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Spirocyclo-quaternary ammonium salt for supercapacitor and preparation method of spirocyclo-quaternary ammonium salt

A spiro quaternary ammonium salt, supercapacitor technology, applied in chemical instruments and methods, hybrid capacitor electrolytes, organic chemistry, etc., can solve problems affecting the electrochemical performance and service life of supercapacitors, and achieve high product quality, production operation Simple, good reaction selectivity

Active Publication Date: 2013-02-27
锦州凯美能源有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the fluorine-containing anion quaternary ammonium salt will dissociate fluoride ions and generate hydrogen fluoride during the working process of the supercapacitor, thus affecting the electrochemical performance and service life of the supercapacitor

Method used

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  • Spirocyclo-quaternary ammonium salt for supercapacitor and preparation method of spirocyclo-quaternary ammonium salt
  • Spirocyclo-quaternary ammonium salt for supercapacitor and preparation method of spirocyclo-quaternary ammonium salt
  • Spirocyclo-quaternary ammonium salt for supercapacitor and preparation method of spirocyclo-quaternary ammonium salt

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Experimental program
Comparison scheme
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Embodiment 1

[0054] Preparation of spiro[4,4]quaternary ammonium bisoxalate borate

[0055] 1.1 Preparation of spiro[4,4]quaternary ammonium salt of p-toluenesulfonate

[0056] In a 2-liter three-necked reaction flask, tetrahydropyrrole (35.5 grams, 0.5 moles) was added dropwise to 1,4-butanediol di-p-toluenesulfonate (238.8 grams, 0.6 moles) and potassium carbonate (103.5 g, 0.75 mol) in deionized water (750 ml), reacted at 25°C for 5 hours, and then heated to reflux for 8 hours. Concentrate under reduced pressure, add ethanol to the obtained residue, and filter. The filtrate was concentrated and recrystallized from ethanol to obtain 130.7 g of spiro[4,4]quaternary ammonium p-toluenesulfonate with a yield of 88%.

[0057] The NMR analysis results are: 1 H NMR (400MHz, D 2 O): δ=2.30-2.35(m, 8H, 4xCH 2 ), 2.44 (s, 3H, CH 3 ), 3.61-3.66 (m, 8H, 4xCH 2 ), 7.51(d, 2H), 7.87(d, 2H).

[0058] 1.2 Preparation of spiro[4,4]quaternary ammonium bisoxalate borate

[0059] The spiro[4,4] qua...

Embodiment 2

[0066] Preparation of spiro[4,4]quaternary ammonium bisoxalate borate

[0067] 2.1 Preparation of spiro[4,4]quaternary ammonium salt of methanesulfonate

[0068] In a 2-liter three-necked reaction flask, tetrahydropyrrole (35.5 grams, 0.5 moles) was added dropwise to 1,4-butanediol dimethylsulfonate (128.4 grams, 0.6 moles) and sodium carbonate ( 91.5 g, 0.75 mol) of deionized water (800 ml), reacted at 25° C. for 4 hours, and then heated to reflux for 6 hours. Concentrate under reduced pressure, add ethanol to the obtained residue, and filter. The filtrate was concentrated and recrystallized from ethanol to obtain 93.9 g of spiro[4,4]quaternary ammonium methanesulfonate with a yield of 85%.

[0069] The NMR analysis results are: 1 H NMR (400MHz, D 2 O): δ=2.33-2.37(m, 8H, 4xCH 2 ), 2.96 (s, 3H, CH 3 ), 3.62-3.67(m, 8H, 4xCH 2 ).

[0070] 2.2 Preparation of spiro[4,4]quaternary ammonium bisoxalate borate

[0071] The spiro[4,4] quaternary ammonium salt of methylsulfon...

Embodiment 3

[0076] Preparation of spiro[4,4]quaternary ammonium bisoxalate borate

[0077] 3.1 Preparation of bromospiro[4,4]quaternary ammonium salt

[0078] In a 2-liter three-necked reaction flask, under stirring, tetrahydropyrrole (35.5 grams, 0.5 moles) was added dropwise to 1,4-dibromobutane (129.6 grams, 0.6 moles) and potassium carbonate (103.5 grams, 0.75 moles). In deionized water (750 ml), react at 25°C for 2 hours, and then heat to reflux for 5 hours. Concentrate under reduced pressure, add ethanol to the obtained residue, and filter. The filtrate was concentrated and recrystallized from ethanol to obtain 84.1 g of bromospiro[4,4]quaternary ammonium salt with a yield of 88%.

[0079] The NMR analysis results are: 1 H NMR (400MHz, D 2 O): δ=2.34-2.37(m, 8H, 4xCH 2 ), 3.62-3.67(m, 8H, 4xCH 2 ).

[0080] 3.2 Preparation of spiro[4,4]quaternary ammonium bisoxalate borate

[0081] The above-obtained bromospiro [4,4] quaternary ammonium salt (47.7 grams, 0.25 moles), lithium...

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Abstract

The invention discloses spirocyclo-quaternary ammonium salt for a supercapacitor and a preparation method of the spirocyclo-quaternary ammonium salt. The spirocyclo-quaternary ammonium salt for the supercapacitor is characterized in that the formula is represented as following, wherein in (A), n, m= 1, 2, 3; in (B) or (C), n, m= 1, 2, 3; and p=1, 2. The preparation method includes that water is used as a reaction medium, cyclic amine and dihalogenation amine or glycol di-sulphonate ester are subjected to condensation reaction under the action of alkali, and obtained spirocyclo-quaternary ammonium salt and lithium bis(oxalato)borate are subjected to ion exchanging and then to purification to obtain the target spirocyclo-quaternary ammonium salt. According to the spirocyclo-quaternary ammonium salt for the supercapacitor and the preparation method of the spirocyclo-quaternary ammonium salt, raw materials are easily obtained, reaction selectivity is good, qualities of the spirocyclo-quaternary ammonium salt are high, and the method is suitable for large scale production, and the supercapacitor which is composed of the spirocyclo-quaternary ammonium salt is low in internal resistance, high in electrostatic capacity and excellent in cycling performances.

Description

technical field [0001] The invention relates to a preparation method of an organic electrolyte for a supercapacitor, in particular to a spirocyclic quaternary ammonium salt for a supercapacitor and a preparation method thereof. Background technique [0002] Supercapacitor (electric double layer capacitor) is a high-energy electric energy storage element developed in recent years. It has the advantages of high power density, high cycle life, fast charging and discharging, and no pollution to the environment. It is widely used in motor regulators Clean energy systems such as sensors, backup power supplies for microcomputer memory, starting devices for motor vehicles, wind power generation and solar power generation systems have attracted attention. Quaternary ammonium salts, as non-aqueous electrolytes for supercapacitors, can be used as supporting electrolytes for chemical batteries for energy storage devices or high-energy capacitors. [0003] So far, as quaternary ammonium...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07D487/10C07D471/10C07D498/10H01G11/62
CPCY02E60/13
Inventor 王道林何铁石金振兴
Owner 锦州凯美能源有限公司
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