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Method for preparing aldehyde or alkone by oxygen catalysis and alcohol oxidation under mild condition

A technology for oxidizing alcohol and oxygen, which is applied in the fields of organic chemistry, carbon-based compound preparation, chemical instruments and methods, etc., can solve problems such as inability to recycle and apply, and achieve the effects of reducing raw material cost, easy operation control, and convenient product separation.

Inactive Publication Date: 2009-10-28
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

[0008] (4) The amount of catalyst TEMPO is 3-8% of the substrate alcohol, which cannot be recycled

Method used

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  • Method for preparing aldehyde or alkone by oxygen catalysis and alcohol oxidation under mild condition
  • Method for preparing aldehyde or alkone by oxygen catalysis and alcohol oxidation under mild condition
  • Method for preparing aldehyde or alkone by oxygen catalysis and alcohol oxidation under mild condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The oxidation reaction was carried out in a long-neck single-necked round bottom flask (50 mL) equipped with a magnet. First add 5.0mmol benzyl alcohol and 0.05mmol TEMPO into the round bottom flask, then add 8mL dichloromethane as the reaction solvent, then add 0.50mmol hydrochloric acid (HCl), and finally add 0.5mmol nitric acid (HNO 3 ), airtight and make the top of the flask communicate directly with a balloon filled with oxygen. After 10 hours of reaction at room temperature, the stirring was stopped. Samples were taken for gas chromatography analysis. After the reaction was complete, the reaction liquid was transferred to a separatory funnel, and then the flask was carefully washed with dichloromethane, and the organic solutions were combined. followed by saturated Na 2 S 2 o 3 Aqueous solution and NaHCO 3 The organic phase was washed with aqueous solution to remove TEMPO and inorganic salts, the organic layer was dried with anhydrous sodium sulfate, and then...

Embodiment 2

[0034] The test method and steps are the same as in Example 1, but the catalyst used is 4-OH-TEMPO, the reaction time is 15 hours, the yield of benzaldehyde is 95%, and the content is more than or equal to 99%.

Embodiment 3

[0036] Test method and step are the same as embodiment 1, but the catalyst used is still TEMPO, but its consumption increases to 0.10mmol. In addition, the top of the flask was open, directly communicated with the atmosphere of the environment, and the reaction was stirred and reacted for a certain period of time. The conversion rate and selectivity of the content of benzyl alcohol were analyzed by GC. The results are shown in Table 1.

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Abstract

The invention relates to a preparation method for aldehyde or alkone, in particular to a method for preparing aldehyde or alkone by oxygen catalysis and alcohol oxidation under the mild condition. Themethod comprises the following steps: according to the 5 mmol of reaction substrate, 1-8 percent of 2,2,6,6-tetramethylpiperidine-oxygen radical (TEMPO) or a derivative thereof, 4-20 percent of halogen-containing compound and 4-20 percent of nitric acid or nitrate are taken as the catalysts, 0.1-0.8 MPa oxygen or air is taken as the oxidant, then the reaction is carried out for 1-36 h at the temperature of 0-80 DEG C, a series of alcohols can be oxidized into aldehyde or alkone with high selectivity, a catalyst TEMPO and the derivative thereof can be circularly and alternately used, the turn-over number (TON) is up to 800 and the cost is greatly reduced. The invention has the advantages of safer reagent with lower price, wider applicability of the substrate, mild reaction conditions, convenient product separation, no pollution to the environment, easy industrialization, and the like.

Description

technical field [0001] The invention relates to the preparation of aldehydes or ketones, in particular to a new method for oxidizing alcohols into aldehydes or ketones without transition metal catalysts and using oxygen or air as an oxidant. 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, 21, 179-185], Dess-Martin reagent [document 5. Dess, D.B.; Martin, J.C.J.Org.Chem., 1983, 48, 4155-4156] and other oxidizing agents. The traditional method, ...

Claims

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Application Information

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IPC IPC(8): C07B41/06C07B33/00C07C45/37C07D231/46C07D333/22B01J31/02
CPCY02P20/582
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
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