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Process for preparing adipic dialdehyde from cyclohexene

A technology for cyclohexene and adipaldehyde, which is applied in the field of preparing adipaldehyde from cyclohexene, can solve the problems of high price, excessive oxidation, hindering industrial application, etc., and achieves high product selectivity, efficient mass transfer, and enhanced material transfer. Effect

Active Publication Date: 2020-05-12
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

[0007] In summary, in the preparation of adipaldehyde by cyclohexene oxidation, metal complexes-NaIO 4 Catalytic system, catalyst preparation method is complex and expensive
When using high-concentration hydrogen peroxide as an oxidant to oxidize cyclohexene, there is a problem of over-oxidation, and it is difficult to obtain high adipaldehyde selectivity, which hinders the further industrial application of this process

Method used

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  • Process for preparing adipic dialdehyde from cyclohexene
  • Process for preparing adipic dialdehyde from cyclohexene

Examples

Experimental program
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Effect test

Embodiment 1

[0053] Cyclohexene is oxidized to adipaldehyde in the microchannel reactor of embodiment 1

[0054] Mix 50g of cyclohexene and 116g of acetone to prepare a cyclohexene solution with a mass concentration of 30%, add 7.78g of ruthenium chloride trihydrate and 6.08g of methyl pyruvate into the cyclohexene solution, and mix well by ultrasonic vibration After that, the mixed solution is obtained;

[0055] A pump is used to inject the mixed solution into the microchannel reactor, the mixed solution flow rate is 10g / min, the mixed gas is injected into the microchannel reactor through a mass flow meter, and the controlled mixed gas flow rate is 15.1L / min, wherein the mixed gas is composed of oxygen and Ozone composition, the ozone concentration is 100mg / L;

[0056] The reaction temperature in the microchannel reactor is 10° C., and the reaction pressure is 0.10 MPa. Samples were taken after 10 minutes of reaction after feeding, and analyzed by gas chromatography.

[0057] Cyclohexe...

Embodiment 14-17

[0060] It is basically the same as Example 1-4, the only difference is that no auxiliary agent is used, and the specific reaction conditions and results are shown in Table 1.

[0061] Table 1 Reaction conditions and result list of cyclohexene oxidation to adipaldehyde in microchannel reactor

[0062]

[0063]

[0064] Remarks: Auxiliary A: methyl pyruvate, Auxiliary B: methyl trifluoropyruvate, Auxiliary C: methyl acetylacetonate, Auxiliary D: methyl acetoacetate.

[0065] It can be seen from Table 1 that in the preparation method provided by the application, adipaldehyde generally has a higher selectivity, especially when using auxiliary agents and the reaction temperature is 0-20°C, the selectivity of adipaldehyde can reach more than 81.3%, the highest It can reach 93.5%, and the conversion rate of cyclohexene can reach more than 85.3%, and the highest can reach 100%. The selectivity of adipaldehyde in the embodiment of the auxiliary agent is higher than that in the em...

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Abstract

The invention discloses a process for preparing adipic dialdehyde from cyclohexene. The preparation method comprises the following steps: respectively injecting a mixed solution and an ozone-containing mixed gas into a micro-channel reactor, and carrying out an oxidation reaction under reaction conditions to obtain adipic dialdehyde, wherein the mixed solution containing cyclohexene and a metal chloride catalyst. According to the method, a metal chloride catalyst is combined with ozone, so that cyclohexene is selectively oxidized into adipic dialdehyde, the defect that precious metal coordination compounds and sodium periodate need to be used in a cyclohexene oxidation reaction is overcome, substance transfer between two-phase materials is effectively enhanced by adopting a micro-channel reactor and utilizing efficient mass transfer and heat transfer efficiency in the micro-reactor, and the product selectivity can reach 93.5%.

Description

technical field [0001] The application relates to a process for preparing adipaldehyde from cyclohexene, which belongs to the field of chemical industry. Background technique [0002] 1,6-Adipaldehyde is an important fine chemical product. It is a quick-acting and broad-spectrum chemical sterilizer. It can not only kill most bacteria, bacterial propagules, fungi, spores and viruses quickly and efficiently, but also does not Corrosion of metal instruments and glass and plastic products, because it is harmless to the human body, it can be widely used in the disinfection and sterilization of medical equipment, food utensils, etc. In addition, adipaldehyde is also used in oil extraction, which can inhibit sulfate-reducing bacteria and increase the sulfur content of crude oil. In addition, as a cross-linking agent, 1,6-hexanedialdehyde has the characteristics of high activity, fast reaction, large binding capacity, stable product, and strong resistance to acid, water, and enzyme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/40C07C47/12
CPCC07C45/40C07C47/12
Inventor 袁扬扬许磊陆标李沛东赵晓炜史鑫
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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