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

Synthesis method of 2-propyn-1-yl 1H-imidazole-1-carboxylic ester

A synthesis method and carboxylic acid ester technology, applied in the direction of organic chemistry and the like, can solve the problems of incomplete preparation and purification methods, unsuitable for industrial production, and limited industrial production, etc., and achieve a process with few reaction steps, simple operation, and easy-to-obtain raw materials. Effect

Pending Publication Date: 2022-04-29
SHIJIAZHUANG SAN TAI CHEM CO LTD
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing transesterification method reacts violently and easily generates by-products, which limits industrial production
[0004] Therefore, the preparation and purification method for 2-propyn-1-yl 1H-imidazole-1-carboxylate is not perfect enough at present, and then causes it to be unsuitable for industrialized production

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
  • Synthesis method of 2-propyn-1-yl 1H-imidazole-1-carboxylic ester
  • Synthesis method of 2-propyn-1-yl 1H-imidazole-1-carboxylic ester
  • Synthesis method of 2-propyn-1-yl 1H-imidazole-1-carboxylic ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The synthetic method of 2-propyn-1-yl 1H-imidazole-1-carboxylate, its synthetic steps are as follows:

[0020] Take 6.16g (0.11mol) of 2-propynyl alcohol and add it to 30mL of dichloromethane, and use it as the dichloromethane solution of 2-propynyl alcohol for later use;

[0021] Under nitrogen protection, dissolve 16.2g (0.1mol) of N,N'-carbonyldiimidazole in 30mL of dichloromethane, add a catalyst composed of 0.65g of alumina and 0.97g of zinc oxide, cool down to 3°C, and slowly drop Add the dichloromethane solution of 2-propynyl alcohol. After the dropwise addition, first maintain the reaction at 3°C ​​for 1h, raise the temperature to 10°C for 1h, then raise the temperature to 20°C for 1h, and finally raise the temperature to reflux for 1.5h. After the reaction is completed , the resulting system was lowered to room temperature, removed the catalyst (aluminum oxide and zinc oxide) by filtration, then adjusted the pH value to 1, and separated the phases. The obtained...

Embodiment 2

[0024] The synthetic method of 2-propyn-1-yl 1H-imidazole-1-carboxylate, its synthetic steps are as follows:

[0025] Take 6g (0.107mol) of 2-propynyl alcohol and add it to 25mL of dichloromethane, and use it as the dichloromethane solution of 2-propynyl alcohol for later use;

[0026] Under nitrogen protection, dissolve 16.2g (0.1mol) of N,N'-carbonyldiimidazole in 30mL of dichloromethane, add a catalyst consisting of 0.405g of alumina and 0.405g of zinc oxide, cool down to 5°C, and slowly drop Add the dichloromethane solution of 2-propynyl alcohol. After the dropwise addition, first maintain the reaction at 5°C for 0.8h, then raise the temperature to 15°C for 0.5h, then raise the temperature to 25°C for 0.6h, and finally raise the temperature to reflux for 2h. After completion, the resulting system was lowered to room temperature, and the catalyst (aluminum oxide and zinc oxide) was removed by filtration, then the pH value was adjusted to 1.5, and the phases were separated. ...

Embodiment 3

[0028] The synthetic method of 2-propyn-1-yl 1H-imidazole-1-carboxylate, its synthetic steps are as follows:

[0029] Take 5.88g (0.105mol) of 2-propynyl alcohol and add it to 25mL of dichloromethane, and use it as the dichloromethane solution of 2-propynyl alcohol for later use;

[0030] Under nitrogen protection, dissolve 16.2g (0.1mol) of N,N'-carbonyldiimidazole in 30mL of dichloromethane, add a catalyst composed of 0.486g of alumina and 0.972g of zinc oxide, cool down to 0°C, and slowly drop Add the dichloromethane solution of 2-propynyl alcohol. After the dropwise addition, first maintain the reaction at 0°C for 0.9h, raise the temperature to 13°C for 0.8h, then raise the temperature to 23°C for 0.5h, and finally raise the temperature to reflux for 1.6h. After the reaction was completed, the resulting system was cooled to room temperature, and the catalyst (aluminum oxide and zinc oxide) was removed by filtration, then the pH value was adjusted to 1.3, and the phases wer...

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 discloses a synthesis method of 2-propyn-1-yl 1H-imidazole-1-carboxylic ester, and relates to the technical field of battery electrolyte additives, the synthesis method comprises the following steps: under the protection of an inert gas, taking N, N-dimethyl formamide, and carrying out a reaction for 2-4 hours to obtain 2-propyn-1-yl 1H-imidazole-1-carboxylic ester; the preparation method comprises the following steps: dissolving N, N '-carbonyldiimidazole in dichloromethane, adding a catalyst consisting of aluminum oxide and zinc oxide, cooling to below 5 DEG C, slowly dropwise adding a dichloromethane solution of 2-propargyl alcohol, carrying out gradient heating after dropwise adding, carrying out ester exchange reaction, and carrying out post-treatment after the reaction is completed, so as to obtain the 2-propargyl-1-yl 1H-imidazole-1-carboxylic ester. According to the invention, the specific catalyst is adopted, so that the ester exchange reaction is effectively controlled to proceed towards the direction of the target product 2-propyn-1-yl 1H-imidazole-1-carboxylic ester; meanwhile, the reaction process is controlled by adopting a gradient heating mode, so that severe reaction of N, N '-carbonyldiimidazole and 2-propargyl alcohol is prevented, side reaction is reduced, and the yield of the target product is effectively improved.

Description

technical field [0001] The invention relates to the technical field of battery electrolyte additives, in particular to a synthesis method of 2-propyn-1-yl 1H-imidazole-1-carboxylate. Background technique [0002] Lithium batteries are widely used due to their high power storage performance, low self-discharge rate, long cycle life and environmental protection. The electrolyte is an important part of the lithium battery, which is responsible for the transmission of ions between the positive and negative electrodes through the interior of the battery. It has an important impact on the capacity, operating temperature range, cycle performance and safety performance of the battery. [0003] 2-propyn-1-yl 1H-imidazole-1-carboxylate, as an important carboxylate additive in lithium battery electrolyte, can effectively improve the safety and cycle performance of lithium batteries. At present, the method for synthesizing 2-propyn-1-yl 1H-imidazole-1-carboxylate is mainly transesterif...

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
IPC IPC(8): C07D233/60
CPCC07D233/60
Inventor 侯荣雪王军葛建民武利斌闫彩桥
Owner SHIJIAZHUANG SAN TAI CHEM 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