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Preparation method for N-[2-(2-hydroxyethoxy)-4-nitrophenyl] ethanol amine

A technology of hydroxyethoxy and nitrophenyl, which is applied in the field of preparation of N-[2--4-nitrophenyl]ethanolamine, can solve the problems of low yield and low purity of ethanolamine, and achieve the production process Mild, high purity, solve the effect of low yield

Active Publication Date: 2015-07-01
ZHEJIANG DINGLONG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the deficiencies in the prior art, the invention provides a method for preparing N-[2-(2-hydroxyethoxy)-4-nitrophenyl]ethanolamine under airtight conditions; Synthesis of N-[2-(2-hydroxyethoxy)-4-nitrophenyl]ethanolamine has high yield, high purity, mild production process, and less waste generation; solves the problem of N-[2-(2 -Hydroxyethoxyl group)-4-nitrophenyl]ethanolamine preparation yield is low, the problem of low purity

Method used

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  • Preparation method for N-[2-(2-hydroxyethoxy)-4-nitrophenyl] ethanol amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 500ml autoclave, add 250.0g DMF, 25.0g (0.16mol) of 2-amino-5-nitrophenol, 9.6g (0.24mol) of sodium hydroxide and 19.3g (0.24mol) of 2-chloroethanol in sequence, Stir to raise the temperature, control the pressure at 0.8MPa, and keep the reaction at 110-120°C for 5h. Sampling analysis, the HPLC content of control raw material is less than 1.0%, promptly stop reaction. After cooling down to room temperature, the reaction solution was diluted in ice water for precipitation, the amount of water used was equivalent to 30% DMF aqueous solution, filtered, and the filter cake was washed with water and dried to obtain a brown solid 2-(3-nitro-6 -aminophenoxy group) ethanol 29.9g, HPLC purity 98.2%, yield is 94.3%.

[0027] HPLC detection conditions: Shimadzu LC-20AT or equivalent precision liquid chromatograph

[0028] Chromatographic column: CLC-ODS-C18 (Φ4.6×250mm)

[0029] Column temperature: 40°C Flow rate: 1.0 ml / min

[0030] Detection wavelength: 254 nm Sample di...

Embodiment 2

[0041] In a 1000ml autoclave, 250.0g of solvent DMAC, 50.0g (0.32mol) of 2-amino-5-nitrophenol, 26.9g (0.48mol) of potassium hydroxide and 38.6g (0.48mol) of 2-chloro Ethanol, stirring to raise the temperature, control the pressure between 0.4-0.5MPa, and keep the reaction at 110-120°C for 8h. Sampling analysis, the HPLC content of control raw material is less than 1.0%, promptly stop reaction. After cooling down to room temperature, the reaction solution was diluted in ice water for precipitation, and the amount of water used was equivalent to 30% of the DMAC solution, filtered, and the filter cake was washed with water and dried to obtain a brown solid 2-(3-nitro- 6-aminophenoxy) ethanol 58.9g, HPLC purity 98.9%, yield is 92.9%.

[0042] Add 50.3g (0.25mol) of the 2-(3-nitro-6-aminophenoxy)ethanol obtained above into a 1000ml autoclave, then add 503.0g of water and 52.9g (0.37mol) of chloroformic acid Ethyl chloride and 10.1g of calcium oxide, stirring to raise the tempera...

Embodiment 3

[0044] In a 500ml autoclave, add 250.0g DMF, 25.0g (0.16mol) of 2-amino-5-nitrophenol, 5.0g of solid base (hydrotalcite loaded with sodium hydroxide) and 19.3g (0.24mol) of 2 -Chloroethanol, stir to raise the temperature, control the pressure between 0.4-0.5MPa, and keep the reaction at 105-110°C for 5h. Sampling analysis, the HPLC content of control raw material is less than 1.0%, promptly stop reaction. After cooling down to room temperature, the reaction solution was diluted in ice water for precipitation, the amount of water used was equivalent to 30% DMF aqueous solution, filtered, and the filter cake was washed with water and dried to obtain a brown solid 2-(3-nitro-6 -aminophenoxy group) ethanol 29.3g, HPLC purity 97.6%, yield is 92.4%.

[0045] Add 22.3g (0.11mol) of the 2-(3-nitro-6-aminophenoxy)ethanol obtained above into a 500 ml autoclave, then add 223.0g (10eq) of water, 23.4g (0.16mol ) of chloroethyl chloroformate and 4.46g of solid base, stirred and heated up...

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Abstract

The invention relates to a preparation method for N-[2-(2-hydroxyethoxy)-4-nitrophenyl] ethanol amine. The preparation method comprises the following steps: mixing 2-amino-5-nitrophenol used as a raw material with an alkali and a solvent, then adding a hydroxyethylation reagent, and reacting at certain pressure and temperature to generate 2-(3-nitro-6-aminophenoxy) ethanol; and then reacting 2-(3-nitro-6-aminophenoxy) ethanol with chloroethyl chloroformate under the action of a catalyst, and obtaining N-[2-(2-hydroxyethoxy)-4-nitrophenyl] ethanol amine through condensation and hydrolysis. The N-[2-(2-hydroxyethoxy)-4-nitrophenyl] ethanol amine disclosed by the invention has the advantages of being high in yield, high in purity, good in quality, moderate in production process, less in three-waste generation, and the like; the preparation method disclosed by the invention is economical and environmentally friendly, and suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of N-[2-(2-hydroxyethoxy)-4-nitrophenyl]ethanolamine. Background technique [0002] N-[2-(2-hydroxyethoxy)-4-nitrophenyl]ethanolamine is an important hair dye intermediate, this product is a non-toxic, permanent hair dye intermediate, compared to the The hair dye using p-phenylenediamine as an intermediate has little harm and no stimulation to the human body, and the production method has the advantages of low cost and little environmental pollution. This compound has been adopted by major cosmetic companies, and its use is increasing year by year. But how to obtain this substance with high purity and high yield is a difficult problem encountered in the development and promotion of this product. [0003] At present, there are few documents about the method for preparing N-[2-(2-hydroxyethoxy)-4-nitrophenyl]ethanolamine, and a synthetic method has been reported in US4337061, which is to react under normal ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/02
Inventor 秦振伟施云龙肖庆军刘琛史元晓朱良
Owner ZHEJIANG DINGLONG TECH
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