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Cyclohexene-based hexamethylenediamine preparation process

A preparation process and technology of cyclohexene, which are applied in the direction of reductive alkylation preparation, ozone oxidation preparation of carboxylic acid, catalyst activation/preparation, etc., can solve the problems of dependence on imports, high toxicity of adiponitrile, high price, etc. Effects of cleaning, improved selectivity and catalyst stability

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

[0005] The raw material adiponitrile in the route of industrialized hydrogenation of adiponitrile to hexamethylenediamine is highly toxic and depends on imports and the price is high

Method used

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  • Cyclohexene-based hexamethylenediamine preparation process
  • Cyclohexene-based hexamethylenediamine preparation process
  • Cyclohexene-based hexamethylenediamine preparation process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Cyclohexene oxidation is adipaldehyde in embodiment 1' microchannel reactor

[0061] 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;

[0062] 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;

[0063] 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

[0064] Cyclohexene is oxidized to adipaldehyde in embodiment 2'-11' microchannel reactor

[0065] 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.

[0066] Table 1 Reaction conditions and result list of cyclohexene oxidation to adipaldehyde in microchannel reactor

[0067]

[0068]

[0069] 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%.

Embodiment 1-10

[0070] The preparation of embodiment 1-10 basic molecular sieve

[0071] Step 1): dissolving an alkali metal salt in water to obtain a precursor solution with a concentration of 0.2-0.6 mol / L, the alkali metal salt being selected from one of potassium nitrate, rubidium nitrate, and cesium nitrate;

[0072] Step 2): Weighing 30g molecular sieves, the molecular sieves are selected from one of NaX, NaY, KL, and NaBeta molecular sieves;

[0073] Step 3) According to the solid-to-liquid ratio of 10:1, use the alkali metal ion precursor solution in step 1) to carry out ion exchange on the molecular sieve weighed in step 2), exchange at 80°C for 4 hours, suction filter and wash 1. After drying, the obtained solid is roasted at 550° C. in a muffle furnace for 6 hours;

[0074] Step 4) Change the object of ion exchange in step 3) from the molecular sieve weighed in step 2) to the molecular sieve obtained after roasting, repeat step 3) twice to obtain a basic molecular sieve sample, an...

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Abstract

The invention discloses a cyclohexene-based hexamethylenediamine preparation process which comprises the steps: introducing a mixed solution containing cyclohexene and a catalyst I and a mixed gas containing ozone into a reactor I, and carrying out a reaction to prepare adipic dialdehyde, the catalyst I being a transition metal complex catalyst; and introducing the obtained adipic dialdehyde, ammonia gas and hydrogen into a reactor II containing a catalyst II to generate hexamethylenediamine under the reaction condition, wherein the catalyst II is a basic molecular sieve supported metal catalyst. Cyclohexene is used as a raw material, hexanediamine is prepared through oxidation and amination, the use of highly toxic raw material adiponitrile is avoided, ozone is used as an oxidizing agent,the heterogeneous catalyst can be used for high-selectivity preparation of adipic dialdehyde, the alkaline molecular sieve supported metal catalyst is further used, the selectivity of the target product and the stability of the catalyst are effectively improved by using the confinement effect of the molecular sieve, and the route is clean and environment-friendly.

Description

technical field [0001] The application relates to a preparation process of hexamethylenediamine based on cyclohexene, which belongs to the field of chemical industry. Background technique [0002] 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. [0003] Domestic adiponitrile is completely dependent on imports, and its price has remained high, seriously affecting the economic benefits and international market competitiveness of my country's nylon industry, and restricting the development of my country's nylon 66 and related industries. Therefore, the development of new technologies for the preparation of hexamethylenediamine has become an urgent problem in ...

Claims

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Application Information

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IPC IPC(8): C07C209/26C07C211/12C07C51/34C07C55/14B01J29/12B01J29/14B01J29/62B01J29/74B01J37/02B01J37/30
CPCB01J29/123B01J29/126B01J29/143B01J29/62B01J29/7415B01J37/0207B01J37/30B01J2229/18C07C51/34C07C209/26C07C211/12C07C55/14
Inventor 袁扬扬许磊李沛东赵晓炜陆标史鑫
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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