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Preparation method of tetrafluoroborate quaternary ammonium salt

A technology of tetrafluoroboric acid and quaternary ammonium salt, which is applied in the field of preparation of tetrafluoroborate quaternary ammonium salt, can solve the problems of complex process conditions, low activity of alkyl carbonate, increased production cost, etc., and achieve the effect of reducing production cost

Active Publication Date: 2018-03-13
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method does not introduce halide ions, the activity of alkyl carbonate is low, the reaction needs to be carried out in an autoclave, the process conditions are complicated, and the production cost is increased.

Method used

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  • Preparation method of tetrafluoroborate quaternary ammonium salt
  • Preparation method of tetrafluoroborate quaternary ammonium salt
  • Preparation method of tetrafluoroborate quaternary ammonium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add trimethyl borate (10.39 g, 0.1 mol), triethylamine (15.15 g, 0.15 mol), and 20 mL of methanol into the autoclave, stir, and react at about 135 ° C for 9 h. After the reaction was completed, the solvent was removed by rotary evaporation to obtain methyltriethylboronic acid quaternary ammonium salt.

[0021] Add 40% hydrofluoric acid aqueous solution (22.51g, 0.45mol) dropwise to the methyltriethylboronic acid quaternary ammonium salt solution, react at about 40°C for 4h, and spin off the solvent to obtain a crude product. It was recrystallized from ethanol to obtain 13.90 g of methyltriethylammonium tetrafluoroborate.

[0022] 1 H-NMR (D 2 O)δ, ppm: 1.29~1.33(t, 9H, N-CH 2 -CH 3 ), 2.93~3.01 (s, 3H, N-CH 3 ), 3..30~3.34 (q, 6H, N-CH 2 ).

[0023] 13 C-NMR (D 2 O):

[0024]

[0025] High resolution mass spectrometry: M + =116.144, M - =87.004.

[0026] Detected by ion chromatography, the results are as follows:

[0027]

Embodiment 2

[0029] Add trimethyl borate (10.39g, 0.1mol), N-methylpyrrolidine (12.77g, 0.15mol), and 20mL of methanol into the autoclave, stir, and react at about 130°C for 9h. After the reaction is completed, the solvent is removed by rotary evaporation to obtain N,N-dimethylpyrrole boric acid quaternary ammonium salt.

[0030] Add 40% hydrofluoric acid aqueous solution (22.51g, 0.45mol) dropwise to the N,N-dimethylpyrrole boric acid quaternary ammonium salt solution, react at about 40°C for 4h, and spin off the solvent to obtain a crude product. Recrystallized from ethanol to obtain 15.75 g of N,N-dimethylpyrrole ammonium tetrafluoroborate.

[0031] 1 H-NMR (D 2 O) δ, ppm: 2.21 ~ 2.35 (t, 4H, CH 2 ), 3.08~3.15 ​​(s, 6H, N-CH 3 ), 3.56~3.64 (q, 4H, N-CH 2 ).

[0032] 13 C-NMR (D 2 O):

[0033]

[0034] High resolution mass spectrometry: M + =100.113, M - =87.004.

[0035] Detected by ion chromatography, the results are as follows:

[0036]

Embodiment 3

[0038] Add trimethyl borate (10.39g, 0.1mol), 1-methylimidazole (12.32g, 0.15mol), and 20mL of methanol into the autoclave, stir, and react at about 125°C for 7h. After the reaction is completed, the solvent is removed by rotary evaporation to obtain 1,3-dimethylimidazole boronic acid quaternary ammonium salt.

[0039] Add 40% hydrofluoric acid aqueous solution (22.51g, 0.45mol) dropwise to 1,3-dimethylimidazole boric acid quaternary ammonium salt solution, react at about 40°C for 4h, and spin evaporate to remove the solvent to obtain a crude product. Recrystallized from ethanol to obtain 14.36 g of 1,3-dimethylimidazolium ammonium tetrafluoroborate.

[0040] 1 H-NMR (D 2 O)δ, ppm: 3.79~3.86(s, 6H, CH 3 ), 7.43-7.52 (s, 2H, CH), 8.70-8.83 (s, 1H, CH).

[0041] 13 C-NMR (D 2 O):

[0042]

[0043] High resolution mass spectrometry: M + =97.135, M - =87.004. Detected by ion chromatography, the results are as follows:

[0044]

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Abstract

The invention provides a preparation method of tetrafluoroborate quaternary ammonium salt. The preparation method includes steps: (1), enabling amine and alkyl borate to be in quaterisation in an organic solvent to generate boric acid type quaternary ammonium salt; (2), enabling the boric acid type quaternary ammonium salt to react with hydrofluoric acid to obtain tetrafluoroborate quaternary ammonium salt. Alkyl borate is used as an alkylation reagent, and chloroalkane or bromoalkane is not used, so that no chlorine ions and bromide ions are left; hydrofluoric acid low in cost is used to replace tetrafluoroboric acid to generate tetrafluoroborate, so that production cost is lowered.

Description

technical field [0001] The invention relates to a preparation method of tetrafluoroborate quaternary ammonium salt, in particular to a preparation method of tetrafluoroborate quaternary ammonium salt used as supercapacitor electrolyte. Background technique [0002] Supercapacitors, also known as double-layer capacitors (Ectrochemical Double-Layer Capacitors, EDLCs), have higher energy density than traditional electrostatic capacitors and greater power density than secondary batteries. They are between ordinary batteries and traditional electrostatic capacitors. new energy storage devices. Due to the advantages of high power density, long cycle life, short charge and discharge time, and wide temperature range, supercapacitors have broad application prospects and become a research hotspot. [0003] Electrolyte is an important part of supercapacitors and has a great influence on the performance of supercapacitors. Quaternary ammonium salts, especially methyltriethylammonium t...

Claims

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Application Information

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IPC IPC(8): C07F5/04C07C211/63C07C209/00C07D233/58C07D295/023C07D295/03
CPCC07C209/00C07D233/58C07D295/023C07D295/03C07F5/04C07C211/63
Inventor 林富荣周海军周永生
Owner CHANGZHOU UNIV
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