Method for preparing N1-(2-aminoethyl)-1,2-ethidene diamine

A technology of ethylenediamine and aminoethyl, applied in the field of organic amine synthesis, can solve the problems of incomplete elimination, process corrosion, complicated molecular sieve regeneration process, etc.

Active Publication Date: 2017-05-10
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dichloroethane method adopts a liquid phase environment, the process is severely corroded, the product is difficult to separate, and a large amount of amine-containing wastewater will be generated, which is difficult to treat, high in energy consumption, and seriously pollutes the environment.
[0011] The prior art also has the method of dehydrating the reaction raw materials to improve the stability of the catalyst. For example, CN103764618 uses molecular sieves to dehydrate the iminodiacetonitrile solution and then adds it to the reactor. However, this method will use a large amount of molecular sieves on an industrial scale , and the molecular sieve regeneration process is complicated and produces three wastes
In addition, using this method only reduces the moisture content, does not completely eliminate it, and cannot completely solve the problem of catalyst deactivation

Method used

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  • Method for preparing N1-(2-aminoethyl)-1,2-ethidene diamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The treated 5g of Raney cobalt and 0.075g of 5% Ru / C were pre-added into a 1L high-pressure stainless steel hydrogenation reactor, and then 500g of iminodiacetonitrile with a mass fraction of 5% iminodiacetonitrile was added. Hexacyclic solution, and then add 17mg of NaOH to the reaction kettle. Replace with 0.3Mpa nitrogen for 3 times, then replace with 0.3MPa hydrogen for 3 times, then raise the temperature to 85°C, add hydrogen and carbon monoxide mixed gas (H 2 : CO=500:1, volume ratio) to a pressure of 5MPa, and stir to 1000 rpm. During the reaction process, the pressure of the mixer was maintained at 5MPa. At the same time, 20wt% formic acid was added dropwise when the amount of hydrogen absorbed by the reaction reached 10% of the theoretical value of hydrogen absorbed by the reaction, and 10% by weight of formic acid was added dropwise for every 10% increase in the amount of hydrogen absorbed later. The method for formic acid is that 25.5mg formic acid is added ...

Embodiment 2

[0069] Other conditions are the same as in Example 1, only the reaction temperature is changed to: 70°C, the reaction pressure is changed to 7.5MPa, the IDAN concentration is changed to 15%, the catalyst 1 quality is 5g, the catalyst 2 quality is 0.05g, and the auxiliary agent base is KOH , the quality is 37.5 mg, the acid added dropwise is glacial acetic acid, and the total mass is 61 mg; when the reaction starts, the volume ratio of feeding hydrogen and carbon monoxide gas mixture is H 2 : CO=1000:1, when the reaction reaches 25%, the system pressure is released to normal pressure, and the hydrogen is switched to high-purity hydrogen with a purity of 99.999%.

[0070] Catalyst application test results are as follows:

[0071] Apply times DETA selectivity % Piperazine selectivity % IDAN Conversion % Response time min 1 95.1 3.3 99.9 55 2 95.2 3.4 99.9 56 3 95.1 3.5 99.9 55 4 95.3 3.4 99.9 55 5 95.2 3.7 99.9 56 6 9...

Embodiment 3

[0073]Other conditions are the same as in Example 1, except that the reaction temperature is changed to 100° C., the reaction pressure is changed to 10 MPa, the IDAN concentration is changed to 25%, the mass of catalyst 1 is 5 g, and the mass of catalyst 2 is 0.025 g. The basic compound is KOH and the acidic compound is acetic acid. The quality of KOH is 66.5mg, and the quality of acetic acid is 133mg; When the reaction starts, the volume ratio of feeding hydrogen and carbon monoxide gas mixture is H 2 : CO=100:1, when the reaction reaches 30%, the system pressure is released to normal pressure, and the hydrogen is switched to high-purity hydrogen with a purity of 99.999%.

[0074] Catalyst application test results are as follows:

[0075] Apply times DETA selectivity % Piperazine selectivity % IDAN Conversion % Response time min 1 95.2 3.5 99.9 47 2 95.3 3.3 99.9 45 3 95.2 3.4 99.9 44 4 95.1 3.6 99.9 44 5 95.2 3.5 99.9...

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Abstract

The invention provides a method for preparing N1-(2-aminoethyl)-1,2-ethidene diamine. The method comprises the following steps: preparing a solution from iminodiacetonitrile and a solvent; adding the solution into a hydrogenation reactor filled with a catalyst 1 and a catalyst 2, and reacting to produce N1-(2-aminoethyl)-1,2-ethidene diamine and a byproduct piperazine under a certain temperature and pressure, wherein the catalyst 1 has the effect of hydrogenating iminodiacetonitrile into N1-(2-aminoethyl)-1,2-ethidene diamine, and the catalyst 2 has the effect of hydrogenating iminodiacetonitrile hydrolysate into diethanolimine. According to the method disclosed by the invention, the stability of the catalyst 1 is greatly improved.

Description

technical field [0001] The present invention relates to a kind of N 1 The invention discloses a preparation method of (2-aminoethyl)-1,2-ethylenediamine, which belongs to the field of synthesis of organic amines. Background technique [0002] N 1 -(2-aminoethyl)-1,2-ethylenediamine, molecular formula C 4 h 13 N 3 , referred to as DETA, commonly known as diethylenetriamine, diethylenetriamine, diethylenetriamine, diethylenetriamine, etc., English name: Diethylenetriamine, is a saturated fatty amine, yellow hygroscopic transparent viscous liquid , has a pungent ammonia odor, and easily absorbs moisture and carbon dioxide in the air. It is mainly used as a solvent and organic synthesis intermediate, and can be used to prepare carbon dioxide absorbers, lubricating oil additives, emulsifiers, photographic chemicals, surfactants, fabric finishing agents, paper strengthening agents, ammonia carboxy complexing agents, ashless additives , metal chelating agent, heavy metal hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/48C07C211/14
Inventor 陈长生丁可黎源
Owner WANHUA CHEM GRP CO LTD
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