Electrochemical catalytic synthesis method of aromaticnitrile

A synthesis method and technology for aromatic nitrile, applied in the field of chemistry, can solve the problems of toxic cyanide source, environmental problems, strict control requirements, etc., and achieve the effects of reducing environmental cost, mild reaction conditions, simple and safe operation

Active Publication Date: 2016-05-04
SHANGHAI LINKCHEM TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantages of this type of synthesis method are: (1) the cyanogen sources used are generally poisonous, and care must be taken during use to avoid the generation of toxic HCN; (2) stoichiometric metal wastes are inevitably generated, resulting in (3) The control requirements of the reaction process are relatively strict
Aromatic nitriles can also be synthesized from aldoximes, but often have the disa

Method used

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  • Electrochemical catalytic synthesis method of aromaticnitrile
  • Electrochemical catalytic synthesis method of aromaticnitrile
  • Electrochemical catalytic synthesis method of aromaticnitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: Preparation of benzonitrile (formula (2-1))

[0027] Add 0.1mol / L sodium perchlorate in acetonitrile solution (10mL), benzaldehyde (formula (1-1), 1mmol, 106mg), TEMPO (0.1mmol, 16mg), HMDS (2.5mmol, 404mg) into a 30ml beaker ) and acetic acid (2.5mmol, 150mg). 25°C, constant potential electrolysis at 1.5V, and the reaction ended after 15 hours. Add saturated sodium sulfite solution to the reaction solution and stir, then extract with dichloromethane, separate the organic layer, distill off the solvent under reduced pressure, and then perform column chromatography separation, and use a mixture of ethyl acetate / petroleum ether with a volume ratio of 1:200 as Eluent, collect the eluate containing the target compound, evaporate the solvent to obtain 82.4 mg of benzonitrile, and the separation yield is 80%.

Embodiment 2

[0028] Embodiment 2: Preparation of p-nitrobenzonitrile (formula (2-2))

[0029] Add 0.1mol / L sodium perchlorate in acetonitrile solution (10mL), p-nitrobenzaldehyde (formula (1-2), 1mmol, 151mg), TEMPO (0.1mmol, 16mg), HMDS (2.5 mmol, 404mg) and acetic acid (2.5mmol, 150mg). 25°C, constant potential electrolysis at 1.5V, and the reaction ended after 12 hours. Add saturated sodium sulfite solution to the reaction solution and stir, then extract with dichloromethane, separate the organic layer, distill off the solvent under reduced pressure, and then perform column chromatography separation, and use a mixture of ethyl acetate / petroleum ether with a volume ratio of 1:200 as Eluent, collect the eluate containing the target compound, evaporate the solvent to obtain 136.2 mg of p-nitrobenzonitrile, and the separation yield is 92%.

Embodiment 3

[0030] Embodiment 3: Preparation of p-nitrobenzonitrile (formula (2-2))

[0031] 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, 130.2 mg of p-nitrobenzonitrile was obtained, and the isolated yield was 88%.

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Abstract

The invention discloses an electrochemical catalytic synthesis method of aromaticnitrile. Aromatic aldehyde is used as a raw material, HMDS (hexamethyldisilazane) is used as a nitrogen source, a three-electrode system is adopted, a negative electrode and a positive electrode adopt platinum electrodes, and a 0.1mol/l silver nitrate acetonitrile solution is used as a reference electrode; aromatic aldehyde, HMDS, TEMPO (2,2,6,6-tetramethyl-1-piperidine-N-oxyl free radicals) and acetic acid are added to an electrolyte acetonitrile solution with certain concentration, the mixture is stirred for an electrolytic reaction at the temperature of 5-40 DEG C and under the constant voltage of 0.5-8.0 V for 5-30 h, a reaction liquid is subjected to aftertreatment, and a product, namely, aromaticnitrile, is obtained; an electrolyte refers to sodium perchlorate, sodium periodate or sodium tetrafluoroborate. The method is simple and safe to operate and easy to implement.

Description

technical field [0001] The invention belongs to the technical field of chemistry, in particular to an electrochemical catalytic synthesis method of aromatic nitriles. Background technique [0002] Nitrile compounds are important building blocks in organic synthesis, especially aromatic nitriles are the key structural units of many dyes, medicines, pesticides and electronic materials. Nitrile compounds are also important intermediates in organic synthesis because the cyano groups contained in them have the ability to transform into other important functional groups such as amino groups, amido groups, aldehyde groups, carboxyl groups, and ester groups. The most traditional synthetic method of aromatic nitriles is through Sandmeyerreaction or Rosenmund–vonBraun reaction, but these two methods have serious defects, both require the use of stoichiometric CuCN, and the reaction conditions are relatively severe. Since then, the cyanation reaction route of aromatic halides catalyze...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 李美超沈振陆陈其国莫卫民
Owner SHANGHAI LINKCHEM TECH CO LTD
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