Method for producing compound containing bis(perfluoroalkylsulfonyl)methyl group and salt thereof, and solid electrolyte membrane produced using same

一种制造方法、化合物的技术，应用在固体电解质、有机化合物的制备、固体电解质燃料电池等方向，能够解决过量使用、化合物不稳定、原料化合物不容易合成等问题

Inactive Publication Date: 2015-05-27
CENT GLASS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0031] In the prior art, there were problems in the synthesis of compounds containing bis(perfluoroalkanesulfonyl)methyl groups: the raw material compound was not easy to synthesize, and in addition, a multi-stage reaction was required, and the compound (reagent) that reacted with the raw material compound Unstable, must be overdose, etc.

Method used

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  • Method for producing compound containing bis(perfluoroalkylsulfonyl)methyl group and salt thereof, and solid electrolyte membrane produced using same
  • Method for producing compound containing bis(perfluoroalkylsulfonyl)methyl group and salt thereof, and solid electrolyte membrane produced using same
  • Method for producing compound containing bis(perfluoroalkylsulfonyl)methyl group and salt thereof, and solid electrolyte membrane produced using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0251] [Production of bis(trifluoromethanesulfonyl)heptane using phenylsilane as a reducing agent]

[0252] The reaction formula of this production method is shown below.

[0253]

[0254] After dissolving 1.1 g of hexanal in 10 ml of dichloromethane, 2.8 g of bis(trifluoromethanesulfonyl)methane was added as the compound (1) in Invention 1, and stirred at room temperature for 15 minutes. Next, 1.1 g of phenylsilane was added as a reducing agent as compound (4), and stirred at room temperature for 14 hours. Magnesium sulfate 1.0 g was added to the reaction liquid after stirring, and it filtered after dehydrating and drying. After the filtrate was concentrated under reduced pressure, it was purified by distillation at a temperature of 90° C. and a pressure of 1.33 Pa to obtain 2.7 g of bis(trifluoromethanesulfonyl)heptane as a compound (5) in a yield of 75%. The measurement results of nuclear magnetic resonance spectroscopy (NMR) are shown below.

[0255] Colorless liquid...

Embodiment 2

[0257] [Production of bis(trifluoromethanesulfonyl)heptane using phenyldimethylsilane as a reducing agent]

[0258] In place of phenylsilane, the compound (4) of Example 1, phenyldimethylsilane having a strong reducing power was used. The reaction formula of this production method is shown below.

[0259]

[0260] 2.8 g of bis(trifluoromethanesulfonyl)methane as the compound (1) was added to a solution of 1.1 g of hexanal in 10 ml of dichloromethane at room temperature, followed by stirring for 15 minutes. To the reaction solution, 1.5 g of phenyldimethylsilane was added as a compound (4), followed by stirring at room temperature for 14 hours. Using 151 mg of trifluoromethylbenzene as an internal standard substance, the reaction solution was 19 According to F-NMR measurement, bis(trifluoromethanesulfonyl)heptane was obtained as compound (5) in an NMR yield of 32%.

[0261] When phenyldimethylsilane having a strong reducing power was used instead of the phenylsilane of Ex...

Embodiment 3

[0268] [production of bis(trifluoromethanesulfonyl)heptane using acetal compound]

[0269] The reaction formula of this production method is shown below.

[0270]

[0271] After dissolving 174 mg of 1,1-diethoxyhexane as compound (3) in 1.0 ml of toluene, 116 mg of triethylsilane as compound (4) was added as a reducing agent, and stirred at room temperature for 15 minutes. To the reaction solution was added 280 mg of bis(trifluoromethanesulfonyl)methane as compound (1), followed by stirring at room temperature for 12 hours. After adding 95 mg of trifluoromethylbenzene as an internal standard substance to the stirred reaction liquid, carry out 19 F-NMR determination. The yield was calculated from the ratio of the integrated value of the internal standard substance, and compound (5) bis(trifluoromethanesulfonyl)heptane was obtained at a yield of 75%.

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Abstract

[Problem] To provide a method for producing a compound having a bis(trifluoroalkanesulfonyl)methyl group, which is a compound having a high acidity degree and hydrophobicity and useful as a raw material compound for a resin, and a salt thereof in a simple manner. [Solution] A method for producing a compound containing a bis(perfluoroalkylsulfonyl)methyl group and represented by formula (5) and a salt of the compound. (In the formula, Rf represents a perfluoroalkyl group having 1 to 12 carbon atoms; A represents a monovalent organic group; and Y represents a single bond, a linear alkylene group having 1 to 4 carbon atoms, a branched alkylene group having 3 to 4 carbon atoms, or a cyclic alkylene group having 3 to 4 carbon atoms, wherein each of some or all of hydrogen atoms in the alkylene group may be substituted by a fluorine atom, a chlorine atom, a bromine atom or an iodine atom and the alkylene group may contain an ether bond or an ester bond.)

Description

technical field [0001] The present invention relates to two (perfluoroalkanesulfonyl) methyl (-CH 2 CH(SO 2 R f ) 2 :R f The production method of the compound and salt of a perfluoroalkyl group, and the solid electrolyte membrane using it are shown. Background technique [0002] Perfluoroalkanesulfonyl (-SO 2 R f ) is known as one of the strongest electron-withdrawing groups. Bis(perfluoroalkanesulfonyl)methyl (-CH(SO) containing 2 perfluoroalkanesulfonyl groups 2 R f ) 2 ) The perfluoroalkanesulfonyl moiety in ) exhibits strong electron-withdrawing property, therefore, H is easily dissociated to exhibit strong acidity. [0003] For example, containing bis(trifluoromethanesulfonyl) group (-CH(SO 2 CF 3 ) 2 ) of bis(trifluoromethanesulfonyl)methane (CH 2 (SO 2 CF 3 ) 2 ) and phenylbis(trifluoromethanesulfonyl)methane (PhCH(SO 2 CF 3 ) 2 ) is known as a strong acid. [0004] Patent Document 1 and Patent Document 2 disclose the introduction of a bis(perfluo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/04C07C317/06C07C317/10C08G61/08H01M8/02H01M8/10H01B1/06
CPCC08G61/08C08G2261/1452C08G2261/146C08G2261/418H01M8/1011H01M8/1032H01M8/04197C07C2601/14C07C2602/42B01J39/20C07C315/04Y02E60/50C07C317/06C07C317/04C07C317/10C08F132/08H01M8/1027H01M8/1039H01M2008/1095H01M2300/0082
Inventor 高桥新铃木克俊小森谷治彦田中彻板桥沙央梨
Owner CENT GLASS CO LTD
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