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A kind of imidazole ionic liquid type chiral stationary phase and its preparation method and application

A technology of chiral stationary phase and ionic liquid, which is applied in separation methods, chemical instruments and methods, solid adsorbent liquid separation, etc. It can solve the problem of poor separation performance of chiral compounds, unsatisfactory separation analysis, insufficient coverage, etc. problems, to achieve good chiral separation effect, novel and stable structure, and easy-to-obtain raw materials

Active Publication Date: 2019-03-12
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, imidazole-based ionic liquid chiral stationary phases have not been reported in the literature, and other types of chiral stationary phases are not very good for the separation of some highly polar, especially chiral compounds with carboxyl groups.
Moreover, considering the diversity of chiral compounds due to the difference in the type and quantity of polar groups and chiral groups, the coverage of existing chiral fixed relative chiral compounds is still not enough to meet the needs of separation and analysis.

Method used

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  • A kind of imidazole ionic liquid type chiral stationary phase and its preparation method and application
  • A kind of imidazole ionic liquid type chiral stationary phase and its preparation method and application
  • A kind of imidazole ionic liquid type chiral stationary phase and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of chiral imidazole

[0039] Mix (S)-1-phenylethylamine (14.69g, >99%, 0.12mol) and ammonia water (8.174g, 25-28%, 0.12mol), and its mixture is called solution A; Glyoxal Aqueous solution (17.41g, >40%, 0.12mol) and formaldehyde aqueous solution (9.74g, >37%, 0.12mol) are mixed uniformly, and its mixture is called solution B. Add solution A and solution B dropwise from two dropping funnels into a 150mL three-necked flask at the same time, keep the reaction slightly boiling under stirring, dropwise is completed in about 10 minutes, continue to stir and reflux for 3 hours and then stop. After the reaction is completed, distill the water under reduced pressure with a water pump, then use an oil pump to distill the product, and collect the fraction at 150-160°C (5-10mmHg). The product chiral N-(α-methylbenzyl)imidazole is a light yellow liquid (17.55g, yield 85%), figure 2 The structure of the product and its 1 H NMR spectrogram, it can b...

Embodiment 2

[0041] Example 2: Preparation of imidazole ionic liquid chiral stationary phase

[0042] Put 13g of blank silica gel into a 250mL three-necked flask, and add 130mL of 10% hydrochloric acid aqueous solution, stir and heat to reflux, suction filter after 8-10hr, wash with distilled water until neutral, then put it in an oven, 110°C Dry for 12 hours to obtain activated silica gel.

[0043] Weigh 12 g of activated silica gel and place it in a 150 mL three-necked flask, add 95 mL of anhydrous toluene, 10.5 mL of 3-chloropropyltrimethoxysilane, and 100 μL of triethylamine as a catalyst through a dropping funnel. Under the protection of nitrogen, the reaction was refluxed for 24 hours. After the reaction was completed, filter, bonded silica gel was extracted with acetone for 24 hours, and after drying, it was capped with 6 mL trimethylchlorosilane, and the reaction time was about 6 hours. After capping and filtering, the bonded silica gel was extracted with acetone for 24 hours, an...

Embodiment 3

[0048] Embodiment 3: the preparation of chiral chromatographic column

[0049] Using the homogenization method, the resulting chiral stationary phase was packed into a 4.6mm×250mm HPLC column: Disperse 3.5g of the target stationary phase filler in 30mL of n-hexane / isopropanol (90 / 10, v / v) A homogenate was made, and 40 mL of n-hexane was used as a displacement liquid, and filled into a stainless steel column under a pressure of 5800 psi. Utilize high-performance liquid chromatography, use biphenyl as the detection substance to measure retention time and column efficiency, the mobile phase is methanol / water=90 / 10 (v / v), isocratic elution, the detection wavelength is DAD 254nm, and the flow rate is 1.0 mL / min. The prepared chromatographic column was tested for column efficiency, and the results are shown in Table 2.

[0050] Table 2 Column efficiency measurement results

[0051]

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Abstract

The invention belongs to an efficient stationary phase of liquid chromatography and particularly relates to an imidazole ionic liquid chiral stationary phase and a preparation method and application. The ionic liquid chiral stationary phase shown in the first formula is obtained by bonding chiral imidazole to a silica gel carrier through a silane coupling agent, wherein R1 is phenyl, benzyl, naphthyl, o-methylphenyl, m-methylphenyl or p-methylphenyl, and R2 is halogen. The preparation process includes the steps that firstly, silica gel is subjected to activating pretreatment, and activated silica gel is prepared; secondly, the activated silica gel is coupled through the silane coupling agent, and silylated silica gel with halogen at the terminal is prepared; thirdly, corresponding chiral imidazole is prepared through a chiral ethylamine raw material; fourthly, the silylated silica gel reacts with chiral imidazole to prepare the imidazole ionic liquid chiral stationary phase. According to the chiral stationary phase prepared through the method, raw materials are easy to obtain, operation steps are simple, the chiral stationary phase has the characteristic of ionic liquid and stability of silica gel in the use process, a good chiral separation effect can be achieved on various polar chiral compounds. Please see the first formula in the description.

Description

technical field [0001] The invention belongs to a stationary phase of high-performance liquid chromatography, and in particular relates to an imidazole ionic liquid chiral stationary phase, a preparation method and an application thereof. Background technique [0002] In recent years, with the development of research fields such as bioengineering, life science, medical science, material science, and environmental science, the separation and determination of chiral enantiomers has gradually become a research hotspot for relevant workers. Although the physical and chemical properties of enantiomers are almost identical, their biochemical and pharmacological effects are often different. After a chiral drug enters a living body, there is a process of recognition, accommodation and interaction between it and the chiral biological system. Different enantiomers have differences in binding to enzymes, ion channels and receptors. However, they show different physiological characteri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29B01J20/30B01D15/38
CPCB01D15/3833B01J20/29
Inventor 黄少华王涛杨海燕
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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