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Adamantyl quaternary ammonium salt and preparation method thereof

A technology of adamantyl and quaternary ammonium salts, applied in the direction of reductive alkylation preparation, preparation of amino compounds, chemical instruments and methods, etc., can solve problems such as poor microbial effect, small antibacterial spectrum, and difficulty in large-scale production, and achieve Low ecotoxicity of the product, mild reaction conditions, simple and easy operation

Inactive Publication Date: 2009-10-28
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Quaternary ammonium compounds are an important class of fine chemicals, which can be used as main components of detergents, bactericides, antistatic agents, softeners, and templating agents. Fields such as medicine, pharmacy, and new material preparation have extensive and important purposes, and the substituting group on the N atom of reported quaternary ammonium salt compound is mostly straight-chain alkyl or aryl, so that the type and range of application of quaternary ammonium salt are limited. Limitations, for example, when polyalkyl quaternary ammonium salt compounds are used as disinfectants, they have good bactericidal activity only at higher concentrations, and they are not effective against some microorganisms, especially for some viruses, with a small antibacterial spectrum, and for clear water Viruses are ineffective, and disinfection applications are limited
In order to expand the types and applications of quaternary ammonium salt compounds, in recent years, the research and development of novel quaternary ammonium salts has been continuously carried out, wherein Gemini quaternary ammonium salt cationic surfactants (CN101385957, CN101337169, CN101279218, US 6,794,345, US 6,777,384) are known for their excellent The surface activity, antistatic, bactericidal and other properties have aroused general interest, but the preparation and purification technology of gemini quaternary ammonium cationic surfactants are relatively complicated, and large-scale production is difficult.

Method used

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  • Adamantyl quaternary ammonium salt and preparation method thereof
  • Adamantyl quaternary ammonium salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 15.1g of amantadine and 189mL of methanol to a 500mL three-necked flask equipped with a reflux condenser, heat while stirring, first add 46g of formic acid at 10°C within 40min, and at 50°C, add 46g of formaldehyde within 4.5h; then raise the temperature To 70°C, react for 30h. After the reaction was completed, the sodium hydroxide solution was used to adjust the alkalinity, the upper solution was separated, and washed with water until the water layer was neutral, and the organic layer was vacuum-dried to obtain adamantyl dimethyl tertiary amine with a yield of 91%.

[0022] Put 15g of adamantyl dimethyl tertiary amine and 185mL of methanol into a 500mL three-necked flask, then add 53.1g of benzyl chloride, raise the temperature to 60°C and continue to stir for 20 hours, then distill off the solvent under reduced pressure, wash with excess ether, vacuum After drying, the corresponding adamantyl dimethyl benzyl quaternary ammonium salt was obtained with a yield of 97...

Embodiment 2

[0024] Add 15.1g of amantadine and 19mL of n-pentanol to a 100mL three-necked flask equipped with a reflux condenser, heat while stirring, add 9.2g of formic acid within 40 minutes at 20°C, and add 6g of formaldehyde within 4.5h at 65°C ; Then the temperature was raised to 120°C, and the reaction was carried out for 5h. After the reaction was completed, the sodium hydroxide solution was used to adjust the alkalinity, the upper layer solution was separated, and washed with water until the water layer was neutral, and the organic layer was vacuum-dried to obtain adamantyl dimethyl tertiary amine with a yield of 88%.

[0025] Put 15g of adamantyl dimethyl tertiary amine and 9.5mL of n-pentanol into a 100mL three-necked flask, then add 10.7g of benzyl chloride, then raise the temperature to 120°C and continue stirring for 3 hours, then distill off the solvent under reduced pressure, and use excess Washing with ether and drying in vacuo gave the corresponding adamantyl dimethyl ben...

Embodiment 3

[0027] Add 30g of amantadine and 200mL of isopropanol to a 500mL three-neck flask equipped with a reflux condenser, heat while stirring, first add 46g of formic acid within 40 minutes at 35°C, and add 24g of formaldehyde within 4.5h at 50°C; then Raise the temperature to 80°C and react for 21h. After the reaction was completed, the sodium hydroxide solution was used to adjust the alkalinity, the upper solution was separated, and washed with water until the water layer was neutral, and the organic layer was vacuum-dried to obtain adamantyl dimethyl tertiary amine with a yield of 92%.

[0028] Put 30g of adamantyl dimethyl tertiary amine and 190mL of isopropanol into a 500mL three-necked flask, then add 25.3g of benzyl chloride, then raise the temperature to 80°C and continue stirring for 9 hours, then distill off the solvent under reduced pressure, and use excess ether Washing, vacuum drying to obtain the corresponding adamantyl dimethyl benzyl quaternary ammonium salt, yield 9...

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Abstract

The invention discloses an adamantyl quaternary ammonium salt and a preparation method thereof. The structural formula of the adamantyl quaternary ammonium salt is shown as right formula, wherein R represents phenmethyl or alkyl containing 1 to 18 carbon atoms; and X represents Cl, Br or I. The preparation method of the adamantyl quaternary ammonium salt adopts amantadine as a material and adopts two-step reaction as follows: adopting amantadine to synthesize adamantyl dimethyl-tert-amine and then synthesizing the adamantyl quaternary ammonium salt through quaterisation of the adamantyl dimethyl-tert-amine. The invention has easy operation, mild reaction process, high yield and purity and low product eco-toxicity. The cation surface active agent of the adamantyl quaternary ammonium salt can be potentially applied to high and new technology fields of micro-electronics, biomedicine, pharmacy, nanometer material and the like.

Description

technical field [0001] The invention relates to an adamantyl quaternary ammonium salt and a preparation method thereof. Background technique [0002] Quaternary ammonium compounds are an important class of fine chemicals, which can be used as main components of detergents, bactericides, antistatic agents, softeners, and templating agents. Fields such as medicine, pharmacy, and new material preparation have extensive and important purposes, and the substituting group on the N atom of reported quaternary ammonium salt compound is mostly straight-chain alkyl or aryl, so that the type and range of application of quaternary ammonium salt are limited. Limitations, for example, when polyalkyl quaternary ammonium salt compounds are used as disinfectants, they have good bactericidal activity only at higher concentrations, and they are not effective against some microorganisms, especially for some viruses, with a small antibacterial spectrum, and for clear water Viruses are ineffecti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/62C07C209/24C07C209/12
Inventor 郭建维朱乐杰关念云刘卅孙保兴
Owner GUANGDONG UNIV OF TECH
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