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Method for synthesizing anisonitrile through indirect electrocatalysis

An anise nitrile and electrocatalysis technology, applied in electrolysis process, electrolysis components, electrolysis organic production and other directions, can solve the problems of large amount of organic solvent, difficult purification treatment, large amount of waste, etc., and achieve no metal residue and atom economy. The effect of strong and lower production cost

Active Publication Date: 2021-02-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has some disadvantages, such as a large amount of organic solvent, expensive reagents, low conversion rate, and difficult purification
There are also some methods that use p-methoxytoluene, p-methoxyaniline and p-methoxyhalogenated benzene as raw materials. In these methods, it is often necessary to use metal oxides as catalysts, or add toxic cyanide reagents, Corrosive dehydrating agent, which will generate a lot of waste and is not conducive to purification

Method used

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  • Method for synthesizing anisonitrile through indirect electrocatalysis
  • Method for synthesizing anisonitrile through indirect electrocatalysis
  • Method for synthesizing anisonitrile through indirect electrocatalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Add 0.0272g p-methoxybenzaldehyde, 0.0040g electrocatalyst 2c, 0.0492g hydroxylamine sulfate, 0.3419g tetrabutylammonium perchlorate, 8mL solvent (volume ratio CH 3 CN:CH 2 Cl 2 =4:1), 2mL distilled water, 50℃, Pt as anode, Pt as cathode, Ag / AgNO 3 (0.01MAgNO 3 Acetonitrile solution) electrode was used as a reference electrode, electrolyzed at a constant potential of 1.5V for 9h to obtain the target product anisonitrile. The yield of electrolysis products was analyzed by gas chromatography GC, and the analysis method was the area normalization method. The product yield is 95% as shown in Table 1. The reaction solution was extracted with anhydrous ether (5mL×3), dried over anhydrous sodium sulfate, purified by column chromatography (petroleum ether / ethyl acetate=15:1), and then characterized.

[0048] The product structure is characterized by: 1 HNMR (500MHz, CDCl 3 )δ: 3.86(s, 3H), 6.96(d, J=8.5Hz, 2H), 7.59(d, J=8.0Hz, 2H) GC-MS (EI, 70eV) m / z: 133.05[M] + .

Embodiment 2-4、 comparative example 1

[0050] Reaction steps and reaction process are the same as embodiment 1, and difference is that electrocatalyst is respectively replaced by equimolar 0.0033g 1c (embodiment 2), 0.0048g 3c (embodiment 3), 0.0045g 4c (embodiment 4) and The above constant potential electrolysis experiment was carried out without adding electrocatalyst (comparative example 1), and the results are listed in Table 1.

[0051] Table 1 Electrolysis of p-methoxybenzaldehyde under the action of different electrocatalysts to generate anisonitrile.

[0052]

[0053]

[0054] It can be seen from Table 1 that all electrocatalysts 1c-4c can be used as electrocatalysts in the field of aromatic aldehyde electrooxidation to synthesize aromatic nitriles. When 2c is used as an electrocatalyst, the yield of the target product is up to 95%, so the electrocatalyst is preferably 2c (Example 1).

Embodiment 5-10

[0056] Reaction steps and reaction process are with embodiment 1, and difference is that temperature of reaction is 5 ℃ (embodiment 5), 20 ℃ (embodiment 6), 25 ℃ (embodiment 7), 30 ℃ (embodiment 8), 40 ℃ ℃ (embodiment 9), 60 ℃ (embodiment 10), carry out above-mentioned constant potential electrolysis experiment, the result is listed in table 2.

[0057] The electrolysis result of table 2 different reaction temperatures

[0058]

[0059] From the above reaction results, it can be seen that the reaction temperature is preferably 50° C. (Example 1).

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Abstract

The invention discloses a method for synthesizing anisonitrile through indirect electrocatalysis. The method comprises the following steps: by taking p-methoxybenzaldehyde or p-methoxybenzyl alcohol as a raw material, hydroxylamine sulfate as a nitrogen source, a carbazole compound as shown in a formula (I) as an electrocatalyst, a platinum electrode as a cathode, a platinum electrode as an anode,and Ag / AgNO3 (0.01 M AgNO3 acetonitrile solution) as a reference electrode, and adopting a three-electrode system, carrying out indirect electrocatalysis in an electrolyte to obtain anisonitrile. Themethod has the characteristics of greenness, economy and high efficiency.

Description

technical field [0001] The invention belongs to the field of organic electrochemical synthesis, in particular to a method for indirect electrocatalytic synthesis of anisonitrile. Background technique [0002] Anisonitrile, also known as p-methoxybenzonitrile, has a strong aroma and is less irritating to the skin. It is an ideal substitute for aldehyde fragrances and is widely used in the fields of fragrances, pesticides, daily medicine and materials. The traditional synthesis method at home and abroad is the anisaldehyde method, which is to prepare anise aldoxime from anisaldehyde, and then generate anisonitrile after catalytic dehydration. This method has some disadvantages, such as a large amount of organic solvent, expensive reagents, low conversion rate, and difficult purification treatment. There are also some methods that use p-methoxytoluene, p-methoxyaniline and p-methoxyhalogenated benzene as raw materials. In these methods, it is often necessary to use metal oxide...

Claims

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Application Information

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IPC IPC(8): C25B3/07C25B3/09C25B3/23
Inventor 朱英红王乙龙焦玉峰葛展榜陈赵扬
Owner ZHEJIANG UNIV OF TECH
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