Method for synthesizing cyclohexanone-oxime from cyclohexane in one step

A technology of cyclohexanone oxime and cyclohexane, which is applied in the field of one-step liquid-phase synthesis of cyclohexanone oxime, can solve the problems of low-value ammonium sulfate by-products, complex process conditions, and serious environmental pollution, and achieve high application value and process conditions Simplicity and efficiency-enhancing effects

Inactive Publication Date: 2011-04-06
XIANGTAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, the industry mainly synthesizes cyclohexanone oxime through multi-step methods, such as the nitric oxide reduction method of the cyclohexanone-hydroxylamine route, the hydroxylammonium sulfate method and the hydroxylamine phospho

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] According to the ratio of cyclohexane: hydrogen peroxide: ammonia water = 1 mL: 2.5 mL: 2 mL, the materials were sequentially loaded into a 100 mL glass reactor in the order of cyclohexane, solvent, catalyst, hydrogen peroxide, and ammonia water, and 6 mL of tert-butanol was used as the solvent. The reaction temperature was 75°C, the reaction time was 8h, and the amount of catalyst accounted for 25% of the cyclohexane.

[0012] The reaction mixture was analyzed by gas chromatography. The conversion of cyclohexane was 18.8%, the selectivity of cyclohexanone oxime was 11.7%, the selectivity of KA oil was 38.9%, and the selectivity of adipic acid was 25.7%.

[0013] The reacted mixed solution was subjected to suction filtration to separate the catalyst and vacuum distillation to obtain 0.32 g of cyclohexanone oxime product and 0.48 g of by-product.

Embodiment 2

[0015] Cyclohexane: hydrogen peroxide: ammonia water=1mL: 5mL: 4mL, the steps are the same as in Example 1, except that 6mL of acetonitrile is added as a solvent, the reaction temperature is 75°C, the reaction time is 8h, and the amount of catalyst accounts for 25% of the cyclohexane. .

[0016] The reaction mixture was analyzed by gas chromatography. The conversion of cyclohexane was 6.8%, the selectivity of cyclohexanone oxime was 10.4%, the selectivity of KA oil was 36.1%, and the selectivity of adipic acid was 17.3%.

[0017] The reacted mixed solution was subjected to suction filtration to separate the catalyst and distillation under reduced pressure to obtain 0.08 g of cyclohexanone oxime product and 0.18 g of by-product.

Embodiment 3

[0019] Cyclohexane: hydrogen peroxide: ammonia water=1mL: 1mL: 1mL, the steps are the same as those in Example 1, except that the reaction temperature is 60°C, the reaction time is 16h, and the amount of catalyst accounts for 20% of the cyclohexane.

[0020] The reaction mixture was analyzed by gas chromatography. The conversion of cyclohexane was 10.1%, the selectivity of cyclohexanone oxime was 13.3%, the selectivity of KA oil was 39.8%, and the selectivity of adipic acid was 28.7%.

[0021] The reacted mixed solution was subjected to suction filtration to separate the catalyst and vacuum distillation to obtain 0.21 g of cyclohexanone oxime product and 0.16 g of by-product.

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Abstract

The invention discloses a method for synthesizing cyclohexanone-oxime from cyclohexane in one step, relating to the field of chemical synthesis. The method comprises the following steps of: adding a titanium-silicate molecular sieve TS-1 used as a catalyst into a synthesis reactor at normal pressure with cyclohexane, H2O2 and ammonia water as raw materials, wherein 0.2g of the catalyst titanium-silicate molecular sieve TS-1is added in 1 mmol of cyclohexane; and controlling the reaction temperature at 25-80 DEG C and the reaction time for 1-30h to synthesize cyclohexanone-oxime in one step, wherein the molar ratio of cyclohexane to H2O2 to ammonia water is 1:1.5-3.5:1.5-2. The method has simple process conditions and mild reaction conditions. Byproducts generated in the reaction process are KA oil and hexanedioic acid which have higher application value, and can greatly improve the utilization rate of resources. The whole process is basically free of environmental pollution and truly realizes zero emission.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for one-step liquid phase synthesis of cyclohexanone oxime using cyclohexane as a raw material. Background technique [0002] At present, cyclohexanone oxime is mainly synthesized by multi-step methods in industry, such as nitrogen oxide reduction method of cyclohexanone-hydroxylamine route, hydroxylamine sulfate method and hydroxylamine phosphate method, etc. These synthesis methods all have complex process conditions, serious environmental pollution and It is accompanied by a large number of low-value ammonium sulfate by-products and other disadvantages. SUMMARY OF THE INVENTION [0003] The purpose of the present invention is to overcome the shortcomings of the prior art, and proposes a one-step method for synthesizing cyclohexanone oxime from cyclohexane, which has simple process conditions, mild reaction conditions, no environmental pollution, and can greatly imp...

Claims

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Application Information

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IPC IPC(8): C07C251/44C07C249/06C07C27/16C07C35/08C07C49/403C07C55/14
Inventor 毛丽秋罗和安尹笃林梁静
Owner XIANGTAN UNIV
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