Preparation method of trifluoromethyl straight-chain carbonate

A technology of straight-chain carbonate and trifluoromethyl, applied in the field of preparation of trifluoromethyl-containing straight-chain carbonate, can solve the problem of reduced hydroxyl activity, impact on synthesis yield, and difficulty in separating alcohols, carbonates and transesterification products and other problems, to achieve the effect of strong stability, simple process, cycle performance and high voltage characteristics improvement.

Active Publication Date: 2012-11-14
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

The invention discloses a preparation method of trifluoromethyl straight-chain carbonate, which comprises the following preparation steps: mixing trifluoromethyl saturated monohydric alcohol or a mixture of trifluoromethyl saturated monohydric alcohol and saturated straight-chain monohydric alcohol with triphosgene; regulating the temperature to 25-80 DEG C in the presence of an organic amine acid-binding agent, and reacting for 1-10 hours to obtain a trifluoromethyl straight-chain carbonate mixed solution; and filtering, separating, and performing distilling purification on the trifluoromethyl straight-chain carbonate mixed solution to obtain the trifluoromethyl straight-chain carbonate. The trifluoromethyl straight-chain carbonate prepared by the process is a high voltage type solvent for a novel power lithium battery, and can greatly enhance the heat stability, cycle performance and high voltage property of the power lithium battery. The preparation method has the advantages of simple process, high yield and low cost; and meanwhile, the triphosgene is high in stability and is decomposed a little at the boiling point of 200 DEG C. Thus, the preparation process has no serious problems on safety, environmental protection and the like.

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