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Synthetic method of bis-(2-dimethylaminoethyl)ether

The technology of a dimethylaminoethyl group and a synthesis method is applied in the synthesis field of organic compounds, and can solve the problems of cumbersome feeding method of sulfur trioxide, unfriendly environment of sulfur trioxide, large recovery and processing capacity, etc., and achieves speeding up the etherification reaction. Speed, reduction of toluene extraction steps, the effect of fast reaction speed

Inactive Publication Date: 2012-11-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Weakness is: there is water to exist in neutralization reaction, can cause chloride hydrolysis; The preparation of sodium alkoxide, reaction time is long; And adopt sodium hydroxide aqueous solution to neutralize chloride hydrochloride, waste water amount is big; Toluene is both as solvent and as solvent. Extractant, large amount of recycling
The main disadvantage of this method is that the feeding method of sulfur trioxide is cumbersome, and sulfur trioxide is not friendly to the environment
The disadvantages of this method are that the reaction temperature is high, the selection is poor, and the yield is low.

Method used

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  • Synthetic method of bis-(2-dimethylaminoethyl)ether

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1, a kind of synthetic method of bis(2-dimethylaminoethyl) ether, take 2-dimethylethanolamine as starting raw material, carry out the following steps successively:

[0042] 1), 2-dimethylethanolamine chlorination:

[0043] Put 66g (0.55mol) of thionyl chloride in a 250mL three-necked flask, add 44.5g (0.5mol) of 2-dimethylethanolamine dropwise, the temperature is controlled at 10°C, and the dropwise is completed within 0.5h. After dropping, the temperature was raised to 30°C, and the reaction was stopped after 2 hours. The resulting reaction solution was removed by rotary evaporation under reduced pressure at room temperature under 10KPa to remove light components (the light components mainly include thionyl chloride, sulfur dioxide, hydrogen chloride), and the precipitated solid was dried (dried at 70°C) To constant weight, about 70.6g of chloride hydrochloride was obtained.

[0044] (2) Put 133.5g (1.5mol) of 2-dimethylethanolamine in a 500mL three-necked...

Embodiment 2

[0049] Embodiment 2, a kind of synthetic method of bis(2-dimethylaminoethyl) ether, take 2-dimethylethanolamine as starting material, carry out the following steps successively:

[0050] (1) Put 59.5g (0.50mol) of thionyl chloride in a 250mL three-necked flask, add 44.5g (0.50mol) of 2-dimethylethanolamine dropwise, and control the temperature at 10°C, and drop it within 0.5h. After dropping, the temperature was raised to 30°C, and the reaction was stopped after 2 hours. The resulting reaction solution was removed by rotary evaporation under reduced pressure at room temperature under 10KPa to remove light components (the light components mainly include thionyl chloride, sulfur dioxide, hydrogen chloride), and the precipitated solid was dried (dried at 70°C) To constant weight, about 68.4g of chloride hydrochloride was obtained.

[0051] (2) Put 133.5g (1.5mol) of 2-dimethylethanolamine in a 500mL three-necked flask, add 24.2g (1.05mol) of sodium metal, the reaction is exother...

Embodiment 3

[0054] Embodiment 3, a kind of synthetic method of bis(2-dimethylaminoethyl) ether, take 2-dimethylethanolamine as starting material, carry out the following steps successively:

[0055] (1) Put 119g (1.0mol) of thionyl chloride in a 250mL three-necked flask, add 44.5g (0.5mol) of 2-dimethylethanolamine dropwise, and control the temperature at 10°C, and drop it within 0.5h. After dropping, the temperature was raised to 30°C, and the reaction was stopped after 2 hours. The resulting reaction solution was removed by rotary evaporation under reduced pressure at room temperature under 10KPa to remove light components (the light components mainly include thionyl chloride, sulfur dioxide, hydrogen chloride), and the precipitated solid was dried (dried at 70°C) To constant weight, about 71.1g of chloride hydrochloride was obtained.

[0056] (2) Put 133.5g (1.5mol) of 2-dimethylethanolamine in a 500mL three-necked flask, add 24.2g (1.05mol) of sodium metal, the reaction is exothermic...

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Abstract

The invention discloses a synthetic method of bis-(2-dimethylaminoethyl)ether. The method comprises the following steps: (1) chlorination is carried out by using 2-dimethylethanolamine as raw material and thionyl chloride as a chlorinating agent to obtain chloride hydrochloride; (2) 2-dimethylethanolamine and sodium are used as the raw material and reacted to obtain a sodium alkoxide solution; (3) etherification: chloride hydrochloride is added into the sodium alkoxide solution, then a catalyst is added for etherification to obtain a reaction solution; the reaction solution is filtered to obtain filtrate; (4) separation and purification: vacuum rectification of the filtrate is carried out to obtain bis-(2-dimethylaminoethyl)ether.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing bis(2-dimethylaminoethyl) ether. Background technique [0002] Bis(2-dimethylaminoethyl) ether, formula C 8 h 20 N 2 O, whose structural formula is shown in S-1, the pure product is a light yellow liquid with a normal pressure boiling point of 190°C, and is a commonly used catalyst for polyurethane foam synthesis. [0003] [0004] S-1 [0005] According to comprehensive literature reports, the preparation of bis(2-dimethylaminoethyl) ether mainly adopts the following methods at present: [0006] 1. Patent US3084675 (1969), which reported a kind of etherification with toluene as solvent, 2-dimethylamino ethyl chloride (hereinafter referred to as chloride) and 2-dimethylamino ethyl alcohol sodium (hereinafter referred to as sodium alcohol), The sodium alkoxide is prepared in toluene with sodium hydroxide and 2-dimethylethanolamine, th...

Claims

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Application Information

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IPC IPC(8): C07C217/08C07C213/06
Inventor 陈新志阮建成钱超
Owner ZHEJIANG UNIV
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