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A kind of preparation method of fullerene polyaza bridge water-soluble derivative

A technology of fullerene polyaza bridges and derivatives, which is applied in the field of carbon nanomaterials, can solve the problems of increasing the difficulty of mass production operations, low dissolution of fullerenes, and inability to achieve large-scale preparation of fullerene products. The effect of excellent solubility in water phase, simple operation method and simple synthesis process

Active Publication Date: 2018-05-18
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Considering that the two have low ability to dissolve fullerenes (such as: toluene and o-dichlorobenzene can respectively dissolve C 60 2.8,27mg / mL, RuoffR.et al.Journal of Physical Chemistry, 1993,97:3379-3383), when carrying out industrialized large-scale preparation, must consume huge volume of toluene or o-dichlorobenzene, so the process will be extremely Greatly increases the operational difficulty of mass production, and cannot achieve economical and reasonable large-scale preparation of water-soluble fullerene products

Method used

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  • A kind of preparation method of fullerene polyaza bridge water-soluble derivative
  • A kind of preparation method of fullerene polyaza bridge water-soluble derivative
  • A kind of preparation method of fullerene polyaza bridge water-soluble derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Large scale preparation of C 60 Water-soluble product C with azide ethanol 60 (NCH 2 CH 2 Oh) 14 (Azafullerol 1)

[0044] (1) Add 60.0g C 60 Solid powder and 362.8g of liquid 2-azidoethanol (substance ratio: 1:50) were respectively fed into a 500mL three-necked reaction bottle, connected to a condenser tube and a mechanical stirring device, without adding an organic solvent, directly in an inert gas atmosphere Under mechanical stirring;

[0045] (2) The reaction system is warmed up to reflux, and after being incubated for 72 hours, the heating is stopped;

[0046] (3) Part of the unreacted 2-azidoethanol is removed by distillation under reduced pressure, and the residue is washed repeatedly with ether and ethyl acetate to further remove unreacted 2-azidoethanol and non-water-soluble alcohols with a small number of additions. Derivatized product, then add deionized water and ultrasonically extract for several times until the supernatant is colorless, th...

Embodiment 2

[0054] Example 2: Preparation C 60 Water-soluble addition product C with azidoethylamine 60 (NCH 2 CH 2 NH 2 ) 12 (Azafulleramine 1)

[0055] (1) 12.0g C 60 The solid powder and 143.5g of liquid 2-azidoethylamine (the amount of material to feed ratio is 1:100) are respectively fed into a 250mL three-port reactor, connected to a condenser tube and a mechanical stirring device, without adding an organic solvent, directly in an inert gas Mechanical stirring under atmosphere;

[0056] (2) The reaction system is warming up to reflux, and after being incubated for 48 hours, the heating is stopped;

[0057] (3) Part of the unreacted 2-azidoethylamine is removed by distillation under reduced pressure, and the residue is washed repeatedly with ether and ethyl acetate to further remove unreacted 2-azidoethylamine and the lesser addition number. The non-water-soluble derivatized product was then ultrasonically extracted with deionized water for several times until the supernatant w...

Embodiment 3

[0059] Example 3: Preparation C 60 A water-soluble derivative of fullerene-based polyglycine with azidoacetic acid C 60 (NCH 2 COOH) 13

[0060] (1) Add 20.0g C 60 The solid powder and 140.4g of liquid 2-azidoacetic acid (the amount of material to feed ratio is 1:100) were respectively fed into a 250mL three-port reactor, connected to a condenser tube and a mechanical stirring device, without adding an organic solvent, directly in an inert gas atmosphere Under mechanical stirring;

[0061] (2) The reaction system is heated to reflux, and after being incubated for 12 hours, the heating is stopped;

[0062] (3) Part of the unreacted 2-azidoacetic acid is removed by distillation under reduced pressure, and the residue is washed repeatedly with ether and ethyl acetate to further remove unreacted 2-azidoacetic acid and non-water-soluble compounds with a small number of additions. The derivatized product was then ultrasonically extracted with deionized water for several times ...

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Abstract

The invention discloses a method for preparing water-soluble derivatives of fullerene polyaza bridges, which comprises the following steps: (1) feeding fullerene and liquid azide organic compounds at room temperature into a reactor without adding The organic solvent is directly mechanically stirred under an inert gas atmosphere, and the ratio of the amount of the two materials fed is 1:50 to 100; one end of the carbon chain of the azide organic compound is linked to a hydrophilic functional group; (2) the reaction system Heat up to reflux, keep warm for 12 to 72 hours, then stop heating; (3) Evaporate part of the unreacted azide organic compound, wash the residue with an organic solvent, then extract it with a solvent, filter the extract and remove the solvent to obtain a solidified (4) refining the crude product to obtain a solid product of pure fullerene polyaza bridge water-soluble derivatives. The invention provides a new method which is convenient in a liquid phase system, avoids adding organic solvents and can prepare water-soluble derivatives of fullerene polyaza bridges on a large scale.

Description

technical field [0001] The invention belongs to the field of carbon nanometer materials, and relates to a preparation method of a fullerene polyaza bridge water-soluble derivative. Background technique [0002] Take the "star molecule" C 60 The typical representative hydrophobic fullerene material can be chemically modified into water-soluble derivatives by specific hydrophilic reagents, such as: fullerene reacts with hydroxylating reagents to generate fullerene alcohols; Bingle-Hirsch reaction generates water-soluble richerenes Multi-addition derivatives of allyl malonic acid; react with a variety of amino acids to form water-soluble derivatives of fullerene amino acids. In addition, our research group has reported that fullerenes in liquid solvent systems undergo polyaddition reactions of nitrates to generate water-soluble derivatives of fullerene polyaza bridges (Chinese invention patent number: Zl201010522925.4.; He R. et al . Nanomedicine: Nanotechnology, Biology and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/04C07C227/40C07C229/14C07C209/00C07C209/84C07C211/41C07C213/02C07C213/10C07C215/08
CPCC07C209/00C07C209/84C07C213/02C07C213/10C07C227/04C07C227/40C07C229/14C07C211/41C07C215/08
Inventor 邰付菊何睿闫凤鸣雷彩燕刘艳杰熊凤霞范宜康
Owner HENAN AGRICULTURAL UNIVERSITY
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