Electrochemical synthesis method of vanillin

A synthesis method and electrochemical technology, which are applied in the electrolysis process, electrolysis components, electrolysis organic production and other directions, can solve the problems of low yield of vanillin, etc., and achieve the effects of simple preparation method, reduced production cost and convenient operation.

Pending Publication Date: 2022-03-18
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a method for the electrochemical synthesis of vanillin, to overcome the low yield of vanillin in the prior art, the use of toxic and harmful transition metals and their oxides or the use of phases in the synthesis process of vanillin. The transfer catalyst produces a large amount of waste water and other defects, providing a green, efficient and economically feasible method for the synthesis of vanillin

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  • Electrochemical synthesis method of vanillin
  • Electrochemical synthesis method of vanillin

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Experimental program
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Effect test

Embodiment 1

[0035] Take 76.1mg 4-hydroxy-3-methoxybenzyl alcohol, 1.5mL H 2 O, 1.5mL CHCl 3 , 3.9mg TEMPO and 14.6mg NaCl were mixed to obtain solution A, and the obtained solution A was used as the electrolyte, the platinum sheet was used as the cathode, and the platinum sheet was used as the anode for electrolysis to obtain solution B. During the electrolysis process, the current was 5mA, the temperature was 50°C, and the electrolysis time was 15h. Solution B was extracted with 20 mL of ethyl acetate to obtain an organic phase, which was detected by thin layer chromatography (TLC). The obtained organic phase was separated and purified by rotary evaporation (pressure: 400 mmHg, temperature: 40°C, rotary evaporation time: 5 min) and column chromatography (developing solvent: petroleum ether / ethyl acetate = 3:1, volume ratio) Finally, a white solid was obtained, and the yield of vanillin was calculated to be 43%.

Embodiment 2

[0037] Take 1.14g 4-hydroxy-3-methoxybenzyl alcohol, 2mL H 2 O, 2mL CHCl 3 , 60mg TEMPO and 219mgNaCl were mixed to obtain a solution A, and the obtained solution A was used as an electrolyte, the platinum sheet was used as a cathode, and the platinum sheet was used as an anode for electrolysis to obtain a solution B. During the electrolysis process, the current was 5mA, the temperature was 50°C, and the electrolysis time was 24h. Solution B was extracted with 80 mL of ethyl acetate to obtain an organic phase, which was detected by thin layer chromatography (TLC). The obtained organic phase was separated and purified by rotary evaporation (pressure: 400 mmHg, temperature: 40°C, rotary evaporation time: 5 min) and column chromatography (developing solvent: petroleum ether / ethyl acetate = 3:1, volume ratio) Finally, a white solid was obtained, and the yield of vanillin was calculated to be 41%.

Embodiment 3

[0039] Take 11.42g 4-hydroxy-3-methoxybenzyl alcohol, 5mL H 2 O, 5mL CHCl 3 , 780mg TEMPO and 2.19gNaCl were mixed to obtain solution A, and the obtained solution A was used as the electrolyte, the platinum sheet was used as the cathode, and the platinum sheet was used as the anode for electrolysis to obtain solution B. During the electrolysis process, the current was 5mA, the temperature was 50°C, and the electrolysis time was 72h. Solution B was extracted with 500 mL of ethyl acetate to obtain an organic phase, which was detected by thin layer chromatography (TLC). The obtained organic phase was separated and purified by rotary evaporation (pressure: 400 mmHg, temperature: 40°C, rotary evaporation time: 5 min) and column chromatography (developing solvent: petroleum ether / ethyl acetate = 3:1, volume ratio) Finally, a white solid was obtained, and the yield of vanillin was calculated to be 38%.

[0040] The product obtained in this embodiment is characterized by NMR, and t...

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Abstract

The invention relates to an electrochemical synthesis method of vanillin, which comprises the following steps: (1) dispersing 4-hydroxy-3-methoxybenzyl alcohol, TEMPO and electrolyte in a solvent to obtain a solution A; (2) carrying out electrolysis by taking the obtained solution A as an electrolyte, a platinum sheet as a cathode and a platinum sheet as an anode to obtain a solution B; and (3) sequentially performing extraction, rotary evaporation and column chromatography separation on the obtained solution B to obtain a target product. According to the method, 4-hydroxy-3-methoxybenzyl alcohol is subjected to selective oxidation reaction in a liquid-liquid two-phase heterogeneous reaction system by adopting an electrochemical synthesis method, and vanillin is prepared. Compared with the prior art, the product yield is high and reaches up to 43%, and the synthesis method is low in solvent consumption, beneficial to reduction of the production cost, environmentally friendly, efficient, economical and convenient to operate and shows a good industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and relates to an electrochemical synthesis method of vanillin. Background technique [0002] Vanillin is also called vanillin, its chemical name is 4-hydroxy-3-methoxybenzaldehyde, and its molecular formula is C 8 h 8 o 3 . Vanillin has the aroma of vanilla bean and strong milky aroma, and acts as an aroma enhancer and fixer. It is widely used in cosmetics, tobacco, pastry, candy, baked food and other industries. It can also be used as a plant growth promoter, fungicide, lubricant defoamer, etc., and is also an important intermediate for the synthesis of drugs and other spices. In addition, it can also be used as a polishing agent in the electroplating industry, as a ripening agent in agriculture, as a deodorant in rubber products, as an anti-hardening agent in plastic products and as a pharmaceutical intermediate, etc. , is widely used. [0003] There are many ways to obtain van...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/07C25B3/23
CPCC25B3/07C25B3/23
Inventor 张兴华项翠灵叶斌楼镓焕杜玉爽
Owner SHANGHAI INST OF TECH
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