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Coumarin derivative and preparation method and application in detecting cyanide ion

A technology of coumarins and cyanide ions, which is applied in the direction of chemical reaction analysis of materials, measurement of color/spectral characteristics, material analysis by observing the influence of chemical indicators, etc., to achieve good selectivity and expand High detection range and high detection sensitivity

Active Publication Date: 2013-04-17
山西永津集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since the intensity change is the only identification signal of the intensity sensor, many factors such as instrument error, environmental change, probe concentration, etc. will affect the signal output and thus affect the determination

Method used

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  • Coumarin derivative and preparation method and application in detecting cyanide ion
  • Coumarin derivative and preparation method and application in detecting cyanide ion
  • Coumarin derivative and preparation method and application in detecting cyanide ion

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation and Application of Coumarin Derivatives (A)

[0031]

[0032] (1) In a dry 50 mL round bottom flask, add 0.91 g (6.6 mmol) 2,4-dihydroxybenzaldehyde, 0.6 mL (4 mmol) diethyl malonate, 10 mL absolute ethanol, 0.1 mL Hexahydropyridine and 2 drops of glacial acetic acid were heated and stirred at 80°C under reflux for 6 h, crystals precipitated after cooling, the solid was collected by suction filtration, washed with absolute ethanol, and dried to obtain the product ethyl 7-hydroxycoumarin-3-carboxylate.

[0033] (2) In a dry 25 mL round bottom flask, add 1.64 g (7.0 mmol) ethyl 7-hydroxycoumarin-3-carboxylate, 1.5 g (10.7 mmol) urotropine (hexamethylene tetra amine) and 10 mL of trifluoroacetic acid, heated and stirred at reflux at 85°C for 24 h, after cooling, add 10 mL of 20% (volume fraction) H 2 SO 4 Stir for 1h. Pour the reaction solution into a 50 mL beaker, add 25 mL of water, let it stand still, crystals precipitate out, collect the sol...

Embodiment 2

[0035] Example 2 Preparation of Coumarin Derivatives (A)

[0036] (1) In a dry 50 mL round bottom flask, add 0.91 g (6.6 mmol) 2,4-dihydroxybenzaldehyde, 0.6 mL (4 mmol) diethyl malonate, 10 mL absolute ethanol, 0.1 mL Hexahydropyridine and 2 drops of glacial acetic acid, heated and stirred at 85°C under reflux for 6 h, crystals precipitated after cooling, the solid was collected by suction filtration, washed with absolute ethanol, and dried to obtain the product ethyl 7-hydroxycoumarin-3-carboxylate.

[0037] (2) In a dry 25 mL round bottom flask, add 1.64 g (7.0 mmol) ethyl 7-hydroxycoumarin-3-carboxylate, 1.5 g (10.7 mmol) urotropine (hexamethylene tetra amine) and 10 mL of trifluoroacetic acid, heated and stirred at reflux at 85°C for 24 h, after cooling, add 10 mL of 20% (volume fraction) H 2 SO 4 Stir for 1h. Pour the reaction solution into a 50 mL beaker, add 25 mL of water, let it stand still, crystals precipitate out, collect the solid by suction filtration, and dr...

Embodiment 3

[0039] Example 3 Application of Coumarin Derivatives (A)

[0040] Determination data of coumarin derivatives (A) prepared by Examples (1) and (2):

[0041] 1 H NMR (400 MHz, DMSO-d 6 ): δ 1.31 (t, J = 6.8 Hz, 3H), 1.79 (s, 6H), 2.33 (s, 1H), 2.67 (s, 1H), 4.01 (s, 3H), 4.29 (q, J = 6.0 Hz, 2H), 7.62 (s, 2H), 7.89 (s, 2H), 8.13 (d, J = 16.0 Hz, 1H), 8.52 (d, J = 16.0 Hz, 1H), 8.72 (s, 1H). FT-IR (KBr, cm -1 ): 3444, 2989, 2451, 1771, 1706, 1601, 1539, 1476, 1373, 1284, 1250, 1026, 832, 751, 681. HRMS (ESI): m / z, calcd for (M + ) 418.1600; Found 418.1598.

[0042] UV spectrum test of coumarin derivatives (A) on cyanide ion concentration: add 0.5 mL of 100 μM solution of coumarin derivatives (A) to a 10 mL colorimetric tube, 1 mL of anhydrous methanol, 1 mL buffer solution (Na 2 CO 3 -NaHCO 3， pH = 9.4), and then add concentrations of 0, 10, 20, 40, 60, 80, 95, 150, 200, 300, 400, 500, 600, 700, 900, 1000, 2000, 4000, 6000, 10000 μM sodium cyanide solution. After cons...

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PUM

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Abstract

The invention discloses a ratio-type coumarin derivative which can be used for detecting cyanide ions. The structural formula (I) of the coumarin derivative is described in the specification, wherein R is shown in the specification. The coumarin derivative is used for detecting cyanide ions; the process of detecting the cyanide ion is carried out in a buffer solution of Na2CO3-NaHCO3; and the pH value of the buffer solution is 9.4. The coumarin derivative provided by the invention can be used for uniquely, efficiently and simply detecting the cyanide ions, is applicable to detection on cyanide ions in wastewater generated in industrial processes such as electroplating, chemical engineering, metallurgy, mineral separation and surface treatment, and is high in detection sensitivity and good in selectivity.

Description

technical field [0001] The invention relates to a coumarin derivative, a preparation method thereof, and an application of the derivative for detecting cyanide ions. Background technique [0002] Cyanide ion salts are widely used in industry, including metallurgy, electroplating, dyes, medicine, etc. Cyanide ion salt is a highly toxic substance with a very small lethal dose to humans. In addition to direct ingestion, its vapor and dust can also enter the human body through the respiratory tract or digestive tract, and even penetrate into the skin. The combination of ferric iron makes the cells unable to use oxygen, loses the function of transferring oxygen, and makes the body hypoxic, causing poisoning and even death. [0003] The quantitative determination methods of cyanide ion can be mainly divided into chromatography, spectrometry, electrochemical method and so on. Among them, the spectroscopic method has the advantages of convenience, high sensitivity, and good select...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06G01N21/33G01N21/64G01N21/78
Inventor 郭媛彭梦姣石博柴斌
Owner 山西永津集团有限公司
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