Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for artificially synthesizing cyclopropanecarbonitrile

The technology of a cyclopropyl nitrile and a synthesis method, which is applied in the field of medicine and chemical industry, can solve the problems of low water content of the product, low yield, equipment destruction yield and the like, and achieves that the temperature control method is simple and easy to operate, the reaction process is gentle, and the separation The effect of purification convenience

Active Publication Date: 2013-11-27
ZHEJIANG HUAHAI PHARMA CO LTD +1
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

US.Pat.No.8843709 has reported taking 4-chlorobutyronitrile as starting raw material, and sodium hydroxide is an acid-binding agent, and the method for synthesizing cyclopropyl nitrile in aprotic dipole solvent, the advantage of this method is that yield is high (98.3%), but the defect is: in the reaction process, there will be sticky insoluble matter, which will hinder the stirring, reduce the mass transfer rate, and the controllability of the temperature is poor. Destruction and yield reduction (about 56%), also can cause the increase of by-product simultaneously; Also there is the separation problem of product in addition
[0003] US.Pat.No.5380911 improves the synthetic method of the above-mentioned patent: the introduction of sodium chloride and catalytic amount of water in the reaction process improves the mass transfer effect, but cannot completely eliminate the explosive heating; and the yield is relatively the former Decrease to some extent (86%); But obtain bigger breakthrough aspect the separation and purification of product: first neutralize reaction solution with concentrated hydrochloric acid, then adopt azeotropic distillation, utilize oil-water separator to separate and obtain a part of product, finally separate The water layer after carrying out secondary azeotropic distillation purification again, the product water content after merging is low and purity is higher (99.9%)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for artificially synthesizing cyclopropanecarbonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of cyclopropylnitrile

[0018] In a 250ml four-neck flask equipped with a mechanical stirrer, a thermometer, a reflux condenser, and a constant pressure dropping funnel, put dimethyl sulfoxide (45ml), anhydrous magnesium sulfate (9.0g), and sodium hydroxide (26.4g) , control the temperature at 60-85° C., and drop 4-chlorobutyronitrile (53.5 g) into the reaction system within 1 hour by means of dropwise addition. After the dropwise addition, it was cooled down to room temperature naturally, and reacted at 80° C. for 5 hours. Cool, and slowly inject 100ml of water into the water bath at room temperature, then slowly add concentrated hydrochloric acid to neutralize the reaction solution, adjust the pH=6.5, and finally adopt the azeotropic distillation method, use the constant pressure dropping funnel to continuously circulate and separate the oil and water, and then obtain the free The color oil was 34.0 g, the yield was 98.0%, and the purity was 99.7%.

Embodiment 2

[0020] Preparation of cyclopropylnitrile

[0021] In a 250ml four-neck flask equipped with a mechanical stirrer, a thermometer, a reflux condenser, and a constant pressure dropping funnel, put dimethyl sulfoxide (45ml), anhydrous sodium sulfate (8.9g), and sodium hydroxide (26.4g) , under the condition of 60-85° C., 4-chlorobutyronitrile (53.5 g) was added dropwise to the reaction system within 1 hour by means of dropwise addition. After the dropwise addition, it was cooled down to room temperature naturally, and reacted at 80° C. for 5 hours. Cool, slowly inject 100ml of water into the water bath at room temperature, then slowly add concentrated hydrochloric acid to neutralize the reaction solution, adjust the pH=6.8, and finally adopt the azeotropic distillation method, and use the constant pressure dropping funnel to continuously circulate and separate the oil and water. The color oil was 33.1 g, the yield was 95.0%, and the purity was 99.3%.

Embodiment 4

[0023] Preparation of cyclopropylnitrile

[0024] In a 250ml four-neck flask equipped with a mechanical stirrer, a thermometer, a reflux condenser, and a constant pressure dropping funnel, put N, N dimethylformyl (45ml), anhydrous magnesium sulfate (9.0g), sodium hydroxide (26.4g), at 60-85°C, dropwise added 4-chlorobutyronitrile (53.5g) into the reaction system within 1 hour. After the dropwise addition, it was cooled down to room temperature naturally, and reacted at 100° C. for 5 hours. Cool, slowly inject 100ml of water into the water bath at room temperature, then slowly add concentrated hydrochloric acid to neutralize the reaction solution, adjust the pH=6.8, and finally adopt the azeotropic distillation method, and use the constant pressure dropping funnel to continuously circulate and separate the oil and water. 32 g of colored oil, yield 92%, purity 99.4%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for artificially synthesizing cyclopropanecarbonitrile, which comprises the following steps of: reacting anhydrous sulfates or anhydrous calcium chloride used as mass transfer acclerants and alkali metal alkali used as acid-binding agents with 4-chlorobutyronitrile at 60 to 90 DEG C in the existence of aprotic solvents to obtain the cyclopropanecarbonitrile. The method belongs to the synthesizing method with the advantages of high yield, safety, economy, easy operation, no explosive heat release and temperature rise and simple separation and purification, and is applicable to large-scale industrial production.

Description

(1) Technical field [0001] The invention relates to a preparation method of cyclopropyl nitrile, which belongs to the technical field of medicine and chemical industry. (2) Background technology [0002] Cyclopropyl nitrile is used as a raw material for the synthesis of thiourea herbicides and anticoagulant prasugrel, and its synthesis method has attracted much attention. US.Pat.No.8843709 has reported taking 4-chlorobutyronitrile as starting raw material, and sodium hydroxide is an acid-binding agent, and the method for synthesizing cyclopropyl nitrile in aprotic dipole solvent, the advantage of this method is that yield is high (98.3%), but the defect is: in the reaction process, there will be sticky insoluble matter, which will hinder the stirring, reduce the mass transfer rate, and the controllability of the temperature is poor. The reduction (about 56%) of destruction and yield also can cause the increase of by-product simultaneously; Also there is the separation probl...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/46C07C253/30
Inventor 刘创伟陈昌辉芦启锋
Owner ZHEJIANG HUAHAI PHARMA CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com