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Synthesis method of 1,3-dimethyl-2-imidazolone

A synthesis method and imidazolinone technology, applied in the first field, can solve the problems of expensive raw materials, unfavorable environmental protection, serious environmental pollution, etc., and achieve the effect of green and clean synthesis process, less discharge of three wastes, and simple production process

Active Publication Date: 2018-04-24
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solid acid catalyst used in this method uses more expensive Gamma-alumina as raw material, and it is modified by loading strong acid. There is waste acid generated, which is not conducive to environmental protection, and the energy consumption in the preparation process is high, which ultimately leads to high production process costs
[0005] In summary, the currently reported 1,3-dimethyl-2-imidazolinone synthesis methods have many deficiencies, or the raw materials are expensive, highly toxic, or the reaction conditions are harsh, or the equipment is severely corroded, or the environment serious pollution

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In the autoclave which can be heated and can be filled and deflated (with stirring device), add 0.2g montmorillonite, 2.0g 2-imidazolidinone (23mmol) and 7.8g concentration in succession and be 37% formaldehyde aqueous solution (96mmol), 159mmol Hydrogen, 0.67g 5% palladium on carbon (water content 55%), stop the reaction after reacting at 145°C for 4h. The reaction solution was naturally cooled to room temperature, and the catalyst was recovered by filtration. After collecting the filtrate, the remaining formaldehyde and by-product water in the filtrate were distilled off to obtain a crude product of 1,3-dimethyl-2-imidazolidinone. Quantitative analysis by gas chromatography, the yield was 91.7%

[0023] NMR analysis results: 1 H NMR (400MHz, D 2 O): δ2.58(s, 6H, CH 3 ); δ3.21(s, 4H, CH 2 ). 13 CNMR (400MHz, D 2 O): δ30.73(2C), 44.88(2C), 163.49(1C).

[0024] Finally, it is purified by rectification to obtain the 1,3-dimethyl-2-imidazolidinone.

Embodiment 2

[0026] In the heatable and inflatable deflation autoclave (with stirring device), add successively 0.2g montmorillonite, 2.0g 2-imidazolidinone (23mmol), 5.9g concentration is 37% formaldehyde aqueous solution (72mmol), 159mmol of hydrogen, 0.67g of 5% palladium carbon (water content 55%), reacted at 145°C for 4h, then stopped the reaction. The reaction solution was naturally cooled to room temperature, and the catalyst was recovered by filtration. After collecting the filtrate, the remaining formaldehyde and by-product water in the filtrate were distilled off to obtain a crude product of 1,3-dimethyl-2-imidazolidinone. Quantitative analysis was carried out by gas chromatography, and the yield was 87.0%. Finally, the 1,3-dimethyl-2-imidazolidinone was obtained by rectification and purification.

Embodiment 3

[0028] In the heatable and inflatable deflation autoclave (with stirring device), add successively 0.2g montmorillonite, 2g 2-imidazolidinone (23mmol), 7.8g concentration is 37% formaldehyde aqueous solution (96mmol), 159mmol Hydrogen, 0.67g 5% palladium on carbon (water content 55%), react at 125°C for 4h, then stop the reaction. The reaction solution was naturally cooled to room temperature, and the catalyst was recovered by filtration. After collecting the filtrate, the remaining formaldehyde and by-product water in the filtrate were distilled off to obtain a crude product of 1,3-dimethyl-2-imidazolidinone. Quantitative analysis was carried out by gas chromatography, and the yield was 84.3%. Finally, the 1,3-dimethyl-2-imidazolidinone was obtained by rectification and purification.

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Abstract

The invention discloses a synthesis method of 1,3-dimethyl-2-imidazolone. The method comprises steps as follows: (1) montmorillonite, palladium on carbon, 2-imidazolidone and a formaldehyde water solution are sequentially added to a heatable and inflatable autoclave, and hydrogen is introduced into the autoclave for a reaction at the temperature of 110-160 DEG C for 1-5 h; (2) a material obtainedin the step (1) is filtered to recover montmorillonite and palladium on carbon, remaining formaldehyde and by-product water in filtrate are removed through distillation after the filtrate is collected, and a crude product is obtained; (3) the crude product is purified by rectification, and 1,3-dimethyl-2-imidazolone is obtained. The used catalyst is montmorillonite which is low in cost, can be directly used without further treatment or modification and is easy to recycle.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 1,3-dimethyl-2-imidazolinone. Background technique [0002] 1,3-Dimethyl-2-imidazolidinone, also known as 1,3-dimethyl-2-imidazolidinone, is a colorless transparent liquid. The compound has strong solubility, can dissolve various organic and inorganic substances, and has the advantages of high boiling point, low melting point, low toxicity, etc., and has good stability under hot strong alkali and acidic conditions, and is resistant to water, It has good light resistance and oxygen resistance, and is widely used in many fields such as chemical industry, and is called "ace solvent". [0003] At present, the chemical synthesis method of 1,3-dimethyl-2-imidazolinone (DMI) mainly includes 1) using N, N-dimethylethylenediamine and carbonylating reagent (such as phosgene, carbon dioxide, trichloro Acetyl chloride, etc.) as raw materials to p...

Claims

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Application Information

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IPC IPC(8): C07D233/32
CPCC07D233/32
Inventor 吐松郑达明毛晨路林新萍叶李艺陈学云尹应武
Owner XIAMEN UNIV
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