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Method for preparing aldehydes or ketones by oxidizing alcohols with oxygen

A technology for oxidizing alcohol and oxygen, applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of unfriendly environment, corrosion of equipment, complicated operation, etc., achieve environmental friendliness, reduce raw material costs, Post-processing simple effects

Inactive Publication Date: 2013-05-01
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] (3) The heating method of autoclave and oil bath is required, and the operation is cumbersome, so that there may be a risk of explosion when the oxidation system is enlarged to the industrial production process;
[0008] (4) The use of halogenated hydrocarbon solvents such as dichloromethane is not environmentally friendly;
[0009] (5) The use of halogen compounds may cause corrosion to equipment in industrial production

Method used

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  • Method for preparing aldehydes or ketones by oxidizing alcohols with oxygen
  • Method for preparing aldehydes or ketones by oxidizing alcohols with oxygen
  • Method for preparing aldehydes or ketones by oxidizing alcohols with oxygen

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Embodiment 1

[0035] The reaction was carried out in a Teflon-lined 316L stainless steel autoclave (300 mL) equipped with a magnet, and the air in the autoclave was not replaced with oxygen before the reaction. First, 10mL of dichloromethane was added to the autoclave, then 10.0mmol of benzyl alcohol and 0.1mmol of TEMPO were added to 10mL of solvent, and then 0.15mmol of ferric nitrate [Fe(NO 3 ) 3 9H 2 O], sealed. Pressurize the kettle to 0.1 MPa, transfer it to an oil bath that has been raised to 80°C in advance, stop stirring after a certain corresponding time, lower the temperature, and release the pressure carefully. After sampling for gas chromatographic analysis, the liquid in the kettle was transferred to a separatory funnel, then the kettle was carefully washed with dichloromethane, and the organic solutions were combined. with saturated Na 2 S 2 o 3 Wash the organic phase with an aqueous solution of TEMPO to remove TEMPO and inorganic salts, dry the organic layer with anhyd...

Embodiment 2

[0037] The transition metal salt used is copper nitrate [Cu(NO 3 ) 2 2.5H 2 O], the test method and steps are the same as in Example 1, the reaction temperature is 80°C, the reaction time is 1h, and the yield is 94%.

Embodiment 3

[0039] The transition metal salt used is chromium nitrate [Cr(NO 3 ) 3 9H 2 O], the test method and steps are the same as in Example 1, the reaction temperature is 80°C, the reaction time is 1h, and the yield is 92%.

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Abstract

The invention provides a method for preparing aldehydes or ketones by oxidizing alcohols with oxygen. According to 5 millimoles of reactants, 1 to 8 mol percent of 4-hydroxy-2,2,6,6-tetramethyl piperidine-oxyl or other like compounds and 1 to 8 mol percent of transition metal nitrates are used as catalysts, 0.1 to 0.8MPa oxygen or air is used as an oxidizer, and a reaction is performed at 0 to 80DEG C for 1 to 36 hours to oxidize a series of alcohols into aldehydes or ketones with high selectivity. The method is characterized by high yield, mild reaction conditions, easy operation control, low cost, safety, environmentally-friendly whole process, no pollution, and the like.

Description

technical field [0001] The invention relates to a method for preparing aldehydes or ketones by oxygen oxidation of alcohols, in particular to a chemical reaction process for preparing aldehydes or ketones by catalyzing oxygen oxidation of alcohols, specifically a method using 4-hydroxyl-2,2,6,6 - Oxygen oxidation of alcohols with tetramethylpiperidine-oxygen free radical (4-OH-TEMPO) as catalyst. Background technique [0002] Oxidation of alcohols to carbonyl compounds is one of the most important unit reactions in organic synthesis, which is widely used in the synthesis of fine chemicals and organic intermediates [document 1.Hudlicky, M.; Oxidations in Organic Chemistry.Washington, DC : ACS, 1990]. Such reactions traditionally employ stoichiometric oxidants such as chromium oxide [2. Muzart, J. Chem. Rev., 1992, 92, 113-140.], manganese oxide [3. Regen, S.L; Koteel, C.J. Am.Chem.Soc., 1977, 99, 3837-3838.], ruthenium oxide [Document 4.: Griffith, W.P.Chem.Soc.Rev., 1992, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/37B01J31/02B01J31/26
Inventor 梁鑫淼王心亮刘仁华徐青薛兴亚章飞芳
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI