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Gemini type quaternary ammonium salt surfactant containing natural terpene structure, synthesis method and application thereof

A technology of surfactants and synthetic methods, applied in the fields of application, chemical instruments and methods, botany equipment and methods, etc., can solve the problem of insufficient research on biological activity and application performance, limited variety and quantity, and restrictions on popularization and application, etc. problems, to achieve the effect of good application prospects, strong surface activity, and good hydrophilicity

Pending Publication Date: 2020-11-06
GUANGXI UNIV FOR NATITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, there are not many varieties and quantities of derivatives containing natural terpene structures, especially the research on biological activity and application performance is not enough, which limits their further promotion and application

Method used

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  • Gemini type quaternary ammonium salt surfactant containing natural terpene structure, synthesis method and application thereof
  • Gemini type quaternary ammonium salt surfactant containing natural terpene structure, synthesis method and application thereof
  • Gemini type quaternary ammonium salt surfactant containing natural terpene structure, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A kind of synthetic method containing natural terpene structure Gemini type quaternary ammonium salt surfactant, its synthetic method comprises the steps:

[0031] In a 50 ml round bottom flask, 3.68 g (20 mmol) ω-chloromethyl camphene and 1.16 g (10 mmol) tetramethylethylenediamine were added, and heated to reflux at 85 °C for 6 h with magnetic stirring. After the reaction was completed, cool to room temperature, add 10 ml of ethyl acetate, and stir thoroughly to precipitate the product, which was collected by decantation and filtration to obtain a gray crude product. The crude product was recrystallized and purified with ethyl acetate as a solvent, and after vacuum drying at 45 °C for 4 h, the off-white N 1 ,N 2 -Bis(camphenylmethyl)-N 1 ,N 1 ,N 2 ,N 2 - 3.50 g of tetramethylethane-1,2-diammonium chloride (Ia), yield 72.2%.

[0032] FT-IR of compound Ia, 1 H-NMR and 13 C-NMR spectroscopy data and attribution are as follows:

[0033] FT-IR υ / cm -1 : 2960, ...

Embodiment 2

[0037] Contain the synthetic method of natural terpene structure Gemini type quaternary ammonium salt surfactant, its synthetic method comprises the steps:

[0038] In a 50 ml round bottom flask, 5.29 g (21 mmol) ω-chloromethyl longifolene and 1.16 g (10 mmol) tetramethylethylenediamine were added, and heated to reflux at 85°C for 6 h with magnetic stirring. After the reaction was completed, cool to room temperature, add 10 ml of ethyl acetate, stir well, and let it stand still to precipitate the product, which was collected by decantation and filtration to obtain a gray crude product. The crude product was purified by recrystallization using ethyl acetate as a solvent, and after vacuum drying at 45 °C for 4 h, the off-white solid N 1 ,N 2 -Bis(longifenylmethyl)-N 1 ,N 1 ,N 2 ,N 2 - Tetramethylethane-1,2-diammonium chloride (Ib) 4.35g, yield 70.0%.

Embodiment 3

[0040] Contain the synthetic method of natural terpene structure Gemini type quaternary ammonium salt surfactant, its synthetic method comprises the steps:

[0041] In a 50 ml round bottom flask, add 3.68 g (20 mmol) ω-chloromethyl camphene and 1.30 g (10 mmol) N,N,N,N-tetramethyl-1,3-propanediamine, in Magnetic stirring was carried out at 90°C and heated to reflux for 5.5 hours. After the reaction was completed, cool to room temperature, add 10 ml of acetone, and stir thoroughly to precipitate the product, which was collected by decantation and filtration to obtain a gray crude product. The crude product was purified by recrystallization using acetone as a solvent, and after vacuum drying at 45 °C for 4 h, the off-white N 1 ,N 3 -Bis(camphenylmethyl)-N 1 ,N 1 ,N 3 ,N 3 - Tetramethylpropane-1,3-diammonium chloride (Ic) 3.75g, yield 75%.

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Abstract

The invention belongs to the technical field of synthesis of forest fine chemicals, and particularly discloses a Gemini type quaternary ammonium salt surfactant containing a natural terpene structure,a synthesis method and application thereof. The surfactant has a natural terpene structure and an allyl quaternary ammonium functional group, and has a structure shown as formula (I), wherein R1 is ahydrophobic group and is allyl containing the natural terpene structure; R2 is a bridging group, and is ethylene group, 1, 3-propylidene or 1, 4-butylidene; and X is chlorine or bromine. According tothe synthesis method of the Gemini type quaternary ammonium salt surfactant containing the natural terpene structure, allyl halide containing the natural terpene structure and binary tertiary amine are used as the raw materials, and a target product is prepared through quaternization reaction. The surfactant has strong surface activity, good hydrophilicity and bacteriostatic activity, can inhibitthe growth of bacteria, fungi and algae, and can be used as a bactericide and an algicide.

Description

technical field [0001] The invention belongs to the technical field of synthesis of forest product fine chemicals, and in particular relates to a Gemini-type quaternary ammonium salt surfactant containing a natural terpene structure and a synthesis method and application thereof. Background technique [0002] α-pinene, β-pinene, camphene, longifolene and other natural terpenes exist in many natural plant essential oils, and are also important turpentine products, with certain biological activities such as anti-inflammatory, analgesic, antibacterial or anticancer, It has important applications and development prospects in the fields of medicine and pesticides. However, due to their volatile and weakly hydrophilic characteristics, it is difficult to directly apply them to hydrophilic systems or environments to exert their due medicinal effects. To this end, people use their chemical properties to modify or derivatize the molecular structure, introduce and construct functional...

Claims

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Application Information

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IPC IPC(8): C07C211/63C07C209/12B01F17/18A01N33/12A01P1/00A01P13/00C09K23/18
CPCC07C211/63C07C209/12A01N33/12C07C2602/42C07C2603/78C09K23/00
Inventor 蓝虹云黄道战霍尚朝莫君明
Owner GUANGXI UNIV FOR NATITIES
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