Synthesis method of bis (2, 2, 2-trifluoroethyl) carbonate

A synthesis method, trifluoroethyl technology, applied in the field of dicarbonate synthesis, can solve the problems of poor exchange reaction ability, complex reaction process, and reduced catalytic activity, achieving mild reaction, simple operation, and few by-products Effect

Pending Publication Date: 2022-05-10
SHIJIAZHUANG SAN TAI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the halofluorination method has a higher yield, the reaction process is more complicated
The transesterification method is a relatively green synthesis method, but since the base-catalyzed transesterification reaction is a nucleophilic substitution reaction, once the alkyl alcohol is changed to a fluorocarbon alcohol, the steric hindrance will increase and the catalytic activity will decrease , the ability to undergo exchange reactions will become poor

Method used

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  • Synthesis method of bis (2, 2, 2-trifluoroethyl) carbonate
  • Synthesis method of bis (2, 2, 2-trifluoroethyl) carbonate
  • Synthesis method of bis (2, 2, 2-trifluoroethyl) carbonate

Examples

Experimental program
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Effect test

Embodiment 1

[0020] The synthetic method of two (2,2,2-trifluoroethyl) carbonates, its synthetic steps are as follows:

[0021] Take 24g (0.24mol) of trifluoroethanol and add it to 100mL of dichloromethane, as a dichloromethane solution of trifluoroethanol for later use;

[0022] Under the protection of nitrogen, take 21.4g (0.1mol) of diphenyl carbonate and 40.95g (0.65mol) of imidazole and stir and mix, add 2.6g of aluminum chloride, heat to 80°C, keep stirring at 80°C for pre-reaction for 2h, and then lower to room temperature, add dropwise a dichloromethane solution containing trifluoroethanol, after the dropwise addition, reflux for 2 h for transesterification, after the reaction is complete, add hydrochloric acid dropwise to adjust the pH to 1, separate the phases, and concentrate the obtained dichloromethane phase , rectification, obtain 19.57g two (2,2,2-trifluoroethyl) carbonate, yield 86.59%, purity 99.97%, concrete chemical reaction formula is as follows:

[0023]

Embodiment 2

[0025] The synthetic method of two (2,2,2-trifluoroethyl) carbonates, its synthetic steps are as follows:

[0026] Take 23g (0.23mol) of trifluoroethanol and add it to 80mL of dichloromethane, as a dichloromethane solution of trifluoroethanol for later use;

[0027] Under nitrogen protection, take 21.4g (0.1mol) of diphenyl carbonate and 41.58g (0.66mol) of imidazole and stir and mix, add 2.14g of aluminum chloride, heat to 70°C, keep stirring at 70°C for pre-reaction for 3h, then drop to room temperature, dropwise add a dichloromethane solution containing trifluoroethanol, after the dropwise addition, reflux for 2.5 h for transesterification reaction, after the reaction is complete, add hydrochloric acid dropwise to adjust to pH = 1.5, separate the phases, and the obtained dichloromethane phase is After concentration and rectification, 19.14 g of bis(2,2,2-trifluoroethyl) carbonate was obtained, with a yield of 84.69% and a purity of 99.91%.

Embodiment 3

[0029] The synthetic method of two (2,2,2-trifluoroethyl) carbonates, its synthetic steps are as follows:

[0030] Take 24g (0.24mol) of trifluoroethanol and add it to 90mL of dichloromethane, as a dichloromethane solution of trifluoroethanol for later use;

[0031] Under the protection of nitrogen, take 21.4g (0.1mol) of diphenyl carbonate and 44.1g (0.7mol) of imidazole and stir and mix, add 3.21g of aluminum chloride, heat to 75°C, keep stirring at 75°C for pre-reaction for 2.5h, then Cool down to room temperature, add dropwise a dichloromethane solution containing trifluoroethanol, after the dropwise addition, reflux for 3 h for transesterification, after the reaction is complete, add hydrochloric acid dropwise to adjust to pH = 2, separate the phases, and the obtained dichloromethane phase is After concentration and rectification, 19.29 g of bis(2,2,2-trifluoroethyl) carbonate was obtained, with a yield of 85.35% and a purity of 99.93%.

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Abstract

The invention discloses a synthesis method of bis (2, 2, 2-trifluoroethyl) carbonate, and relates to the technical field of battery electrolyte additives, and the synthesis method comprises the following steps: under the protection of an inert gas, taking diphenyl carbonate, under the catalytic action of aluminum chloride, carrying out a pre-reaction on diphenyl carbonate and imidazole, cooling to room temperature, dropwise adding a dichloromethane solution containing trifluoroethanol, after dropwise adding, carrying out a reaction at room temperature, cooling to room temperature, and carrying out a reaction at room temperature to obtain the bis (2, 2, 2-trifluoroethyl) carbonate. The preparation method comprises the following steps: adding 2, 2, 2, 2-trifluoroethyl carbonate into a reaction kettle, refluxing to carry out ester exchange reaction, dropwise adding hydrochloric acid after the reaction is completed to adjust to be acidic, carrying out phase splitting, and concentrating and rectifying an obtained dichloromethane phase to obtain the bis (2, 2, 2-trifluoroethyl) carbonate. According to the preparation method, diphenyl carbonate is taken as a raw material and is firstly subjected to pre-reaction with imidazole, so that the ester exchange reaction difficulty of trifluoroethoxy is reduced, and meanwhile, compared with a reaction which is carried out by directly adopting N, N-carbonyldiimidazole as a raw material, the reaction is milder, fewer by-products are produced, and the yield is higher.

Description

technical field [0001] The invention relates to the technical field of battery electrolyte additives, in particular to a synthesis method of bis(2,2,2-trifluoroethyl)carbonate. Background technique [0002] Lithium-ion batteries have the advantages of high energy density, high output voltage, long cycle life, no memory effect, and less environmental pollution. They are the most attractive and potential secondary batteries. At present, the solvents used in lithium-ion battery electrolytes are usually carbonates, which can improve the charge-discharge capacity and cycle life of lithium-ion batteries, but their flash point is low. In recent years, fires caused by lithium-ion batteries There are even reports of explosions. The safety of lithium-ion batteries has been widely concerned by people, and safety is also the bottleneck restricting the development of lithium-ion batteries in the direction of high energy and large scale. [0003] Fluorinated solvents usually have a high...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07C68/00C07C69/96C07D233/56
CPCC07C68/00C07D233/56C07C69/96
Inventor郝俊侯荣雪王军葛建民武利斌
OwnerSHIJIAZHUANG SAN TAI CHEM CO LTD