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Method for catalyzing and condensing aromatic aldehyde and active methylene compound by using multi-amino ionic liquid

An active methylene and ionic liquid technology, which is applied in the field of polyamino ionic liquid catalytic condensation of aromatic aldehydes and active methylene compounds, can solve the problems of low efficiency, large loss of ionic liquid, weak alkalinity, etc., and achieve catalytic activity. High, economical post-treatment, high alkali density effect

Inactive Publication Date: 2014-12-10
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The basic ionic liquid used above contains only one amino group, which leads to its weak alkalinity, and its catalytic effect is poor in the reaction process of catalytic condensation of aromatic aldehydes and active methylene compounds, and the amount of ionic liquid used is relatively large.
In addition, the loss of ionic liquids during recycling is also relatively large, which makes the entire process less efficient and difficult to use on a large scale in industrial production.

Method used

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  • Method for catalyzing and condensing aromatic aldehyde and active methylene compound by using multi-amino ionic liquid
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  • Method for catalyzing and condensing aromatic aldehyde and active methylene compound by using multi-amino ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: 5mmol benzaldehyde, 5mmol malononitrile, 25mL water and 0.1mmol polyamino ionic liquid were respectively added into a 100mL single-necked bottle with a stirring bar. Vigorously stirred and reacted at 25°C for 15 minutes, TLC (thin plate chromatography) detected that the raw material point disappeared, and suction filtered, and the obtained filter residue was recrystallized with 95% ethanol aqueous solution, and dried to obtain the pure product benzallonitrile with a yield of 92%. Add benzaldehyde and malononitrile directly to the filtrate for repeated use.

[0021] Benzymalononitrile: 1 H NMR (400MHz, CDCl 3 ):δ=7.92(d, J=7.7Hz, 2H), 7.80(s, 1H), 7.64(t, J=7.4Hz, 1H), 7.55(t, J=7.6Hz, 2H); 13 C NMR (101MHz, CDCl 3 ): δ=160.01, 134.68, 130.97, 130.74, 129.67, 113.73, 112.60, 82.71

Embodiment 2

[0022] Example 2: 5mmol of 3-hydroxybenzaldehyde, 5mmol of malononitrile, 30mL of water and 0.1mmol of polyamino ionic liquid were respectively added into a 100mL single-necked bottle with a stirring bar. Vigorously stirred and reacted at 25°C for 30 minutes, detected by TLC (thin plate chromatography), the raw material point disappeared, filtered with suction, and the obtained filter residue was recrystallized with 95% ethanol aqueous solution, dried to obtain the pure product 2-(3-hydroxybenzyl) propane Nitrile, yield 91%. Add 3-hydroxybenzaldehyde and malononitrile directly to the filtrate for repeated use.

[0023] 2-(3-Hydroxybenzyl)malononitrile: 1 H NMR (400MHz, CDCl 3 ):δ=7.92(d, J=7.7Hz, 2H), 7.80(s, 1H), 7.64(t, J=7.4Hz, 1H), 7.55(t, J=7.6Hz, 2H); 13 C NMR (101MHz, CDCl 3 ): δ=160.01, 134.68, 130.97, 130.74, 129.67, 113.73, 112.60, 82.71

Embodiment 3

[0024] Example 3: 5mmol of 4-methoxybenzaldehyde, 5mmol of malononitrile, 30mL of water and 0.15mmol of polyamino ionic liquid were respectively added to a 100mL single-necked bottle with a stirring bar. Vigorously stirred and reacted at 30°C for 45 minutes, detected by TLC (thin plate chromatography), the raw material point disappeared, filtered with suction, and the obtained filter residue was recrystallized with 95% ethanol aqueous solution, dried to obtain the pure product 2-(4-methoxybenzyl) Malononitrile, yield 92%. Add 4-methoxybenzaldehyde and malononitrile directly to the filtrate for repeated use.

[0025] 2-(4-Methoxybenzyl)malononitrile: 1 H NMR (400MHz, CDCl 3 ):δ=7.92(d, J=7.7Hz, 2H), 7.80(s, 1H), 7.64(t, J=7.4Hz, 1H), 7.55(t, J=7.6Hz, 2H); 13 C NMR (101MHz, CDCl 3 ): δ=160.01, 134.68, 130.97, 130.74, 129.67, 113.73, 112.60, 82.71

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Abstract

The invention provides a method for catalyzing and condensing aromatic aldehyde and an active methylene compound by using a multi-amino ionic liquid, belonging to the technical field of organic chemicals. In the condensation reaction, the mole ratio of the ionic liquid to the active methylene compound is 1:1; the molar weight of the multi-amino ionic liquid catalyst is 2-5% of that of the used aromatic aldehyde; the volume (mL) of reaction solvent water is 5-10 times of the molar weight (mmol) of the aromatic aldehyde; the reaction temperature is 25-35 DEG C; the reaction pressure is of one atmosphere; the reaction time is 5-200 minutes; and after the reaction is accomplished, the components are subjected to suction filtration, and the obtained filter residue is recrystallized by using a 95% ethanol water solution and is dried so as to obtain pure E-type olefin. Compared with methods employing other catalysts, the method has the characteristics that the catalysis activity is high, the catalyst can be recycled, the post treatment is simple, the reaction condition is gentle, and the like.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and in particular relates to a method for catalytic condensation of aromatic aldehydes and active methylene compounds by polyamino ionic liquids. Background technique [0002] Carbonyl compounds, especially the condensation reaction between aromatic aldehydes and active methylene compounds (Knoevenagel condensation reaction) is an important method for the formation of carbon-carbon double bonds in organic synthesis. It has been highly valued and widely used for a long time, and has become Classic reactions in synthetic organic chemistry. It can use ammonium salt, primary amine, secondary ammonia or their salts, TiCl 4 / pyridine, Al 2 o 3 , AlPO 4 -Al 2 o 3 and ZnCl 2 Catalyze. However, these catalysts, whether they are homogeneous or heterogeneous, have their disadvantages, such as the catalyst cannot be recycled or the post-treatment method is complicated. Therefore, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/34C07C255/36C07C255/37C07C255/41
CPCY02P20/584
Inventor 岳彩波朱琳吴胜华储昭莲
Owner ANHUI UNIVERSITY OF TECHNOLOGY