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Preparation method of trifluoromethyl straight-chain carbonate

A technology of straight-chain carbonate and trifluoromethyl, which is applied in the field of preparation of trifluoromethyl-containing straight-chain carbonate, which can solve the problem of decreased activity of hydroxyl groups, difficulties in separating alcohols, carbonates and transesterification products, and affecting the synthesis yield and other issues, to achieve the effects of strong stability, cycle performance and high voltage characteristics, and simple process

Active Publication Date: 2014-04-02
ZHANGJIAGANG HUASHENG CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this method, due to the strong electron-pulling effect of the trifluoromethyl group, the activity of the hydroxyl group is greatly reduced, which greatly affects the synthesis yield. The yield is 40-50%, and unreacted alcohols, carbonates and esters are increased simultaneously. Difficulty separating exchange products

Method used

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  • Preparation method of trifluoromethyl straight-chain carbonate
  • Preparation method of trifluoromethyl straight-chain carbonate
  • Preparation method of trifluoromethyl straight-chain carbonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 297.0g (1.0mol) of triphosgene and 600.0g (6.0mol) of trifluoroethanol into a three-necked flask, stir and mix well, add 620.0g ((6.14mol) of triethylamine dropwise at 25°C, and keep warm for 4 hours after the addition Finally, the content of trifluoroethanol in the sampling filtrate is less than 1%; cooling and filtration obtains 578.6g of filtrate, through Agilent 7890A, analysis and detection product bistrifluoroethyl carbonate content 93.6178%, triethylamine content 2.8156%, trifluoroethanol 0.4679% The obtained filtrate was rectified under normal pressure with reflux adjustment to recover residual trifluoroethanol and excess trifluoroethanol, collected 523.6 g of bis-trifluoroethyl carbonate at 112~116°C / 100kPa, and analyzed and detected by Agilent 7890A (RT2 .525), the content is 99.94Wt.%, and the yield is 77.2%.

Embodiment 2

[0030] Add 297.0g (1.0mol) of triphosgene and 1368.0g (12.0mol) of trifluoropropanol into a three-necked flask, stir and mix well, add 620.0g (6.14mol) of triethylamine dropwise at 80°C, and keep warm for 10 hours after the addition Finally, triethylamine content is less than 3% in the sampling filtrate; Cooling filtration obtains 1485.6 filtrate, by Agilent 7890A, analysis and detection product bistrifluoropropyl carbonate content 58.6358%, triethylamine content 1.2313%, trifluoropropanol 40.1637% . The obtained filtrate was rectified under normal pressure with reflux regulation to recover residual trifluoropropanol and excess triethylamine, and 815.6 g of bis-trifluoropropyl carbonate at 75~85°C / 10~30kPa was collected under reduced pressure, and analyzed by Agilent 7890A Detection (RT5.596), the content is 99.91Wt.%, and the yield is 95.1%.

Embodiment 3

[0032] Add 297.0g (1.0mol) of triphosgene, 400.0g (4.0mol) of trifluoroethanol and 96.0g of methanol (3.0mol) into a three-necked flask and stir well, then add 452.6g (6.2mol) of n-butylamine dropwise at 50°C, After incubation for 1 hour after the dropwise addition, the content of n-butylamine in the sampled filtrate was less than 3%; 565.8g of filtrate was obtained by cooling and filtration, which was analyzed and detected by Agilent 7890A. The content of methyl trifluoroethyl carbonate was 72.0718%, and the content of n-butylamine was 1.9156 %, trifluoroethanol 18.4679%, bistrifluoroethyl carbonate content 4.1135%, dimethyl carbonate 3.4312%. The obtained filtrate was subjected to rectification under normal pressure with reflux adjustment to recover residual trifluoroethanol and excess n-butylamine, collected 385.4 g of trifluoroethyl methyl carbonate at 102~106°C / 100kPa, and analyzed and detected by Agilent 7890A (RT1. 586), the content is 99.90Wt.%, and the yield is 67.5%....

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Abstract

Disclosed is a trifluoromethyl straight-chain carbonic ester preparation method. Preparation steps are: mixing trifluoromethyl saturated monohydric alcohol or a mixture of trifluoromethyl saturated monohydric alcohol and saturated straight-chain monohydric alcohol with triphosgene; and under an organic amine acid-binding agent, adjusting a temperature to 25 to 80 °C, reacting for 1 to 10 h, to obtain mixed liquor containing the trifluoromethyl straight-chain carbonic ester; and performing filtering and separation, and performing distillation and purification on the mixed liquor containing the trifluoromethyl straight-chain carbonic ester, to obtain the trifluoromethyl straight-chain carbonic ester. The trifluoromethyl straight-chain carbonic acid obtained by using the process disclosed by the present invention is a high-voltage solvent of a power lithium battery, which can greatly improve thermal stability, cycle performance, and high-voltage characteristics of the power lithium battery. The preparation method has simple process, high yield, and low costs. At the same time, the triphosgene has strong stability, and has little resolution under a boiling point of 200°C, and therefore, problems of major security and environmental protection do not exist in the preparation process.

Description

technical field [0001] The invention relates to a preparation method of trifluoromethyl-containing straight-chain carbonate, in particular to a preparation method of directly substituting saturated monoalcohol with trifluoromethyl and triphosgene. Background technique [0002] Trifluoromethyl-containing linear carbonate is a new type of high-voltage lithium battery solvent. The electrochemical window reaches above 5V. At the same time, the molecule contains a large amount of fluorine. It participates in part of the lithium solvation reaction under the electrochemical field of the lithium battery. And participate in the formation of fluorine-containing SEI film, which enhances the thermal stability of lithium batteries, and then greatly improves the cycle performance of batteries. The application prospect of new solvents for power-type high-voltage lithium battery electrolytes is very broad. [0003] At present, the most commonly used preparation method in China is to use a s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/96C07C68/02C07C68/08
CPCC07C68/06C07C68/02C07C69/96
Inventor 张先林杨志勇张丽亚吴国栋陆海媛
Owner ZHANGJIAGANG HUASHENG CHEM CO LTD