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Synthesis method and application of indole derivative capable of efficiently degrading perfluorinated compounds

A technology of indole derivatives and perfluorinated compounds, which is applied in the field of synthesis of indole derivatives, can solve the problems of insufficient utilization of hydrated electrons, reduced operability, and large dosage of pharmaceuticals, achieving high utilization, Improvement of utilization rate and effect of high utilization rate

Active Publication Date: 2020-08-11
NANJING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Chinese patent number is 200910051114.8, and the application publication date is November 17, 2010. The patent discloses a method for degrading perfluorinated compounds through photoreduction and desorption. Ultraviolet light is used to stimulate the production of reducing substances such as potassium thiosulfate and potassium sulfite. Hydrated electrons efficiently reduce PFOA, but this method needs to be carried out under anaerobic conditions and alkaline solutions, which will lead to increased treatment costs and reduced operability in practical applications
The existing method of using indole acetic acid to generate hydration electrons to degrade PFCs still has the disadvantages that the utilization rate of hydration electrons is not high enough and the dosage of chemicals is large.

Method used

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  • Synthesis method and application of indole derivative capable of efficiently degrading perfluorinated compounds
  • Synthesis method and application of indole derivative capable of efficiently degrading perfluorinated compounds
  • Synthesis method and application of indole derivative capable of efficiently degrading perfluorinated compounds

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Experimental program
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Effect test

Embodiment 1

[0028] Chemical synthesis of a novel indole derivative:

[0029] 5g of indole, 5.2g of n-hexadecylamine and 3.3mL of 35% formaldehyde solution were dissolved in 50mL of ethanol solution, and 1.2g of ZnCl was added 2 as a catalyst reaction. The reaction was refluxed at 55°C for 10 hours. The reacted product was filtered, evaporated to dryness to 10mL, separated and purified through a silica gel column (200-300 mesh), and finally obtained 3g of product A ( figure 1 ), the yield is 60%.

Embodiment 2

[0031] Chemical synthesis of a novel indole derivative:

[0032] (1) adopt indole, n-hexadecylamine, formaldehyde and Virahol identical with embodiment 1, take 5.1g glacial acetic acid as catalyst reaction, through same preparation and purification method, finally obtain 9.2g product A, synthetic The yield was 87%.

[0033] (2) The obtained product A was dissolved in isopropanol at a concentration of 10 mg / L. Agilent 1200 liquid chromatograph was used in series with Agilent 6120 mass spectrometer detector and electrospray ionization source was used to determine the purity of product A. Use Waters X-BrigdeShield C18 chromatographic column (50mm*4.6mm*3.5um) to separate, use water (containing 0.5% trifluoroacetic acid) and acetonitrile (containing 0.5% trifluoroacetic acid) as the mobile phase for gradient elution, and the flow rate is 2mL / min, the organic phase increased from 5% to 100% within 1.6min and kept for 1.4min. The purity of product A finally obtained was >88%. C...

Embodiment 3

[0036]This synthetic method is also suitable for synthesizing derivatives with different alkyl chain lengths, and the n-hexadecylamine of Example 2 is replaced with other carbon chain lengths of alkylamines, including n-dodecylamine (H 2 N-C 12 h 25 ), n-octylamine (H 2 N-C 8 h 17 ), n-pentylamine (H 2 N-C 5 h 11 ), with glacial acetic acid as catalyst reaction, through the same preparation and purification method, synthesize product B respectively, product C, product D ( figure 1 ), the synthetic yields were all over 80%.

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Abstract

The invention relates to a synthesis method and application of an indole derivative capable of efficiently degrading perfluorinated compounds. The synthesis method comprises the following steps: dissolving a proper amount of indole, alkylamine and formaldehyde in an ethanol solution, and carrying out reflux reaction for a period of time under proper conditions by using ZnCl2 or glacial acetic acidas a catalyst; and carrying out vacuum drying on the reaction product, and carrying out column chromatography purification and separation to finally obtain the product indole derivative. The alkyl chain of the indole derivative obtained by the invention has certain hydrophobicity, in addition, the positively charged amino groups can effectively capture PFCs in a polluted water body and form a self-assembled inclusion with the PFCs, so that hydrated electrons generated by illumination directly attack the PFCs in the inclusion without long-distance mass transfer, the hydrated electron utilization rate is greatly improved, and the material adding proportion is reduced. Degradation application of the indole derivative can be suitable for neutral pH conditions, interference of dissolved oxygenis avoided, and the toxicity of a solution after reaction is low.

Description

technical field [0001] The invention relates to the field of highly efficient degradation of fluorine compounds, in particular to a synthesis method and application of indole derivatives capable of efficiently degrading perfluorinated compounds. Background technique [0002] Perfluorinated compounds (PFCs), a family of synthetic aliphatic chemicals in which all C atoms are saturated with F atoms, are widely used in industrial and commercial products, including waxes, varnishes, high-temperature lubricants, protective coatings, and foam fire extinguishing agents , carpets, clothing, furniture, fabrics and food packaging, etc. Due to the mass production and use of such chemicals, they have been widely detected in various environmental media (such as surface water, bottom sediment, atmospheric particles, and sludge). Because PFCs are environmentally persistent and bioaccumulative, they have developmental toxicity, endocrine disruption, immunotoxicity and potential carcinogenic...

Claims

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Application Information

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IPC IPC(8): C07D209/14C02F1/28C02F1/58C02F101/36C02F101/34
CPCC07D209/14C02F1/285C02F1/583C02F2101/36C02F2101/34Y02C20/30C02F2305/00C02F1/68
Inventor 金鑫谷成
Owner NANJING UNIV
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