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Preparation method of 4,5-dicyan base-2-trifluoro-methylimidazole and prepared intermediate and salt thereof

A technology of trifluoromethyl imidazole salt and trifluoromethyl imidazole, which is applied in the field of chemical synthesis, can solve the problems of low boiling point, volatile measurement, inconvenience of use, etc. , the effect of simple process

Active Publication Date: 2016-10-12
武汉海斯普林科技发展有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] It is currently known that 4,5-dicyano-2-trifluoromethylimidazole and its salts are mostly synthesized by the reaction of diaminomalenitrile with fluorinated anhydride, but the fluorinated anhydride has a low boiling point, is volatile and irritating. Strong sex, tear gas, sensitive to water, decomposed into toxic fluoride gas when in contact with water, and toxic fluoride smoke when burned, etc., poor safety, in addition, because the substance is extremely volatile, it can also cause scale deviations such as measurement deviations It is inconvenient to use in chemical production. If the substance is not stirred in time when it is added in production, it will cause a high local concentration, so that the two amino acids on diaminomalenitrile will be acylated to form by-products, resulting in a decrease in yield and removal of impurities. Difficulties, product quality decline and other adverse consequences

Method used

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  • Preparation method of 4,5-dicyan base-2-trifluoro-methylimidazole and prepared intermediate and salt thereof
  • Preparation method of 4,5-dicyan base-2-trifluoro-methylimidazole and prepared intermediate and salt thereof
  • Preparation method of 4,5-dicyan base-2-trifluoro-methylimidazole and prepared intermediate and salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] In a 1L four-necked round-bottom flask equipped with an electric stirrer, reflux condenser, thermometer, and gas guide tube, add 43.24 g (0.4 mol) of diaminomaleonitrile and 51.22 g of methyl trifluoroacetate in a glove box at room temperature (0.4mol), 1,4-dioxane 500mL, set up the device, turn on the ventilation equipment to ensure that there is dry argon protection throughout the reaction. Stir at 25°C for 2 hours to fully react the two reactants to form an amide, and then raise the temperature to the boiling point of 1,4-dioxane (101°C) to ensure the reflux of the system. At this temperature, the amide dehydrates to form imidazole, and stops after 2 hours of reflux After the heating reaction, a mixed solution containing 4,5-dicyano-2-trifluoromethylimidazole was obtained.

[0048] Evaporate the solvent and residual methyl trifluoroacetate under the protection of dry argon, add 600ml of water to the system, add 24g of activated carbon to remove color, heat slightly b...

Embodiment 2

[0051] In a 250mL four-necked round-bottom flask equipped with an electric stirrer, reflux condenser, thermometer, and gas guide tube, add 43.24g (0.4mol) of diaminomalenitrile and 68.05g of butyl trifluoroacetate in a glove box at room temperature (0.4mol), set up the device, turn on the ventilation equipment to ensure that there is dry argon protection throughout the reaction. Heating to 100°C, the boiling point of butyl trifluoroacetate, facilitates the reflux of the system. At this temperature, the two reactants first form an amide, and then the amide is dehydrated to form an imidazole ring. The reaction lasts for 3 hours. After the reaction, stop heating and wait for the reaction system to cool. A mixed solution containing 4,5-dicyano-2-trifluoromethylimidazole can be obtained.

[0052] Transfer the mixed solution containing 4,5-dicyano-2-trifluoromethylimidazole into a 1L flask, add 600ml of water, add 24g of activated carbon to remove color, and heat it slightly before ...

Embodiment 3

[0055] In a 1L four-necked round-bottom flask equipped with an electric stirrer, reflux condenser, thermometer, and gas guide tube, add 43.24 g (0.4 mol) of diaminomalenitrile and 142.08 g of ethyl trifluoroacetate in a glove box at room temperature (1mol), 1,4-dioxane 500mL, set up the device, turn on the ventilation equipment to ensure that there is dry argon protection throughout the reaction. Stir at 50°C for 2 hours to fully react the two reactants to form an amide, and then raise the temperature to the boiling point of 1,4-dioxane (101°C) to ensure the reflux of the system. At this temperature, the amide dehydrates to form imidazole, and stops after 2 hours of reflux After the heating reaction, a mixed solution containing 4,5-dicyano-2-trifluoromethylimidazole was obtained.

[0056] Evaporate and remove the solvent and residual ethyl trifluoroacetate under the protection of dry argon, add 600ml of water to the system, add 24g of activated carbon to remove the color, and ...

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Abstract

The invention belongs to the technical field of chemical synthesis and particularly relates to a preparation method of 4,5-dicyan base-2-trifluoro-methylimidazole and a prepared intermediate and salt thereof. Diaminoaleo dinitrile and trifluoroacetic acid ester are subjected to aminolysis of ester with solvent or without solvent, amide is obtained, the amide is then subjected to intramolecular dehydration, a crude product of the 4,5-dicyan base-2-trifluoro-methylimidazole is obtained, after the crude product is purified, high-purity dehydrate of the 4,5-dicyan base-2-trifluoro-methylimidazole is obtained, then the high-purity dehydrate is mixed with water phase suspension liquid of salt of metal elements and stirred for a reaction, after the reaction is ended, filtering is conducted to remove an undissolved substance, filtrate is evaporated to be dry in a rotary evaporation mode, after dissolution with solvent is conducted again, filtering, rotary evaporation and vacuum drying are conducted, and the high-purity 4,5-dicyan base-2-trifluoro-methylimidazole salt is obtained. The condition of the whole technological process is safer and milder compared with those of other processes for producing the 4,5-dicyan base-2-trifluoro-methylimidazole, and the preparation method meets the requirement for scaled production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of 4,5-dicyano-2-trifluoromethylimidazole, its preparation intermediate and its salt. Background technique [0002] In recent years, small electronic devices such as mobile power banks, mobile phones, and tablets have been widely used in daily life, and large electric tools such as electric vehicles are also developing rapidly under the promotion of national policies. The demand for secondary batteries will increase. [0003] At present, the lithium secondary battery using lithium reaction as the charging and discharging reaction is the most common and has wide application prospects. In the industrially produced lithium ion battery, LiPF 6 still dominates. But in actual use, LiPF 6 It has been exposed that it is easy to hydrolyze and quickly decompose at high temperature. This not only easily causes safety problems but also greatly r...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/30C07D233/90
CPCC07C253/30C07C255/30C07D233/90
Inventor 周永妍周宜海杨光黄迅陈丹陈杰潘君王文周阳
Owner 武汉海斯普林科技发展有限公司
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