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Preparation method of high-purity 4,5-dicyano-2-trifluoromethylimidazole and salts thereof

A technology of trifluoromethyl imidazole salt and trifluoromethyl imidazole is applied in the field of preparation of high-purity 4,5-dicyano-2-trifluoromethyl imidazole and its salt, and can solve the problem of volatile, measurement deviation , inconvenient use and other problems, to achieve the effect of improving yield, mild process conditions and reducing pollution

Active Publication Date: 2015-03-25
GUANGZHOU TINCI MATERIALS TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the synthetic methods of 4,5-dicyano-2 trifluoromethylimidazole and its salts are mostly prepared by reacting diaminomalenitrile (DAMN) with acid derivatives such as fluorinated anhydrides. The problem includes two aspects. One is that the trifluoroacetic anhydride (TFAA) used has a boiling point of 40°C and is extremely volatile at room temperature, which is inconvenient to use and easily causes measurement deviations. On the other hand, the system is partially When the concentration is high, it will inevitably cause the acylation of both amino groups on DAMN to generate colored by-products, reducing the yield and increasing the post-processing burden
The lithium salt obtained after treatment still contains more colored impurities, which cannot meet the requirements of the electronic chemical industry for high-purity raw materials

Method used

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  • Preparation method of high-purity 4,5-dicyano-2-trifluoromethylimidazole and salts thereof
  • Preparation method of high-purity 4,5-dicyano-2-trifluoromethylimidazole and salts thereof
  • Preparation method of high-purity 4,5-dicyano-2-trifluoromethylimidazole and salts thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0043] In a 1000 ml three-neck flask equipped with an electric stirrer, a reflux condenser, and a thermometer, 43.24 g (0.4 mol) of diaminomaleonitrile, 600 mL of 1,4-dioxane, and 50.17 g of trifluoroacetic acid ( 0.44mol), P 2 o 5 28.39g (0.2mol), heated to 80°C for 3h. After the reaction was completed, the solvent and most of the remaining trifluoroacetic acid were removed by evaporation, 600 ml of water was added to the system, and 20 g of activated carbon was added to remove the color. The filtrate was concentrated to 200 mL, crystallized by cooling, filtered to obtain crystals and washed with 100 mL of ice water, the obtained crystals were recrystallized with 200 mL of water, filtered to obtain crystals and washed with 100 mL of ice water. The resulting filtrate and washings were used in the next purification. The crystals were dried at 60°C for 6 hours under reduced pressure and then used 19 F NMR (solvent is acetonitrile) detection, no obvious impurity peak ( figure ...

Embodiment 2

[0045] In a 1000 ml three-neck flask equipped with an electric stirrer, a reflux condenser, and a thermometer, 43.24 g (0.4 mol) of diaminomaleonitrile, 600 mL of 1,4-dioxane, and 91.22 g of trifluoroacetic acid ( 0.8mol), P 2 o 5 56.78g (0.4mol), heated to 120°C for 1h. After the reaction was completed, the solvent and most of the remaining trifluoroacetic acid were removed by evaporation, and 600 ml of the filtrate and washing liquid from the previous experiment were added to the system, and 25 g of activated carbon was added to remove the color. The filtrate was concentrated to 200 mL, crystallized by cooling, filtered to obtain crystals and washed with 100 mL of ice water, the obtained crystals were recrystallized with 200 mL of water, filtered to obtain crystals and washed with 100 mL of ice water. The resulting filtrate and washings were used in the next purification. The crystals do not need to be dried, and LiOH aqueous solution is added thereto until the pH is 7. ...

Embodiment 3

[0047] In a 1000 ml three-neck flask equipped with an electric stirrer, a reflux condenser, and a thermometer, 43.24 g (0.4 mol) of diaminomaleonitrile, 500 mL of 1,4-dioxane, and 228.05 g of trifluoroacetic acid ( 2mol), P 2 o 5 85.17g (0.6mol), heated to 100°C for 2h. After the reaction was completed, the solvent and most of the remaining trifluoroacetic acid were removed by evaporation, and 600 ml of the filtrate and washing liquid from the previous experiment were added to the system, and 25 g of activated carbon was added to remove the color. The filtrate was concentrated to 200 mL, crystallized by cooling, filtered to obtain crystals and washed with 100 mL of ice water, the obtained crystals were recrystallized with 200 mL of water, filtered to obtain crystals and washed with 100 mL of ice water. The resulting filtrate and washings were used in the next purification. The crystal does not need to be dried, Na is added to it 2 CO 3 Aqueous solution, stop when the pH i...

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Abstract

The invention discloses a preparation method of high-purity 4,5-dicyano-2-trifluoromethylimidazole and salts thereof. The preparation method comprises the following steps: placing diaminomaleonitrile, trifluoroacetic acid and phosphorus pentoxide at a molar ratio of 1:(1-10):(0.5-2) in a reactor, adding a solvent or not, reacting at a reaction temperature of 40-140 DEG C for a reaction time of 0.5-8 hours, after the reaction, evaporating to remove the solvent and residual trifluoroacetic acid to obtain an intermediate product 4,5-dicyano-2-trifluoromethyl-imidazole; purifying the intermediate product 4,5-dicyano-2-trifluoromethyl-imidazole; and reacting the purified 4,5-dicyano-2-trifluoromethyl-imidazole and salts or hydroxide of a metal element to obtain 4,5-dicyano-2-trifluoromethylimidazole salts. The preparation method has mild entire process conditions and relatively low device investment and is suitable for requirements of large-scale production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of high-purity 4,5-dicyano-2-trifluoromethylimidazole and salts thereof. Background technique [0002] At present, the main obstacle to the development of battery vehicles is the high price of power batteries, which account for about 50% of the manufacturing cost. Therefore, for manufacturers, it is urgent to reduce the manufacturing cost of batteries. Electrolyte accounts for 14-23% of the material cost of lithium-ion battery cells, which mainly comes from lithium salts. Until now, in the industrial production of lithium-ion batteries, LiPF 6 The use of the battery still occupies a dominant position, but in the application, there are problems of easy hydrolysis and rapid decomposition at high temperature, which greatly reduce the battery life. Based on this, the development of a series of new lithium salts has become a hotspot, among which 4,5-d...

Claims

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Application Information

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IPC IPC(8): C07D233/90
CPCC07D233/90
Inventor 陈晓军张利萍徐三善
Owner GUANGZHOU TINCI MATERIALS TECH
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