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Organic solid base catalyst for synthesizing alpha-cyanoethyl cinnamate, and preparation method and application thereof

A technology of ethyl cinnamate and organic solids, which is applied in the chemical industry, can solve the problems of complicated separation, difficult separation, and harsh preparation process requirements, and achieve the effect of simple preparation method, easy operation, and good reusability

Inactive Publication Date: 2012-10-17
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are homogeneous and heterogeneous methods for industrially synthesizing ethyl α-cyanocinnamate. Generally, alkali is used as a catalyst. Homogeneous alkali catalysts mainly include NaOH, amines, and basic ionic liquids. High efficiency, but there are problems such as complicated separation, equipment corrosion and waste liquid treatment
Among them, alkaline ionic liquid is a new type of catalyst, which has the advantages of high activity and selectivity, but the preparation process is demanding and the cycle is long, and because it is a homogeneous catalyst, it is not easy to separate, the dosage is large, and it is not easy to Disadvantages such as repeated use

Method used

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  • Organic solid base catalyst for synthesizing alpha-cyanoethyl cinnamate, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Preparation and application of organic solid base catalyst

[0032] Add 10.0g of chloropropyltrimethoxysilane to 60.0g of cyclohexane to prepare a solution, and ultrasonically (KQ-50DB desktop CNC ultrasonic cleaner, working frequency 40KHz) disperses evenly, then add 10.0g of silica gel to it, and seal it. The reaction system was ultrasonically oscillated for 1 h. The sample was extracted with toluene for 8 hours, and dried in vacuum at 100°C for 8 hours. Get Cl / SiO 2 . Then 4.0g imidazole was added to 50g cyclohexane solution, and the above 10.0gCl / SiO 2 Dip it in, and seal it. After the reaction system was ultrasonically oscillated for 0.5h, 6g of n-butane bromide was added, and after ultrasonically oscillating for 1h, 2g of NaOH was added for ultrasonically oscillating for 0.5h, the sample was extracted with toluene for 8h, and vacuum-dried at 100°C for 8h. That is, the catalyst for this reaction is obtained. Add benzaldehyde, ethyl cyanoacetate ...

Embodiment 2

[0033] Embodiment 2: Preparation and application of organic solid base catalyst

[0034] Add 10.0g of chloropropyltrimethoxysilane to 65g of cyclohexane to prepare a solution, and ultrasonically (KQ-50DB desktop CNC ultrasonic cleaner, working frequency 40KHz) disperses evenly, then add 11.5g of silica gel to it, and seal it. The reaction system was ultrasonically oscillated for 1.2 h. The sample was extracted with toluene for 9 hours, and dried in vacuum at 95°C for 9 hours. Get Cl / SiO 2 . Then 5g imidazole was added to 50g cyclohexane solution, and the above 10.0gCl / SiO 2 Dip it in, and seal it. After the reaction system was ultrasonically oscillated for 0.6h, 7g of n-butane bromide was added. After ultrasonically oscillating for 1.1h, 3g of NaOH was added for ultrasonically oscillating for 0.6h. The sample was extracted with toluene for 9h and vacuum-dried at 95°C for 9h. That is, the reaction catalyst is obtained. Add methanol, propylene oxide and catalyst into a 100...

Embodiment 3

[0035] Embodiment 3: Preparation and application of organic solid base catalyst

[0036] Add 10.0g of chloropropyltrimethoxysilane to 70g of cyclohexane to prepare a solution, and ultrasonically (KQ-50DB desktop CNC ultrasonic cleaner, working frequency 40KHz) disperses evenly, then add 13.0g of silica gel to it, and seal it. The reaction system was ultrasonically oscillated for 1.4 h. The sample was extracted with toluene for 10 hours, and dried in vacuum at 90°C for 10 hours. Get Cl / SiO 2 . Then 6g of imidazole was added to 50g of cyclohexane solution, and the above 10.0g of Cl / SiO 2 Dip it in, and seal it. After the reaction system was ultrasonically oscillated for 0.8h, 8g of n-butane bromide was added. After ultrasonically oscillating for 1.2h, 4g of NaOH was added for ultrasonically oscillating for 0.7h. The sample was extracted with toluene for 10h, and vacuum-dried at 90°C for 10h. That is, the reaction catalyst is obtained. Add methanol, propylene oxide and cata...

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Abstract

The invention discloses an organic solid base catalyst for synthesizing alpha-cyanoethyl cinnamate. The preparation method of the organic solid base catalyst for synthesizing alpha-cyanoethyl cinnamate comprises the following steps: by using chloropropyltrimethoxysilane as a coupling agent and cyclohexane as a solvent, grafting an N-butylimidazole basic ionic liquid onto a silica gel supporter by ultrasonic technology, thereby obtaining the organic solid base catalyst for synthesizing alpha-cyanoethyl cinnamate. The method for synthesizing alpha-cyanoethyl cinnamate by using the catalyst comprises the following steps: evenly mixing benzaldehyde and ethyl cyanoacetate in a mol ratio of 1:(0.9-1.1), adding the organic solid base catalyst which accounts for 2 wt% of the reactants into the reaction kettle, heating to 80-110 DEG C while stirring to react for 5-12 hours, and centrifugally settling to obtain the product, wherein the organic solid base catalyst can be recycled and used repeatedly. The catalyst disclosed by the invention has high catalytic activity and can be used repeatedly.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to an organic solid base catalyst used in the reaction of Nowengel condensation to synthesize ethyl α-cyanocinnamate. Background technique [0002] The Knoevenagel reaction was proposed by Knoevenagel in the 1890s. It is one of the important methods for forming carbon-carbon double bonds in organic synthesis. It has been highly valued and widely used for a long time. The Knoevenagel condensation reaction is a reaction between aldehydes or ketones and compounds containing active methylene groups to form unsaturated compounds and water. The equation is as follows: [0003] [0004] In the formula, X and Y are electro-absorbing groups, such as cyano and carbonyl. This reaction forms a carbon-carbon double bond, which can be further added or hydrogenated, so it has a wide range of applications in organic synthesis, such as the synthesis of cinnamic acid, the synthesis of c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02B01J37/34C07C255/41C07C253/30
CPCY02P20/54Y02P20/584
Inventor 张雪红刘树彬杨晓辉张云霄刘会茹胡瑞省
Owner SHIJIAZHUANG UNIVERSITY
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