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Aromatic aldehyde preparation method employing oxygen to catalyze and oxidize aromatic primary alcohol

A technology for the catalytic oxidation of aromatic primary alcohols, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds. The effect of less dosage, high product yield and mild reaction conditions

Inactive Publication Date: 2010-07-07
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

As reported, triphenylphosphine ruthenium chloride / TEMPO, Chinese patent CN1796349A, CN1789225A respectively reported NaNO 2 / Br 2 / TEMPO,NaNO 2 / HCl / TEMPO, this type of system has high catalytic activity, but the halogen is highly corrosive, and it is easy to produce halogenated by-products with alcohol
Nitroxide radicals, such as TEMPO, are expensive and, as organic compounds, are not conducive to product separation

Method used

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  • Aromatic aldehyde preparation method employing oxygen to catalyze and oxidize aromatic primary alcohol
  • Aromatic aldehyde preparation method employing oxygen to catalyze and oxidize aromatic primary alcohol
  • Aromatic aldehyde preparation method employing oxygen to catalyze and oxidize aromatic primary alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Add 5.4g of benzyl alcohol, 0.427g of vanadyl sulfate, and 0.175g of sodium nitrite into a 500mL reaction kettle, add 50mL of acetonitrile, add 250μL of water, close the kettle, fill it with oxygen at a pressure of 0.5MPa, and raise the temperature under stirring To 80 ℃, and keep 2h, if the partial pressure of oxygen drops, add oxygen. After the reaction, cool to room temperature. Sampling is analyzed by gas chromatography, and the conversion rate of benzyl alcohol is greater than 99%, and the selectivity of benzaldehyde is greater than 98%. The separation yield of benzaldehyde was 93%. through 1 HNMR, 13 CNMR, GC-MS identified benzaldehyde.

Embodiment 2

[0021] Example 2: Add 5.4g of benzyl alcohol, 0.427g of vanadyl sulfate, and 0.175g of sodium nitrite into a 500mL reaction kettle, add 50mL of acetonitrile, close the kettle, fill it with oxygen at a pressure of 0.5MPa, and heat up to 80°C under stirring. And keep 2h, if the oxygen partial pressure drops, add oxygen. After the reaction, cool to room temperature. Sampling was analyzed by gas chromatography, the conversion rate of benzyl alcohol was 11.3%, and the selectivity of benzaldehyde was greater than 98%.

Embodiment 3

[0022] Example 3: 5.4g of benzyl alcohol, 0.427g of vanadyl sulfate, and 0.253g of potassium nitrite were added to a 500mL reaction kettle, 50mL of acetonitrile was added, and 500 μL of water was added, the kettle was closed, and the pressure of oxygen was 0.5MPa, and the temperature was raised under stirring To 50 ℃, and keep 10h, if the oxygen partial pressure drops, add oxygen. After the reaction, cool to room temperature. Sampling is analyzed by gas chromatography, the conversion rate is greater than 99%, and the selectivity is greater than 98%.

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Abstract

Disclosed is an aromatic aldehyde preparation method employing oxygen to catalyze and oxidize aromatic primary alcohol; the method takes air or oxygen as the oxygen source and adopts the catalyst system composed of vanadium oxides and nitrogen-containing compounds to selectively and highly oxidize the aromatic primary alcohol into corresponding aromatic aldehyde at temperature of 30-120 DEG C. The method has high oxidation efficiency, less side products, mild reaction conditions, has cheap and obtainable catalyst, is easy to separate and purify products, has high practicality and economy.

Description

technical field [0001] The invention relates to a method for preparing corresponding aromatic aldehydes by catalytically oxidizing primary aromatic alcohols. Specifically, it uses a two-component catalyst system, uses air or oxygen as the oxygen source, and oxidizes primary aromatic alcohols with high activity and selectivity under mild conditions to prepare the corresponding aromatic aldehydes. Background technique [0002] The oxidation of aromatic alcohols to aromatic aldehydes is one of the important basic functional group conversion reactions in organic chemistry, and has important applications in fine chemical industries such as pharmaceuticals. It has been a difficult point to develop an efficient and economical catalytic oxidation system using oxygen as the oxygen source. In the past few decades, scientists at home and abroad have developed a lot of catalytic oxidation systems. However, most of these catalyst systems use noble metals, such as palladium, ruthenium, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/54C07C45/38
Inventor 徐杰杜中田苗虹马继平孙志强马红
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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