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Synthetic method of N-substituent-3-amino acrolein

A technology of amino acrolein and synthesis method, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problem of low catalyst activity, and achieve the effects of short reaction time, high activity and high yield

Inactive Publication Date: 2014-07-02
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the catalyst activity of this method is not high, and generally equimolar active manganese dioxide is used as a catalyst, and the yield of 3-N, N-diethylaminoacrolein is only about 75%.

Method used

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  • Synthetic method of N-substituent-3-amino acrolein
  • Synthetic method of N-substituent-3-amino acrolein
  • Synthetic method of N-substituent-3-amino acrolein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: silicon-manganese composite catalyst Si 2 MnO 6 preparation of

[0029] In a 250mL three-necked flask, add 9.6g (60mmol) potassium permanganate, 19.5g (250mmol) silica gel and 100mL water, stir and raise the temperature to 90°C, dissolve 11.4g (75mmol) manganese sulfate in 50mL water, drop in 30min Add it into a three-necked flask, keep it warm for 2 hours, filter it while it is hot, wash the filter cake with water until the aqueous solution is colorless, dry it at 90°C, and then activate it at 140°C for 2 hours to obtain the chemical composition of Si 2 MnO 6 30.4g of the silico-manganese composite catalyst.

Embodiment 2

[0030] Embodiment 2: silicon-manganese composite catalyst Si 4 MnO 10 preparation of

[0031] Change the amount of silica gel to 39g (500mmol), and other operations are the same as in Example 1, and the obtained chemical composition is Si 4 MnO 10 49.5g of the silico-manganese composite catalyst.

Embodiment 3

[0032] Embodiment 3: silicon-manganese composite catalyst Si 6 MnO 14 preparation of

[0033] Change the amount of silica gel to 58.5g (750mmol), and other operations are the same as in Example 1, and the obtained chemical composition is Si 6 MnO 14 The silico-manganese composite catalyst 68g.

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Abstract

The invention discloses a synthetic method of N-substituent-3-amino acrolein, comprising the following steps: secondary amine and propargyl alcohol are used as raw materials to react under the effect of a silicomanganese composite catalyst for 3-20h in an organic solvent in air environment in the following conditions: a pressure of 1-4MPa and a temperature of 50-180 DEG C; and after the reaction is finished, N-substituent-3-amino acrolein derivatives are obtained by after-treatment of the reaction solution. A structural formula of the catalyst in the synthetic method is expressed by SixMnO2(1+x), wherein x is any value from 0 to 10; and x is a molar ratio of silicon to manganese in the silicomanganese composite catalyst. Compared with active manganese dioxide, the catalyst used in the synthetic method of the invention has the advantages of less dosage, high activity and yield and the like, and the yields of a plurality of Nsubstituent-3-amino acrolein derivatives are up to above 90% in a condition that the use amount of the catalyst is 20% of the mole number of acraldehyde.

Description

(1) Technical field [0001] The invention relates to a synthesis method of N-substituent-3-aminoacrolein. (2) Background technology [0002] N-substituent-3-aminoacrolein is an important pharmaceutical and pesticide intermediate. It mainly has the following two types of synthesis methods: [0003] 1. N-substituted formamide first reacts with phosgene, oxalyl chloride, phosphorus oxychloride and bis(trichloromethyl)carbonate to generate Vilsmerier reagent, then adds vinyl ether to heat and react, and the obtained solution is again in alkaline Under the condition of hydrolysis, N-substituent-3-aminoacrolein can be obtained. For example, DE19825200 and US3974159 use N, N-dimethylformamide, phosgene and vinyl ether as raw materials to prepare N, N-dimethyl-3-aminoacrolein; EP0363934 reports N-formaldehyde under nitrogen protection N-methyl-N-phenyl-3-aminoacrolein is synthesized from oxalyl anilide, oxalyl chloride and vinyl ether; Acyl bromide and vinyl ether are raw materia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C223/02C07C221/00
Inventor 杜晓华周显峰田晓宏谢思勉
Owner ZHEJIANG UNIV OF TECH