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Method for preparing aldehydes and ketones by using oxygen gas to oxidize alcohols

A technology for oxidizing alcohol and oxygen, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of environmental pollution by waste, increase the cost of raw materials, etc., achieve environmental friendliness, reduce the cost of raw materials, react mild conditions

Inactive Publication Date: 2008-03-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the traditional method needs to use a large amount of heavy metal reagents, which increases the cost of raw materials; on the other hand, a large amount of waste generated during the reaction process seriously pollutes the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 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 add 10mL of dichloromethane into the autoclave, then add 10.0mmol of benzyl alcohol and 0.1mmol of TEMPO into 10mL of solvent, and then add 0.5mmol of FeCl 3 , and finally add 0.5mmolNaNO 2 ,seal. Pressurize the kettle to 0.1MPa, transfer it to an oil bath that has been raised to 80°C in advance, stop stirring after a certain period of time, cool down, 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 anhydrous sodium sulfate, and...

Embodiment 2

[0020] The reaction temperature is room temperature, the test method and steps are the same as in Example 1, the reaction time is 6 hours, and the yield is 95%.

Embodiment 3

[0022] The transition metal ion used is Cu(NO 3 ) 2 , 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%.

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PUM

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Abstract

The present invention relates to chemical reaction process of oxidizing alcohol with oxygen to prepare aldehyde or ketone, and is especially an alcohol oxidizing process with 2, 2, 6, 6-tetramethyl piperidine nitroxide free radical as catalyst. In organic solvent, and in the presence of catalyst comprising TEMPO, sodium nitrite and transition metal salt, alcohol is oxidized to produce aldehyde or ketone. The process has the alcohol, TEMPO, sodium nitrite and transition metal salt in the weight ratio of 100 to 1-5 to 1-10 to 1-10, oxygen pressure of 0.1-0.8 MPa, reaction temperature of 0-80 deg.c and reaction time of 1-24 hr. The present invention has the advantages of mild reaction condition, easy control, low cost, high safety and environment friendship.

Description

technical field [0001] The present invention relates to the chemical reaction process of preparing aldehyde or ketone by catalytic oxygen oxidation alcohol, specifically a kind of oxygen oxidation alcohol utilizing 2,2,6,6-tetramethylpiperidine nitroxide free radical (TEMPO) as catalyst new method. Background technique [0002] The oxidation of alcohols to carbonyl compounds is an important unit reaction 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 [Document 2: Muzart, J. Chem. Rev., 1992, 92, 113-140.], manganese oxide [Document 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, 21, 179-185], Dess-Martin reagent [Document 5: Dess, D.B.; Martin, J.C.J.Org.Chem., 1983,...

Claims

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Application Information

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IPC IPC(8): C07C45/38C07C47/54C07C47/55C07C47/228C07C47/02C07C49/395C07C49/407C07D213/48C07D333/22
Inventor 梁鑫淼王乃伟刘仁华徐青
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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