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Preparation method of N,N-bis(2-hydroxyethyl)methacrylamide

A technology of methacrylamide and hydroxyethyl, applied in the N field, can solve the problems of low yield of synthesis process, difficult purification, poor economic benefits, etc., and achieves the advantages of good process reproducibility, simple operation and reduced production cost. Effect

Active Publication Date: 2017-12-05
SHANGHAI ZAIQI BIO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the whole, the yield of the existing synthesis process is low, it is difficult to purify, and the economic benefits are not good

Method used

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  • Preparation method of N,N-bis(2-hydroxyethyl)methacrylamide
  • Preparation method of N,N-bis(2-hydroxyethyl)methacrylamide
  • Preparation method of N,N-bis(2-hydroxyethyl)methacrylamide

Examples

Experimental program
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Effect test

Embodiment 1

[0036] The first step: the synthesis of 2,2-dimethyl-1,3-dioxo-6-azacyclooctane.

[0037] Diethanol ammonia (5 kg, 47.58 mol, 1.00 eq) was added to 22 kg of methanol, and hydrogen chloride (1.02 eq) was passed through at 0-10 °C. The resulting solution was stirred at room temperature for 1 hour, 2,2-dimethoxypropane (27kg, 259mol, 5.4 eq) and p-toluenesulfonic acid (326 g, 1.90 mmol, 0.04 eq) were added, and the resulting solution was refluxed for reaction 3-4 Hour. Filter, wash the filter cake with acetone, add it to the dichloromethane solution, adjust the pH value to 9-10 with 2N aqueous sodium hydroxide solution, separate the organic phase, extract the aqueous phase twice with dichloromethane, and combine the organic phases with rotary evaporation 6.49 kg of pale yellow oil were obtained, with a yield of 94%.

[0038] After detection, the mass spectrometry data are as follows, and it is determined that the oily substance is 2,2-dimethyl-1,3-dioxo-6-azacyclooctane.

[00...

Embodiment 2

[0051] The first step: the synthesis of 2,2-dimethyl-1,3-dioxo-6-azacyclooctane.

[0052] Diethanolamine ( 5 kg, 47.58 mol, 1.00 eq) was added to 22 kg of methanol, and hydrogen bromide (1.02 eq) was introduced at 0-10 °C. The resulting solution was stirred at room temperature for 1 hour, 2,2-dimethoxypropane (34.7 kg, 333 mol, 7 eq) and p-toluenesulfonic acid (406 g, 2.37 mmol, 0.05 eq) were added to the resulting solution at 85°C Stir for 3-4 hours. Filter, wash the filter cake with acetone, dissolve it with dichloromethane, adjust the pH value to 9-10 with 2N aqueous sodium hydroxide solution, separate the organic phase, and extract the aqueous phase twice with dichloromethane. Dry with sodium sulfate, filter and spin dry to obtain 6.50kg of light yellow oil, the yield is 94%.

[0053] After detection, the mass spectrometry data are as follows, and it is determined that the oily substance is 2,2-dimethyl-1,3-dioxo-6-azacyclooctane.

[0054] ESI / MS: m / z=146.2[MH] +

[0...

Embodiment 3

[0065] The first step: the synthesis of 2,2-dimethyl-1,3-dioxo-6-azacyclooctane.

[0066] Diethanolamine (500 g, 4.76 mol, 1.00 eq) was added to dioxane (1.5 L), and hydrogen chloride (1.02 eq) was passed through at 0-10°C. The resulting solution was stirred at room temperature for 1 hour, and 2,2-dimethoxypropane (1.49 kg, 14.28 mol, 3 eq) and p-toluenesulfonic acid (24 g, 0.14 mmol, 0.03 eq) were added. The resulting solution was stirred at 85°C for 3-4 hours. After filtering, the filter cake was washed with acetone, added to dichloromethane solution, adjusted to pH 9 with 2N aqueous sodium hydroxide solution, the organic phase was separated, the aqueous phase was extracted twice with dichloromethane, and the organic phases were combined with anhydrous Dry over sodium sulfate, filter and spin dry to obtain 669 g of light yellow oil, with a yield of 97%.

[0067] After detection, the mass spectrometry data are as follows, and it is determined that the oily substance is 2,2-...

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Abstract

The invention discloses a preparation method of N,N-bis(2-hydroxyethyl)methacrylamide. The N,N-bis(2-hydroxyethyl)methacrylamide is prepared mainly from diethanolamine, 2,2-dimethoxypropane and methyl methacrylate through a three-step reaction. The method has the advantages of simplicity and stability in process operation, easy separation and high yield of products in all steps, environmental protection, realization of the comprehensive yield of 85% or above, cheap and easily available raw materials, great reduction of the production cost, and facilitation of industrial scale production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of N,N-bis(2-hydroxyethyl)methacrylamide. Background technique [0002] N,N-bis(2-hydroxyethyl)methacrylamide, a modified acrylamide monomer, colorless oily substance, English name: N,N-bis(2-hydroxyethyl)-2-methylprop -2-enamide, the chemical structure is as follows: [0003] [0004] The double bond of the compound itself can undergo a polymerization reaction with acrylate or methacrylate monomers. At the same time, after the water volatilizes, the nitrohydroxyethyl group can undergo a self-crosslinking reaction, resulting in very good water resistance and resistance to water. Scrub performance. Double bonds and hydroxyl groups can also react with other groups, so it is a good biological, pharmaceutical and chemical intermediates. [0005] Among the existing synthetic methods, the document WO 2012049453 A2 reports that diethanolamine and methacryloyl ...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/20
CPCC07C231/12C07D273/00C07C233/20
Inventor 王治国宋艳红马秀娟张欣李世江李超李强田贝贝李涛
Owner SHANGHAI ZAIQI BIO TECH
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