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Industrial preparation method of hexamethylenediamine

A hexamethylenediamine, industrial technology, applied in the field of industrial preparation of hexamethylenediamine, can solve the problems of synthetic route, complex synthesis technology, dependence on imports of adiponitrile, complex catalyst technology, etc., and achieves simple and fast reaction operation and route, and reaction The effect of low cost and good use prospects

Active Publication Date: 2021-06-11
山西铁峰化工有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the adiponitrile method has the following problems: 1) adiponitrile as a raw material is highly toxic; 2) adiponitrile is dependent on imports and the price is high; 3) the synthetic route and synthesis technology of adiponitrile to hexamethylenediamine are complex and difficult to construct High cost, not suitable for widespread promotion
The catalyst technology used in this method is complex and needs to be further improved
In addition, Chinese patent CN104262168A discloses a method for aminating dialdehyde to prepare hexamethylenediamine using a nickel-based hydrogenation catalyst supported on a silica carrier. Although the process flow of this method is simple, it is still in the stage of laboratory research and needs to be developed. Further research for application in industrial production
And Chinese patent CN111072487A discloses a method for preparing hexamethylenediamine based on cyclohexene. This method adopts ozonation reaction to prepare cyclohexene into adialdehyde, and then uses Ni-containing 2+ The hydrotalcite catalyst prepared by oxidation and amination of hexamethylenediamine; this method has a simple route and is green and concise, but the process technology requirements are high and the conditions are difficult to control, so it needs to be further improved

Method used

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  • Industrial preparation method of hexamethylenediamine
  • Industrial preparation method of hexamethylenediamine
  • Industrial preparation method of hexamethylenediamine

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preparation example Construction

[0022] A kind of industrial preparation method of hexamethylenediamine of the present invention comprises the following steps:

[0023] 1) After dissolving cyclohexene in the first organic solvent, electrocatalytic oxidation reaction is carried out in the reaction kettle, and the reaction solution is obtained by constant potential electrolysis, and then adipaldehyde is obtained by vacuum distillation;

[0024] 2) dissolving the adipaldehyde obtained in step 1 in the second organic solvent, passing through ammonia and hydrogen, and performing reductive amination reaction under the action of a supported nickel catalyst to obtain hexamethylenediamine;

[0025] Concrete reaction general formula is as follows:

[0026] .

[0027] In the step 1, the electrode used in the electrocatalytic oxidation reaction is a platinum-graphite electrode or a Pb-Ti electrode or a Ni-Cu electrode, and the platinum-graphite electrode is to place the burnt platinum electrode in a sulfuric acid solu...

Embodiment 1

[0040] Using 0.5mol / L sulfuric acid as the supporting electrolyte, the platinum-graphite electrode constitutes the electrolysis system: the polished and cleaned graphite rod is used as the cathode, and the polished, burned and cleaned platinum sheet is used as the anode (with an area of ​​4 cm 2 ), placed in a dry electrolyzer without a diaphragm, and the electrolyte is a 0.5mol / L sulfuric acid solution. Under magnetic stirring, constant potential electrolysis was performed, and cyclic voltammetry scanning was performed until a reproducible and stable CV curve appeared, and the electrode potential was controlled at 1.5V.

[0041] Add 80ml of acetone to 10ml of cyclohexene and stir thoroughly to dissolve cyclohexene in acetone to obtain a cyclohexene solution, then add the cyclohexene solution to the reaction kettle, and pass through a 1.5V constant potential, -10°C, 5MPa state, the electrocatalytic oxidation reaction was carried out for 2 h. The obtained reaction liquid was d...

Embodiment 2

[0045] Using 0.1mol / L sulfuric acid as the supporting electrolyte, platinum-graphite electrodes constitute the electrolytic system: the polished and cleaned graphite rod is used as the cathode, and the polished, burned and cleaned platinum sheet is used as the anode (with an area of ​​4 cm 2 ), placed in a dry electrolytic cell without a diaphragm, and the electrolyte is a 0.1mol / L sulfuric acid solution. Under magnetic stirring, electrolyze at constant potential, and perform cyclic voltammetry scanning until a reproducible and stable CV curve appears, and the electrode potential is controlled at 1.3V.

[0046] Add 40ml of acetone to 10ml of cyclohexene and stir thoroughly to dissolve cyclohexene in acetone to obtain a cyclohexene solution, then add the cyclohexene solution to the reaction kettle, and pass through a 1.5V constant potential, 0°C, 8MPa state , the electrocatalytic oxidation reaction was carried out for 3 h. The obtained reaction liquid was distilled under reduc...

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Abstract

The invention discloses an industrial preparation method of hexamethylenediamine, wherein the industrial preparation method comprises the following steps: 1) dissolving cyclohexene in a first organic solvent, carrying out electrocatalytic oxidation reaction in a reaction kettle, carrying out constant potential electrolysis to obtain a reaction solution, and carrying out reduced pressure distillation to obtain adipic dialdehyde; and 2) dissolving adipic dialdehyde in a second organic solvent, introducing ammonia gas and hydrogen, and carrying out reductive amination reaction under the action of a supported nickel catalyst to obtain the hexamethylenediamine. The reaction adopts an electrocatalytic oxidation mode, and the selectivity is controlled by utilizing electrode potential, so that the reaction is more accurate and sufficient, the product conversion rate is improved, and the product is easy to separate, clean and environment-friendly; according to the method, hexamethylenediamine can be prepared through rectification operation, the product conversion rate of the method reaches 98.70%, the total yield reaches 98.02%, the purity reaches 95.14%-98.13%, the requirements of industrial production are met, and the method has good application prospects in industry; in addition, raw materials and auxiliary materials are simple and easy to obtain, the price is low, the input cost is low, and the construction scale is not limited.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to an industrial preparation method of hexamethylenediamine. Background technique [0002] Hexamethylenediamine, with a relative molecular mass of 116.20, a melting point of 42°C, and a boiling point of 204°C to 205°C, is a white flaky crystal with an ammonia odor at room temperature, and is a strongly basic organic compound. The main purpose of hexamethylenediamine is neutralization reaction with adipic acid, polycondensation can get nylon-66 product; neutralization reaction with sebacic acid, polycondensation can get nylon-610 product, it is a rare intermediate in synthetic materials. Nylon-66 and Nylon-610 products can be processed to produce engineering plastics, military-grade and civilian-grade fibers and other products. The materials with strong stretchability and weather resistance of these products can replace traditional metal materials, and are use...

Claims

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Application Information

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IPC IPC(8): C07C209/26C07C211/12C25B3/23C25B3/03
CPCC07C209/26C07C211/12
Inventor 朱远斌樊保敏和振秀
Owner 山西铁峰化工有限公司
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