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Method for preparing hexamethylenediamine

A technology of hexamethylenediamine and adipaldehyde, which is applied in reductive alkylation preparation, chemical instruments and methods, molecular sieve catalysts, etc., can solve the problems of dependence on imports, high toxicity of adiponitrile, high price, etc., and achieves a clean route, The effect of improving selectivity and catalyst stability

Active Publication Date: 2020-05-08
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] 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
  • Method for preparing hexamethylenediamine
  • Method for preparing hexamethylenediamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] The preparation of embodiment 1 metal@molecular sieve catalyst

[0081] (1) 2.48gNi(NO 3 ) 2 ·6H 2 O was dissolved in water, and the volume was adjusted to 12mL, and 10g of HBeta molecular sieves (SiO 2 / Al 2 o 3 Molar ratio = 800, SiO 2 The mass content is 98.9%), the Ni element is loaded on the HBeta by the equal volume impregnation method, placed in a 100 ° C oven for 12 hours, and then placed in the HBeta 2 Reduction at 500°C for 4 hours in the atmosphere to obtain metal-loaded Ni / HBeta molecular sieves;

[0082] (2) Place metal-loaded Ni / HBeta molecular sieves in 15 mL of TPAOH aqueous solution with a mass fraction of 35.0%, immerse at room temperature for 2 h, and dry in an oven at 100° C. for 12 h to obtain TPAOH / HBeta molecular sieves adsorbed in the pores;

[0083] (3) Mix the / HBeta molecular sieve with TPAOH adsorbed in the channel with 0.60g sodium hydroxide and 20mL deionized water, and crystallize at 90°C for 6 hours to obtain Ni@ZSM-5 molecular sie...

Embodiment 2-10

[0086] Embodiment 2-10 Preparation of transition metal@molecular sieve catalyst

[0087] The same steps in Example 1 were used to prepare M@ZSM-5, and the metal type and loading amount were adjusted by changing the type and concentration of the metal salt solution. The specific synthesis conditions are listed in Table 1.

[0088] The specific synthetic conditions of each embodiment of table 1

[0089]

[0090] In the table, in the catalyst nA@ZSM-5, A represents the transition metal, ZSM-5 is the abbreviation of HZSM-5, n represents the transition metal mass loading in M / Hbeta, W(%) represents the metal content in M@ZSM-5 mass content.

[0091] Embodiment 1-10 Characterization of metal@molecular sieve catalyst

[0092] figure 1 It is the XRD spectrogram of the HBeta molecular sieve used in Example 1; the catalyst obtained in Examples 1 to 10 is a ZSM-5 molecular sieve, and a typical representative is as figure 2 The XRD spectrogram of embodiment 1 catalyst in. The XRD...

Embodiment 11-20

[0093] Reaction Performance Evaluation of Embodiment 11-20 Metal @ Molecular Sieve Catalyst

[0094] Pack 2.0g of the above-mentioned catalyst in a stainless steel fixed-bed reactor with an inner diameter of 10mm and a length of 300mm. Both ends of the catalyst are filled with quartz sand. First, a reducing gas is introduced at a flow rate of 30mL / min, and the catalyst is reduced at 400°C for 4 hours. , wherein the reducing gas composition is H 2 / N 2 The volume ratio is 1 / 4.

[0095] After the reduction, the temperature of the reactor dropped to 130°C, the reaction pressure rose to 6.0Mpa, and H 2 , liquid ammonia and adipaldehyde for reductive amination reaction, wherein liquid ammonia and adipaldehyde are respectively injected into the reaction system through a high-pressure micro feed pump, and the mass space velocity of adipaldehyde is 1.0h -1 , H 2 :NH 3 : adipaldehyde=15:30:1, reaction 10h sampling adopts gas chromatography analysis, and reaction result is listed i...

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Abstract

The invention discloses a method for preparing hexamethylenediamine, which comprises the step of reacting a raw material containing adipic dialdehyde in the presence of ammonia gas, hydrogen and a catalyst to generate the hexamethylenediamine, and the catalyst is an HZSM-5 molecular sieve encapsulated transition metal catalyst. According to the method, the hexamethylenediamine is prepared throughcatalytic reductive amination of the adipic dialdehyde by encapsulating a transition metal in pore channels of a molecular sieve, so that the use of a highly toxic raw material adiponitrile is avoided, and the route is clean and environment-friendly.

Description

technical field [0001] The application relates to a method for preparing hexamethylenediamine from adipaldehyde, which belongs to the field of chemistry and chemical engineering. 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] The production of hexamethylenediamine is mainly monopolized by some large multinational companies. INVISTA, BASF and Ascend together account for 74% of the global production capacity, and are in a highly oligopoly industry. China Shenma, which ranks fourth, accounts for 9% of the global production capacity . The only manufacturers in my country that can produce hexamethylenediamine are PetroCh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/26C07C211/12B01J29/46
CPCB01J29/46B01J2229/18C07C209/26C07C211/12
Inventor 许磊袁扬扬赵晓炜李沛东陆标史鑫
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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