Method for preparing aromatic aldehyde by catalytic oxidation of toluene compound

A technology for catalytic oxidation and compounds, which is applied in the preparation of carbon-based compounds, the preparation of organic compounds, chemical instruments and methods, etc. It can solve the problems of difficult to control oxidation depth, pollute the environment, equipment corrosion, etc., and achieve reaction selectivity and yield. The effect of high reaction selectivity and yield, and simple process

Inactive Publication Date: 2014-06-25
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the industry, the chlorination and hydrolysis of toluene compounds is mainly used to produce aromatic aldehydes. The method has the disadvantages of difficult to control the oxidation depth and serious equipment corrosion, and has brought serious environmental problems.
The traditional oxidation method of toluene compounds is to use heavy metal oxides such as potassium dichromate, potassium permanganate, chromium trioxide-pyridine, etc., and the reaction generates a large amount of heavy metal waste, which serious

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  • Method for preparing aromatic aldehyde by catalytic oxidation of toluene compound
  • Method for preparing aromatic aldehyde by catalytic oxidation of toluene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 0.2g of cobalt isomorphously substituted ZSM-5 molecular sieve, 0.5g of potassium bromide, 1mL of toluene, and 10mL of glacial acetic acid into the three-necked flask in sequence, feed oxygen at a flow rate of 100mL / min, and react under stirring at 100°C After 12 hours, the gas chromatography-mass spectrometry analysis results showed that the product was the target product benzaldehyde, and the gas chromatography analysis results showed that the conversion rate of toluene was 90.2%, and the selectivity and yield of benzaldehyde were 78.4% and 70.7%, respectively.

Embodiment 2

[0027] Add 0.2 g of zirconium isomorphic substituted ZSM-5 molecular sieves, 2.0 g of hydrogen bromide with a mass fraction of 30.0%, 1 mL of o-chlorotoluene, and 10 mL of glacial acetic acid into the three-necked flask, and feed oxygen at a flow rate of 100 mL / min. After reacting at 80°C for 14h under stirring, the gas chromatography-mass spectrometry analysis results showed that the product was the target product o-chlorobenzaldehyde, and the gas chromatography analysis results showed that the conversion rate of o-chlorotoluene was 91.2%, and the selection of o-chlorobenzaldehyde The yield and yield were 68.6% and 62.6%, respectively.

Embodiment 3

[0029] Add 0.3 g of ZSM-5 molecular sieves substituted by manganese isomorphs, 2.0 g of hydrogen bromide with a mass fraction of 40%, 1 mL of p-bromotoluene, and 10 mL of acetonitrile in the three-necked flask, and feed oxygen at an oxygen flow rate of 160 mL / min. Under 80 DEG C, react 8h, gas chromatography-mass spectrometry analysis result shows that product is target product p-bromobenzaldehyde, and gas chromatography analysis result shows that the conversion rate of p-bromobenzaldehyde is 94.4%, the selectivity of p-bromobenzaldehyde and The yields were 71.3% and 67.3%, respectively.

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Abstract

The invention discloses a method for preparing aromatic aldehyde by selective catalytic oxidation of a toluene compound through a transition metal modified MFI molecular sieve. The method comprises the following steps: under the catalytic action of the transition metal modified MFI molecular sieve, with bromide or molecular bromine as an initiator and with oxygen or air as an oxygen source, performing reaction on a substrate toluene compound, and adding a polar organic solvent in the reaction system. The preparation method of the aromatic aldehyde by catalytic oxidation has the advantages that the percent conversions of reactants are high and the selectivity of a target product is high. In addition, a catalyst is simple to prepare, easy to separate and long in service life; the reaction conditions are mild and environmental friendly, and the application prospect is good.

Description

【Technical field】 [0001] The invention relates to the field of catalytic organic synthesis, in particular to a method for preparing aromatic aldehydes by catalytic oxidation of toluene compounds. 【Background technique】 [0002] Aromatic aldehydes are important raw materials in the production of fine chemicals. As intermediates in medicine, dyes, spices, pesticides, etc., they have good market prospects. For example, nitrobenzaldehyde is the main raw material for the synthesis of new cardiovascular drugs such as nifedipine and nimodipine; o-chlorobenzaldehyde can be directly used as an electroplating whitening agent, and also as an intermediate for tear gas products; p-chlorobenzaldehyde can be used It is used in the synthesis of herbicide Maidi San, plant growth regulator paclobutrazol and uniconazole; p-bromobenzaldehyde is also the main intermediate in the industrial synthesis of benzene-containing compounds. [0003] In the industry, the chlorination and hydrolysis of to...

Claims

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Application Information

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IPC IPC(8): C07B41/06C07C47/54C07C47/55C07C47/542C07C45/36C07C205/44C07C201/12
Inventor 尹双凤周伟芳邓益强陈浪周永波陈铁桥邱仁华
Owner HUNAN UNIV
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