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Method of preparing adipic acid by directly oxidizing cyclohexane

A technology of cyclohexane and adipic acid, applied in the field of direct oxidation of cyclohexane to adipic acid, which can solve the problems of low conversion rate of cyclohexane and low yield of adipic acid

Active Publication Date: 2014-10-22
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is that the direct oxidation of cyclohexane to adipate cyclohexane in the prior art has low conversion rate and low yield of adipic acid, and a new direct oxidation of cyclohexane is provided. Oxidation method for producing adipic acid

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 5mol acetic acid, 0.025mol NHPI, 0.025mol NAPI, 0.0025mol cobalt acetate, 0.0025mol manganese acetate, 0.005mol PEG2000 and 1mol cyclohexane (that is, the molar ratio of solvent, free radical catalyst, metal catalyst, cocatalyst, cyclohexane 5:0.05:0.005:0.005:1) into a 1-liter high-pressure reactor (with a reflux condensing device, the reflux condensing device is connected to the atmosphere through a backup pressure valve), sealed and stirred, heated to 100 ° C, and 5 liters / Continuously feed air in minutes, control the internal pressure of the kettle and keep it at 1MPa. After reacting for 5 hours, cool to room temperature, take out the reaction mixture for analysis, and the analysis results: the conversion rate of cyclohexane is 80%, and the yield of adipic acid is 45%. The main reaction conditions and reaction results are listed in Table 1 for comparison.

Embodiment 2

[0019] 5mol acetic acid, 0.025mol NHPI, 0.025mol NAPI, 0.0025mol cobalt acetate, 0.0025mol manganese acetate, 0.005mol PEG400 and 1mol cyclohexane (that is, the molar ratio of solvent, free radical catalyst, metal catalyst, cocatalyst, cyclohexane 5:0.05:0.005:0.005:1) into a 1-liter high-pressure reactor (with a reflux condensing device, the reflux condensing device is connected to the atmosphere through a backup pressure valve), sealed and stirred, heated to 100 ° C, and 5 liters / Continuously feed air in minutes, control the internal pressure of the kettle and keep it at 1MPa. After reacting for 5 hours, cool to room temperature, take out the reaction mixture for analysis, and the analysis results: the conversion rate of cyclohexane is 65%, and the yield of adipic acid is 30%. The main reaction conditions and reaction results are listed in Table 1 for comparison.

Embodiment 3

[0021]5mol acetic acid, 0.025mol NHPI, 0.025mol NAPI, 0.0025mol cobalt acetate, 0.0025mol manganese acetate, 0.005mol 18-crown-6 and 1mol cyclohexane (i.e. solvent, free radical catalyst, metal catalyst, promoter, cyclohexane The molar ratio of alkanes is 5:0.05:0.005:0.005:1) into a 1-liter high-pressure reactor (with a reflux condensing device, which is connected to the atmosphere through a backup pressure valve), sealed and stirred, and heated to 100 ° C. Air was continuously fed in at 5 liters / minute, and the pressure in the kettle was kept at 1 MPa. After 5 hours of reaction, it was cooled to room temperature, and the reaction mixture was taken out for analysis. The analysis results showed that the conversion rate of cyclohexane was 90%, and the yield of adipic acid was 50%. %, for the convenience of comparison, the main reaction conditions and reaction results are listed in Table 1.

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Abstract

The invention relates to a method for preparing adipic acid by directly oxidizing cyclohexane. The problems of low cyclohexane conversion rate and low adipic acid yield of preparation of adipic acid by directly oxidizing cyclohexane in the prior art are mainly solved. The method for preparing adipic acid by directly oxidizing cyclohexane comprises is characterized in that adipic acid is obtained by oxidizing cyclohexane with an oxygen-containing gas as an oxidant in the presence of a solvent, a free radical catalyst, a metal catalyst and a cocatalyst; the solvent is at least one selected from acetic acid, acetonitrile and ethyl acetate; the free radical catalyst is at least one selected from NHPI (N-hydroxyphthalimide) and NAPI (N-acetoxylphthalimide); the metal catalyst is at least one selected from cobalt and manganese; and the cocatalyst is at least one selected from polyethylene glycol and crown ether. The method well solves the problems, and can be used in the industrial production of adipic acid.

Description

technical field [0001] The invention relates to a method for directly oxidizing cyclohexane to prepare adipic acid. Background technique [0002] Adipic acid, also known as fatty acid, is an important organic dibasic acid and an important raw material for the preparation of polyurethane and nylon 66. In the world, adipic acid is used in more than 70% of nylon 66 fields, and in my country, adipic acid is used in polyurethane fields reaching 78%. At present, there are four production methods of adipic acid in the world: phenol method, cyclohexane method, cyclohexene method and butadiene method. Before the 1950s, the production of adipic acid mainly used phenol as the raw material. The production of adipic acid by the phenol method is a relatively classical method. The advantages of this method are high product purity, mature production technology, and no stainless steel materials. However, phenol resources are limited and expensive, and the product cost is high, so it has be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/215C07C55/14
CPCC07C51/313C07C55/14
Inventor 唐泓干丰丰
Owner CHINA PETROLEUM & CHEM CORP
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