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Method for preparing amide compounds through ionic liquid catalysis in high-pressure environment

A technology of amide compounds and ionic liquids, which is applied in the field of catalytic preparation of amide compounds by ionic liquids under high-pressure environments, achieving the effects of fewer steps, low cost of raw materials and technologies, and easy operation

Active Publication Date: 2021-01-12
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that the traditional synthetic methods of directly converting alcohols into amides must use heavy metals as catalysts, and usually must be used in conjunction with additives to promote the reaction.

Method used

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  • Method for preparing amide compounds through ionic liquid catalysis in high-pressure environment
  • Method for preparing amide compounds through ionic liquid catalysis in high-pressure environment
  • Method for preparing amide compounds through ionic liquid catalysis in high-pressure environment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1, the synthesis of N-p-phenylpropyl-phenylacetamide.

[0039] Dissolve 0.122g of phenylethyl alcohol and 0.135g of n-phenylpropylamine in 1.00mL of 1-ethyl-3-methylimidazolium acetate ionic liquid, apply a pressure of 5.0MPa under the condition of feeding oxygen, and heat to 110 °C and continued to stir for 24 hours. After the reaction was completed, the high pressure was removed and the heating was stopped, and the reaction product was extracted from the reaction mixture with methyl acetate, and separated and purified by high performance liquid chromatography to obtain the target product 2-phenyl-N-p-phenylpropylacetamide. Its reaction formula is as follows:

[0040]

[0041] Mass spectrometry, high performance liquid chromatography ( figure 1) and NMR analysis confirm that the resulting target product is 2-phenyl-N-p-phenylpropylacetamide, and the total yield is 94.42% (m / z[M+H] + =254.15437, 1 H NMR (500MHz, Chloroform-d) δ7.31,7.30,7.30,7.29,7.29,...

Embodiment 2

[0047] Example 2, the synthesis of N-hexyl-2-phenylacetamide.

[0048] Dissolve 0.122g of phenylethyl alcohol and 0.101g of n-hexylamine in 1.00mL of 1-ethyl-3-methylimidazolium acetate ionic liquid, apply a pressure of 5.0MPa under the condition of feeding oxygen, heat to 110°C, and Stirring was continued for 12 hours. After the reaction was completed, the high pressure was removed and the heating was stopped, and the reaction product was extracted from the reaction mixture with methyl acetate, separated and purified by high performance liquid chromatography to obtain the target product N-hexyl-2-phenylacetamide. Its reaction formula is as follows:

[0049]

[0050] Mass spectrometry, high performance liquid chromatography ( figure 2 ) and NMR analysis confirm that the resulting target product is N-hexyl-2-phenylacetamide, and the total yield is 83.02% (m / z[M+H] + =220.16478, 1 H NMR (500MHz, Chloroform-d) δ7.31,7.30,7.30,7.29,7.29,7.28,7.28,7.27,7.26,7.26,7.25,7.25,7...

Embodiment 3

[0051] Example 3, the synthesis of N-benzyl-2-phenylacetamide.

[0052] Dissolve 0.122g of phenylethyl alcohol and 0.107g of benzylamine in 1.00mL of 1-ethyl-3-methylimidazolium acetate ionic liquid, apply a pressure of 5.0MPa under the condition of feeding oxygen, and heat to 110°C, And keep stirring for 8 hours. After the reaction was completed, the high pressure was removed and the heating was stopped, and the reaction product was extracted from the reaction mixture with methyl acetate, separated and purified by high performance liquid chromatography to obtain the target product N-benzyl-2-phenylacetamide. Its reaction formula is as follows:

[0053]

[0054] Mass spectrometry, high performance liquid chromatography ( image 3 ) and NMR analysis confirm that the resulting target product is N-benzyl-2-phenylacetamide, and the total yield is 93.51% (m / z[M+H] + =256.12572, 1 H NMR (500MHz, Chloroform-d) δ7.31,7.31,7.30,7.30,7.29,7.29,7.29,7.29,7.29,7.28,7.28,7.27,7.27,7...

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Abstract

The invention relates to a method for preparing amide compounds through ionic liquid catalysis in a high-pressure environment. According to the method, ionic liquid 1-ethyl-3-methylimidazolium acetateis used as a catalyst and a solvent, oxygen is used as an oxidizing agent, and aromatic methanol or alkyl alcohol is converted into an amide compound under the conditions of high pressure and heating. The synthesis method provided by the invention has the advantages that the raw material and technical cost is low; compared with other traditional methods, the method is safe, low in toxicity, economical and environmentally friendly; and the method has few steps, is simple and convenient to operate, is beneficial to large-scale synthesis, and has important significance for synthesis of amide compounds and large-scale industrialization of preparation.

Description

technical field [0001] The present invention relates to the application of ionic liquid in catalytic amidation reaction under high pressure environment, specifically: using imidazolium acetate ionic liquid as catalyst, oxygen as oxidant, under high pressure and heating conditions, combined oxidation and amidation The reaction converts aromatic methanol or alkyl alcohols to amides. Background technique [0002] Amidation reaction is one of the most important reactions in organic synthesis and chemical industry. Amide compounds are important building blocks of synthetic chemical intermediates and commercial chemicals, and have a wide range of applications in biopharmaceuticals, material synthesis, medical diagnosis, and food processing. In practice, amides are usually synthesized by condensation reactions between carboxylic acids and amines. Although this traditional method is very mature, due to the need to deal with corrosive acids and / or their derivatives and the use of a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/10C07C233/11C07C233/22C07C233/13C07D213/40C07D295/182C07C233/05C07C233/58C07C235/46C07C233/65C07D307/68
CPCC07C231/10C07D213/40C07D295/182C07D307/68C07C2601/02C07C233/11C07C233/22C07C233/13C07C233/05C07C233/58C07C235/46C07C233/65
Inventor 陈铭
Owner YANTAI UNIV
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