is used for solving the problem that the product prepared from N1-n-octyl-N2-[2-(n-octylamino) ethyl]-1, 2-ethidene diamine raw medicines in the prior art is low in content and yield and more in byproducts and the post treatment is complex. The preparation method disclosed by the invention is mainly used for preparing N1-n-octyl amine-N2-[2-(n-octylamino) ethyl]-1, 2-ethidene diamine. The obtained product can be used for bactericides in oil fields, farms and papermaking. The structure of N1-n-octyl amine-N2-[2-(n-octylamino) ethyl]-1,2-ethidene diamine is shown in the specification.

Description

Technical field: [0001] The present invention relates to a kind of preparation method of bactericide, particularly relate to a kind of N 1 -n-octyl-N 2 - a preparation method of [2-(n-octylamino)ethyl]-1,2-ethylenediamine. Background technique [0002] N 1 -n-octyl-N 2 -[2-(n-octylamino)ethyl]-1,2-ethylenediamine is one of the main active ingredients of octoprodil (formerly known as Junduqing), and it is a typical systemic drug developed in my country. Broad-spectrum fungicide. The bactericidal mechanism of octoprodil is to coagulate the protein of the bacteria, destroy the cell membrane of the bacteria, inhibit the respiration of the bacteria, and denature the enzyme system of the bacteria, thereby killing the bacteria. It has the characteristics of high efficiency, low toxicity, no residue and good permeability. It has a certain eradication effect on latent germs and can be used to prevent and control diseases caused by various fungi, bacteria and viruses. N in the in...

Claims

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Application Information

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IPC IPC(8): C07C211/14C07C209/52
Inventor 张晓光宁斌科刘康云薛超林双政张媛媛王威王列平王安勇
Owner XIAN MODERN CHEM RES INST
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