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Tripod hexaurea neutral ligand as well as preparation method and application thereof

A neutral ligand and ligand technology, applied in the preparation of urea derivatives, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of low reusability and high cost of heavy metal barium salts, and achieve a wide range of applications. High stability, easy availability of raw materials, and high reproducibility

Pending Publication Date: 2022-07-01
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the nitro group at the tail of the ligand is prone to enhanced reduction reaction, which has certain limitations in practical application; and affected by solubility, the reusability of the ligand is low; at the same time, the ligand is recovered using BaCl 2 Precipitation method, the cost of introducing heavy metal barium salt is relatively high, and there is a greater risk of environmental pollution

Method used

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  • Tripod hexaurea neutral ligand as well as preparation method and application thereof
  • Tripod hexaurea neutral ligand as well as preparation method and application thereof
  • Tripod hexaurea neutral ligand as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A preparation method of compound I, the method steps are as follows:

[0035] (1) In a 250mL two-necked flask, o-nitrophenyl isocyanate (5.0g, 30.5mmol, 3.2eq) was dissolved in toluene (80mL) to obtain solution I; in a 25mL dropping funnel, tris(2-aminoethyl)amine ( 1.4g, 9.6mmol, 1eq) was dissolved in dry THF (10mL) to obtain solution II, solution I was added dropwise to solution II at a rate of 2 seconds / drop, and tris(2-aminoethyl)amine was detected by TLC The reaction is complete, and the product point (the ratio shift value R f = 0.6, developing solvent: dichloromethane (DCM) and methanol (CH 3 The volume ratio of OH) was 50:2), the reaction was completed, the solid-liquid was separated, the solid was washed with toluene (10 mL×3) and diethyl ether (10 mL×3) in turn, and dried in vacuo to obtain the intermediate product 1 (5.9 g, yield is 98%); 1 H NMR (400MHz, 298K, DMSO-d 6 , ppm): δ=9.35 (s, 3H), 8.24 (d, 3H, J=8.48Hz), 7.99 (d, 3H, J=9.84Hz), 7.57 (t, 3H, J...

Embodiment 2

[0043] A kind of preparation method of tripodal hexaurea neutral ligand, described method steps are as follows:

[0044] (1) Dissolve hexylamine (1.91g, 18.8mmol, 1.0eq) in dry THF (60mL) in a 125mL dropping funnel to obtain solution VI; under nitrogen atmosphere, add 4-nitrophenyl chloroformate in a 250mL three-necked flask (4.50g, 22.4mmol, 1.2eq) was dissolved in dry THF (60mL) to obtain solution VII and heated to 80°C, then solution VI was added dropwise at a rate of 2 seconds / drop, and after 14 hours of reaction, TLC detected 4 -Nitrophenyl chloroformate reacts completely, generates product point (specific shift value R f = 0.7, developing solvent: DCM), the reaction was completed, the system was clear, concentrated to dryness under reduced pressure, cooled to room temperature, added n-hexane (150 mL), fully ultrasonically stirred until the precipitation was complete, filtered the precipitate, n-hexane (10 mL × 3 ) washed the precipitate and dried to obtain the intermedi...

Embodiment 3

[0051] A kind of preparation method of tripodal hexaurea neutral ligand, described method steps are as follows:

[0052] (1) Dodecylamine (3.0g, 16.2mmol, 1.0eq) was dissolved in dry THF (60mL) in a 125mL dropping funnel to obtain solution VI; under nitrogen atmosphere, 4-nitrophenylchloroformic acid was placed in a 250mL three-necked flask Ester (5.0 g, 24.9 mmol, 1.5 eq) was dissolved in dry THF (60 mL) to obtain solution VII and heated to 80°C, then solution VI was added dropwise at a rate of 2 sec / drop, after 14 hours of reaction, TLC detection 4-Nitrophenyl chloroformate reacts completely, generates product point (ratio shift value R f = 0.7, developing solvent: DCM), the reaction was completed, the system was clarified, cooled to room temperature, a large amount of white precipitate was precipitated, the precipitate was removed by filtration, the filtrate was concentrated to dryness under reduced pressure, cooled to room temperature, added methanol (150 mL), and fully ul...

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Abstract

The invention relates to a tripodal hexaurea neutral ligand as well as a preparation method and application thereof, and belongs to the technical field of high polymer materials. A triamine bridging group is used as a framework, a repeatable o-phenylenediurea structure is used as a basic unit, and a tripodal hexaurea neutral ligand is formed through tail end substituents of-CnH2n + 1,-PhCnH2n + 1 or-PhOCnH2n + 1. The preparation method comprises the following steps: directly reacting isocyanate with a compound I to obtain a tripodal hexaurea neutral ligand; or the amine substance is converted into carbamate, and then the carbamate reacts with the compound I to obtain the tripodal hexaurea neutral ligand. The ligand can be used for identifying anions, and especially has high extraction efficiency and high selectivity on sulfate radicals.

Description

technical field [0001] The invention relates to a tripodal hexaurea neutral ligand, a preparation method and an application thereof, and belongs to the technical field of polymer materials. Background technique [0002] Anions play an important role in research fields such as environmental science, life science, biology and medicine. For example, high concentrations of SO 4 2- It can easily lead to mineralization of water body, high permanent hardness index, and induce the formation of industrial scale; while NO 3 - and Cl - It is the main component of industrial pollution. Therefore, the identification and separation of anions has important research and application value. The current wastewater treatment methods have the characteristics of high cost, low selectivity and complex process, which are difficult to meet the actual production needs. Wu Biao et al. reported a tripodal hexaurea neutral ligand with a nitro group at the tail, which can specifically bind to sulf...

Claims

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Application Information

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IPC IPC(8): C07C273/18C07C275/40C07C269/04C07C271/44C07C271/58B01D11/04
CPCC07C273/1827C07C273/1836C07C275/40C07C269/04B01D11/0492C07C271/44C07C271/58Y02P10/20
Inventor 吴彪陈思琪赵伟
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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