Aliphatic nitrile catalytic oxidation synthesis method

A technology of catalytic oxidation and synthesis method, applied in the field of chemistry, can solve the problems of unsuitable fatty aldehyde, strict control requirements, unavoidable metal waste, etc., and achieve the effects of reducing environmental cost, easy and safe operation

Active Publication Date: 2016-04-13
邳州市润宏实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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
JinhoKim (J.Org.Chem.201

Method used

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  • Aliphatic nitrile catalytic oxidation synthesis method
  • Aliphatic nitrile catalytic oxidation synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of n-dodecanonitrile (formula (2-1))

[0026] In a 100ml flask, add 50mL acetonitrile, 10mmolHMDS, 0.4mmol TEMPO, 0.4mmol KPF 6 And 0.6mmol of TBN, replace the air in the bottle with oxygen, seal the mouth of the bottle with a rubber stopper, insert an oxygen balloon, put the reaction bottle into a pre-heated water bath and heat to 30℃, slowly add 4mmol of dodecaldehyde (formula (1-1)), react for 8h. Sodium thiosulfate solution was added to the reaction solution and stirred, and then extracted with ether, the organic layer was separated, the solvent was distilled off under reduced pressure, and column chromatography was performed. The mixture of ethyl acetate / petroleum ether volume ratio 1:200 was used as Eluent, collect the eluent containing the target compound, evaporate the solvent to obtain dodeconitrile, the separation yield is 75%.

Embodiment 2

[0027] Example 2: Preparation of n-dodecanonitrile (formula (2-1))

[0028] The reaction steps are the same as in Example 1, except that acetonitrile is changed to N,N'-dimethylformamide and reacted for 20 hours. The isolated yield of dodeconitrile is 46%.

Embodiment 3

[0029] Example 3: Preparation of n-dodecanonitrile (formula (2-1))

[0030] The reaction steps are the same as in Example 1, except that acetonitrile is changed to dimethyl sulfoxide and reacted for 20 hours. The separation yield of dodeconitrile is 53%.

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Abstract

The invention discloses an aliphatic nitrile catalytic oxidation synthesis method. With aliphatic aldehyde serving as reaction substrate, 2, 2, 6, 6-tetramethylpiperidine-1-oxygen radical (TEMPO), alkali metal salt and tert-butyl nitrite (TBN) as catalysts, hexamethyl-disilazane (HMDS) as the nitrogen source and oxygen as an oxidizing agent, the reaction substrate is reacted in organic solvent at normal pressure at the temperature of 25-50 DEG C, and aftertreatment is performed after reaction to obtain the aliphatic nitrile. The method is easy and safe to operate, and environment cost is lowered.

Description

Technical field [0001] The invention belongs to the technical field of chemistry, and particularly relates to a method for catalytic oxidation synthesis of fatty nitrile. Background technique [0002] Nitriles are important building blocks in organic synthesis, and are key structural units for many dyes, medicines, pesticides and electronic materials. Since the cyano group contained in it has the ability to transform into other important functional groups such as amino, amide, aldehyde, carboxyl and ester groups, nitrile compounds are also important intermediates in organic synthesis. The most traditional synthesis method of nitriles is through Sandmeyer reaction or Rosenmund–vonBraun reaction, but these two methods have serious drawbacks. Both require the use of stoichiometric CuCN and the reaction conditions are relatively severe. Since then, a transition metal-catalyzed cyanidation reaction route of aromatic halides has been developed to synthesize aromatic nitriles. KCN, NaC...

Claims

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Application Information

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IPC IPC(8): C07B43/08C07C253/24C07C255/03C07C255/46C07C255/47C07C255/33C07C255/34C07D317/60C07D211/62
CPCC07B43/08C07C253/24C07D211/62C07D317/60C07C255/03C07C255/46C07C255/47C07C255/33C07C255/34
Inventor 李美超沈振陆方朝杰莫卫民
Owner 邳州市润宏实业有限公司
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