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A kind of organic compound and application thereof for measuring metal ion content in water environment

A technology for organic compounds and water environment, applied in organic chemistry, measurement devices, and analysis by making materials undergo chemical reactions, etc., can solve the problems of special ion identification, cannot be used continuously, cannot realize automatic detection, etc., and achieve mild reaction conditions. , the effect of improving efficiency

Active Publication Date: 2015-11-11
TIANJIN HEOWNS BIOCHEM TECH
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0009] However, although the selectivity of the currently used mercury ion recognition carrier has been further improved, it still cannot specifically identify special ions in the environment, and the currently used mercury ion recognition carrier can only be used for a single determination. If it cannot be used continuously, it will not be able to realize automatic detection

Method used

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  • A kind of organic compound and application thereof for measuring metal ion content in water environment
  • A kind of organic compound and application thereof for measuring metal ion content in water environment
  • A kind of organic compound and application thereof for measuring metal ion content in water environment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the synthesis of ion complexing group

[0061] Synthesis of compound Hg31:

[0062] Hg30 (38g0.25), 1,2-dibromoethane (108ml, 1.25mol), and potassium carbonate (34.60g, 0.25mol) were added to DMF (200ml), heated to 100°C, and kept for 2 After 1 hour, TLC detected that the reaction of the raw materials was complete, spin-dried, and recrystallized from methanol to obtain 46 g of the product. 1H NMR (CDCl3) δ = 2.40 (s, 3H), 3.65 (t, 2H) 6.85 (d, 2H), 7.75 (d, 1H).

[0063] Synthesis of compound Hg32:

[0064] At room temperature, Hg31 (80.0g, 1.5mol), o-methoxyaniline (25.0g, 1mol), potassium carbonate (56.0g, 2.0mol), potassium iodide 1(, 33.5g, 1mol) were added to 300ml of acetonitrile , refluxed overnight, TLC detection, the reaction of the raw materials was completed, spin-dried, and passed through the column to obtain 44g of the product. 1HNMR (CDCl3)8 = 2.38(s, 3), 3.61(t, 2H), 3.85(s, 3H), 4.29(t, 2H), 6.69-6.85(m, 6H) 7.81(d, 1H).

[0065] Synth...

Embodiment 2

[0072] Synthesis of compound Hg35:

[0073] Under ice bath, phosphorus oxychloride (14.2g, 0.09mol) was slowly added dropwise to DMF (14.2ml), stirred in ice bath for 0.5 hour, then a solution of Hg34 (10.0g, 0.018mol) in DMF (10ml) was added dropwise Add it to the above solution, turn it to room temperature and react overnight, TLC detects 50% reaction, pour it into water, extract with EA, dry, spin dry, and pass through the column to obtain 0.8g of the product. 1HNMR (CDCl3) δ=(1.20, 9H), 2.48(s, 3H) 2.57(m, 12H), 3.25(t, 4H), 3.51(t, 2H), 3.81(t, 2H), 3.88(s, 3H) 4.09 (t, 2H), 6.61-7.35 (m, 7H), 9.78 (s, 1H).

[0074] Synthesis of compound Hg36:

[0075] Compound Hg35 (0.1g, 1.77*10 -4 mol) and 2-methyl-1-(3-sulfonylpropyl)naphtho[1,2-d]thiazolium hydroxide inner salt monohydrate (0.06g, 1.8*10 -4 mol) was added to the mixed solution of 0.5ml of acetic acid and 0.5ml of acetic anhydride, reacted at 100°C overnight, the solution turned red, TLC detected the completion of...

Embodiment 3

[0078] Synthesis of Compound Hg37:

[0079] Dissolve 2ml of p-nitroaniline (0.038g, 0.27mmol) in THF: water = 1:1 solution, add sodium nitrite (0.019g, 0.27mmol, under ice-cooling, add dropwise concentrated hydrochloric acid 0.05ml, ice-bath Stir for 1 hour, then add compound 34 (0.1g, 0.18mmol) in THF: water=1: 1 solution in 2ml, stir in ice bath for 2 hours, turn to room temperature overnight, TLC detects that new spots are generated, raw materials are not Complete the reaction, add water, extract three times with EA, dry over anhydrous sodium sulfate, and scrape to obtain an orange-yellow product. 1HNMR (CDCl3) δ=1.38 (m, 9H) 2.26 (s, 3H), 2.46-2.71 (m, 12H), 3.28(t, 4H), 3.57(t, 2H), 3.64(t, 2H), 3.96(s, 3H), 4.04(t, 2H), 6.64(m, 2H), 6.87(m, 2H), 7.05 (m, 1H), 7.50(d, 1H), 7.98(d, 2H), 8.37(d, 2H).

[0080] Test of compound Hg37: 4 mg of the above product (Hg37) was dissolved in 1 mL of a mixture of methanol and water (1:1), and then the solution was prepared into a 50 ...

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Abstract

The invention discloses an organic compound for measuring the content of metal ions in a water environment. The compound is characterized in that N-[2-(N'N'-bi(alkylthiolethyl)aminophenyloxyethyl]-N-alkylthiolethyl-2-alkoxyphenylamine is used as a metal ion complex, a chromophore or fluorophore is introduced to a molecule of the N-[2-(N'N'-bi(alkylthiolethyl)aminophenyloxyethyl]-N-alkylthiolethyl-2-alkoxyphenylamine, and then, a color development indicator or fluorescent indicator of metal ions and particularly mercury, lead and silver ions is generated. The compound disclosed by the invention can also be fixed on a hydrophilic superpolymer, can be prepared into a nonexpendable reversible metal ion fluorescent probe by utilizing the characteristic of the chromophore or fluorophore, and can be suitable for continuously detecting the concentration of metal ions in various environments and particularly suitable for continuously detecting the concentration of mercury ions.

Description

technical field [0001] The invention belongs to the field of organic compounds, and in particular relates to an organic compound which can be used to detect the content of metal ions in water environment and related applications. Background technique [0002] Mercury ion and its derivative methylmercury are one of the most harmful heavy metal pollutants to the environment. It poses an increasing threat to the living environment of human beings. According to the statistics of the US Environmental Protection Agency (EPA), the annual total amount of mercury discharged to the environment due to human daily activities has reached 7,500 tons. The burning of coal, metal smelting, domestic waste disposal, especially the widespread use of energy-saving fluorescent lamps further aggravate mercury pollution [1]. Elemental mercury discharged into the environment is oxidized in the air into ionized mercury with better water solubility, especially divalent mercury, which seeps into rive...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/84C07C323/25C07C319/20C07D311/82C07D311/92C09K11/06G01N21/78G01N21/64
CPCC07C319/20C07C323/25C07D277/84C07D311/82C07D311/92C09K11/06C09K2211/1014C09K2211/1037C09K2211/1088G01N21/6428G01N21/78G01N2021/7786
Inventor 何华瑞王邦臣王蕊娜刘大颖常河西
Owner TIANJIN HEOWNS BIOCHEM TECH
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