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Calixarene amide derivative stationary phase and preparation method and application thereof

An aromatic hydrocarbon amide and derivative technology, which is applied in the field of a calixarene amide derivative stationary phase and its preparation, can solve the problems of low separation efficiency and low separation purity, and achieves a simple preparation method, good application prospect and high bonding amount. Effect

Active Publication Date: 2016-07-20
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The currently reported derivatization groups are mainly calixarene derivatives such as ether, ester, amide, carboxyl, hydroxime and other calixarene derivatives obtained by modifying the lower edge of calixarene. However, the above studies all choose to modify the lower edge of calixarene. The method will affect the selective coordination of each group on the lower edge of the calixarene and the metal ion, and the calixarene derivatives prepared by the above modification method can usually only show one kind when used in the above technical fields. Separation mode, resulting in low separation efficiency and low separation purity

Method used

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  • Calixarene amide derivative stationary phase and preparation method and application thereof
  • Calixarene amide derivative stationary phase and preparation method and application thereof
  • Calixarene amide derivative stationary phase and preparation method and application thereof

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Embodiment 1

[0024] like figure 1 As shown, the stationary phase of a calixarene amide derivative provided in this example includes a calixarene group, a proline group and an aminopropyltriethoxy bonded silica gel group, and its structural formula is shown in the following formula, The spheres represent the activated silica chains:

[0025] .

[0026] The calixarene amide derivative stationary phase described in this embodiment can be passed such as figure 2 Shown reaction process obtains, and concrete preparation process comprises the following steps:

[0027] Synthesis of calixarene proline derivatives (I): Take 0.8g of de-tert-butylcalixarene in a 50mL round bottom flask, add 20mL of tetrahydrofuran solution under magnetic stirring, then add 1g of L-proline, 2mL of Glacial acetic acid and 1 mL of formaldehyde aqueous solution with a mass fraction of 37% were reacted at room temperature for 36 hours, filtered and washed 5 times with tetrahydrofuran, and the obtained solid was recry...

Embodiment 2

[0037] The calixarene amide derivative stationary phase provided in this example has the same structural formula as that in Example 1.

[0038] This embodiment also provides a preparation method for preparing the stationary phase of the calixarene amide derivative, the whole reaction process is as follows figure 2 As shown, the specific preparation process is roughly the same as the preparation steps in Example 1, except that:

[0039] In the synthesis step of calixarene proline derivatives (I), 1.5 g of de-tert-butyl calixarene dissolved in 40 mL of tetrahydrofuran solution and 5 g of L-proline, 3 mL of glacial acetic acid and 2 mL of mass percent are 30% aqueous formaldehyde solution was used for the reaction.

[0040] In the acid chlorination step of the calixarene proline derivative, 1.9 g of the calixarene proline derivative was reacted with 3 mL of oxalyl chloride in anhydrous dichloromethane.

[0041] In the preparation step of aminopropyltriethoxysilane-bonded silic...

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Abstract

The invention provides a calixarene amide derivative stationary phase and a preparation method and application thereof. The stationary phase comprises calixarene groups, praline groups and aminopropyl triethoxy bonded silica gel groups. It is found through research that the stationary phase has RPLC / HILIC mixed mode behaviors and has obvious advantages in the aspect of separation and analysis of complex samples, that is, hydrophobic retention characteristics are displayed under an organic phase in a low proportion; hydrophilic retention characteristics are displayed under the organic phase in a high proportion; hydrophobic compounds can be separated out under the RPLC mode, and polar micromolecular compounds or biological samples can be separated out under the HILIC mode. The preparation method includes the steps of synthesis of a calixarene amide derivative, acylating chlorination of the calixarene amide derivative, preparation of aminopropyl triethoxy bonded silica gel and preparation of a calixarene amide derivative stationary phase finished product. The preparation method is simple, mild, high in bonding amount, small in toxicity and good in reproducibility.

Description

technical field [0001] The invention relates to the field of materials, in particular to a stationary phase of calixarene amide derivatives, a preparation method and application thereof. Background technique [0002] Calixarene substances have a unique chemical structure, and their skeleton is a three-dimensional cavity structure composed of benzene rings, which can have hydrophobic, inclusion, and π-π interactions with guest molecules. As the third-generation supramolecular compound, calixarene integrates the advantages of crown ether and cyclodextrin. It is not only easy to obtain raw materials, but also has low toxicity; the cavity size of the molecule is adjustable; the lower edge is a lively hydroxyl group, which can be introduced by reaction A wide variety of groups; the tert-butyl group on the upper edge can be easily removed to introduce other functional groups. According to the number n of benzene rings, it is named calix[n]arene. Calix[4]arene, calix[6]arene and ...

Claims

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Application Information

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IPC IPC(8): B01J20/282B01J20/30B01D15/08
CPCB01D15/08B01J20/282B01J2220/52
Inventor 张永明张文芬杜慧芳张书胜班付国吴宁鹏
Owner ZHENGZHOU UNIV
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