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Adamantane-containing quaternary ammonium salt ionic liquid and preparation method thereof

A quaternary ammonium salt ion, adamantane technology is applied in the preparation of organic compounds, chemical instruments and methods, preparation of aminohydroxy compounds, etc., to achieve mild reaction conditions, easy availability of raw materials, and improved amphiphilicity.

Inactive Publication Date: 2019-06-14
HEZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the adamantane-containing quaternary ammonium salt compounds reported in the literature are in the form of solid powder, with a melting point generally higher than 100°C, and those in the form of ionic liquids are rare

Method used

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  • Adamantane-containing quaternary ammonium salt ionic liquid and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0019] Embodiment 1: the synthesis of the quaternary ammonium salt ionic liquid (n=11) containing adamantane

[0020] Weigh 1.8g (0.01mol) of 1-adamantanecarboxylic acid and add it to a 100mL three-neck flask (installed with a thermometer, constant pressure dropping funnel, condenser tube, magnetic stirring), and drop 2.4g of thionyl chloride into the bottle to form a suspension , under the protection of nitrogen, the temperature was raised to 80° C. to react until the solution was a transparent clear liquid, and then evaporated to dryness under reduced pressure to obtain a yellow 1-adamantanecarbonyl chloride solid with a yield of 95%.

[0021] Under nitrogen protection, in a 250mL single-necked flask, 3.3g of 11-bromo-1-undecanol was added to dichloromethane, placed in an ice bath and 4.2mL of triethylamine was added, and 2.0g of 1-adamantanecarbonyl chloride The solution formed with dichloromethane was added dropwise, after the dropwise addition was completed, stirred at ro...

Embodiment 2

[0023] Embodiment 2: the synthesis of quaternary ammonium salt ionic liquid (n=9) containing adamantane

[0024] Weigh 1.8g (0.01mol) of 1-adamantanecarboxylic acid and add it to a 100mL three-neck flask (installed with a thermometer, constant pressure dropping funnel, condenser tube, magnetic stirring), and drop 6.0g of thionyl chloride into the bottle to form a suspension , N 2 In the atmosphere, the temperature was raised to 60° C. to react until the solution was a transparent clear liquid, and then evaporated to dryness under reduced pressure to obtain a yellow 1-adamantanecarbonyl chloride solid with a yield of 97%.

[0025] Under nitrogen protection, in a 250mL single-necked flask, 2.7g of 9-bromo-1-nonanol was added to 1,2-dichloroethane, placed in an ice bath and 3.5mL of triethylamine was added, and 2.0g of 1- The solution formed by adamantanecarbonyl chloride and 1,2-dichloroethane was added dropwise. After the dropwise addition, the reaction was stirred at room tem...

Embodiment 3

[0027] Embodiment 3: the synthesis of quaternary ammonium salt ionic liquid (n=6) containing adamantane

[0028]Weigh 1.8g (0.01mol) of 1-adamantanecarboxylic acid and add it to a 100mL three-necked flask (installed with a thermometer, constant pressure dropping funnel, condenser tube, magnetic stirring), and drop 4.8g of thionyl chloride into the bottle to form a suspension , N 2 In the atmosphere, the temperature was raised to 70° C. to react until the solution was a transparent clear liquid. After completion, it was evaporated to dryness under reduced pressure to obtain a yellow 1-adamantanecarbonyl chloride solid with a yield of 96%.

[0029] Under nitrogen protection, in a 250mL single-necked flask, 2.2g of 6-bromo-n-hexanol was added to tetrahydrofuran, placed in an ice bath, 2.8mL of triethylamine was added, and the solution formed by 2.0g of 1-adamantanecarbonyl chloride and tetrahydrofuran was dropped After the dropwise addition, stir at room temperature for 12 hours...

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Abstract

The invention relates to an adamantane-containing quaternary ammonium salt ionic liquid and a preparation method thereof. The structural formula of the adamantane-containing quaternary ammonium salt ionic liquid designed and prepared by the invention is shown in the specification, and in the formula, n is equal to 6, 9 or 11. According to the adamantane-containing quaternary ammonium salt ionic liquid disclosed by the invention, 1-adamantanecarboxylic acid is used as a raw material, and the ionic liquid is prepared by the following three steps: firstly, carrying out acylating chlorination reaction on 1-adamantanecarboxylic acid and thionyl chloride to synthesize 1-adamantanecarbonyl chloride, carrying out esterification reaction on the 1-adamantanecarbonyl chloride and OH(CH2)nBr, and thencarrying out quaternization with N,N-dimethylbenzylamine to form the adamantane-containing quaternary ammonium salt ionic liquid. The adamantane-containing quaternary ammonium salt ionic liquid obtained in the invention has the characteristics of mild reaction conditions, easily available raw materials and high product purity, and has potential application prospects in the fields of supramolecular chemistry, catalysis, batteries, nano materials and the like.

Description

technical field [0001] The invention relates to an adamantane-containing quaternary ammonium salt ionic liquid and a preparation method thereof. Background technique [0002] As a new type of environmentally friendly "green solvent", ionic liquids have many unique properties and have attractive application prospects in many fields. Adamantane (tricyclo[3.3.1.1 3,7 ]Decane) is a cyclic tetrahedral hydrocarbon composed of 10 carbon atoms and 16 hydrogen atoms, and the entire ring system has a symmetrical and highly stable structural feature. This rigid ring system and positive symmetric structure determine that adamantane and its derivatives have unique physical and chemical properties: non-toxic, tasteless, high density, high melting point, good thermal stability, good fat solubility, high biological activity, antiviral Strong, extremely lipophilic, etc. By introducing adamantyl groups into ionic liquids, various types of ionic liquids can be designed and synthesized, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C219/12B01F17/18C09K23/18
Inventor 钟星胡彩霞严小威邓慧秋刘伟珍郭建维林海芳
Owner HEZHOU UNIV
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