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Cholesterol zwitterionic compound containing double bond, preparation method thereof, and ionic liquid multiphase emulsion prepared therefrom

A technology of zwitterions and ionic liquids, applied in the fields of steroids, organic chemistry, etc., to achieve the effect of stable interface and simple preparation method

Active Publication Date: 2019-05-14
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of a single small molecule ionic compound as a stabilizer to prepare an ionic liquid multiphase emulsion has not been reported.

Method used

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  • Cholesterol zwitterionic compound containing double bond, preparation method thereof, and ionic liquid multiphase emulsion prepared therefrom
  • Cholesterol zwitterionic compound containing double bond, preparation method thereof, and ionic liquid multiphase emulsion prepared therefrom
  • Cholesterol zwitterionic compound containing double bond, preparation method thereof, and ionic liquid multiphase emulsion prepared therefrom

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The cholesterol-like zwitterionic compounds containing double bonds shown in Synthesis III-1, the specific synthetic route and synthetic method are as follows:

[0037]

[0038]1. Under nitrogen protection, add 10mL dichloromethane and 0.27g (0.4386mmol) compound of formula I-1 to the three-necked flask, inject 0.3668mL (2.6316mmol) triethylamine with a needle; The acid chloride was dissolved in 10 mL of dichloromethane, stirred in an ice bath, then added dropwise to a three-necked flask, and reacted for 4 hours under an ice bath. After the reaction was completed, it was extracted with saturated saline (twice), and extracted with secondary water ( 2 times), rotary evaporation removes dichloromethane, obtains yellow colloidal solid, room temperature vacuum drying, obtains the compound of formula II-1, and its structural characterization result is: 1 H-NMR (400MHz, CDCl 3 )δ (ppm): 6.44 (1H, CHHCHCOO-), 6.16 (1H, CHHCHCOO-), 5.83 (1H, CHHCHCOO-), 5.35 (1H, -CH-(choles...

Embodiment 2

[0041] The ionic liquid multiphase emulsion was prepared by adopting the cholesterol-like zwitterionic compound containing double bonds in Example 1, and the specific method was as follows:

[0042] Dissolve 0.005g of cholesterol-like zwitterionic compounds containing double bonds in 100 μL of cyclohexane, and dissolve 0.01 g of 1-butyl-3-methylimidazole chloride in 100 μL of distilled water, then mix the two solutions, and place at room temperature Under mechanical stirring for 2 minutes, the rotating speed was 11400 rpm to obtain the ionic liquid multiphase emulsion (see figure 1 ), it can be seen from the figure that the droplet size in the obtained multiphase emulsion is uniform.

Embodiment 3

[0044] In Example 2, the chlorinated 1-butyl-3-methylimidazole used was replaced with an equal mass of 1-allyl-3-vinylimidazolium chloride salt, and the other steps were the same as in Example 2 to obtain an ionic liquid poly phase emulsion (see figure 2 ).

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Abstract

The invention discloses a double-bond-containing cholesterol zwitterionic compound, a preparation method thereof and an ionic liquid based multiphase emulsion prepared from the double-bond-containing cholesterol zwitterionic compound. The structural formula of the compound is shown in the specification, wherein R in the formula represents C1-C4 alkyl groups, m is an integer in the range of 6-12, and n is 3 or 4. The double-bond-containing cholesterol zwitterionic compound has obvious amphipathicity, the ionic liquid based multiphase emulsion can be prepared from the double-bond-containing cholesterol zwitterionic compound only serving as a stabilizer and an ionic liquid serving as one phase with a one-step method, the preparation method is simple, and the obtained multiphase emulsion has good stability and is applicable to various oil-phase systems.

Description

technical field [0001] The invention relates to a cholesterol type zwitterionic compound containing double bonds, a preparation method of the compound and an ionic liquid multiphase emulsion prepared by using the compound as a stabilizer. Background technique [0002] Ionic liquid (IL: Ionic Liquid) is composed of anions and cations, and is a salt compound that is liquid at room temperature or near room temperature. It is generally composed of organic cations and inorganic or organic anions. Common cations include quaternary ammonium salt ions, quaternary Phosphonium salt ions, imidazolium salt ions, pyrrole salt ions, etc., and anions include halogen ions, tetrafluoroborate ions, hexafluorophosphate ions, and the like. Ionic liquids have properties such as low vapor pressure, low melting point, wide liquid range, designability, recyclability, and high stability, which are unmatched by many traditional solvents and are a kind of "green solvent". Due to their unique physical...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J41/00
CPCC07J41/0044
Inventor 彭军霞田晴张媛媛张红霞
Owner SHAANXI NORMAL UNIV
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