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Method for preparing 3-methylthio propylamine

A technology of methylthiopropylamine and methylthiopropylphthalimide, which is applied in the fields of sulfide preparation and organic chemistry, and can solve problems such as inconvenient operation, low total yield, and low yield , achieve the effects of shortened reaction time, low reaction temperature and less by-products

Active Publication Date: 2018-03-09
BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the above methods, the total yield (56.6%) of the first method is lower, and the price of 1,3-dibromopropane is higher; in the second method, methyl mercaptan gas needs to be used, which is inconvenient to operate and always The yield is not high; the third method is not effective for the decarboxylation of methionine, and there are other by-products in the final product except 3-methylthiopropylamine; the fourth method takes a long time and the yield is not very high

Method used

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  • Method for preparing 3-methylthio propylamine
  • Method for preparing 3-methylthio propylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Put the 250mL three-necked flask equipped with a reflux condenser (connected to the drying tube) and a constant pressure dropping funnel into a microwave ultrasonic combined synthesizer, and add a certain amount of 42.4g 3-methylthiopropanol and 70mL chloroform to the three-necked flask , set the microwave power to 500w, and the ultrasonic power to 400w. After the microwave-ultrasonic combined synthesizer starts to work, after the mixture is refluxed, slowly drop the mixture of 57.2g of thionyl chloride and 30mL of chloroform into the three ports through a constant pressure dropping funnel. In the flask; after the dropwise addition, continue the reflux reaction for 30min. After the reaction was finished, rotary evaporation removed unreacted raw materials and solvent chloroform in the reaction mixture, and the content of 3-methylthio-1-chloropropane was analyzed by gas chromatography, and its yield was calculated to be 95.2%; under reduced pressure, 33 to 37 The distilla...

Embodiment 2

[0025] Put the 500mL three-necked flask equipped with a reflux condenser (connected to the drying tube) and a constant pressure dropping funnel into a microwave ultrasonic combined synthesizer, and add a certain amount of 84.8g 3-methylthiopropanol and 150mL chloroform to the three-necked flask , set the microwave power to 600w, the ultrasonic power to 500w, and the microwave-ultrasonic combined synthesizer starts to work. After the mixture is refluxed, slowly drop the mixture of 114.4g of thionyl chloride and 60mL of chloroform into the three-necked flask through the constant pressure dropping funnel After the dropwise addition, continue the reflux reaction for 40min. After the reaction was finished, rotary evaporation removed unreacted raw materials and solvent chloroform in the reaction mixture, and the content of 3-methylthio-1-chloropropane was analyzed by gas chromatography, and its yield was calculated to be 95.6%; vacuum distillation collected 33 to 37 The distillate a...

Embodiment 3

[0029] The 1000mL three-necked flask equipped with a reflux condenser (connected to the drying pipe) and a constant pressure dropping funnel is put into a combined microwave-ultrasonic synthesizer, and a certain amount of 170g 3-methylthiopropanol and 300mL chloroform are added to the three-necked flask, Set the microwave power to 800w, the ultrasonic power to 800w, and the microwave-ultrasonic combined synthesizer starts to work. After the mixture is refluxed, slowly drop the mixture of 230g of thionyl chloride and 120mL of chloroform into the three-necked flask through the constant pressure dropping funnel; After the dropwise addition, the reflux reaction was continued for 60 min. After the reaction was finished, rotary evaporation removed unreacted raw materials and solvent chloroform in the reaction mixture, and the content of 3-methylthio-1-chloropropane was analyzed by gas chromatography, and its yield was calculated to be 95.8%; vacuum distillation collected 33 to 37 Th...

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Abstract

The invention provides a preparation method of 3-methylthio propylamine. The method is characterized in that under the effects of microwaves and ultrasonic waves, flavoring essence of 3-methylthio propyl alcohol capable of being easily obtained in China is used as a starting raw material; the reaction time is short; the total yield is relatively high. Under the effects of microwaves and ultrasonicwaves, firstly, 3-methylthio propyl alcohol and thionyl chloride react for 20 to 60 min under the back flow condition to prepare 3-methylthio-1-chloropropane, and the yield is greater than 95 percent; then, at 80 to 90 DEG C, the 3-methylthio-1-chloropropane and phthalimide potassium react for 0.5 to 2.5h to prepare N-3-methylthio propyl phthalimide, and the yield is greater than 94 percent; finally, the N-3-methylthio propyl phthalimide and hydrazine hydrate perform backflow reaction in absolute ethyl alcohol for 20 to 60min to prepare the 3-methylthio propylamine, and the yield is greater than 85 percent.

Description

technical field [0001] The invention relates to a method for preparing 3-methylthiopropylamine under the action of microwave and ultrasonic waves. 3-Methylthiopropylamine is a spice compound, which is an edible flavor approved by the American Food Flavor and Extract Manufacturers Association (Flavour Extract Manufacturer's Association, FEMA) and the Joint Expert Committee on Food Additives (JECFA); as a flavor, It can be used to prepare food flavors, flavoring fish products, fast food, soup and other foods. Background technique [0002] The existing method for preparing 3-methylthiopropylamine mainly contains the following: (1) 1,3-dibromopropane reacts with phthalimide potassium salt to obtain N-3-bromopropyl phthalic Formimide, the productive rate is 74%; N-3-bromopropylphthalimide reacts with sodium methylmercaptide to obtain N-3-methylthiopropylphthalimide, producing The rate is 90%; N-3-methylthiopropylphthalimide undergoes hydrazinolysis to obtain 3-methylthiopropyla...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/25
Inventor 刘玉平李燕敏于洋孙宝国
Owner BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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