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A kind of method of molecular oxygen phase oxidation cyclohexylamine to prepare cyclohexanone oxime and caprolactam

A technology for the production of cyclohexanone oxime and cyclohexylamine, which is applied in the field of one-step co-production of cyclohexanone oxime and caprolactam by oxidation rearrangement, which can solve the problems of difficult production, high cycle energy consumption, and low product quality, and achieve resource improvement. Utilization rate, low cost, cost reduction effect

Inactive Publication Date: 2015-10-07
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above processes all have problems such as difficulty in product separation and purification, low product quality, and excessive energy consumption in the cycle, and there are still great difficulties in production realization.
[0005] U.S. patents such as US 4337358, US 4504681, US 4504791, and US 4624939 disclose that silica gel, aluminum oxide, or silica gel and aluminum oxide loaded with tungsten oxide are used as catalysts to prepare cyclohexanone oxime by gas-phase molecular oxygen oxidation of cyclohexylamine These methods have a common technical problem, the catalyst life is too short (the reaction time is only 1~4h), the problem that the catalyst is easy to deactivate has not been solved at present, and the reaction only stays in the preparation stage of cyclohexanone oxime

Method used

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  • A kind of method of molecular oxygen phase oxidation cyclohexylamine to prepare cyclohexanone oxime and caprolactam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In this example, the flow rate of cyclohexylamine is 0.06mL / min, and the air flow rate is 25 mL / min. Cyclohexylamine is continuously injected into the fixed-bed reactor from the air end of the reaction tube through a plunger-type advection pump, and the reaction solution is vaporized in the preheating section. Enter the mesoporous silicon catalyst bed layer for reaction, the reaction temperature is 190°C, the reaction time is 5h, and the product is condensed by water flow into the collection bottle. After the product was analyzed by gas-phase internal standard method and liquid-phase external standard method, the conversion rate of cyclohexylamine was 16% and the selectivity of cyclohexanone oxime was 92% through material balance calculation.

[0018] The conversion rate of cyclohexylamine, the selectivity of cyclohexanone oxime are calculated according to the following formula:

[0019]

Embodiment 2

[0021] The procedure of this example is the same as that of Example 1, except that the aluminum-loaded mesoporous silicon material is used as the catalyst, the reaction time is 0.5 h, the conversion rate of cyclohexylamine is 21%, and the selectivity of cyclohexanone oxime is 88%.

Embodiment 3

[0023] The steps of this example are the same as in Example 1, except that the flow rate of cyclohexylamine is 0.03ml / min, the reaction time is 10h, the conversion rate of cyclohexylamine is 38%, and the selectivity of cyclohexanone oxime is 78%.

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Abstract

The invention relates to a method for preparing cyclohexane oxime and caprolactam by oxidizing cyclohexylamine through molecular oxygen in gas phase. The cyclohexane oxime is continuously prepared by selectively oxidizing cyclohexylamine through molecular oxygen in a fixed bed reactor, and caprolactam can be synthesized by one step through oxidation rearrangement. The catalyst is meso-porous silicon material or metal or nonmetal loaded meso-porous silicon material and has dual catalytic functions of oxidization and rearrangement. The method can be used for avoiding the technical barrier problem in the existing method for synthesizing cyclohexanone, the cyclohexane can be prepared by nitrobenzene, aniline and nitrocyclohexane through hydrogenation and also can be prepared by cyclohexanol and cyclohexene through ammoniation, and the source of feed is wide. The method not only can be used for greatly simplifying the steps and lowering the cost, but also can be used for sharply improving the resource utilization rate, thus being an environment-friendly synthesis method.

Description

technical field [0001] The invention relates to a preparation method of cyclohexanone oxime and caprolactam, in particular to a method for preparing cyclohexanone oxime by selectively oxidizing cyclohexylamine in a fixed-bed reactor with molecular oxygen, which can also be oxidized and rearranged for one-step co-production Methods for cyclohexanone oxime and caprolactam. Background technique [0002] Cyclohexanone oxime and caprolactam are important chemical raw materials for the production of nylon-6 and nylon-66. The current industrial production methods mainly include cyclohexanone-hydroxylamine method, photonitrosation method and toluene method, etc. Cyclohexanone needs to be used in the cyclohexanone-hydroxylamine method process, and the industrial production of cyclohexanone by oxidation of cyclohexane The technical barriers limit its further wide application; the photonitrosation method needs to use ultraviolet light radiation, and the reaction process consumes too m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/04C07C251/44C07D223/10C07D201/04
Inventor 钟文周毛丽秋尹笃林毛小龙李永强邹国强王思捷
Owner HUNAN NORMAL UNIVERSITY