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Preparation method of spiro quaternary ammonium salt for organic electrolyte of super capacitor

A technology of spirocyclic quaternary ammonium salt and organic electrolyte, which is applied in the direction of organic chemistry, can solve the problems of low yield and difficult to meet the requirements of electrochemical products, and achieve the effect of high yield, good quality and good selectivity

Inactive Publication Date: 2013-02-27
BOHAI UNIV
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Problems solved by technology

[0004] As a spirocyclic quaternary ammonium salt synthesis method, in patents (US: 2007-49750, JP2005-294332, US: 3055171) and journal papers (ARKIVOC, 2002 (iii), 63-70; Chem.Ber., 1924, 57, 187; Chem.Ber., 1916,49,970) describes the nucleophilic substitution reaction between cyclic amines and dihalogenated hydrocarbons, first synthesizing the corresponding halogenated salts, and then preparing the synthesis of spirocyclic quaternary ammonium salts by ion exchange process, the yield of this method is low, and a large amount of organic solvents are used in the preparation process, so there are obvious deficiencies as a large-scale production method
Especially the product contains a large amount of halide ions, it is difficult to meet the requirements of electrochemical products

Method used

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  • Preparation method of spiro quaternary ammonium salt for organic electrolyte of super capacitor
  • Preparation method of spiro quaternary ammonium salt for organic electrolyte of super capacitor
  • Preparation method of spiro quaternary ammonium salt for organic electrolyte of super capacitor

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Preparation of spiro-1,1'-pyrrole quaternary ammonium salt

[0039] 1.1 Preparation of p-toluenesulfonic acid spiro-1,1'-pyrrole quaternary ammonium salt

[0040] 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-1,1'-pyrrole quaternary ammonium p-toluenesulfonate with a yield of 88%.

[0041] The structural analysis is as follows:

[0042] 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).

[0043] 1.2 Preparation of spiro-1,1’-p...

Embodiment 2

[0061] Preparation of spiro-1,1'-pyrrole quaternary ammonium salt

[0062] 2.1 Preparation of spiro-1,1'-pyrrole quaternary ammonium salt of methanesulfonate

[0063] 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 6 hours, and then heated to reflux for 10 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-1,1'-pyrrole quaternary ammonium methanesulfonate with a yield of 85%.

[0064] The structural analysis is as follows:

[0065] 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 ).

[0066] 2.2 Preparation of spiro-1,1’-pyrrole quaternary ammonium tetrafluor...

Embodiment 3

[0077] Preparation of spiro(piperidine-1,1'-pyrrole) quaternary ammonium salt

[0078] 3.1 Preparation of spiro(piperidine-1,1'-pyrrole) quaternary ammonium salt of p-toluenesulfonate

[0079] In a 2-liter three-necked reaction flask, under stirring, hexahydropiperidine (51.0 grams, 0.6 moles) was added dropwise to 1,4-butanediol di-p-toluenesulfonate (238.8 grams, 0.6 moles) and sodium carbonate (91.5 g, 0.75 mol) in deionized water (800 ml), reacted at 25° C. for 5 hours, and then heated to reflux for 10 hours. Concentrate under reduced pressure, add ethanol to the obtained residue, and filter. The filtrate was concentrated and recrystallized from ethanol to obtain 149.3 g of p-toluenesulfonate spiro(piperidine-1,1'-pyrrole) quaternary ammonium salt with a yield of 80%.

[0080] The structural analysis is as follows:

[0081] The NMR analysis results are: 1 H NMR (400MHz, D 2 O): δ=1.71-1.76(m, 2H), 1.91-1.96(m, 4H, 2xCH 2 ), 2.30-2.35(m, 4H, 2xCH 2 ), 2.46(s, 3H, CH ...

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Abstract

The invention discloses a preparation method of a spiro quaternary ammonium salt for an organic electrolyte of a super capacitor, which comprises the following steps: by using water as a reaction medium, enabling cyclic diamine and diol disulfonate to be subjected to condensation reaction at a certain temperature to obtain a corresponding spiro quaternary ammonium salt; carrying out ion exchange on the ammonium salt to obtain a corresponding spiro quaternary ammonium salt; and finally, purifying to obtain the target product. The method disclosed by the invention has good selectivity, increases the yield of the target product, improves the quality, and can lower the impurity content in the electrolyte to 5 ppm or below, thereby meeting the requirements of the organic electrolyte of a super capacitor.

Description

technical field [0001] The invention relates to a method for synthesizing an organic electrolyte for a supercapacitor, in particular to a method for preparing a spirocyclic quaternary ammonium salt. technical background [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 ions, including aliphatic qu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/10C07D471/10
Inventor 王道林金振兴曹亮李帝
Owner BOHAI UNIV
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