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Method of preparing methyl ketone through cobalt catalysis

A technology for catalytic preparation and methyl ketone, applied in the field of chemistry, can solve the problems of incapable of large-scale production, harsh reaction conditions, expensive catalysts, etc., and achieve the effects of fast reaction speed, mild reaction temperature, safety and feasibility guarantee.

Active Publication Date: 2017-07-28
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the disadvantages of expensive catalysts in the prior art, harsh reaction conditions, pollution to the environment, and inability to produce on a large scale

Method used

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  • Method of preparing methyl ketone through cobalt catalysis
  • Method of preparing methyl ketone through cobalt catalysis
  • Method of preparing methyl ketone through cobalt catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] P-Chlorophenylacetylene (10g, 73.2mmol) was added to a 250mL round bottom flask filled with methanol (117mL) solution, a magnet was added, and after stirring evenly, the catalyst (616mg, 1.46mmol) was added thereto. Then the reaction system was heated to 65° C., and after 20 h of reaction, it was quenched with water, and the reaction bottle was cooled to room temperature. After spinning off the solvent, it was separated by silica gel column chromatography to obtain a colorless oily liquid.

[0010] The reaction formula is:

[0011]

[0012] The following examples are helpful in understanding the present invention. In the table below are examples of the hydrolysis of alkynes to methyl ketones. Reaction conditions refer to embodiment example 1.

[0013]

[0014]

[0015]

[0016]

[0017]

Embodiment 2

[0019] Add 0.25mmol of an alkynyl compound (such as phenylacetylene, p-methoxyphenylacetylene, etc.) linked to an aromatic system into a 5mL round-bottomed flask filled with 1mL of methanol solution, add a magnet, and after stirring evenly, add 5mol% catalyst in. Then the reaction system was heated to 65° C., and after 4.5 h of reaction, it was quenched with water, and the reaction bottle was cooled to room temperature. After spinning off the solvent, it was separated by silica gel column chromatography to obtain a colorless oily liquid.

Embodiment 3

[0021] Add 0.25mmol of an acid-sensitive terminal alkyne compound (such as a compound containing Boc-, MOMO-, etc.) into a 10ml sealed tube containing 1mL of methanol solution, add a magnet, and after stirring evenly, add 5mol% catalyst in. Then the reaction system was heated to 60° C., and after 10-20 h of reaction, it was quenched with water, and the reaction bottle was cooled to room temperature. After spinning off the solvent, it was separated by silica gel column chromatography to obtain a colorless oily liquid.

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Abstract

The invention particularly discloses a method of preparing methyl ketone through cobalt catalysis and aims at the defect that the prior art for preparing methyl ketone uses expensive catalysts, is harsh in reaction conditions, causes environmental pollution and cannot realize large-scale production. Triple bonds in alkyne are activated through lewis acid of metal cobalt coordinated with oxime, so that alkyne can be efficiently hydrolyzed into methyl ketone. Methanol is used as a solvent, concentration of reaction substance is 0.25mol / L, a catalyst is added into a reaction system according to 5% of molar weight of raw materials, reaction temperature is 65 DEG C, and alkyne can be efficiently hydrolyzed into methyl ketone. Catalysis performance can be on a par with other catalysts. Reaction temperature is comparatively mild, reaction speed is high, and no acidic substance needs to be added in the process of reaction. Environmental pollution is lowered to minimum extent, the operation process of reaction is simplified to maximum extent, and safety of an operator and feasibility of reaction are guaranteed to maximum extent. Therefore, the method has more obvious industrialization trend.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a cobalt-catalyzed method for preparing methyl ketone. Background technique [0002] The catalytic hydrolysis of alkynes plays a very important role in functional group conversion. The key to this reaction is the economical and environmentally friendly conversion of alkynyl atoms to carbonyl compounds via suitable catalysts. [0003] The reaction is usually carried out in acidic medium with HgO-H 2 SO 4 (Kucherov catalyst) and HgO-BF 3 (Hennion-Nieuwland catalyst) as catalyst. However, environmental concerns due to the toxicity of mercury salts have hindered their full application. Therefore, in the past few decades, researchers have done a lot of research on alkyne hydrolysis, including Rh catalysts, Ru catalysts, Pt catalysts, Ir catalysts, Pd catalysts, Cu(II) catalysts, Fe(III) catalysts , Ag(I) catalysts, and Au catalysts for the catalytic performance of this type ...

Claims

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Application Information

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IPC IPC(8): C07C45/26C07C49/78C07C49/807C07C49/84C07C49/788C07C49/16C07C49/175C07C201/12C07C205/45C07C67/29C07C69/78C07F7/18C07C68/06C07C69/96C07D207/408C07D209/48
CPCC07C45/26C07C67/29C07C68/06C07C201/12C07D207/408C07D209/48C07F7/1804C07F7/1892C07C49/78C07C49/807C07C49/84C07C49/788C07C49/16C07C205/45C07C69/78C07C49/175C07C69/96
Inventor 李云侯胜泰
Owner LANZHOU UNIVERSITY
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