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Vinyl sulfite derivative as well as preparation method and application thereof

A technology of vinyl sulfite and dihalogenated vinyl sulfite, which is applied in the field of vinyl sulfite derivatives and its preparation and application, can solve problems such as battery explosion, potential safety hazards, and impact on battery high-voltage cycle performance, and achieve Short production cycle, low production cost, and improved high-pressure cycle performance

Active Publication Date: 2020-11-10
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, increasing the charge cut-off voltage will cause a series of interface electrochemical problems, which will affect the high-voltage cycle performance of the battery.
In addition, the organic solvent in the electrolyte of lithium-ion batteries is flammable, and will be oxidized and decomposed to produce gas as the voltage increases during the working process. The accumulated heat and gas may eventually cause the battery to explode, posing a safety hazard

Method used

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  • Vinyl sulfite derivative as well as preparation method and application thereof
  • Vinyl sulfite derivative as well as preparation method and application thereof
  • Vinyl sulfite derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of 4-trifluoromethyl vinyl sulfite:

[0034] 1) Disperse 5 mmol of 3,3,3-trifluoropropene in 50 mL of dichloromethane, add 5 mmol of potassium permanganate and 12 mmol of deionized water at 25°C, and react for 6 hours to obtain 3,3,3 - trifluoropropane-1,2-diol;

[0035] 2) Disperse 3mmol of 3,3,3-trifluoropropane-1,2-diol and 4mmol of trichloromethanesulfonyl chloride in 25mL of tetrahydrofuran, add 1mmol of triethylamine, and react at 25°C for 5h to obtain 4 - trifluoromethyl vinyl sulfite (structural formula: Yield: 93.33%, purity: 98.2%).

[0036] Performance Testing:

[0037] 1) Structural characterization: It was confirmed by hydrogen nuclear magnetic resonance that the prepared product was indeed 4-trifluoromethyl vinyl sulfite;

[0038] 2) Capacity retention test: Lithium-ion battery electrolyte was prepared with 4-trifluoromethylethylene sulfite (abbreviated as TFES) as an additive, in which lithium hexafluorophosphate (LiPF 6 ) content is 1.0...

Embodiment 2

[0043] Preparation of 4-perfluorobutyl vinyl sulfite:

[0044] 1) Disperse 5 mmol of perfluorobutylethylene in 50 mL of dichloromethane, add 5 mmol of potassium permanganate and 15 mmol of deionized water at 25°C, and react for 5 hours to obtain perfluorobutyl glycol;

[0045] 2) Disperse 3mmol of perfluorobutyl glycol and 4mmol of trichloromethanesulfonyl chloride in 50mL of tetrahydrofuran, then add 1mmol of triethylamine, and react at 25°C for 5h to obtain 4-perfluorobutyl vinyl sulfite (structural formula: Yield: 92.00%, purity: 99.0%).

[0046] Performance Testing:

[0047] 1) Structural characterization: It was confirmed by H NMR spectroscopy that the prepared product was indeed 4-perfluorobutyl vinyl sulfite;

[0048] 2) Capacity retention rate test: the test method is the same as in Example 1, and the test results: the capacity retention rate of the battery with 1wt% 4-perfluorobutyl vinyl sulfite added in the electrolyte is 86% after 100 cycles, while the electrol...

Embodiment 3

[0051] Preparation of 4-perfluorooctyl vinyl sulfite:

[0052] 1) Disperse 5 mmol of perfluorooctylethylene in 50 mL of dichloromethane, add 7 mmol of potassium permanganate and 10 mmol of deionized water at 25°C, and react for 7 hours to obtain perfluorooctyl glycol;

[0053] 2) Disperse 3mmol of perfluorooctyl glycol and 4mmol of trichloromethanesulfonyl chloride in 50mL of tetrahydrofuran, then add 1mmol of triethylamine, and react at 25°C for 8h to obtain 4-perfluorooctyl vinyl sulfite (structural formula: Yield: 80.10%, purity: 96.0%).

[0054] Performance Testing:

[0055] 1) Structural characterization: It was confirmed by H NMR spectroscopy that the prepared product was indeed 4-perfluorooctyl vinyl sulfite;

[0056] 2) Capacity retention rate test: The test method is the same as in Example 1, and the test results: the capacity retention rate of the battery with 1wt% 4-perfluorooctyl vinyl sulfite added in the electrolyte is 84% ​​after 100 cycles, while the electr...

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Abstract

The invention discloses a vinyl sulfite derivative as well as a preparation method and application thereof. The structural formula of the vinyl sulfite derivative is shown in the specification, wherein R is a C1-C8 perfluoroalkyl group. The preparation method of the vinyl sulfite derivative comprises the following steps: firstly, carrying out halogenation reaction on vinyl sulfite to obtain 4,4-dihalogenated vinyl sulfite; and then carrying out halogen replacement reaction on the 4,4-dihalogenated vinyl sulfite and a fluorinating reagent; or carrying out oxidation reaction on perfluoroalkyl ethylene to obtain perfluoroalkyl ethylene glycol; or carrying out oxidation reaction on perfluoroalkyl ethylene to obtain perfluoroalkyl ethylene glycol and carrying out cyclization reaction with trichloromethylsulfonyl chloride. The preparation method of the vinyl sulfite derivative is simple, short in production period, low in production cost and high in product purity, and can broaden the electrochemical window of an electrolyte system, improve the high-voltage interface stability of a battery and improve the high-voltage cycle performance of the battery after being added into the electrolyte of the lithium ion battery.

Description

technical field [0001] The invention relates to a vinyl sulfite derivative and its preparation method and application. Background technique [0002] Since its birth in the 1990s, lithium-ion secondary batteries have developed vigorously. Lithium-ion secondary batteries have the advantages of long service life, high working voltage, high energy density, and less environmental pollution. main power source. As countries begin to impose restrictions on fuel vehicles, lithium-ion electric vehicles may become the future development direction. At the same time, people have higher and higher performance requirements for lithium-ion batteries. [0003] At present, improving the energy density of lithium-ion batteries is a research hotspot, and one of the methods is to increase the charge cut-off voltage of the battery. However, increasing the charge cut-off voltage will cause a series of interface electrochemical problems, which will affect the high-voltage cycle performance of th...

Claims

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Application Information

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IPC IPC(8): C07D327/10H01M10/0525H01M10/0567H01M10/42
CPCC07D327/10H01M10/0567H01M10/4235H01M10/0525H01M2300/0025Y02E60/10
Inventor 左晓希章塄丹南俊民
Owner SOUTH CHINA NORMAL UNIVERSITY