Preparation method of 1,2-di(2-aminophenoxy)ethane

An aminophenoxy, ethane technology, applied in the field of compound preparation, can solve the problems of low purity, high cost, low condensation reaction yield, etc., and achieve the effects of high reaction yield and high product purity

Active Publication Date: 2016-06-15
CHANGZHOU YONGHE FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is: (1) the condensation reaction yield is low, only about 75% when no sodium carbonate is added; less than 65% when more sodium carbonate is added; The highest is only about 90%; (2) The hydrazine hydrate used in the reduction reaction is highly toxic and expensive, and is not suitable for industrial production
The disadvantages of this method are: (1) the condensation reaction yield is also low, and the highest yield is only 85% after repeated experiments by the applicant; (2) the catalytic hydrogenation yield is also low, only about 90%, especially the purity Low, less than 99.3%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0016] This embodiment is the preparation method of 1,2-di(2-nitrophenoxy)ethane, specifically as follows:

[0017] Add 100.0g (0.635mol) of o-nitrochlorobenzene, 10.0g (0.044mol) of phase transfer catalyst TEBAC and 15.7g ( 0.253mol) of ethylene glycol, slowly warming up to 75°C under stirring, uniformly drop 61.4g of 50wt% sodium hydroxide aqueous solution (0.768mol) into the reaction system within 2 hours, and keep the temperature of the reaction system at 75~ Continue to react at 80°C for 20h.

[0018] The temperature of the reaction system was lowered to 30-35° C., filtered, and the filtrate was allowed to stand for separation to obtain 53.8 g of an oil layer.

[0019] After the filter cake was rinsed with 100 mL of water, it was dried at 70°C to obtain 77.8 g of crude 1,2-bis(2-nitrophenoxy)ethane.

[0020] Add the crude product to 150g of DMF, then add 0.5g of activated carbon, heat up to 95°C, filter while it is hot, cool the filtrate to below 10°C, then filter with ...

Embodiment 2）

[0022] This embodiment is still the preparation method of 1,2-di(2-nitrophenoxy)ethane, specifically as follows:

[0023] Add 80.0g (0.508mol) of o-nitrochlorobenzene, 1.0g (0.0044mol) of phase transfer catalyst TEBAC, 15.7g ( 0.253mol) of ethylene glycol and the 53.8g oil layer obtained in Example 1, slowly warming up to 75°C under stirring, and uniformly dropwise adding 61.4g of 50wt% sodium hydroxide aqueous solution (0.768mol) to the reaction system within 2h, dropwise After completion, keep the temperature of the reaction system at 75-80°C and continue the reaction for 20 hours.

[0024] The temperature of the reaction system was lowered to 30-35° C., filtered, and the filtrate was allowed to stand for separation to obtain 52.6 g of an oil layer.

[0025] After the filter cake was rinsed with 100 mL of water, it was dried at 70°C to obtain 78.2 g of crude 1,2-bis(2-nitrophenoxy)ethane.

[0026] Add the crude product to 150g of DMF, then add 0.5g of activated carbon, hea...

Embodiment 3～ Embodiment 5）

[0028] The preparation method of each embodiment is basically the same as that of Example 2, and the differences are shown in Table 1.

[0029] Table 1

[0030]

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PUM

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Abstract

The invention discloses a preparation method of 1,2-di(2-aminophenoxy)ethane. According to the method, o-nitrochlorobenzene which is used as a starting material and glycol firstly undergo a condensation reaction under the alkaline condition and in the presence of a phase transfer catalyst so as to prepare 1,2-di(2-nitrophenoxy)ethane; and then, the 1,2-di(2-nitrophenoxy)ethane undergoes catalytic hydrogenation so as to prepare 1,2-di(2-aminophenoxy)ethane. The phase transfer catalyst is triethylbenzylammonium chloride. molar ratio of o-nitrochlorobenzene to glycol is 2.2:1-3.0:1. By selecting the proper phase transfer catalyst TEBAC and using excess o-nitrochlorobenzene in the condensation reaction, high-purity 1,2-di(2-aminophenoxy)ethane can be obtained. Especially, yield of the condensation reaction can reach 95% and above. Thus, the preparation method is suitable for industrial mass production.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and in particular relates to a preparation method of 1,2-bis(2-aminophenoxy)ethane. Background technique [0002] 1,2-bis(2-aminophenoxy)ethane, also known as 2,2'-diaminoethylene glycol diphenyl ether, is an important raw material for the synthesis of Pigment Yellow 180, pesticides, composite resins, etc. [0003] Chinese patent document CN101863781A discloses a preparation method of 1,2-bis(o-aminophenoxy)ethane, which uses o-nitrochlorobenzene as the starting material, and first mixes with equimolar ethylene glycol in alkali Under neutral conditions, 1,2-di(o-nitrophenoxy)ethane was prepared by condensation reaction in the presence of phase transfer catalyst dodecyltrimethylammonium chloride (DTAC); then reduced by hydrazine hydrate 1,2-Bis(2-o-aminophenoxy)ethane is obtained. The disadvantage of this method is: (1) the condensation reaction yield is low, only about 75% when not...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/84
CPCC07C201/12C07C213/02C07C205/37C07C217/84
Inventor 栾永勤陆海峰姜友林许晓春
Owner CHANGZHOU YONGHE FINE CHEM
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