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A kind of method of synthesizing 2-carboxamide cyclohexanone

A technology of cyclohexanone and formamide, which is applied in the field of synthesizing 2-formamide cyclohexanone, can solve the problems of low utilization rate of cyclohexanone, pollute the environment and the like, and achieve the advantages of shortened reaction time, low energy consumption and good promotion prospects. Effect

Inactive Publication Date: 2016-01-20
CHINA UNIV OF MINING & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the process still has the defects that the utilization rate of cyclohexanone is not high and pollutes the environment

Method used

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  • A kind of method of synthesizing 2-carboxamide cyclohexanone
  • A kind of method of synthesizing 2-carboxamide cyclohexanone
  • A kind of method of synthesizing 2-carboxamide cyclohexanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0028] Add 124g of cyclohexanone, 42g of urea, 0.6g of 85.0% phosphoric acid and 15g of xylene into a 1000ml three-neck flask, reflux at 138°C for 2.5 hours, then add 320g of 1M dilute H 2 SO 4 The spiro ring was hydrolyzed by heating. After the reaction was completed, 77 g of the xylene cyclohexanone mixture was collected to obtain 58 g of 2-carboxamide cyclohexanone, mp: 127.1-129.0°C. Based on the consumption of cyclohexanone (62 g), the total yield was 65.3%.

Embodiment 3

[0030] 77g of xylene cyclohexanone mixture collected in Example 2 and 62g of neocyclohexanone, 42g of urea, 0.6g of 85.0% phosphoric acid were added to a 1000ml three-necked flask, and 322g was added after reflux reaction at 135°C for 3 hours to prepare by recovering water from Example 2 1M dilute H2SO4 was heated to hydrolyze the spiro ring. After the reaction was completed, 89 g of the xylene cyclohexanone mixture was collected to obtain 56.2 g of 2-carboxamide cyclohexanone. Yield 78.1%.

Embodiment 4

[0032] Add 124g of cyclohexanone, 42g of urea, 0.6g of 85.0% phosphoric acid and 15g of toluene into a 1000ml three-neck flask, reflux at 136°C for 3 hours, then add 320g of 1M dilute H 2 SO 4 Heated and hydrolyzed the spiro ring. After the reaction was completed, 78.4 g of the tolyl cyclohexanone mixture was collected to obtain 57.8 g of 2-carboxamide cyclohexanone, mp: 127.2-129.5°C. Based on the consumption of 60.6 g of cyclohexanone, the total yield was 66.3%.

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Abstract

The invention discloses a synthetic method for 2-formamide cyclohexanone with low emission and low consumption, and belongs to the technical field of medicinal chemistry and organic synthesis. According to the method, a non-oxide proton acid or salt thereof is used as a catalyst, arene is used as a solvent and a water-carrying agent, and cyclohexanone and urea are used as raw materials, so that the 2-formamide cyclohexanone can be prepared through a one-pot reaction. The screw ring synthetized through the technology provided by the invention is not needed to be cooled and separated, so that a great amount of scouring water is eliminated; besides, condensation generated water saturated by cyclohexanone, evaporated water generated during the screw ring hydrolysis and aqueous phase mother solution generated after the product is separated out are used for preparing hydrolyzing diluted acid to realize cyclic utilization, so that the loss caused by the cyclohexanone dissolution in water is eliminated, the use ratio of cyclohexanone is increased and the zero release of sewage is realized; the method is simple and convenient to operate and is suitable for industrial application.

Description

technical field [0001] The invention relates to a method for synthesizing 2-carboxamide cyclohexanone, belonging to the technical fields of medicinal chemistry and organic synthesis. Background technique [0002] 2-Carboxamide cyclohexanone is an important raw material for the hypoglycemic drug gliclazide and herbicides. The existing synthesis method is as follows: method one [Journalfprakt. Ketone and urea were used as raw materials, p-toluenesulfonic acid was used as a catalyst, and toluene was hydrated to synthesize a spiro ring (91.0% yield). Since the catalyst p-toluenesulfonic acid is an oxidizing organic acid, during the reaction, especially at high temperature, the oxidized part of cyclohexanone will generate a brownish-red syrupy impurity, which will make the intermediate spiro ring darker in color, and must be cooled and passed through water Hydrolysis can only be carried out after purification with organic solvents. However, the step-by-step operation not only i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/82C07C231/10
Inventor 李国防高庆宇马啸华潘长伟刘晓娟王绍荣
Owner CHINA UNIV OF MINING & TECH
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