A kind of preparation method of symmetrical spirocyclic ammonium salt electrolyte

A spiro quaternary ammonium salt and electrolyte technology, which is applied in the directions of hybrid capacitor electrolytes, electrolytic capacitors, double-layer capacitors, etc., can solve the problems of strong acid safety hazards, long synthesis process, high energy consumption, and achieve high safety and good selectivity. , the effect of high product yield

Active Publication Date: 2016-08-24
JIANGSU GUOTAI SUPER POWER NEW MATERIALS
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AI Technical Summary

Problems solved by technology

This method has a long synthesis process, and the use of strong acid in the ion exchange process has certain safety hazards. The purification process often requires recrystallization in an organic solvent, and the energy consumption is high.

Method used

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  • A kind of preparation method of symmetrical spirocyclic ammonium salt electrolyte
  • A kind of preparation method of symmetrical spirocyclic ammonium salt electrolyte

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: Preparation of tetrafluoroborate spiro 1,1'-bispyrrole quaternary ammonium salt

[0027] In the three-necked flask, put 105g (1mol) NH 4 BF 4 , 254g (2mol) 1,4-dichlorobutane, 276g (2.1mol) K 2 CO 3 and 2000ml of deionized water, after reflux reaction at normal pressure for 10h, the resulting reaction solution was concentrated to a product content of 21%.

[0028] After cooling the concentrated solution, filter to remove the filter residue, and further concentrate the obtained filtrate to a paste solid with a product content of 75%, add an appropriate amount of ethanol, stir and crystallize at -10°C for 10 hours, and filter to obtain colorless transparent crystals.

[0029] The above crystals were dried under vacuum for 24 hours to obtain 184 g of spiro 1,1'-bispyrrole quaternary ammonium tetrafluoroborate in the form of colorless crystals. The molar yield is 86.3%.

[0030] Proton NMR spectrum results: 1H NMR (400MHz, D 2 O): δ=2.17(8*H,4*CH 2 ), δ...

Embodiment 2

[0034] Embodiment 2: Preparation of spiro trifluoromethanesulfonate 1,1'-bispyrrole quaternary ammonium salt

[0035] In the three-necked flask, put 167g (1mol) NH 4 SO 3 CF 3 , 254g (2mol) 1,4-dichlorobutane, 212g (2mol) Na 2 CO 3 and 2000ml of deionized water, after reflux reaction at normal pressure for 18h, the resulting reaction solution was concentrated to a product content of 20%.

[0036] After cooling the concentrated solution, filter to remove the filter residue, and further concentrate the obtained filtrate to a paste solid with a product content of 70%, add an appropriate amount of isopropanol, stir and crystallize at -5°C for 10 h, and filter to obtain colorless transparent crystals.

[0037] The above crystals were dried under vacuum for 24 hours to obtain 224 g of colorless crystals of spiro 1,1'-bispyrrole quaternary ammonium trifluoromethanesulfonate, with a molar yield of 81.5%.

[0038] The product purity calculated by ion chromatography is 99.9%

[00...

Embodiment 3

[0041] Example 3: Preparation of difluorooxalate borate spiro 1,1'-bispyrrole quaternary ammonium salt

[0042] In the three-necked flask, put 155g (1mol) NH 4 B(C 2 o 4 )F 2 , 516g (2mol) 1,4-dibromobutane, 212gNa 2 CO 3 (2mol) and 2000ml of deionized water, reflux reaction at normal pressure for 20h, and then concentrate the resulting reaction solution to a product content of 19%.

[0043] After cooling the concentrated solution, filter to remove the filter residue, and further concentrate the obtained filtrate to a paste solid with a product content of 70%, add an appropriate amount of n-butanol, stir and crystallize at 0°C for 10 h, and filter to obtain colorless transparent crystals.

[0044] The above-mentioned crystals were dried under vacuum for 24 hours to obtain 240 g of colorless crystalline difluorooxalate borate spiro 1,1'-bispyrrole quaternary ammonium salt. The molar yield is 91.3%.

[0045] The product purity calculated by ion chromatography is 99.9%

...

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Abstract

The invention relates to a preparation method of a symmetric spiro-quaternary ammonium salt electrolyte. The preparation method comprises the following steps: with water as a reaction medium, subjecting ammonium salt and alkyl dihalide to normal pressure reflux reaction for 10-20 hours in the presence of an acid-binding agent, then concentrating the product until the mass of symmetric spiro-quaternary ammonium salt is 15-25% of that of a symmetric spiro-quaternary ammonium salt reaction liquid, and carrying out filtration and purification to obtain the symmetric spiro-quaternary ammonium salt electrolyte, wherein the ammonium salt is any one of ammonium fluoroborate, ammonium trifluoromethanesulfonate and ammonium difluoro(oxalate)borate; alkyl dihalide is any one of 1,4-dichlorobutane, 1,5-dichloropentane, 1,4-dibromobutane and 1,5-dibromopentane; the feed mole ratio of the ammonium salt to alkyl dihalide to the acid-binding agent is 1 to (2-2.2) to (2-2.3); at the beginning of the reaction, the concentration of the ammonium salt is less than or equal to 0.5mol / l. The preparation method has the advantages that the raw materials are cheap; the whole preparation process has high safety; the synthetic reaction is good in selectivity; the product has high yield and high purity; the preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing a symmetrical spirocyclic quaternary ammonium salt electrolyte. Background technique [0002] Because electrochemical energy storage devices, especially supercapacitors, have excellent pulse charge-discharge performance and large-capacity energy storage performance that traditional physical capacitors do not have, their applications in high-energy pulsed lasers have attracted widespread attention. At the same time, it is used as a backup power supply for computer systems and wireless communication equipment because of its large storage energy, light weight, and multiple charge and discharge. With the rise of research on environmentally friendly electric vehicles, electrochemical capacitors are used in conjunction with lead-acid batteries and other batteries to form composite batteries, which are used in the power starting system of electric veh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/10C07D487/10H01G11/62
CPCC07D471/10C07D487/10H01G11/00H01G11/62Y02E60/13
Inventor 何永刚邹凯熊鲲施苏萍闻立新郭军关士友李建中
Owner JIANGSU GUOTAI SUPER POWER NEW MATERIALS
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