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A kind of method of indirect electrocatalytic synthesis of anisonitrile

An anise nitrile and electrocatalysis technology, applied in the directions of organic chemistry, electrolysis components, electrolysis process, etc., can solve the problems of large amount of organic solvent, difficult purification treatment, large amount of waste, etc., and achieve environmental friendliness, strong atom economy, The effect of reducing production costs

Active Publication Date: 2021-12-07
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A kind of method of indirect electrocatalytic synthesis of anisonitrile
  • A kind of method of indirect electrocatalytic synthesis of anisonitrile
  • A kind of method of indirect electrocatalytic synthesis of anisonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Add 0.0272 g p-methoxybenzaldehyde, 0.0040 g electrocatalyst 2c, 0.0492 g hydroxylamine sulfate, 0.3419 g tetrabutylammonium perchlorate, 8 mL solvent (volume ratio CH 3 CN:CH 2 Cl 2 =4:1), 2 mL distilled water, 50 ℃, Pt as anode, Pt as cathode, Ag / AgNO 3 (0.01 M AgNO 3 Acetonitrile solution) electrode was used as a reference electrode, and the target product anisonitrile was obtained by electrolysis at a constant potential of 1.5 V for 9 h. 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 (5 mL×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 (500 MHz, CDCl 3 )δ: 3.86 (s, 3H), 6.96 (d, J=8.5Hz, 2H), 7.59 (d, J=8.0 Hz, 2H)GC-MS (EI, ...

Embodiment 2-4、 comparative example 1

[0050] The reaction steps and reaction process are the same as in Example 1, except that the electrocatalyst is replaced by equimolar 0.0033 g 1c (Example 2), 0.0048 g 3c (Example 3), 0.0045 g 4c (Example 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 to generate anisonitrile under the action of different electrocatalysts.

[0052]

[0053] 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 was used as the electrocatalyst, the yield of the target product was up to 95%, so the electrocatalyst was preferably 2c (Example 1).

Embodiment 5-10

[0055] The reaction steps and reaction process are the same as in Example 1, except that the reaction temperature is 5°C (Example 5), 20°C (Example 6), 25°C (Example 7), 30°C (Example 8), 40°C °C (Example 9) and 60 °C (Example 10), the above constant potential electrolysis experiments were carried out, and the results are listed in Table 2.

[0056] Table 2 Electrolysis results at different reaction temperatures

[0057]

[0058] From the above reaction results, it can be known that the reaction temperature is preferably 50° C. (Example 1).

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Abstract

The invention discloses a method for indirect electrocatalytic synthesis of anisonitrile. The method is as follows: using p-methoxybenzaldehyde or p-methoxybenzyl alcohol as raw material, hydroxylamine sulfate as nitrogen source, and formula (I) The carbazole compounds shown are electrocatalysts, using a three-electrode system, the cathode and anode are platinum electrodes, Ag / AgNO 3 (0.01MAgNO 3 Acetonitrile solution) is used as reference electrode, carries out indirect electrocatalysis in electrolyte and obtains anisonitrile. The invention 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 anisaldehyde 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 meta...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/82C25B3/07C25B3/09C25B3/23
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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