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Method for synthesizing (E)-alpha, beta-unsaturated carbonyl compound

A carbonyl compound and unsaturated technology, applied in the field of synthesis-α, can solve the problems affecting catalyst activity, separation of catalyst and product, target product selectivity cannot reach 100%, and achieves significant industrialization prospects, green preparation process, and source of raw materials broad effect

Inactive Publication Date: 2014-05-07
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method adopts direct carbon-carbon bond condensation reaction to obtain the target compound, and protic solvents such as water can be used, but the catalyst needs to be separated after the reaction is completed, which affects the activity of the catalyst and the separation of the catalyst and the product to a certain extent, and The selectivity of the target product cannot reach 100% when water is used as the solvent

Method used

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  • Method for synthesizing (E)-alpha, beta-unsaturated carbonyl compound
  • Method for synthesizing (E)-alpha, beta-unsaturated carbonyl compound

Examples

Experimental program
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Effect test

preparation example 1

[0024] Add 0.001mol of organic bismuth ion compound (X=OSO) to a 100mL single-necked flask 2 C 8 F 17 ) and 5.0mL [Bmim]BF 4 , 0.1mol benzaldehyde (R 1 =Ph) and 0.1mol n-propylamine (R 4 =n-C 3 H 7 ), after stirring the material for 5 minutes, add 0.3 mol of cyclohexanone (R 2 -R 3 =-(CH 2 ) 4 -). The flask was then placed in a water bath reactor with magnetic stirring, and the reaction was carried out at 25°C for 3 hours. The reaction was followed by TLC to completion. The reaction results were as follows: the yield of (E)-2-benzenecyclohexanone was 99%, and the selectivity was 100%; after the catalyst system was reused 10 times, its catalytic performance did not decrease.

preparation example 2

[0026] Add 0.003mol of organic bismuth ion compound (X=OSO) to a 100mL single-necked flask 2 C 6 F 5 ) and 5.0mL [Bmim]BF 4 , 0.1mol benzaldehyde (R 1 =Ph) and 0.1mol n-propylamine (R 4 =n-C 3 H 7 ), after stirring for 5 minutes, add 0.3 mmol of acetophenone (R 2 =Ph,R 3 =H). The flask was then placed in a water bath reactor with magnetic stirring, and the reaction was carried out at 110°C for 1 hour. The reaction was followed by TLC to completion. The reaction results were as follows: the yield of (E)-chalcone was 97%, and the selectivity was 100%; after the catalyst system was reused 10 times, its catalytic performance did not decrease.

preparation example 3

[0028] Add 0.005mol organic bismuth ion compound (X=OSO) to a 100mL single-necked flask 2 CF 3 ) and 5.0mL [Bmim]PF 6 , 0.1mol benzaldehyde (R 1 =Ph) and 1.0 mmol n-propylamine (R 4 =n-C 3 H 7 ), after stirring for 5 minutes, add 0.3 mmol of acetone (R 2 =CH 3 , R 3 =H). The flask was then placed in a water bath reactor with magnetic stirring, and the reaction was carried out at 25°C for 12 hours. The reaction was followed by TLC to completion. The reaction results were as follows: (E)-4-phenylbut-3-en-2-one had a yield of 100% and a selectivity of 100%; after the catalyst system was reused 10 times, its catalytic performance did not decrease.

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Abstract

The invention provides a method for synthesizing (E)-alpha, beta-unsaturated carbonyl compound by adopting reaction control and self-separation technology. The method takes ionic liquid as solvent, aldehyde and ketone as materials, bridge sulfur atom ligand-containing organic bismuth ion complex as main catalyst and fatty amine as auxiliary catalyst for reaction. The synthesis method opens up a new environment-friendly approach for preparing (E)-alpha, beta-unsaturated carbonyl compound with low cost, and has the advantages that both the selectivity and the yield of the target product are nearly 100%; the reaction is homogeneous reaction and products are separated to two phases automatically after the reaction; the catalysts can be directly recycled in the ionic liquid; pure (E)-alpha, beta-unsaturated carbonyl compound can be obtained by separating the products simply through distillation under reduced pressure; and no normal organic solvents are necessary in the whole reaction and separation process, so the method is environment-friendly.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, in particular to a method for synthesizing (E)-α,β-unsaturated carbonyl compounds. 【Background technique】 [0002] Homogeneous catalysis has a series of advantages, for example, all catalytically active sites can be fully contacted with the reaction substrate. More importantly, the chemoselectivity, stereoselectivity or enantioselectivity of homogeneous catalysts can be easily tuned. Despite the many advantages, many homogeneous catalytic systems have not been commercialized for one very important reason: the separation of product and catalyst is difficult. [0003] To overcome the separation challenges in homogeneous catalytic systems, many researchers have proposed some solutions. These schemes can be divided into two categories. One is that homogeneous catalysts are immobilized on soluble or insoluble supports, and the separation of product and catalyst can be achieved by simple...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/02C07C49/683C07C45/74C07C49/796C07C49/794C07C49/697C07C49/753C07C49/647C07C49/217C07D307/46C07C69/618C07C67/343B01J31/22B01J31/02
CPCY02P20/54
Inventor 尹双凤邱仁华罗胜联宋星星邱一苗孟振功许新华夏军谭年元张晓文
Owner HUNAN UNIV
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