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Free radical protective agent for preparing hexanedioic acid through direct oxidation of cyclohexane

A technology of free radicals and cyclohexane, applied in the field of free radical protection agents, can solve the problems of reducing the decomposition rate of free radical catalysts, easy deactivation and decomposition of free radical catalysts, etc.

Active Publication Date: 2018-12-28
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] One of the technical problems to be solved by the present invention is the problem that the free radical catalyst is easily deactivated and decomposed in the reaction of direct oxidation of cyclohexane to adipic acid existing in the prior art, and the freedom to directly oxidize cyclohexane to adipic acid is provided. Radical protection agent, the use of this protection agent has the characteristics of reducing the decomposition rate of free radical catalysts

Method used

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  • Free radical protective agent for preparing hexanedioic acid through direct oxidation of cyclohexane
  • Free radical protective agent for preparing hexanedioic acid through direct oxidation of cyclohexane
  • Free radical protective agent for preparing hexanedioic acid through direct oxidation of cyclohexane

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Embodiment 1

[0029] Add 5mol acetic acid, 0.02mol NHS, 0.01mol cobalt acetate, 0.01mol manganese acetate, 0.01mol copper acetate, 1mol cyclohexane, 0.01mol p-tert-butylphenol, 0.01mol citric acid and 0.01mol triphenyl phosphite to In a 1-liter high-pressure reactor (with a reflux condensing device, the reflux condensing device communicates with the atmosphere through a backup pressure valve), seal and stir, heat to 90°C, and continuously feed air at 5 liters / minute to control the pressure inside the kettle. 3MPa, after reacting for 5 hours, cool to room temperature, take out the reaction mixture for analysis, the analysis results: the conversion rate of cyclohexane is 52%, the selectivity of adipic acid is 83%, and the NHS decomposition rate after the reaction is 6%. For the convenience of comparison, the main The reaction conditions and reaction results are listed in Table 1.

Embodiment 2

[0031] 5mol acetic acid, 0.02mol NHPI, 0.01mol cobalt acetate, 0.01mol manganese acetate, 0.01mol copper acetate, 1mol cyclohexane, 0.01mol p-tert-butylphenol, and 0.01mol triphenyl phosphite were added to a 1-liter high-pressure reactor ( Equipped with a reflux condensing device, the reflux condensing device is connected to the atmosphere through a backup pressure valve), sealed and stirred, heated to 90°C, continuously fed with air at 5 liters / min, and kept at 3MPa to control the internal pressure of the kettle. After 5 hours of reaction , cooled to room temperature, and the reaction mixture was taken out for analysis. The analysis results showed that the conversion rate of cyclohexane was 47%, the selectivity of adipic acid was 81%, and the NHS decomposition rate after the reaction was 12%. For the convenience of comparison, the main reaction conditions and reaction results are listed in Table 1.

Embodiment 3

[0033] 5mol acetic acid, 0.02mol NHS, 0.01mol cobalt acetate, 0.01mol manganese acetate, 0.01mol copper acetate, 1mol cyclohexane, 0.01mol citric acid and 0.01mol triphenyl phosphite were added to a 1-liter high-pressure reactor (with reflux The condensing device, the reflux condensing device is connected to the atmosphere through the backup pressure valve), sealed and stirred, heated to 90°C, continuously fed with air at 5 liters / min, and kept at 3MPa to control the pressure in the kettle. After 5 hours of reaction, cool To room temperature, take out the reaction mixture for analysis, analysis results: cyclohexane conversion rate 42%, adipic acid selectivity 78%, NHS decomposition rate after the reaction is 18%, for the convenience of comparison, the main reaction conditions and reaction results are listed in the table 1.

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Abstract

The invention relates to a free radical protective agent for preparing hexanedioic acid through direct oxidation of cyclohexane, and mainly solves the problem in the prior art that a free radical catalyst inactivates and decomposes easily in the reaction of preparing the hexanedioic acid through the direct oxidation of the cyclohexane. The free radical protective agent comprises citric acid and / orat least one of substituted phenol shown in the formula in the description, wherein the technical scheme that X and Y are independently selected from H or tertiary butyl, and X and Y are not used inH at the same time better solves the problem, and the free radical protective agent for preparing the hexanedioic acid through the direct oxidation of the cyclohexane can be applied to the industrialproduction of preparing the hexanedioic acid through the direct oxidation of the cyclohexane.

Description

technical field [0001] The invention relates to a free radical protecting agent for directly oxidizing cyclohexane to produce 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 to reach 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 cos...

Claims

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Application Information

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IPC IPC(8): C07C55/14C07C51/31C07B60/00
CPCC07B61/02C07C51/313C07C55/14
Inventor 干丰丰唐泓
Owner CHINA PETROLEUM & CHEM CORP
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