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Method for preparing hexamethylenediamine from cyclohexene

A technology of cyclohexene and hexamethylene diamine, which is applied in chemical instruments and methods, preparation of amino-substituted functional groups, preparation of carbonyl compounds by oxidation, etc., can solve the problems of high toxicity of adiponitrile, dependence on imports, high price, etc., to improve the choice performance, catalyst stability, route cleaning effect

Active Publication Date: 2020-04-24
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

[0006] 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 from cyclohexene
  • Method for preparing hexamethylenediamine from cyclohexene
  • Method for preparing hexamethylenediamine from cyclohexene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0111]The preparation of embodiment 1-10 supported type W, Mo catalyst

[0112] Firstly, the carrier was calcined at 550 °C for 4 h in a nitrogen atmosphere to remove species adsorbed in the pores. Dissolve a certain amount of ammonium tungstate and ammonium molybdate in water, and set the volume according to the saturated water absorption of the carrier (when using MCM-41, set the volume to 50 ml, when using SBA-15, set the volume to 30 ml, use medium When using porous silica, set the volume to 20 ml), take 10 g of the carrier and use the equal volume impregnation method to load the metal salt solution on the carrier, then place it in an oven at 100 ° C for 12 h, and then bake it in a muffle furnace at 500 ° C for 4 h Prepare the catalyst. The types and qualities of carriers and metal salts are shown in Table 1.

[0113] The preparation parameter of table 1 catalyst

[0114]

[0115] Wherein, in the name of the catalyst aW-bMo / X, a represents the mass loading of the met...

Embodiment 11

[0116] Example 11 Cyclohexene oxidation to adipaldehyde

[0117] In a 250mL round-bottomed flask, add 1.0g of cyclohexene, 0.10g of methyl pyruvate, 25mL of acetonitrile, 0.5W-1.0Mo / MCM-41 catalyst (0.10g), rise to 20°C, and feed ozone with a concentration of The mixed gas of 100mg / L, described mixed gas is made up of ozone and oxygen, and described mixed gas flow rate is 80mL / min, is down to room temperature rapidly after reacting 1h, analyzes product composition with gas chromatograph.

Embodiment 12-20

[0118] Example 12-20 Cyclohexene oxidation to adipaldehyde

[0119] The cyclohexene oxidation reaction was carried out according to the same steps as in Example 11, and the specific differences and results of the reaction conditions are shown in Table 2.

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Abstract

The invention discloses a method for preparing hexamethylenediamine from cyclohexene, wherein the method comprises the following steps: a cyclohexene-containing mixed solution and an ozone-containingmixed gas are subjected to a reaction under reaction conditions I to obtain adipic dialdehyde, wherein the reaction conditions I comprise that a supported metal oxide is used as a catalyst I; the obtained adipic dialdehyde, ammonia gas and hydrogen are introduced into a reactor containing a catalyst II, and hexamethylenediamine is generated under the reaction condition II, wherein the catalyst IIis an HZSM-5 molecular sieve encapsulated metal catalyst. Cyclohexene is used as a raw material; hexamethylenediamine is prepared through oxidation and amination; the use of highly toxic raw materialadiponitrile is avoided, ozone is used as an oxidizing agent, the heterogeneous catalyst can be used for preparing adipic dialdehyde with high selectivity, the HZSM-5 molecular sieve encapsulated metal catalyst is further adopted, the selectivity of a target product and the stability of the catalyst are effectively improved by utilizing the confinement effect of the molecular sieve, and the routeis clean and environment-friendly.

Description

technical field [0001] The application relates to a method for preparing hexamethylenediamine from 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. React with sebacic acid to produce polyhexamethylene sebacamide (PA610), also known as polyamide 610 or nylon 610. Nylon 610 can be made into various nylon resins, nylon fibers and engineering plastic products, and is a rare intermediate in synthetic materials. HDI (1,6-hexamethylene diisocyanate) can be produced through photochemical reaction. HDI is a new type of polyureth...

Claims

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Application Information

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IPC IPC(8): C07C211/12C07C209/22B01J29/04
CPCB01J29/045C07C45/28C07C209/22C07C211/12C07C47/12
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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