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A method for electrochemically catalytically synthesizing aromatic nitriles with alcohol as raw material
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A technology of raw material electrochemistry and aromatic nitrile, applied in the direction of electrolytic components, electrolytic process, electrolytic organic production, etc., can solve the problems of harsh experimental conditions, human health hazards, and inability to completely avoid environmental pollution, etc., to achieve simple and safe operation, The effect of reducing environmental costs
Active Publication Date: 2018-11-09
ZHEJIANG UNIV OF TECH
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The method for the synthesis of nitriles originally proposed is mainly the exchange of cyanide ions in halogen groups and metal cyanides, which usually needs to be carried out under conditions such as high temperature and high pressure, and the metal cyanides used in these methods are highly toxic and harmful to the environment. heavy metal pollution
In later reports, although the source of metal cyanide has been improved, it still cannot completely avoid environmental pollution and hazards to personnel health
Since then, various methods for the synthesis of nitrile compounds starting from different substrates have been proposed successively. However, in most routes, catalysts containing transition metals need to be used, or relatively harsh experimental conditions are still required, which greatly affects Its application in actual production
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Embodiment 1
[0024] Embodiment 1: the preparation of benzonitrile (formula (2-1))
[0025] In a 30ml beaker, add 0.1mol / L sodium perchlorate in acetonitrile (15mL), benzyl alcohol (formula (1-1), 1mmol, 108mg), 2,2,6,6-tetramethylpiperidine nitrogen Oxygen radical (TEMPO) (0.15 mmol, 23 mg) and ammonium acetate (3 mmol, 231 mg). 25°C, constant potential electrolysis at 1.5V, the reaction ends after 10h. Add saturated sodium bisulfite solution to the reaction solution and stir, then extract with ethyl acetate, separate the organic layer, distill off the solvent under reduced pressure, and then perform column chromatography separation, using ethyl acetate / n-hexane volume ratio 1:5 The mixed solution was used as the eluent, and the eluate containing the target compound was collected, and the solvent was evaporated to obtain 78.3 mg of benzonitrile, with an isolation yield of 76%.
Embodiment 2
[0026] Embodiment 2: the preparation of p-chlorobenzonitrile (formula (2-2))
[0027] Add 0.1mol / L sodium perchlorate in acetonitrile solution (10mL), p-chlorobenzyl alcohol (formula (1-2), 1mmol, 143mg), TEMPO (0.15mmol, 23mg) and ammonium acetate (3mmol) in a 30ml beaker , 231 mg). 25°C, constant potential electrolysis at 1.5V, the reaction ends after 10h. Add saturated sodium bisulfite solution to the reaction solution and stir, then extract with ethyl acetate, separate the organic layer, distill off the solvent under reduced pressure, and then perform column chromatography separation, using ethyl acetate / n-hexane volume ratio 1:5 The mixed solution was used as the eluent, and the eluate containing the target compound was collected, and the solvent was evaporated to obtain 118.3 mg of p-chlorobenzonitrile, with an isolation yield of 86%.
Embodiment 3
[0028] Embodiment 3: the preparation of p-chlorobenzonitrile (formula (2-2))
[0029] The reaction steps were the same as in Example 2, except that the voltage was changed to 1.0V, and the reaction was performed for 15 hours. Finally, 115.6 mg of p-chlorobenzonitrile was obtained with an isolated yield of 84%.
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Abstract
The invention discloses a method for electrochemically catalyzing and synthesizing aromatic nitriles using alcohol as a raw material. The reaction adopts a three-electrode system, the cathode and the anode are both platinum electrodes, and 0.1mol / L silver nitrate acetonitrile solution is used as a reference electrode. A reaction substrate is added to the solution, and the electrolyte is sodium perchlorate, sodium periodate or sodium tetrafluoroborate with a molar concentration of 0.05-0.2mol / L; the reaction substrate is benzyl alcohol compound, ammonium acetate and 2 , 2,6,6-tetramethylpiperidine nitroxide radical, the reaction substrate benzyl alcohol compound, ammonium acetate and 2,2,6,6-tetramethylpiperidine nitroxide radical three feeding The molar ratio is 100:200~400:5~30; after stirring the electrolysis reaction for 5~30 hours under the condition of temperature 5~40℃ and electrolysis voltage 0.6~2.5V, the reaction solution is post-treated to obtain the product aromatic nitrile. The beneficial effects mainly lie in that the raw materials of the invention are cheap and easy to obtain; the reaction conditions are relatively mild; clean electric energy is used as the oxidation-reduction agent, and the environmental cost is greatly reduced.
Description
technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a method for electrochemically catalytically synthesizing aromatic nitriles by using alcohol as a raw material. Background technique [0002] Nitrile compounds are widely used in the production of dyeing agents, pesticides, herbicides, etc., and are important chemical raw materials. At the same time, because the cyano group can be converted into other groups under mild conditions, such as carboxyl group, amino group, etc., nitrile compounds are often used as intermediates in drug synthesis. The method for the synthesis of nitriles originally proposed is mainly the exchange of cyanide ions in halogen groups and metal cyanides, which usually needs to be carried out under conditions such as high temperature and high pressure, and the metal cyanides used in these methods are highly toxic and harmful to the environment. It can also cause heavy metal pollution. I...
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