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Novel synthesis method for L-menthyl-N,N-dimethyl succinamide

A technology of dimethylsuccinamide and synthesis method is applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., and can solve the problems of high production cost, low reaction yield, complicated post-processing and the like, and achieves The three wastes are small, the purity and yield are improved, and the post-processing is easy.

Active Publication Date: 2014-05-14
ANHUI FENGLE PERFUME
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The L-menthyl-N,N-dimethylsuccinamide product prepared by this method is a colorless to light yellow transparent liquid, and the yield is only 50.4%; however, the reaction generates more by-products, and the post-treatment is relatively difficult. Complicated, and the reaction yield is low, the production cost is high, and the three wastes are relatively large

Method used

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  • Novel synthesis method for L-menthyl-N,N-dimethyl succinamide

Examples

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preparation example Construction

[0016] (1) Preparation of Menthyl Succinic Acid Monochloride

[0017] Add 1mol L-monomenthyl succinate, 0.005mol DMF catalyst, 3.5mol 1,2-dichloroethane into a 2000ml four-necked round bottom flask, and add dropwise triphosgene solution (0.3mol triphosgene dissolved in 0.24mol1,2-dichloroethane), keep the internal temperature at 83°C during the dropwise addition, stir and react for 30h; stop the reaction to obtain menthyl succinic acid chloride.

[0018] (2) Preparation of menthyl methyl succinate

[0019] Gained menthyl succinic acid chloride, the control temperature is 50 ℃. Add 1 mol of methanol into a constant pressure titration funnel, and slowly drop it into the prepared menthyl succinic monochloride reaction solution. During the dropping process, control the temperature at 50°C, stir for 20 hours, add water to destroy the system, and let it stand for water separation. The water phase was extracted by adding 1,2-dichloroethane, and the oil phases were combined. Adjust...

Embodiment 2

[0023] This example relates to a new method for the synthesis of L-menthyl-N,N-dimethylsuccinamide

[0024] (1) Preparation of Menthyl Succinic Acid Monochloride

[0025] Add 1mol L-monomenthyl succinate, 0.1mol DMF catalyst, 1mol1,2-dichloroethane in a 2000ml four-neck round bottom flask, and drop triphosgene solution (3mol triphosgene dissolved in 9mol1, 2-dichloroethane), maintain the internal temperature at 15°C during the dropwise addition, and stir the reaction for 20 minutes; stop the reaction to obtain menthyl succinic acid chloride.

[0026] (2) Preparation of menthyl methyl succinate

[0027] The resulting menthyl succinic acid chloride was cooled to -30°C. Add 50 mol of methanol into a constant pressure titration funnel, and slowly drop it into the prepared menthyl succinic monochloride reaction solution. During the dropping process, control the temperature at -30°C, stir for 30 minutes, add water to destroy the system, and let stand to separate the water. The wa...

Embodiment 3

[0031] This example relates to a new method for the synthesis of L-menthyl-N,N-dimethylsuccinamide

[0032] (1) Preparation of Menthyl Succinic Acid Monochloride

[0033] Add 1mol L-monomenthyl succinate, 0.02mol DMF catalyst, 2.5mol1,2-dichloroethane into a 2000ml four-neck round bottom flask, and add triphosgene solution (2mol triphosgene dissolved in 5mol1 , 2-dichloroethane), maintain the internal temperature at 50°C during the dropwise addition, and stir the reaction for 16h; stop the reaction to obtain menthyl succinic acid chloride.

[0034] (2) Preparation of menthyl methyl succinate

[0035] The resulting menthyl succinic acid chloride was cooled to 0°C. Add 24 mol of methanol into a constant pressure titration funnel, and slowly drop it into the prepared menthyl succinic monochloride reaction solution. During the dropwise addition, control the temperature at 0°C, stir for 13 hours, add water to destroy the system, and let stand to separate the water. The water pha...

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Abstract

The invention discloses a novel synthesis method for L-menthyl-N,N-dimethyl succinamide. The method specifically comprises the following steps: adding L-mono-methyl succinate, DMF (Dimethyl Formamide) and dichloromethane into a dry four-mouth flask with a thermometer, a backflow condensing tube and a tail gas recycling device, under the condition of stirring, dropping a triphosgene solution to perform acylating chlorination reaction, dropping methanol into prepared menthyl succinic acid mono acyl chloride at low temperature to perform esterification reaction, dropping a dimethylamine solution into the prepared methyl succinic acid menthyl acetate for reaction at low temperature, adding water, stirring, standing to layer, collecting the organic phase, washing the organic phase till being neutral, depressurizing to distill so as to obtain a product, namely, L-menthyl-N,N-dimethyl succinamide. The yield of the product is 75.4%, and the product is a faint yellow liquid with the purity of 99.0%. By using the method, the purity and the yield of the product are improved, a small amount of byproducts are produced, the aftertreatment is easy to carry out, a small deal of industrial waste is generated, the production cost is lowered, and large-scale production application in industry is achieved.

Description

technical field [0001] The invention relates to the technical field of cooling agent preparation, in particular to a new synthesis method of L-menthyl-N,N-dimethylsuccinamide ester. Background technique [0002] L-menthyl-N,N-dimethylsuccinamide is a new type of liquid cooling agent, which belongs to a kind of menthyl derivatives. L-menthyl-N,N-dimethylsuccinamide not only has a long-lasting cooling effect and mild skin feeling, but also overcomes the shortcomings of menthol such as bitterness, short action time, and easy volatility, and can also be used in conjunction with other cooling agents. Has a fragrance-enhancing effect. Widely used in food, medicine, daily chemical, tobacco and other industries. [0003] At present, the method for synthesizing L-menthyl-N,N-dimethylsuccinamide is to use L-succinic acid monomenthyl as a raw material, and undergo acid chloride reamination reaction or esterification reamination reaction to obtain the target product. [0004] For exa...

Claims

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Application Information

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IPC IPC(8): C07C233/05C07C231/02
Inventor 张勤夏晋张文朱俊峰赵彬郭希凯刘德娟
Owner ANHUI FENGLE PERFUME
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