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Method for synthesizing dinitrile ethyl tertiary amine from aliphatic primary amine by one-step method

A technology of aliphatic primary amines and tertiary amines, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid nitriles, etc., can solve problems such as increasing the complexity of the reaction process, complex reaction process, and large amount of three wastes

Active Publication Date: 2021-09-10
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] 2. The production of three wastes is large
[0010] 3. The reaction process is complicated
Two-step nitrile ethylation reaction increases the complexity of the reaction process

Method used

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  • Method for synthesizing dinitrile ethyl tertiary amine from aliphatic primary amine by one-step method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] reaction process:

[0039] Add 132.5g acrylonitrile and 2.65g glycolic acid aqueous solution (glycolic acid concentration is 70wt%, with the total weight of aqueous solution) in the 500ml three-neck flask that magneton is housed, adopt constant pressure dropping funnel to 73g n-butylamine in 30min Add it dropwise to a three-necked flask, and stir at reflux for 6h at 90°C.

[0040] Post-processing process:

[0041] The above reaction mother liquor was kept at 110°C and an absolute pressure of 5KPa, and a vacuum pump was used to remove light components such as acrylonitrile for about 3 hours, and the product liquid was analyzed by gas chromatography. , the mononitrile ethyl substituted n-butylamine content is 0.8wt%, and the n-butylamine content is 0.7wt%.

Embodiment 2

[0043] reaction process:

[0044] Add 116.6g acrylonitrile and 5.83g glycolic acid aqueous solution (glycolic acid concentration is 60wt%, with aqueous solution gross weight) in the 500ml three-neck flask that magneton is housed, adopt constant pressure dropping funnel to 99g cyclohexylamine in 40min Add it dropwise to a three-necked flask, and stir at reflux for 5h at 80°C.

[0045] Post-processing process:

[0046] The above reaction mother liquid was removed at 120°C and an absolute pressure of 10KPa, and light components such as acrylonitrile were removed by a vacuum pump for about 2 hours. The product liquid was analyzed by gas chromatography, and the content of dinitrile ethyl substituted cyclohexylamine was 98.8wt%. , the content of mononitrile ethyl substituted cyclohexylamine is 0.8wt%, and the content of cyclohexylamine is 0.4wt%.

Embodiment 3

[0048] reaction process:

[0049]Add 127.2g acrylonitrile and 6.36g glycolic acid aqueous solution (glycolic acid concentration is 70wt%, with the total weight of aqueous solution) in the 500ml three-necked flask that magneton is housed, adopt constant pressure dropping funnel to 113g 2-methylcyclohexane The amine was added dropwise to the three-necked flask within 60 minutes, and stirred at reflux at 90°C for 5 hours.

[0050] Post-processing process:

[0051] The above reaction mother liquid is at 120°C and the absolute pressure is 5KPa, and the light components such as acrylonitrile are removed by vacuum pump for about 3 hours, and the product liquid is analyzed by gas chromatography. It can be seen that the content of dinitrile ethyl substituted methylcyclohexylamine is 98.1 wt%, the content of mononitrile ethyl substituted methylcyclohexylamine is 1.2wt%, and the content of methylcyclohexylamine is 0.7wt%.

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Abstract

The invention provides a method for synthesizing dinitrile ethyl tertiary amine from aliphatic primary amine by a one-step method, which comprises the steps of adding aliphatic primary amine into acrylonitrile by using a glycollic acid aqueous solution as a catalyst, synthesizing a dinitrile ethyl tertiary amine compound by a one-step method under heating reflux, and after the reaction is finished, carrying out reduced pressure distillation treatment to remove low-boiling-point components, and obtaining the dinitrile ethyl tertiary amine compound with the yield being higher than 95%. The process provided by the invention has the following advantages: 1) single nitrile ethylation reaction and double nitrile ethylation reaction are carried out at the same time, so that the reaction efficiency is improved; 2) the glycollic acid is weak in acidity and basically has no corrosion to reaction equipment, so that the equipment investment is reduced; and 3) the reaction mother liquor does not need to be neutralized by adding alkali, so that a large amount of salt-containing wastewater is avoided, and the post-treatment process is simplified.

Description

technical field [0001] The invention relates to a method for carrying out a dinitrile ethylation reaction with an aliphatic primary amine, in particular to a method for synthesizing a bisnitrile ethylated tertiary amine compound with an aliphatic primary amine in one step. Background technique [0002] Nitrile ethylation of organic amines has many industrial uses. The cyanoethylamine compound prepared after the reaction of acrylonitrile with primary amine or secondary amine can be used to prepare the coupling agent in the synthetic process of azo dyes. At the same time, the amines of epoxy curing agent can After modification, the reactivity of the amine curing agent can be appropriately reduced to increase its pot life, which has a very wide range of application scenarios. [0003] Due to the high reactivity of the amino group, the addition reaction of primary amines and acrylonitrile is easier than that of general compounds. Usually, no special catalyst is needed, or water...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/24
CPCC07C253/30C07C2601/14C07C255/24
Inventor 李鑫吴健张聪颖姜庆梅
Owner WANHUA CHEM GRP CO LTD
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