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Preparation method of 2-aryl propionitrile compounds

A technology for arylpropionitrile and compound is applied in the field of preparation of 2-arylpropionitrile compounds, and can solve the problems of easy deactivation of catalyst, high reaction temperature, low yield of 2-phenylpropionitrile and the like

Active Publication Date: 2009-10-28
浙江优创材料科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Tanaka et al. use metal ruthenium to catalyze aldehydes and nitriles containing active methylene to react at a reaction temperature of 130-230°C. The experimental results are ideal, but the disadvantage is that expensive metal ruthenium catalysts are used. The system is easy to deactivate, and the reaction temperature is relatively high, and the operation is troublesome
[0004] From the analysis point of view, the second method uses dimethyl carbonate as the methylation reagent to carry out the methylation of substituted phenylacetonitrile compounds, which solves the problem of using toxic and harmful methylation reagents, but there are many problems in the existing catalyst system. A big disadvantage is that when obtaining ideal selectivity, noble metals must be used as catalysts; if heterogeneous catalysts such as NaY zeolite are used, although the separation at the end of the reaction is more convenient, the yield of 2-phenylpropionitrile is relatively low. Low; also use such as potassium carbonate as a catalyst, can get very high selectivity, but the reaction temperature is very high

Method used

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  • Preparation method of 2-aryl propionitrile compounds
  • Preparation method of 2-aryl propionitrile compounds
  • Preparation method of 2-aryl propionitrile compounds

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Experimental program
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Effect test

Embodiment 1

[0043]

[0044] Add benzyl cyanide (0.234g, 2mmol), [Bmim]OAc (39.6mg, 0.2mmol), dimethyl carbonate (10mL) and a stir bar to a 40mL autoclave; put the reaction vessel containing the sample mixture in It is heated in an oil bath equipped with stirring and thermocouple until the internal temperature of the reactor reaches 130°C; at this temperature, the reaction is stirred for 10 hours under this catalyst. At the end of the reaction, the reactor was cooled to room temperature, 10 mL of deionized water was added, and then 3×10 mL of anhydrous ether was used for extraction. The ionic liquid was dissolved in the water phase, and the reactants and products were dissolved in the ether phase, and the ether phases were combined. , The ether was removed with a water pump to obtain a colorless liquid 2-phenylpropionitrile (0.257g, 98%).

Embodiment 2

[0046]

[0047] To a 40 mL autoclave were added p-toluene acetonitrile (0.262 g, 2 mmol), [Bmim]OAc (39.6 mg, 0.2 mmol), dimethyl carbonate (10 mL) and a stir bar. The reactor containing the sample mixture was heated in an oil bath equipped with stirring and thermocouple until the internal temperature of the reactor reached 130°C. At this temperature, the reaction was stirred under this catalyst for 10 hours. At the end of the reaction, the reactor was cooled to room temperature. Add 10 mL of deionized water, and then extract with 3×10 mL of anhydrous ether. The ionic liquid is dissolved in the water phase, while the reactants and products are dissolved in the ether phase. Combine the ether phases and remove the ether with a water pump to obtain a colorless liquid 2-(p-methyl)phenylpropionitrile (0.244 g, 84%).

Embodiment 3

[0049]

[0050] To a 40 mL autoclave were added p-ethylbenzeneacetonitrile (0.290 g, 2 mmol), [Bmim]OAc (39.6 mg, 0.2 mmol), dimethyl carbonate (10 mL) and a stir bar. The reactor containing the sample mixture was heated in an oil bath equipped with stirring and thermocouple until the internal temperature of the reactor reached 130°C. At this temperature, the reaction was stirred under this catalyst for 10 hours. At the end of the reaction, the reactor was cooled to room temperature. Add 10 mL of deionized water, and then extract with 3×10 mL of anhydrous ether. The ionic liquid is dissolved in the water phase, while the reactants and products are dissolved in the ether phase. Combine the ether phases and remove the ether with a water pump to obtain a colorless liquid 2-(p-ethyl)phenylpropionitrile (0.256 g, 82%).

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Abstract

The invention discloses a preparation method of 2-aryl propionitrile compounds, which belongs to the technical field of chemical preparation. The preparation method of 2-aryl propionitrile compounds comprises the steps of: dissolving substituted phenylacetonitrile in methyl carbonate and adding a catalytic amount of ionic liquid to react for 1 to 15 hours at a temperature ranging from 25 to 180 DEG C to prepare 2-aryl propionitrile compounds. The preparation method of 2-aryl propionitrile compounds has the advantages that the green catalyst, namely the ionic liquid, is used instead of the traditional catalyst which has poor catalytic activity and is difficult to recycle; the reaction conditions are mild and the yield and selectivity are very high; in addition, the green reagent, namely the methyl carbonate, is used for avoiding the use of toxic and hazardous reagents, therefore, the preparation method is safe and convenient in operation.

Description

Technical field [0001] The invention relates to the technical field of chemical preparation, in particular to a method for preparing 2-arylpropionitrile compounds. Background technique [0002] 2-Arylpropionitrile compounds are important organic raw materials and chemical products. Such compounds can be hydrolyzed to generate carboxylic acids, reduced to generate amines, and many other functional groups can be derived, not only for the preparation of painkillers (such as ketoprofen, Naproxen, Ibuprofen) is an important intermediate and a precursor for dye preparation. Therefore, such compounds have a wide range of applications in the fields of industry, agriculture and medicine. There are many methods for methylation of substituted benzyl cyanide compounds. According to the current literature reports, it can be roughly divided into two methods. One is the traditional methylation method of substituted benzyl cyanide compounds. The methylation reagents are methyl halide and sulfuri...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/33B01J31/02B01J31/04
Inventor 高国华付贤磊杨榆安莹张利锋
Owner 浙江优创材料科技股份有限公司