Pyrrolidine type chiral Gemini surfactant with linking groups containing ester groups and preparation method thereof

A technology of surfactant and pyrrolidine, which is applied in the field of pyrrolidine chiral Gemini surfactant and its preparation, can solve the problems of synthesis and performance vacancy, and achieve the effect of easy separation and purification, easy degradation, and simple synthesis steps

Active Publication Date: 2018-11-23
长治学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention aims at the problem of the lack of synthesis and performance of existing pyrrole chiral Gemini surfactants, and provides a linker-containing pyrrolidine chiral Gemini surfactant with an ester group and a preparation method thereof

Method used

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  • Pyrrolidine type chiral Gemini surfactant with linking groups containing ester groups and preparation method thereof
  • Pyrrolidine type chiral Gemini surfactant with linking groups containing ester groups and preparation method thereof
  • Pyrrolidine type chiral Gemini surfactant with linking groups containing ester groups and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The structural formula of surfactant (I) is as follows:

[0043] .

[0044] The preparation method of surfactant (I) comprises the steps:

[0045] The first step, the synthesis of bis(N-methyl-L-prolinol) adipate

[0046] Add 9.30 g (80.74 mmol) of N-methyl-L-prolinol, 50 mL of dichloromethane and 12.26 g (121.11 mmol) of triethylamine into a 250 mL three-neck flask, blow in nitrogen, and cool to 0 in an ice bath. ~10°C. Slowly add 7.39 g (40.37 mmol) of adipoyl chloride dropwise, and react for 8 h after the addition of adipyl chloride is complete. After the reaction was over, 100 mL of saturated sodium carbonate was added, and the mixture was stirred for 3 min to separate the layers. The organic layer was washed with water, dried with an appropriate amount of anhydrous magnesium sulfate, decolorized with activated carbon, and rotary evaporated to obtain a colorless viscous liquid, namely bis(N-methyl-L-prolinol) adipate.

[0047] The second step, the synthesis o...

Embodiment 2

[0051] The structural formula of surfactant (II) is as follows:

[0052] .

[0053] The preparation method of surfactant (II) comprises the steps:

[0054] The first step, the synthesis of bis(N-methyl-L-prolinol) adipate

[0055] Add 9.30g (80.74 mmol) of N-methyl-L-prolinol, 80mL of chloroform and 25.68g (242.22mmol) of anhydrous sodium carbonate into a 250mL three-neck flask, blow in nitrogen, and cool in an ice bath to 0~ 10°C. Slowly add 7.39 g (40.37 mmol) of adipoyl chloride dropwise, and react for 6 hours after the addition of adipoyl chloride is complete. After the reaction was over, 100 mL of saturated sodium carbonate was added, and the mixture was stirred for 3 min to separate the layers. The organic layer was washed with water, dried with an appropriate amount of anhydrous magnesium sulfate, decolorized with activated carbon, and rotary evaporated to obtain a colorless viscous liquid, namely bis(N-methyl-L-prolinol) adipate.

[0056] The second step, the sy...

Embodiment 3

[0060] The structural formula of surfactant (III) is as follows:

[0061] .

[0062] The preparation method of surfactant (III) comprises the steps:

[0063] The first step, the synthesis of bis(N-methyl-L-prolinol) succinate

[0064] Add 9.30 g (80.74 mmol) of N-methyl-L-prolinol, 100 mL of anhydrous acetone and 25.55 g (322.96 mmol) of pyridine into a 250 mL three-neck flask, blow in nitrogen gas, and cool in an ice bath to 0-10°C . Slowly add 6.26 g (40.37 mmol) of succinoyl chloride dropwise, and react for 3 h after the addition of succinoyl chloride is complete. After the reaction was completed, 100 mL of saturated sodium carbonate was added, and the mixture was stirred for 3 min to separate the layers. The organic layer was washed with water, dried with anhydrous magnesium sulfate, decolorized with activated carbon, and rotary evaporated to obtain a colorless viscous liquid, that is, bis(N-methyl-L-prolinol) succinate.

[0065] The second step, the synthesis of su...

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Abstract

The invention relates to a pyrrolidine type chiral Gemini surfactant with linking groups containing ester groups and a preparation method thereof, and belongs to the technical field of surfactants, which can solve the problem of lack of synthesizing and property in the existing pyrrolidine type chiral Gemini surfactant. The preparation method comprises the following steps of using pyrrolidine as ahydrophilic head group; using the ester group as a linkage group; firstly, synthesizing alkyl diacid di (N-methyl-L-prolinol) ester; then, synthesizing the surfactant. The preparation method has theadvantages that the synthesizing steps are simple, and the separating and purifying are easy. The prepared pyrrolidine type chiral Gemini surfactant has optical activity and good surface activity.

Description

technical field [0001] The invention belongs to the technical field of surfactants, and in particular relates to a linker-containing ester group-containing pyrrolidine chiral Gemini surfactant and a preparation method thereof. Background technique [0002] Surfactant is an important product in the field of fine chemicals. It has a series of unique application properties such as wetting, penetration and waterproofing, emulsification and demulsification, foaming and defoaming, so it has the reputation of "industrial monosodium glutamate". Many fields such as food, pesticide, medicine and oil extraction have received extensive attention and application. At present, most surfactants are based on petroleum-based raw materials, which have problems such as non-renewable raw materials and low chemical safety. At the same time, the residual surfactants after use will cause serious environmental pollution. Therefore, in order to meet consumers' growing environmental awareness and ind...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/32C07D207/08C09K23/32
CPCC07D207/08C07B2200/07C09K23/00
Inventor 梁亚琴申婧翔李梦瑶王佳佳李慧毛晓明李燕
Owner 长治学院
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