Preparation of o-nitrobenzaldehyde by biomimetic catalysis oxidation of o-nitrotoluene with oxygen

A technology for o-nitrobenzaldehyde and o-nitrotoluene, which is applied in the field of biomimetic catalytic oxygen oxidation of o-nitrotoluene to prepare o-nitrobenzaldehyde, can solve the problems of high equipment cost, large equipment corrosion, complicated operation and the like, and achieves a reaction Low temperature, reduced reaction cost and small dosage

Inactive Publication Date: 2004-11-17
BEIJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of the multi-step method is that the equipment used for the reaction is expensive, the operation is cumbersome, and time-consuming; moreover, the reaction needs to be carried out in an acidic environment, which causes great corrosion to the equipment.
In addition, most of the above reactions use metal compounds for oxidation, which has caused serious pollution to the environment.
CN1111615A discloses a kind of method that uses manganese salt as catalyst, alkoxyalkylamine as solvent, carries out oxidation with pure oxygen or air in the presence of strong alkali, and the shortcoming of this method is to use the pollution Environmental metal salt catalysts and expensive alkoxyalkylamine solvents

Method used

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  • Preparation of o-nitrobenzaldehyde by biomimetic catalysis oxidation of o-nitrotoluene with oxygen
  • Preparation of o-nitrobenzaldehyde by biomimetic catalysis oxidation of o-nitrotoluene with oxygen
  • Preparation of o-nitrobenzaldehyde by biomimetic catalysis oxidation of o-nitrotoluene with oxygen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Get 7mg cobalt phthalocyanine (i.e. R=H in general formula (I), M 1 =Co), 3.5g of o-nitrotoluene and 5.6g of sodium hydroxide were charged into a 200ml autoclave, 30ml of methanol was added, and oxygen at a pressure of 2.5MPa was introduced, and the reaction was carried out in a water bath at a temperature of 40°C for 12h. The mixed solution after the reaction removes the catalyzer first through suction filtration, then adds 30ml distilled water, adds dilute hydrochloric acid to neutralize, filters, and uses high-pressure liquid chromatography to analyze and detect after purification, and the yield of o-nitrobenzaldehyde is 15.6%. The product purity is 98.5%.

Embodiment 2

[0025] Get 15mg iron phthalocyanine (i.e. R=H in general formula (I), M 1 =Fe), 2.5g of o-nitrotoluene and 3.6g of sodium hydroxide were put into an autoclave, 30ml of methanol was added, the oxygen pressure was 3.0MPa, the temperature was controlled at 40°C in a water bath, and the reaction was carried out for 18h. The processing steps are the same as Example 1, and the product obtained is analyzed and detected by high-pressure liquid chromatography, and the yield of o-nitrobenzaldehyde is 13.5%, and the product purity after purification is 99.0%.

Embodiment 3

[0027] Get 14mg copper phthalocyanine (being R=H in the general formula (I), M 1 =Cu), 3.5g of o-nitrotoluene and 6.4g of sodium hydroxide were put into an autoclave, 30ml of methanol was added, the oxygen pressure was 1.0MPa, the temperature was controlled at 25°C in a water bath, and the reaction was carried out for 48h. The processing steps are the same as in Example 1, and the resulting product is analyzed and detected by high-pressure liquid chromatography. The yield of o-nitrobenzaldehyde is 18.4%, and the purified product has a purity of 99.2%.

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Abstract

The invention relates to a process for preparing aromatic aldehydes, in particular a process for preparing o-nitrobenzaldehyde through bionic catalytic oxidation of ortho-methylnitro benzene, wherein metallic phthalocyanine, single nuclear metalloporphyrin or mu-oxy-double nuclear metalloporphyrin having the similar structure as the biological enzymes are selected as the catalyst for the disclosed process, whose dose is 0.2-1.0% weight of ortho-methylnitro benzene, and methyl alcohol is used as solvent, 0.8-3.0 MPa oxygen is let into 3.0-6.0 mol/L strong alkaline methyl alcohol solution, the reaction temperature is controlled between 25 deg. C to 60 deg. C, the reaction time being 6-48 hrs.

Description

technical field [0001] The invention relates to a method for preparing aromatic aldehydes, in particular to a method for preparing o-nitrobenzaldehyde by biomimetic catalyzing oxygen oxidation of o-nitrotoluene. Background technique [0002] At present, the preparation methods of o-nitrobenzaldehyde mainly include benzaldehyde method, o-nitrotoluene oxidation method, o-nitrotoluene side chain methyl chloride hydrolysis method and o-nitrobenzoyl chloride method, and these methods all adopt multi-step Reaction method. The disadvantage of the multi-step method is that the equipment used for the reaction is expensive, and the operation is cumbersome and time-consuming; moreover, the reaction needs to be carried out in an acidic environment, which causes great corrosion to the equipment. In addition, most of the above reactions use metal compounds for oxidation, which has caused serious pollution to the environment. CN1111615A discloses a kind of method that uses manganese salt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/14
Inventor 佘远斌钟儒刚范莉莉吴胜周周贤太
Owner BEIJING UNIV OF TECH
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