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Method for preparing hexamethylenediamine on basis of cyclohexene

A technology of cyclohexene and hexamethylene diamine, which is applied in the preparation of reductive alkylation, chemical instruments and methods, and preparation of carboxylic acid by ozone oxidation, can solve the problems of dependence on imports, high price, and high toxicity of adiponitrile, and achieves Low cost, convenient operation, and the effect of reducing the occurrence of side reactions

Active Publication Date: 2020-04-28
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

[0004] Judging from the existing literature and technology, the raw material adiponitrile in the route of industrialized hydrogenation of adiponitrile to hexamethylenediamine is highly toxic, and it depends on imports and the price is high.

Method used

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  • Method for preparing hexamethylenediamine on basis of cyclohexene
  • Method for preparing hexamethylenediamine on basis of cyclohexene
  • Method for preparing hexamethylenediamine on basis of cyclohexene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Cyclohexene oxidation is adipaldehyde in embodiment 1' microchannel reactor

[0075] 50 g of cyclohexene and 116 g of acetone were mixed to prepare a cyclohexene solution with a mass concentration of 30%, and 7.89 g of vanadyl acetylacetonate was added to the cyclohexene solution, and the mixed solution was obtained after ultrasonic vibration and uniform mixing;

[0076] A pump is used to inject the mixed solution into the microchannel reactor, and the flow rate of the mixed solution is 10g / min. At the same time, the mixed gas is injected into the microchannel reactor through a mass flow meter, and the flow rate of the mixed gas is controlled to be 15.1L / min. Composed of ozone, the ozone concentration is 100mg / L;

[0077] The reaction temperature in the microchannel reactor was 10° C., the reaction pressure was 0.10 MPa, and the materials were collected after 10 minutes of reaction, and analyzed by gas chromatography.

Embodiment 2

[0078] Cyclohexene is oxidized to adipaldehyde in embodiment 2'-11' microchannel reactor

[0079] Adopt the described operation of embodiment 1 ', change the pressure of reaction, solvent, catalyzer and temperature of reaction to react, concrete reaction condition and result are shown in Table 1.

[0080] Table 1 Reaction conditions and result list of cyclohexene oxidation to adipaldehyde in microchannel reactor

[0081]

[0082]

[0083] As can be seen from Table 1, in the preparation process provided by the application, adipaldehyde generally has higher selectivity, and the selectivity of adipaldehyde can reach more than 53.8%, the highest can reach 91.2%, and the conversion rate of cyclohexene can reach 35.2% above, up to 100%.

[0084] Preparation of Ni-based catalyst: The ratios of ions in the following examples are all molar ratios unless otherwise specified.

[0085] Embodiment 1 prepares NiMgAl-01 catalyst with hydrotalcite as precursor, (Ni 2+ +Mg 2+ ):Al 3...

Embodiment 3

[0089] Embodiment 3 prepares NiMgAl-03 catalyst with hydrotalcite as precursor, (Ni 2+ +Mg 2+ ):Al 3+ The ratio is 3:1, Ni 2+ : Mg 2+ The ratio is 3.0

[0090] 78.52gNi(NO 3 ) 2 ·6H 2 O, 46.89gAl(NO 3 ) 3 9H 2 O and 23.07gMg(NO 3 ) 2 ·6H 2 O is completely dissolved in 500ml of water to obtain mixed solution I; weigh 26.5gNa 2 CO 3 and 70g of NaOH were completely dissolved in 1L of water to obtain the mixed solution II; the two mixed solutions were slowly added dropwise to 200mL of water at the same time, vigorously stirred at a speed of 600r / min, and the pH was maintained at 10. After the addition was completed, the obtained colloidal suspension Transfer to an oven, age at 65°C for 72h, wash with distilled water until neutral, and dry to obtain Ni-based hydrotalcite, and further roast the obtained Ni-based hydrotalcite precursor at 500°C for 4h to obtain highly dispersed Ni base catalyst.

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Abstract

The invention discloses a method for preparing hexamethylenediamine on basis of cyclohexene. The method comprises the steps: respectively injecting a mixed solution and an ozone-containing mixed gas into a micro-channel reactor, and carrying out an oxidation reaction under a reaction condition to obtain adipic dialdehyde, the mixed solution containing cyclohexene and a metal compound catalyst; andreacting the raw material containing the adipic dialdehyde in the presence of ammonia gas, hydrogen and a Ni-based catalyst to generate hexamethylenediamine, wherein the Ni-based catalyst is preparedfrom hydrotalcite containing Ni < 2 + >. Cyclohexene is adopted as a raw material, hexamethylenediamine is prepared through oxidation and amination, highly toxic raw material adiponitrile is prevented from being used, ozone is adopted as an oxidizing agent, the heterogeneous catalyst can be used for high-selectivity preparation of adipic dialdehyde, the Ni-based catalyst is further adopted to catalyze adipic dialdehyde to prepare hexamethylenediamine through reductive amination, the highly toxic raw material adiponitrile is prevented from being used, and the route is clean and environment-friendly.

Description

technical field [0001] The application relates to a method for preparing hexamethylenediamine based on cyclohexene, which belongs to the field of chemical engineering. Background technique [0002] Hexamethylenediamine is an important organic chemical raw material, which can be polycondensed with adipic acid to produce polyhexamethylene adipamide, also known as polyamide 66 (PA66) or nylon 66. Nylon 66 can be used for injection molding, extrusion, blow molding, spraying, casting, machining, welding, and bonding. About 90% of hexamethylenediamine produced in the world is used in the production of nylon 66. The production technologies of hexamethylenediamine mainly include adiponitrile method, hexanediol method and caprolactam method. At present, almost all hexamethylenediamine is prepared by hydrogenation of adiponitrile, and the production methods of adiponitrile include catalytic amination of adipic acid, electrolytic dimerization of acrylonitrile and butadiene method. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/26C07C211/12C07C51/34C07C55/14B01J23/78B01J23/80B01J23/755
CPCB01J23/78B01J23/80C07C51/34C07C209/26C07C211/12C07C55/14
Inventor 许磊袁扬扬李沛东陆标赵晓炜史鑫
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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