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Method for continuously preparing adiponitrile by hydrocyanation of 1, 3-butadiene

A technology of hydrocyanation and adiponitrile, which is applied in the direction of hydrogen cyanide addition preparation, chemical instruments and methods, organic compound/hydride/coordination complex catalyst, etc., which can solve the problem of low yield and complex synthesis method, etc. problem, achieve the effect of reducing production cost, improving activity and selectivity, and reducing usage

Active Publication Date: 2022-03-01
北京道思克矿山装备技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a method for continuously preparing adiponitrile by hydrocyanation of 1,3-butadiene, so as to solve the problems of complex synthesis methods and low yields of conventional methods

Method used

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Examples

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Effect test

Embodiment 1

[0024] This embodiment provides a method for continuously preparing adiponitrile by hydrocyanation of 1,3-butadiene, comprising the following steps:

[0025] S1: After passing 1,3-butadiene through the first catalyst system, a hydrocyanation reaction occurs to generate a product containing 3-pentenenitrile and by-products; the step S1 also includes isomerization of by-products again Operations for the preparation of 3-pentenenitrile;

[0026] S2: pass the 3-pentenenitrile described in step S1 through the second catalyst system, and hydrocyanation reaction occurs again to produce a mixed solution containing adiponitrile, and the product and by-products obtained from the mixed solution are distilled out respectively after vacuum distillation and recycle;

[0027] The step S2 also includes the operation of adding a cocatalyst Lewis acid, and the molar ratio of the Lewis acid to zero-valent nickel is 2.5:1.

[0028] S3: Repeat the hydrocyanation reaction of step S2 to continuous...

Embodiment 2

[0050] This embodiment provides a method for continuously preparing adiponitrile by hydrocyanation of 1,3-butadiene, comprising the following steps:

[0051] S1: After passing 1,3-butadiene through the first catalyst system, a hydrocyanation reaction occurs to generate a product containing 3-pentenenitrile and by-products; the step S1 also includes isomerization of by-products again Operations for the preparation of 3-pentenenitrile;

[0052] S2: pass the 3-pentenenitrile described in step S1 through the second catalyst system, and hydrocyanation reaction occurs again to produce a mixed solution containing adiponitrile, and the product and by-products obtained from the mixed solution are distilled out respectively after vacuum distillation and recycle;

[0053] The step S2 also includes the operation of adding a cocatalyst Lewis acid, and the molar ratio of the Lewis acid to zero-valent nickel is 5:1.

[0054] S3: Repeat the hydrocyanation reaction of step S2 to continuously...

Embodiment 4

[0063] The raw material, raw material quality and reaction conditions and productive rate that add during specific operation are provided in embodiment 4, specifically as follows:

[0064] Preparation of catalyst 1-(diphenylphosphine)-2-(ethyldiphenylphosphine) ferrocene:

[0065] (1) Synthesis of 1-(diphenylphosphino)ferrocene, synthesis of vinyldiphenylphosphine

[0066] Under the protection of argon, ferrocene (1mol, 186g) and n-butyl lithium n-BuLi (700mL, 1.1mol, 1.6M n-hexane solution) injection. In an inert gas atmosphere, inject N,N,N',N'-tetramethylethylenediamine (TMEDA) (1mL, 6.7mmol) with a 20ml disposable syringe and stir for 2 hours, then drop it into the system at -20°C Add diphenylphosphine chloride (1mol, 180g), then react at -20°C for 3 hours, add water to the system to quench, then separate the layers, dry the organic layer with anhydrous magnesium sulfate, filter, and distill off the solvent under reduced pressure Finally, a yellow solid was obtained, wh...

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Abstract

The invention discloses a method for continuously preparing adiponitrile by hydrocyanation of 1, 3-butadiene, which mainly comprises the following steps: S1, enabling 1, 3-butadiene to pass through a catalyst system, and carrying out hydrocyanation reaction to generate a product containing 3-pentenenitrile; s2, enabling the product obtained in the step S1 to pass through a catalyst system, carrying out hydrocyanation reaction again to produce a mixed solution containing adiponitrile, carrying out reduced pressure distillation, and respectively steaming out and recovering a product obtained from the mixed solution and a by-product; s3, supplementing a catalyst to the liquid subjected to reduced pressure distillation in the step S2, and repeating the hydrocyanation reaction in the step S2 to continuously prepare adiponitrile; the catalyst system comprises a mixture consisting of 1-(diphenylphosphine)-2-(ethyl diphenylphosphine) ferrocene, zero-valent nickel and a monodentate phosphine ligand. According to the present invention, the service life of the catalyst system can be significantly prolonged, and the use amount of the catalyst can be significantly reduced so as to reduce the production cost of the adiponitrile, improve the production efficiency of the adiponitrile, and provide the new catalyst technology for the industrial application of the adiponitrile.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a method for continuously preparing adiponitrile by hydrocyanation of 1,3-butadiene. Background technique [0002] The hydrocyanation reaction is used industrially to synthesize compounds containing nitrile functionality from compounds containing unsaturation. In the hydrocyanation reaction, adiponitrile is an important chemical intermediate, especially an important intermediate for the production of nylon 66, and is obtained by the secondary hydrocyanation of 1,3-butadiene. In the first hydrocyanation, 1,3-butadiene is reacted with hydrogen cyanide in the presence of zerovalent nickel(0) stabilized with phosphorus-containing ligands to give pentenenitriles, forming linear 3-pentenenitriles and branched pentenenitrile (2-methyl-3-butenenitrile) isomerization mixture. In the second process step, branched pentenenitriles are generally isomerized to linear pentenenitriles. Finall...

Claims

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Application Information

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IPC IPC(8): C07C253/10C07C255/04C07C255/07B01J31/22B01J31/24
CPCC07C253/10B01J31/2409B01J31/2295B01J31/2495B01J23/755B01J2231/322B01J2531/842B01J2531/847B01J35/19C07C255/04C07C255/07
Inventor 耿海涛应国海
Owner 北京道思克矿山装备技术有限公司
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