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Method for preparing aldehyde or ketone by alcohol selective oxidation under catalysis of copper complex

A copper complex and selective technology, which is applied in the direction of oxidation preparation of carbonyl compounds, organic compound/hydride/coordination complex catalysts, chemical instruments and methods, etc., can solve the problems of poor solvents and achieve convenient preparation and low price , a wide range of effects

Inactive Publication Date: 2016-08-10
JINGCHU UNIV OF TECH
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Problems solved by technology

However, most existing catalytic oxidation processes require the use of environmentally unfavorable solvents such as toluene and chlorinated hydrocarbons

Method used

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  • Method for preparing aldehyde or ketone by alcohol selective oxidation under catalysis of copper complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the synthesis of copper complex

[0022] Dissolve N-methylimidazole (82 mg, 0.001 mol), 2,2,6,6-tetramethyl-1-oxopiperidine (31.2 mg, 0.0005 mol) in 20 ml of ethanol, and add dihydrate to it A solution of copper acetate (108.5 mg, 0.0005 mol) in water (50 mL). The resulting light brown solution was stirred in air at room temperature for 30 minutes, then the gray-green precipitate was filtered off, the filtrate was extracted with ethyl acetate, the organic phase was dried and filtered, and the solvent was distilled off under reduced pressure to obtain a brown crude product. The crude product was dissolved in ethanol and slowly volatilized in the air for 2 days to obtain yellow-brown blocky crystals. Yield: 147 mg (85%). UV-Vis spectrum UV-Vis: λ max / nm (1.0 × 10 -5 mol dm -3 , CH 2 Cl 2 ) 270 (ε / 10 3 dm 3 mol −1 cm −1 53.6), 372 (8.5), 430 (6.70), 610 (0.33). Infrared spectrum FT-IR (solid, cm -1 ): 1655s,160s, 1536s, 1442m, 1370s, 1309w, 1...

Embodiment 2

[0023] Embodiment 2: the synthesis of benzaldehyde

[0024] Add the above copper catalyst (13.8 mg, 0.02 mmol, 2%), 2,2,6,6-tetramethyl-1-oxopiperidine (TEMPO) (0.050 mmol, 5%) into a 25 mL round bottom flask , phenylethyl alcohol (108 mg, 1 mole) and 5 mL of deionized water. The reaction was exposed to air at room temperature and stirred for 2 hours. After the resulting solution was extracted with ethyl acetate, the organic phase was washed with water and washed with anhydrous sulfuric acid. Magnesium is dried and easily removed under reduced pressure to obtain benzaldehyde (purity greater than 98%). Yield: 101 mg (95%). H NMR spectrum 1 H NMR (400 MHz, CDCl 3 ) δ 9.92 (s, 1H), 7.83-7.78 (m, 2H), 7.55-7.38 (m, 3H). Mass Spectrum GC-MS (m / z): 106 (calc. 106).

Embodiment 3

[0025] Embodiment 3: the synthesis of 4-methoxybenzaldehyde

[0026] Add the above copper catalyst (13.8 mg, 0.02 mmol, 2%), 2,2,6,6-tetramethyl-1-oxopiperidine (TEMPO) (0.050 mmol, 5%) into a 25 mL round bottom flask , 4-methoxyphenethyl alcohol (138 mg, 1 mmol) and 5 mL of deionized water, the reaction was exposed to air at room temperature and stirred for 2 hours, the resulting solution was extracted with ethyl acetate, and the organic phase was washed with water , dried with anhydrous magnesium sulfate, and easily removed under reduced pressure to obtain 4-methoxybenzaldehyde (purity greater than 98%). Yield: 126 mg (93%). H NMR spectrum 1 H NMR (400 MHz, CDCl 3 ) δ 9.97 (s, 1H), 7.84 (d, J =8.7 Hz, 2H), 7.01 (d, J = 8.8 Hz, 2H), 3.90 (s, 3H, H OCH3 ). Mass Spectrum GC-MS (m / z): 136 (calc. 136).

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Abstract

The invention relates to a method for preparing aldehyde or ketone by alcohol selective oxidation under catalysis of a copper complex. The preparation method comprises the following steps: adding ethanol, N-methylimidazole, copper acetate dihydrate, 2,2,6,6-tetramethyl-1-oxo piperidine and deionized water into a round-bottom flask, and reacting to obtain reaction products; extracting the reaction products with ethyl acetate to obtain a crude product; recrystallizing the crude product in ethanol to obtain a copper complex catalyst; and adding the copper catalyst, 2,2,6,6-tetramethyl-1-oxo piperidine primary alcohol or secondary alcohol and deionized water, reacting, and extracting reaction products with ethyl acetate, so that the aldehyde or ketone product is obtained. The method provided by the invention has the advantages that the metal complex is taken as the catalyst, water is taken as solvent, and alcohol is oxidized under catalysis to obtain aldehyde or ketone; and preparation is convenient, price is relatively low, yield is high, purity is higher than 98%, mass synthesis can be carried out, and the method provided by the invention is applicable to industrial production application.

Description

technical field [0001] The invention relates to a method for preparing aldehydes or ketones by catalyzing the selective oxidation of alcohols, in particular to a method for synthesizing aldehydes or ketones by catalyzing alcohols with metal copper complexes. Background technique [0002] The selective oxidation of alcohols to aldehydes or ketones is a key reaction widely used in modern synthetic chemistry and industry. In recent years, atom-economical oxidation methods, including catalytic oxidation, have made significant progress, and catalytic oxidation is most attractive because of its low cost and environmental friendliness. However, most existing catalytic oxidation processes require the use of environmentally poor solvents, such as toluene and chlorinated hydrocarbons. If the reaction is carried out in water instead of organic solvents, there are clear advantages from a "green" chemical and technological point of view. Oxidation reactions in water, for example, are c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07C47/54C07C47/575C07C49/14B01J31/22
CPCB01J31/181B01J2231/70B01J2531/0213B01J2531/16C07C45/29C07C47/54C07C47/575C07C49/14
Inventor 刘娥刘金丽李立威
Owner JINGCHU UNIV OF TECH
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