Preparation method of N,N'-dicyclohexylurea

A technology of dicyclohexyl urea and cyclohexylamine, which is applied to the preparation of urea derivatives, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of high pressure reaction temperature, reduce reaction temperature and pressure, promote activation, The effect of large absorption capacity

Inactive Publication Date: 2016-10-12
SHAOXING UNIVERSITY
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, due to CO 2 The thermodynamic stability and kinetic inertness make CO 2 The conditions for directly reacting with organic amines to prepare disubstituted ureas are relatively harsh, generally requiring catalysts (transition metal salts or bases), dehydrating agents and solvents, and CO 2 The pressure (~5.5MPa) and reaction temperature (~170°C) are also high (Green.Chem., 9, 158, 2007)

Method used

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  • Preparation method of N,N'-dicyclohexylurea
  • Preparation method of N,N'-dicyclohexylurea
  • Preparation method of N,N'-dicyclohexylurea

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Effect test

Embodiment 1

[0030] When [P 66614 ]Im anion functionalized ionic liquid for CO absorption 2 After reaching the absorption equilibrium, according to the CO2 Saturation absorption capacity, when absorbing CO 2 Add 2 times the molar amount of cyclohexylamine to the final ionic liquid system, mix it evenly, transfer it to a stainless steel autoclave at 60°C and carry out the in-situ conversion reaction under normal pressure, stop the reaction after reacting for 8 hours, and add a certain amount of distilled water, separated the crude product from the ionic liquid, and recrystallized to obtain N,N'-dicyclohexylurea with a yield of 65%.

Embodiment 2-14

[0031] Embodiment 2-14: the influence of different reaction temperature, pressure and time on product yield.

[0032] According to the preparation method of embodiment 1, adopt [P 66614 ] Im anion-functionalized ionic liquid absorbed CO 2 In situ reaction of carbon source and cyclohexylamine with 2 times the molar amount, the temperature, pressure and time of the reaction were changed, and the yield of N,N'-dicyclohexylurea was calculated as shown in Table 1:

[0033] Table 1, the influence of temperature of reaction, pressure and time on product yield

[0034]

[0035]

[0036] As shown in Table 1, due to the anion functionalization of ionic liquids with CO 2 chemical interaction to activate CO 2 molecules, thereby effectively reducing the CO 2 Reaction temperature and pressure with cyclohexylamine, under mild conditions (reaction temperature is 40-80°C, pressure is 0.1-0.3Mpa, reaction time is 6-10 hours) to achieve 2 In situ transformation and preparation of N,N'...

Embodiment 15-34

[0038] Examples 15-34: Effects of different types of anion-functionalized ionic liquids on product yield.

[0039] According to the preparation method of Example 1, the difference is: change the type of anion-functionalized ionic liquid, and the CO absorbed by the anion-functionalized ionic liquid 2 In situ reaction of carbon source with 2 times the molar amount of cyclohexylamine, reacted at 60°C and normal pressure for 8 hours, and investigated the effect of the type of anion functionalized ionic liquid on CO 2 The effect of in situ conversion to N,N'-dicyclohexylurea, the results are shown in Table 2.

[0040] Table 2. The effect of the type of anionic functionalized ionic liquid on the product yield

[0041]

[0042]

[0043] As shown in Table 2, different anion functionalized ionic liquids, for CO 2的 Absorption capacity and absorption rate are different, for CO 2 The activation of the molecule is also different, therefore, its impact on the yield is more obvious,...

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Abstract

The invention discloses a preparation method of N,N'-dicyclohexyl urea, which is characterized in that: anionic functionalized ionic liquid absorbs CO through chemical action 2 In situ reaction of carbon source and cyclohexylamine, N,N'-dicyclohexylurea was prepared under mild conditions. with traditional CO 2 Compared with the method of preparing N,N'-dicyclohexyl urea directly with cyclohexylamine reaction, this method has the advantages of low reaction temperature and pressure, CO 2 The utilization rate is high, the anionic functionalized ionic liquid can be recycled, and no additional catalyst, dehydrating agent and solvent are needed. It is a preparation method of N,N'-dicyclohexyl urea with industrial application potential.

Description

Technical field: [0001] The present invention relates to a preparation method of N,N'-dicyclohexyl urea, more specifically refers to CO absorbed by functionalized ionic liquid through chemical action 2 Preparation of N,N'-dicyclohexylurea for in situ reaction of carbon source with cyclohexylamine. Background technique: [0002] At present, the preparation method of N,N'-dicyclohexyl urea mainly adopts cyclohexylamine as a raw material, which is prepared by reacting with urea or carbon disulfide. [0003] Traditionally, carbon disulfide is used as a raw material and water is used as a solvent to prepare N,N'-dicyclohexyl urea. The main problem is that the hydrogen sulfide produced is not easy to come out, which causes safety and environmental problems in production. [0004] On the other hand, using urea (urea) and cyclohexylamine as raw materials to prepare N,N'-dicyclohexyl urea under heating reaction in the presence of isoamyl alcohol solvent has the disadvantage of large...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C273/18C07C275/26
CPCC07C273/1809
Inventor 许映杰
Owner SHAOXING UNIVERSITY
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