Compound for determining content of metal ions in water environment, and its application

A metal ion, water environment technology, applied in the direction of analysis by chemical reaction of materials, organic chemistry, chemical instruments and methods, etc., can solve the problem of lack of selectivity of zinc ions

Active Publication Date: 2015-01-21
FORLIGHTS DETECTION TECH LLC SUZHOU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Another object of the present invention is to provide an organic compound used in the detection of cadmium and mercury ion content in the water environment, which

Method used

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  • Compound for determining content of metal ions in water environment, and its application
  • Compound for determining content of metal ions in water environment, and its application
  • Compound for determining content of metal ions in water environment, and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1: the synthesis of ion complexing group

[0084] Synthesis of compound C22: 2-nitro-4,5-dimethylaniline (C21) (29.9g0.18mol), 1,2-dibromoethane (235ml, 2.71mol), N,N-di Isopropylethylamine (DIEA, 90ml, 0.543mol) and 4-N, N-dimethylaminopyridine (DNAP, 3.10g, 0.025mol) were added to a three-necked flask, heated to 120°C, and kept warm for 18 After 1 hour, TLC detects that 2 / 3 of the raw materials have reacted, cooled, spin-dried the excess 1,2-dibromoethane, dissolved the solid in 100ml dichloromethane and 100ml water, washed the organic phase 3 times with water, and dried over anhydrous sodium sulfate , filtered, the solvent was spin-dried, the solid was purified through a column, and recrystallized from methanol to obtain 17 g of a yellow product (yield 30%). 1H NMR (CDCl3) δ=2.20(s, 3H), 2.25(s, 3H), 3.60(t, 2H), 3.78(t, 2H), 6.85(m, 1H), 7.25(m, 1H), 8.06 (s, 1H).

[0085]Synthesis of compound C23: C22 (6.8g0.025mol), aniline (2.31g, 0.025mol), potassi...

Embodiment 2

[0094] Synthesis of compound C50: 2 ml of p-nitroaniline (0.035 g, 0.27 mmol) was dissolved in tetrahydrofuran (THF) THF: water = 1:1 solution, sodium nitrite (0.017 g, 0.27 mmol was added, under ice-cooling, Add 0.05 ml of concentrated hydrochloric acid dropwise, stir in an ice bath for 1 hour, then add compound C25 (0.1 g, 0.18 mmol) in 2 ml of a solution of THF:water=1:1, stir in an ice bath for 2 hours, and turn to room temperature overnight. TLC detects that there is a new point to generate, a small amount of raw material has not reacted, add water, extract three times with EA, dry over anhydrous sodium sulfate, scraper, obtain orange-yellow product 0.06g (51%).1H NMR (CDCl ) δ=1.23( m, 12H), 2.26(m, 6H), 3.60(m, 4H), 4.00-4.20(m, 16H), 6.55-6.85(m, 5H), 7.15(m, 2H), 7.98(d, 2H) , 8.37(d, 2H).

[0095] Synthesis of compound C51: Dissolve compound C50 (0.06g, 0.08mmol) in methanol (2ml), add 0.1N sodium hydroxide (6ml), heat to 80°C, keep for 5min, cool, and stir overnigh...

Embodiment 3

[0097] Example 3: Synthesis of compound C27: under ice bath, phosphorus oxychloride (7.7g, 0.05mol) was slowly added dropwise in DMF (8.0ml), stirred in ice bath for 0.5 hour, and then C25 (6.0g, 0.01 mol) of DMF (10ml) solution was added dropwise to the above solution, turned to room temperature and reacted overnight, TLC detected that the reaction was complete, poured into water, extracted with EA, dried, spin-dried, and passed through the column to obtain 3.0g of product (yield 48 %). 1H NMR (CDCl3) δ=1.23(m, 12H), 2.20(m, 6H), 3.55(m, 4H), 4.00-4.20(m, 16H), 6.60-6.85(m, 4H), 7.15(m, 2H), 9.80 (s, 1H).

[0098] Synthesis of compound C60: compound C27 (0.2g, 3.2*10 -4 mol) and 2-methyl-1-(3-sulfonylpropyl)naphtho[1,2-d]thiazolium hydroxide inner salt monohydrate (0.1g, 3.2*10 -4 mol) was added to the mixed solution of acetic acid (1.0ml) and acetic anhydride (1.0ml), reacted overnight at 100°C, the solution turned red, TLC detected that the reaction was complete, spin-dr...

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Abstract

The invention discloses an organic compound for detecting the content of metal ions. The compound adopts diethylenetriamine as a complexation main body, allows one ethylidene and amino groups to be aromatized and converted into 1,2-diaminobenzene and aniline in order to form anilinoethyl phenylenediamine, three amino groups are connected with different complexing groups, and a series of organic compounds formed in the invention can be used as metal ion complexes. The complexes and metal ion complexes, especially cadmium and mercury ion complexes, form a complex capable of causing the color or fluorescence change of an indicator in order to detect the content of metal ions. The compound can be applied in environmental detection, and can also be applied in the detection of the field of biomedicines.

Description

technical field [0001] The invention relates to a compound for detecting the content of metal ions in the water environment and its application, in particular to an organic compound which can be used for detecting the content of cadmium and mercury ions in the water environment and its application. Background technique [0002] Metal cadmium is one of the very important industrial raw materials, widely used in metallurgy, electroplating, battery and pigment industries. Over-exploitation and use of cadmium ore and immature smelting technology in recent decades have made cadmium metal one of the most serious heavy metal pollutants to the environment, especially the pollution of natural water systems, which has seriously affected people's daily life. Life, such as cadmium-containing rice has appeared in many rice-growing areas in southern my country. my country has also made very strict regulations on the content of cadmium metal in drinking water quality standards. However, a...

Claims

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Application Information

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IPC IPC(8): C07D311/90C07C245/08C07D221/06C07D401/14C09K11/06G01N21/78G01N21/64
CPCC07C245/08C07D221/06C07D311/90C07D401/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/64G01N21/78
Inventor 何华瑞
Owner FORLIGHTS DETECTION TECH LLC SUZHOU
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