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Preparation method of N,N-diallyl aniline

A diallyl aniline and allyl technology, applied in the field of N, can solve the problems of expensive metal catalysts, achieve good industrial application prospects, high efficiency, and mild reaction conditions

Inactive Publication Date: 2011-05-04
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this metal catalyst is expensive

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 A kind of N, the preparation method of N-diallyl aniline, comprises the following steps:

[0023] (1) Allyl halide--allyl bromide, amine compounds--aniline, alkali-potassium carbonate are put into reaction solvent-dehydrated alcohol / water (the volume ratio of dehydrated alcohol and water is 2ml:1ml), the reaction was carried out at 70°C for 2h. The whole reaction process is tracked by thin layer chromatography, that is, samples are taken every 5 minutes, and the reaction solution and the raw material aniline are dropped on the silica gel plate with a capillary tube, and the two spots are on the same straight line, and then the The silica gel plate was placed in a display bottle filled with a mixture of petroleum ether and ethyl acetate at a volume ratio of 10:1. After the plate transfer is completed, put the silica gel plate under an ultraviolet lamp or in an iodine bottle for observation. If there is no point flush with the aniline of the raw material liq...

Embodiment 2

[0027] Embodiment 2 A kind of N, the preparation method of N-diallyl aniline is the same as embodiment 1.

[0028] Wherein the allyl halide is allyl bromide, the amine compound is m-nitroaniline, the base is potassium carbonate, and the reaction solvent is absolute ethanol / water (the volume ratio of absolute ethanol to water is 2ml: 1ml).

[0029] Wherein the mol ratio of m-nitroaniline and allyl bromide is 1: 3, the mol ratio of m-nitroaniline and potassium carbonate is 1: 4, and the mol ratio of m-nitroaniline and reaction solvent dehydrated alcohol is 1: 68 , and the molar ratio of water is 1:111.

[0030] The reaction temperature is 70° C., the reaction time is 5 h, and the yield is 80%.

Embodiment 3

[0031] Embodiment 3 A kind of N, the preparation method of N-diallyl aniline is the same as embodiment 1.

[0032] Wherein the allyl halide is allyl chloride, the amine compound is p-methoxyaniline, the alkali is potassium carbonate, and the reaction solvent is water.

[0033] Wherein the mol ratio of p-methoxyaniline and allyl chloride is 1: 2.5, the mol ratio of p-methoxyaniline and potassium carbonate is 1: 6, and the mol ratio of p-methoxyaniline and reaction solvent water is 1: 333.

[0034] The reaction temperature is 40°C, the reaction time is 6h, and the yield is 86%.

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Abstract

The invention relates to a preparation method of N,N-diallyl aniline, which comprises the following steps of: (1) sequentially adding allyl halide, an amine compound and alkali into a reaction solvent, reacting at the temperature of 20-70 DEG C, and obtaining a reaction liquid after complete reaction; (2) extracting the reaction solvent to obtain an extraction liquid; and (3) drying, concentrating and carrying out column chromatography separation on the extraction liquid to obtain the N,N-diallyl aniline. The preparation method has the advantages of mild condition, short reaction time, simple postprocessing and high yield, and a noble metal is not needed to be used as a catalyst in the method, therefore, the preparation method is a green synthesis technology conforming to an environment-friendly standard, can realize large-scale production and has better industry application prospect.

Description

technical field [0001] The invention relates to N, N-diallyl aniline in the field of organic synthetic chemistry, in particular to a preparation method of N, N-diallyl aniline. Background technique [0002] N, N-diallyl aniline, as a class of important organic synthesis intermediates, is a valuable intermediate in pharmaceuticals, agrochemical industry, dyes and plastics. [0003] The traditional preparation of N, N-diallyl aniline is to react with mineral acid as catalyst and halogenated hydrocarbon or dimethyl sulfate as alkylating agent and amine in solution. At present, attacking halogenated hydrocarbons with anilines with electrophilic groups is the best way to synthesize N-alkyl substituted anilines, but its yield and selectivity have not been significantly improved. The main reason for this is that the alkylation of amines is also undergoing its competing reactions, such as the formation of secondary amines, tertiary amines and quaternary ammonium salts. [0004] St...

Claims

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Application Information

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IPC IPC(8): C07C211/45C07C209/10
Inventor 杜正银魏小红张源民张雯雯
Owner NORTHWEST NORMAL UNIVERSITY
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