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Chelating agent having multidentate aminocarboxylic-type dimer, preparation method and application thereof, and separation medium therewith

A technology for separating medium and dimer, which is applied in the direction of solid adsorbent liquid separation, ion exchange of chelate, separation method, etc., can solve the problems of only suitable synthesis method, uncommon, complicated steps, etc., and achieve experimental operation. The effect of convenience and safety, short steps and simple reaction device

Inactive Publication Date: 2017-07-14
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned dimer synthesis steps are cumbersome, some uncommon reagents are involved in the reaction, and the synthesis method is only suitable for NTA or EDTA monomers

Method used

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  • Chelating agent having multidentate aminocarboxylic-type dimer, preparation method and application thereof, and separation medium therewith
  • Chelating agent having multidentate aminocarboxylic-type dimer, preparation method and application thereof, and separation medium therewith
  • Chelating agent having multidentate aminocarboxylic-type dimer, preparation method and application thereof, and separation medium therewith

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preparation example Construction

[0082] A kind of preparation method of described polydentate aminocarboxyl dimer chelating agent, it comprises the steps:

[0083] 1) Diethylenetriamine reacts with an amino protection reagent to protect the primary amino group;

[0084] 2) Diethylenetriamine after primary amino group protection reacts with γ-glycidyl etheroxypropyltrimethoxysilane;

[0085] 3) The product obtained in step 2) is subjected to a deprotection reaction to remove the protecting group of the primary amine;

[0086] 4) The primary amino group of the product obtained in step 3) reacts with the aminocarboxyl ester to form an amide bond.

[0087] Preferably, in step 1), the molar ratio of the diethylenetriamine to the amino-protecting reagent is 1:1.9 to 2.1; more preferably, the molar ratio of the diethylenetriamine to the amino-protecting reagent is 1: 2.

[0088] Preferably, in step 1), the protecting group for protecting the primary amine includes one of tert-butoxycarbonyl, methoxycarbonyl, etho...

Embodiment 1

[0099] Preparation of TM1

[0100]

[0101] In a 150mL flask, dissolve 1.10mL (10.30mmol) of diethylenetriamine (DETA) in 20mL of tetrahydrofuran, then add 4.28mL (30.90mmol) of triethylamine, and stir in a low-temperature reaction bath at 0°C for 30min; weigh 5.2131 g (20.60mmol) 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (Boc-on), and dissolved in 60mL tetrahydrofuran, placed in a constant pressure dropping funnel, added dropwise to the above in solution. After 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile was completely dropped into the flask, the reaction was continued at 0° C. for 4 h in a low-temperature reaction bath, and then left at room temperature for 3 h.

[0102] 1.1 TLC analysis

[0103] This step reaction carries out thin-layer chromatography to each reactant, developing agent is dichloromethane (DCM):methanol (MeOH)=9:1, the R of raw material DETA f The value is 0.16, because there are three amino groups in the molecular structure of DETA...

Embodiment 2

[0110] Under alkaline conditions, TM1 reacts with γ-GLDP to generate TM2:

[0111]

[0112] Measure 20mL of ethanol (EtOH) and put it in a beaker, then weigh 1.3g of sodium metal, cut it into small pieces and place it in it, and transfer it to a 150mL flask after the sodium metal has completely reacted; weigh 2.9160g (9.61mmol) of TM1 Add to the flask and stir to dissolve completely; accurately measure 1.5mL (6.79mmol) of γ-glycidyl etheroxypropyltrimethoxysilane (γ-GLDP), dissolve it in 3mL of ethanol, and add it dropwise under rapid stirring in the flask. The flask was placed in a water bath at 80°C and refluxed for 12h under rapid stirring.

[0113] After the reaction finished, the ethanol in the flask was completely steamed out with a rotary evaporator; 50 mL of distilled water was added to the flask to hydrolyze EtONa; the solution was rotary evaporated again at a temperature of 55° C., and the ethanol in the aqueous solution was steamed; 6 mol / L HCl was added to the...

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Abstract

The invention provides a chelating agent having a multidentate aminocarboxylic-type dimer, a preparation method and an application thereof, and a separation medium therewith. The structure of the chelating agent is represented as the formula (A). The chelating agent has strong chelating capability, is easy to prepare, and can be used for producing a novel separation medium with the multidentate aminocarboxylic-type dimer as a ligand. The invention also provides a novel separation medium with the multidentate aminocarboxylic-type dimer as the ligand, and a preparation method and an application thereof, wherein the novel separation medium is produced by modifying a stationary phase with the chelating agent having the multidentate aminocarboxylic-type dimer. The synthesis method is simple. The separation medium has dual functions of ion exchange chromatography and metal-chelating chromatography and can significantly improve stability of an IMAC column.

Description

technical field [0001] The invention relates to a class of chelating agents, in particular to a multidentate aminocarboxyl dimer chelating agent and its preparation method, application and separation medium. Background technique [0002] Since the concept of immobilized metal affinity chromatography (IMAC) was proposed in 1975 [Porath, et al. Nature, 1975, 197-204], ion exchangers and metal chelating agents with aminocarboxyl separation media as ligands are traditional Chinese medicine, One of the commonly used methods for separation and purification of target components in the fields of chemical engineering and biological engineering. In this method, the separation medium is the key material in the whole separation technology, and its consumption accounts for about 50% of the production cost. For this type of separation medium, unfixed metal ions can be used as cation exchangers to separate some positively charged target components under a wide range of acidity. Remove me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18B01J20/22B01D15/36
CPCY02P20/55B01D15/361B01J20/223B01J2220/44C07F7/1804C07F7/1892
Inventor 李蓉陈斌张开言栗时玉马晓迅
Owner NORTHWEST UNIV(CN)
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