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Preparation method of N,N-di-n-butylethylenediamine

A technology of di-n-butylethylenediamine and di-n-butylamine, which is applied in the field of synthesis of organic compounds, can solve the problems of long reaction time, cumbersome process, and inconvenient operation, and achieves low environmental hazards, simple process flow, and low cost Effect

Inactive Publication Date: 2013-04-03
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, it is reported in Patent US2318729 that using di-n-butylamine and ethyleneimine as raw materials, catalytic reaction at 90°C to 95°C for 16 hours produces N,N-di-n-butylethylenediamine, and the yield is only 23%.
These two methods all have low yield, long reaction time, complex process and inconvenient operation.

Method used

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  • Preparation method of N,N-di-n-butylethylenediamine

Examples

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Embodiment 1

[0017] Embodiment 1, a preparation method of N,N-di-n-butylethylenediamine, using di-n-butylamine and 2-chloroethylamine hydrochloride as starting materials, the following steps are carried out in sequence:

[0018] In autoclave, add di-n-butylamine 85ml (0.5mol), 2-chloroethylamine hydrochloride 11.6g (0.1mol), the methanol solution of the sodium methylate of mass concentration 30% (which contains sodium methylate 5.4g (0.1 mol), methanol 16ml), close the kettle lid. The temperature was raised to 150° C., and the reaction pressure was 0.8 MPa at this time, and the reaction was maintained at this temperature for 5 hours. After the reaction, add saturated aqueous sodium hydroxide solution to the reaction solution to adjust the pH to 12, take the upper oil phase for rectification, collect fractions at 109-114°C, and obtain 77.9 g of the product N,N-di-n-butylethylenediamine, The yield was 74.7%, and the structure of the obtained product was confirmed by mass spectrometry.

Embodiment 2～6

[0020] Change the following reaction conditions in embodiment 1: di-n-butylamine consumption (abbreviation V 1 ), the amount of sodium methoxide (M 2 ), methanol dosage (V 2 ), reaction temperature (abbreviated T), reaction time (abbreviated t), reaction pressure (abbreviated P); 1 ), to obtain Examples 2-6, thereby obtaining the corresponding yield of N,N-di-n-butylethylenediamine (abbreviated as y). See Table 1 for details and data results.

[0021] Table 1

[0022] Example

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Abstract

The invention discloses a preparation method of N,N-di-n-butylethylenediamine, which comprises the following steps: 1) adding a sodium methoxide methanol solution to carry out reaction on raw materials di-n-butylamine and 2-chlorethamin hydrochloride in a high-pressure autoclave, wherein the mol ratio of di-n-butylamine to 2-chlorethamin hydrochloride is (4-6):1, the mol ratio of sodium methoxide to 2-chlorethamin hydrochloride is (0.5-2):1, the reaction temperature is 100-200 DEG C, the reaction time is 2-9 hours, and the reaction pressure is 0.5-1.0 MPa; and 2) adding alkali solution into the obtained reaction solution in the step 1) to regulate the pH value to 12-13, and carrying out liquid separation and rectification to obtain the N,N-di-n-butylethylenediamine. The method disclosed by the invention has the characteristics of simple technique, high yield and low cost.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing N,N-di-n-butylethylenediamine. Background technique [0002] N,N-Di-n-butylethylenediamine (N,N-Di-n-butylethylenediamine) is an important organic chemical intermediate. [0003] According to comprehensive literature reports, there are not many synthesis methods of N,N-di-n-butylethylenediamine at present, and there is no method for directly preparing di-n-butylamine and 2-chloroethylamine hydrochloride as raw materials. In The Journal of Organic Chemistry, 1984. 49(25): p. 4889-4893, it was reported in an article titled Nucleophilic ring opening of 2-oxazolines with amines: a convenient synthesis for unsymmetrically substituted ethylenediamines, with two positive Butylamine and 2-ethyl-2-oxazoline were used as raw materials, zinc acetate was used as a catalyst, and reacted at 180°C for 24 hours to generate N-(2-(dibutylamino)ethyl)propiona...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/10C07C209/08
Inventor 陈新志李于钢钱超
Owner ZHEJIANG UNIV
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