Adamantane-containing Gemini surfactant and synthesis method thereof

A technique for surfactants and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of Gemini surfactants that have not been reported in literature, and achieve improved amphiphilicity and easy availability of raw materials , the effect of mild reaction conditions

Active Publication Date: 2019-06-04
HEZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Gemini surfactants that simultaneously introduce two amphiphilic molecules at position 1 have not been reported in the literature.

Method used

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  • Adamantane-containing Gemini surfactant and synthesis method thereof
  • Adamantane-containing Gemini surfactant and synthesis method thereof
  • Adamantane-containing Gemini surfactant and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: Gemini surfactant containing adamantane (R=C 12 h 25 )Synthesis

[0025] Weigh 1.8g (0.01mol) of 1-adamantanecarboxylic acid into a 100mL three-necked 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 liquid, heated up to 80°C under the protection of nitrogen to react until the solution was a transparent clear liquid, and evaporated to dryness under reduced pressure after completion to obtain yellow 1-adamantanecarbonyl chloride solid with a yield of 95%.

[0026] Under the protection of nitrogen, dissolve 2.0g (0.01mol) of 1-adamantanecarbonyl chloride in ether, keep the temperature at 0°C, and add 2.4g (0.013mol) of 3,3'-iminobis(N, The solution formed by N-dimethylpropylamine) and diethyl ether has a white precipitate. After the dropwise addition, the temperature is raised to 40°C for 5 hours. The precipitate is filtered to ...

Embodiment 2

[0028] Embodiment 2: Gemini surfactant containing adamantane (R=C 16 h 33 )Synthesis

[0029] 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%.

[0030] Under the protection of nitrogen, dissolve 2.0g (0.01mol) of 1-adamantanecarbonyl chloride in ether, keep the temperature at 20°C, and add 2.2g (0.012mol) of 3,3'-iminobis(N, The solution formed by N-dimethylpropylamine) and diethyl ether has a white precipitate. After the dropwise addition, the temperature is raised to 30°C for 10 hours. The precipitate is filtered ...

Embodiment 3

[0032] Embodiment 3: Gemini surfactant containing adamantane (R=C 18 h 37 )Synthesis

[0033] 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%.

[0034] Under the protection of nitrogen, dissolve 2.0g (0.01mol) of 1-adamantanecarbonyl chloride in diethyl ether, keep the temperature at 15°C, and add 2.1g (0.011mol) of 3,3'-iminobis(N, The solution formed by N-dimethylpropylamine) and diethyl ether produced white precipitates. After the dropwise addition, the temperature was raised to 25°C for 8 hours, ...

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Abstract

The invention belongs to the technical field of organic chemical industry surface activity, and particularly relates to synthesis of an adamantane-containing Gemini surfactant, wherein the adamantane-containing Gemini surfactant has a structural formula defined in the specification, R represents CnH2n+1, and n is 12,16 or 18. According to the present invention, the Gemini surfactant is obtained byusing 1-adamantanecarboxylic acid as a raw material through a three-step reaction, wherein the three-step reaction comprises that 1-adamantanecarboxylic acid and thionyl chloride are subjected to anacyl chlorination reaction to synthesize 1-adamantanecarbonyl chloride, the 1-adamantanecarbonyl chloride and 3,3'-iminobis(N,N-dimethylpropylamine) are subjected to an amidation reaction to prepare akey intermediate bis(N,N-dimethylpropylamine)adamantane-1-formamide, and finally the intermediate and a long chain brominated alkane are subjected to quaternization to form the adamantane-containingGemini surfactant. According to the present invention, the obtained adamantane-containing Gemini surfactant has characteristics of mild reaction condition, easily available raw materials and simple and easy-performing operation, and has potential application prospects in the fields of supramolecular chemistry, nanometer materials, special washing and the like.

Description

technical field [0001] The invention relates to an adamantane-containing Gemini surfactant and a synthesis method thereof. Background technique [0002] Gemini surfactants, also known as gemini surfactants, are formed by two identical or almost identical amphiphilic molecules linked together by chemical bonds at or near their hydrophilic headgroups A new class of surfactants. Compared with traditional surfactants, Gemini surfactants have higher surface activity, very low Krafft point, good water solubility, and better application performance, and are known as a new generation of surfactants. 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 ...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/62B01F17/22C09K23/22
Inventor 钟星严小威胡彩霞朱东建郭建维邓慧秋刘伟珍王邦均
Owner HEZHOU UNIV
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