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2-imidazolidone synthesis method

A technology of imidazolidinone and synthesis method, which is applied in the field of synthesis of 2-imidazolidinone, can solve the problems of expensive raw materials, relatively expensive ethylene carbonate, and high boiling point of by-products, and achieve simple and easy-to-operate reaction process and synthetic method The effect of green cleaning and mild reaction conditions

Inactive Publication Date: 2014-01-08
XIAMEN UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Japanese patent JP62265268 proposes to react ethylenediamine and phosgene in aqueous sodium hydroxide solution, and then recrystallize the crude product obtained after vacuum distillation with chloroform to obtain 2-imidazolidinone. This method uses highly toxic raw material phosgene, and uses To the highly toxic solvent chloroform, there are great potential safety hazards, and there are problems such as equipment corrosion and environmental pollution.
Chinese patent CN101270088A improved Japanese patent JP62265268, and proposed to prepare 2-imidazolidinone by reacting ethylenediamine and solid phosgene in an aqueous solution of sodium hydroxide, and then recrystallize the extracted and concentrated crude product to obtain 2- Imidazolidinone, although this method overcomes some of the weaknesses of the phosgene method, the price of solid phosgene is relatively expensive, and the yield of this method is not high, and there is a problem of wastewater treatment
Chinese patent CN101817764 proposes to use ethylenediamine and carbon dioxide as raw materials to prepare 2-imidazolidinone, but this method requires high temperature and high pressure, which has a large safety hazard, and the utilization rate of raw material ethylenediamine is low, resulting in a low yield of the target product
Patent WO2010062490 proposes to use chloroform as solvent, disalicylate carbonate and ethylenediamine as raw materials to synthesize 2-imidazolidinone (Formula 1). The raw material disalicylate carbonate used in this method is expensive, and the highly toxic solvent chloroform is used , and the utilization rate of atoms is low (the by-product of methyl salicylate is generated), the by-product has a high boiling point, and the product is not easy to refine
Chinese patent CN101195606 proposes to use ethylene carbonate and ethylenediamine as raw materials to synthesize 2-imidazolidinone (Formula 2). The raw material ethylene carbonate used in this method is more expensive, and the atom utilization rate is low (generation of ethylene glycol by-product ), the by-product ethylene glycol has a high boiling point, is not easy to recycle, and brings certain difficulties to product refining
[0005] In summary, the methods reported so far have many deficiencies, such as the use of highly toxic raw materials and solvents in the synthesis process, the reaction needs to be carried out under high temperature and high pressure, or the raw materials are expensive, the atom utilization rate is low, or the expensive, corrosive strong catalyst

Method used

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Experimental program
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Embodiment 1

[0025] Into the heatable reactor (with stirring device), add 1.0g sulfamic acid (0.01mol), 6mL methanol, 3.0g ethylenediamine (0.05mol), 5.4g dimethyl carbonate (0.06mol), 60 After reacting at ℃ for 3h, the temperature was increased to 160℃, and the reaction was stopped after 15h. The reaction liquid is naturally cooled to room temperature, the catalyst is removed by filtration, and then the solvent is removed to obtain the crude product 2-imidazolidinone. The quantitative analysis was carried out by gas chromatograph, and the yield was 62.1%.

[0026] NMR analysis results:

[0027] 1 H NMR(400MHz, D 2 O): δ3.47 (s, 4H). 13 C NMR(100MHz, D 2 O): δ 40.69 (2C), 167.07 (1C).

Embodiment 2

[0029] Into the heatable reactor (with a stirring device), add 1.0g sulfamic acid (0.01mol), 6mL methanol, 3.0g ethylenediamine (0.05mol), 6.3g dimethyl carbonate (0.07mol), 60 After reacting at ℃ for 3h, the temperature was increased to 160℃, and the reaction was stopped after 15h. The reaction liquid is naturally cooled to room temperature, the catalyst is removed by filtration, and then the solvent is removed to obtain the crude product 2-imidazolidinone. Quantitative analysis by gas chromatograph showed that the yield was 63.4%.

Embodiment 3

[0031] Into a heatable reactor (with a stirring device), add 1.0g sulfamic acid (0.01mol), 6mL methanol, 3.0g ethylenediamine (0.05mol), 7.2g dimethyl carbonate (0.08mol), 60 After reacting at ℃ for 3h, the temperature was increased to 160℃, and the reaction was stopped after 15h. The reaction liquid is naturally cooled to room temperature, the catalyst is removed by filtration, and then the solvent is removed to obtain the crude product 2-imidazolidinone. The quantitative analysis was carried out by gas chromatograph, and the yield was 63.0%.

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Abstract

The invention relates to 2-imidazolidone, and provides a 2-imidazolidone synthesis method simple in process and low in cost. The method includes: (1) sequentially adding a catalyst of sulfamic acid, a solvent of methyl alcohol, ethylenediamine and dimethyl carbonate into a heatable reactor for reacting at the temperature of 20-80 DEG C for 1-5 hours; (2) continuously raising the temperature to 120-180 DEG C, and reacting for 10-24 hours prior to generating a target product 2-imidazolidone; (3) after reaction is ended, filtering to remove the catalyst of sulfamic acid and remove the solvent of methyl alcohol so as to obtain a coarse product 2-imidazolidone; (4) refining the coarse product 2-imidazolidone obtained in the step (3) to obtain the product 2-imidazolidone. The defects that an existing synthesis process is carried out at high temperature under high pressure, high-corrosivity catalysts, toxic materials and high boiling solvent are used, atom utilization rate is low and the like are overcome.

Description

Technical field [0001] The present invention relates to 2-imidazolidinone, in particular to a method for synthesizing 2-imidazolidinone under mild reaction conditions. Background technique [0002] 2-imidazolidinone, also known as cycloethylene urea, is a colorless needle crystal. Because this compound can effectively remove the residual formaldehyde in the fabric after finishing with 2D-resin, KB resin, urea-formaldehyde resin, melamine-formaldehyde resin, etc., it can be used to synthesize high-performance formaldehyde scavengers, home air formaldehyde powerful enzymes, etc.; It is also used as an intermediate of fine chemicals for the manufacture of resins, plasticizers, spray paints, adhesives, etc.; in the pharmaceutical industry, 2-imidazolidinone is a key intermediate for a variety of new antibiotics, used for Merlot It can be used for the preparation of various antibiotics such as cillin and azlocillin, and can be used as the basic raw material of the third generation pe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/34
CPCY02P20/584C07D233/34
Inventor 吐松刘建设卢英华肖宗源蓝家勇阮鹭韩
Owner XIAMEN UNIV
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