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Method for preparing adiponitrile by catalytic ammonia oxidation cracking of cyclohexanol

A technology of cyclohexanol and adiponitrile, which is applied in the field of ammoxidative cracking of cyclohexanol to prepare adiponitrile, can solve the problems of alicyclic hydroxyl groups, low catalytic activity, catalyst deactivation, etc., and achieve easy separation, catalyst The effect of simple system and less by-products

Active Publication Date: 2019-07-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the alicyclic hydroxyl group is difficult to activate, and the traditional oxidative cracking catalytic system will face problems such as low catalytic activity and catalyst deactivation in the presence of ammonia.
On the other hand, the selectivity of the ammoxidation reaction of the aldehyde group is difficult to control, and the nitrile is easily further hydrolyzed to form an amide, which has a negative impact on the downstream conversion and application of the product.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Mix 1mmol cyclohexanol with 0.050g Rh / MnO 2 (Rh / cyclohexanol = 1mol%) was put into a 20mL lined reaction kettle, 10mL of acetonitrile was added, and 3MPa NH 3 With 0.1MPa air, the temperature was programmed to 30°C for 48 hours, and then cooled. The qualitative analysis of the obtained samples was performed by gas chromatography-mass spectrometry, and the quantitative analysis was realized by gas chromatography. The conversion rate of cyclohexanol was 73.0%, and the selectivity of adiponitrile was 95.2%. The isolated yield of adiponitrile was 50.5%, and the purity by gas chromatography was 99.1%.

Embodiment 2

[0024] Mix 1mmol cyclohexanol with 0.100g Ru / MnO 2 (Ru / cyclohexanol = 2mol%) was put into a 20mL lined reaction kettle, 10mL of dioxane was added, and 3.6MPa NH 3 With 0.5MPa oxygen, the temperature was programmed to 50°C for 15 hours, and then cooled. The qualitative analysis of the obtained samples was performed by gas chromatography-mass spectrometry, and the quantitative analysis was realized by gas chromatography. The conversion rate of cyclohexanol was 83.6%, and the selectivity of adiponitrile was 91.4%. The isolated yield of adiponitrile was 71.7%, and the purity by gas chromatography was 99.0%.

Embodiment 3

[0026] Mix 1mmol cyclohexanol with 0.150g Pd / MnO 2 (Pd / cyclohexanol=3mol%) was put into a 20mL lined reaction kettle, 10mL tert-butanol was added, and 5MPa NH 3 and 0.3MPa oxygen, the temperature was programmed to 70°C for 10 hours, and then cooled. The qualitative analysis of the obtained samples was performed by gas chromatography-mass spectrometry, and the quantitative analysis was realized by gas chromatography. The conversion rate of cyclohexanol was 87.7%, and the selectivity of adiponitrile was 90.2%. The isolated yield of adiponitrile was 71.6%, and the purity by gas chromatography was 99.0%.

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Abstract

The invention relates to a method for preparing adiponitrile by the catalytic ammonia oxidation cracking of cyclohexanol. In the method, ammonia gas is used as the nitrogen source, air and / or oxygen is used as the oxygen source, and cyclohexanol is subjected to the ammonia oxidation cracking to prepare adiponitrile under the catalytic action. According to the method, the ammonia oxidation efficiency is high, and the product yield is high; the air is used as the oxygen source, so that the method is economic and environment-friendly; and the product and the catalyst are easy to separate, and thepost-treatment is simple, so that the method has good application prospect.

Description

technical field [0001] The invention relates to a method for preparing adiponitrile by ammoxidation cracking of cyclohexanol. Background technique [0002] Adiponitrile is an important organic chemical intermediate, the most important industrial use of which is the production of hexamethylenediamine, which is a monomer for the synthesis of nylon 66. In addition, adiponitrile is also widely used in the fields of electronics, light industry and organic synthesis. For example, adiponitrile is hydrolyzed to produce adipic acid; it is used as plasticizer and auxiliary material in textile industry; it is used as solvent and extractant, etc. At present, the production methods of adiponitrile include adipic acid ammonification dehydration method, acrylonitrile electrolytic dimerization method, and butadiene hydrocyanation method, and its production is monopolized by some large multinational companies. The development of clean and efficient adiponitrile preparation technology can n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/24C07C255/04
CPCC07C253/24C07C255/04
Inventor 徐杰贾秀全马继平李晓芳苗虹徐永明夏飞
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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