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Preparation method of p-nitrobenzaldehyde

A technology of p-nitrobenzaldehyde and p-nitrotoluene, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve problems such as low process yield, pollution, and unfavorable economic benefits, and achieve improvement The effect of yield and purity, optimized reaction process, and simple process flow

Pending Publication Date: 2020-09-15
山东卓俊实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 2) The reaction solvent often uses halogenated alkanes such as dichloromethane or aromatics such as toluene. These solvents are highly toxic or polluting, which is not conducive to the green development of the process
[0006] 3) Chromium trioxide and acid system are used in the oxidation process. Due to the use of heavy metal oxidants and the production of a large amount of acid, the process has a great pollution to the environment;
[0007] 4) The oxidation process uses expensive oxidants such as sodium periodate, which is unfavorable to economic benefits;
[0008] 5) the process yield of prior art is generally not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 0.01mol p-nitrotoluene and 12ml methanol to a reactor capable of passing ultraviolet light, stir with a magnetic stirrer, turn on the ultraviolet lamp, and slowly add liquid bromine (0.01mol) dropwise to the reactor, and continue stirring at room temperature Reaction, the dropwise addition time is 5min, then add 40g of sodium bicarbonate solution with a mass concentration of 5%, slowly raise the temperature to reflux for 2h, slowly lower to room temperature, and extract with dichloromethane (15mL×3) , collected the organic phase, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized with water and ethanol (v / v=1:1) to obtain the product p-nitrobenzaldehyde with a yield of 83% and a purity of 99%.

Embodiment 2

[0030] Add 0.01mol p-nitrotoluene and 15ml ethanol to a reactor capable of passing ultraviolet light, stir with a magnetic stirrer, turn on the ultraviolet lamp, and slowly add liquid bromine (0.02mol) dropwise to the reactor, and continue stirring at room temperature Reaction, the dropwise addition time is 12min, then add 50g of sodium bicarbonate solution with a mass concentration of 10%, slowly raise the temperature to reflux for 2.5h, slowly drop to room temperature, and extract with dichloromethane (15mL×3 ), collected the organic phase, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized with water and ethanol (v / v=2:1) ​​to obtain the product p-nitrobenzaldehyde with a yield of 86% and a purity of 99.8%.

Embodiment 3

[0032] Add 0.1mol p-nitrotoluene and 100ml ethanol to a reactor capable of passing ultraviolet light, stir with a magnetic stirrer, turn on the ultraviolet lamp, and slowly add liquid bromine (0.15mol) dropwise to the reactor, and continue stirring at room temperature Reaction, dropwise time is 30min, then add 180g of sodium bicarbonate solution with a mass concentration of 15%, slowly raise the temperature to reflux for 3h, slowly drop to room temperature, use chloroform extraction (100mL×6), collect The organic phase was dried over anhydrous calcium sulfate, concentrated under reduced pressure, and recrystallized with water and ethanol (v / v=4:1) to obtain the product p-nitrobenzaldehyde with a yield of 81% and a purity of 99.7%.

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Abstract

The invention provides a preparation method of p-nitrobenzaldehyde. The method is characterized by comprising the following steps of: adding p-nitrotoluene and an alcohol solvent into a reactor; continuously stirring, controlling the temperature to be 20 to 30 DEG C; dropwise adding liquid bromine, simultaneously using ultraviolet light to catalyze a reaction, reacting for 5-30 min, adding a sodium bicarbonate solution, heating to reflux, adjusting the temperature to room temperature, extracting, drying, concentrating and recrystallizing to obtain the product p-nitrobenzaldehyde. According tothe invention, ultraviolet light is adopted as a catalyst, a mixed solvent of water and alcohol is adopted for recrystallization, the yield of the obtained product is larger than 80%, and the purity of the obtained product is larger than 99%.

Description

technical field [0001] The invention relates to a preparation method of a known compound, specifically a preparation method of p-nitrobenzaldehyde, belonging to the field of organic synthesis Background technique [0002] p-Nitrobenzaldehyde is white or light yellow prismatic crystal, with a melting point of 105-108°C and a relative density of 1.496. This product is an intermediate in organic synthesis of dyes and medicines, such as the synthesis of nitrobenzene-2-butenone, p-aminobenzaldehyde, p-acetamidobenzaldehyde, trimethoprim, thiosulfuron, and p-thiourea , Acetaminophen, Hydrazone, Chloramphenicol, etc. [0003] Using p-nitrotoluene as a starting material, preparing p-nitrobenzaldehyde through bromination, hydrolysis, oxidation and other processes is the most common method in this field for preparing p-nitrobenzaldehyde, but the following disadvantages often exist in the prior art: [0004] 1) An azo reagent or a peroxide reagent is used as a free radical initiator ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/44
CPCC07C201/12C07C205/44
Inventor 李娟
Owner 山东卓俊实业有限公司
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