Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of alpha, beta-unsaturated ketone

An unsaturated, acetone-based technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemical methods, etc., can solve solid strong alkaline waste that is difficult to handle, does not conform to the spirit of green chemistry, and restricts large-scale production applications, etc. problems, to achieve the effect of simple synthesis method, high yield and mild reaction conditions

Active Publication Date: 2017-02-15
YANGZHOU UNIV
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, about α, β - There have been many reports in the literature on the research methods of unsaturated ketones, and in these methods, alkaline catalysts and organic solvents are mostly used. The catalysts and solvents used in these methods are harmful to the environment and will cause corrosion to equipment in industrial production , and the solid strong alkaline waste produced after the reaction is also difficult to deal with. These shortcomings limit its large-scale production and application in industry, and it does not conform to the spirit of green chemistry.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of alpha, beta-unsaturated ketone
  • Preparation method of alpha, beta-unsaturated ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] In a 15mL high-pressure sealed tube, add immobilized proline and 2,6-dimethylpiperazine, dissolve benzaldehyde in 1 mL of acetone, and add this mixed solution into the high-pressure sealed tube under nitrogen protection at 50 Under the condition of ℃, stir for 48 hours (the feeding amount is shown in Table 1), the reaction solution gradually turns light yellow. After the reaction, petroleum ether was added to the reaction solution until no precipitate was precipitated, filtered, washed with petroleum ether, and dried to obtain a solid catalyst for next use. The filtrate was separated and purified by thin-layer chromatography (developing solvent: petroleum ether and ethyl acetate mixed at a volume ratio of 10:1) or purified by column chromatography to obtain the final product - ɑ, β-unsaturated ketone, with a yield of 81.2% .

[0013] substance molecular weight millimoles Mass / g Benzaldehyde 106 1 0.1060 acetone 58 3 0.1740 Immobilize...

Embodiment 2

[0016] Embodiment 2: other conditions are the same as embodiment 1, and the reaction is checked under different temperatures, and the experimental results are shown in Table 2.

[0017] serial number temperature(℃) Yield 1 20 46.6 2 30 53.8 3 40 64.5 4 50 81.2 5 60 76.1

[0018] It can be seen from the above table that the reaction temperature is the best under the condition of 50° C., and the yield is the highest.

Embodiment 3

[0019] Embodiment 3: other conditions are the same as embodiment 1, and the reaction under different co-catalyst conditions is checked, and the experimental results are shown in Table 3.

[0020] Table 3: Comparison table of the influence of different cocatalysts on the reaction

[0021]

[0022] It can be seen from the above table that the effect of using 2,6-dimethylpiperazine as the cocatalyst is the best, and the yield is the highest.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a preparation method of alpha-beta-unsaturated ketone and relates to the technical field of preparation of alpha, beta-unsaturated ketone compound. According to the preparation method, immobilized proline is utilized as a catalyst, 2,6-dimethylpiperazine is utilized as cocatalyst, and aldehyde and acetone are utilized as reaction raw materials in catalysis and are condensed to generate the alpha, beta-unsaturated ketone. The preparation method has the advantages: 1, the reaction conditions are moderate, and the synthetic method is convenient; 2, the catalyst is stable and can be recycled, and the yield is still higher than 70% after tenth circulation; 3, the catalyst is high in tolerance to an acidic functional group of substrate.

Description

technical field [0001] The invention relates to a synthetic method for preparing ɑ, β-unsaturated ketones. Background technique [0002] α, β -Unsaturated ketones are not only important synthetic building blocks in organic synthesis, but also widely used in many other fields, such as: spices, biopharmaceuticals, pesticides, food and material science, etc. Therefore, this kind of compound has very important research value. Currently, about α, β - There have been many reports in the literature on the research methods of unsaturated ketones, and in these methods, alkaline catalysts and organic solvents are mostly used. The catalysts and solvents used in these methods are harmful to the environment and will cause corrosion to equipment in industrial production , and the solid strong alkaline waste produced after the reaction is also difficult to deal with. These shortcomings limit its large-scale production and application in industry, and at the same time, it does not confor...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07B37/00C07C45/72C07C49/217C07C49/235C07C49/255C07C49/248C07C49/21C07C201/12C07C205/45
CPCY02P20/584C07B37/00C07C45/72C07C201/12C07C49/217C07C49/235C07C49/255C07C49/248C07C49/21C07C205/45
Inventor 韩梦婷俞磊
Owner YANGZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products