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Cyclohexene-based hexanediamine preparation process

A preparation process, cyclohexene technology, applied in the direction of reductive alkylation preparation, ozonolysis preparation, including molecular sieve catalysts, etc., can solve the problems of dependence on imports, high toxicity of adiponitrile, high price, etc., to achieve clean routes and improve Catalyst stability and selectivity improvement effect

Active Publication Date: 2020-05-12
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • 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 hexanediamine preparation process
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  • Cyclohexene-based hexanediamine preparation process

Examples

Experimental program
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Effect test

preparation example Construction

[0059] The preparation parameter of table 1 catalyst

[0060] Example catalyst Ammonium tungstate quality (g) Ammonium molybdate mass (g) Carrier mass (g) 1’ 0.5W-1.0Mo / MCM-41 0.07 0.18 10.00 2’ 1.0W-1.0Mo / MCM-41 0.14 0.18 10.00 3’ 2.0W-1.0Mo / MCM-41 0.28 0.18 10.00 4’ 3.0W-1.0Mo / MCM-41 0.42 0.18 10.00 5’ 5.0W-1.0Mo / MCM-41 0.69 0.18 10.00 6’ 5.0W-2.0Mo / MCM-41 0.69 0.37 10.00 7’ 3.0W-1.0Mo / SBA-15 0.42 0.18 10.00 8’ 3.0W-2.0Mo / SBA-15 0.42 0.37 10.00 9’ 3.0W-0.5Mo / SiO 2

[0061] Wherein, in the name of the catalyst aW-bMo / X, a represents the mass loading of the metal W element, b represents the mass loading of the metal Mo element, and X represents the support.

Embodiment 11

[0062] Embodiment 11' cyclohexene oxidation produces adipaldehyde

[0063] 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.

[0064] Embodiment 12'-20' cyclohexene oxidation produces adipaldehyde

[0065] Carry out cyclohexene oxidation reaction according to the same step of embodiment 11', the specific differences and results of reaction conditions are shown in Table 2.

[0066] Example 21'

[0067] The preparation method is basically the same as that of Example 13', except that methyl trifluoropyruvate is not added, and the test results are shown in Table 2.

[0068] Example 22'

[0069] The prepara...

Embodiment 1-10

[0078] The preparation of embodiment 1-10 basic molecular sieve

[0079] 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;

[0080] Step 2): Weighing 30g molecular sieves, the molecular sieves are selected from one of NaX, NaY, KL, and NaBeta molecular sieves;

[0081] 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;

[0082] 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 hexanediamine preparation process, which comprises: carrying out an oxidation reaction on a cyclohexene-containing mixed solution and an ozone-containing mixed gas under a reaction condition I to obtain adipic dialdehyde, wherein the reaction condition I comprises using a supported metal oxide as a catalyst I; and introducing the obtained adipic dialdehyde, ammonia gas and hydrogen into a reactor containing a catalyst II, and generating hexanediamine under reaction conditions, wherein the catalyst II is an alkaline molecular sieve supported metal catalyst. According to the invention, cyclohexene is used as a raw material, and hexanediamine is prepared through oxidation and amination, so that the use of highly toxic raw material adiponitrile is avoided; and ozone is used as an oxidizing agent, a heterogeneous catalyst can be used for high-selectivity preparation of adipic dialdehyde, an alkaline molecular sieve supported metal catalyst is further used, and the selectivity of the target product and the stability of the catalyst are effectively improved by using the confinement effect of the molecular sieve, so that 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): C07C211/12C07C209/26
CPCC07C45/40C07C209/26C07C2523/30C07C2529/03C07C211/12C07C47/12
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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