2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative, its preparation method and application

Abstract

The invention provides a 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative, its preparation method and application, the 2-(5-bromo-2-pyridylazo) The ‑5‑diethylaminophenol derivative has a structure shown in formula (I), can selectively recognize uranyl ions, has a lower detection limit, and has better specificity and anti-interference ability. Combining the above 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivatives with basic materials to make colorimetric test paper can effectively identify uranyl ions specifically, and this The derivatives are made into color-changing inks for writing, and the written handwriting can produce obvious color-changing effects after spraying uranyl ions. At the same time, the detection limit is low and the colorimetric effect is remarkable. The detection is simple, fast and efficient, which not only eliminates the expensive and cumbersome instrument characterization process, but also has good real-time and on-site detection capabilities, and is suitable for the analysis and detection of uranyl in environmental samples.

Description

technical field

[0001] The invention relates to the technical field of analysis, in particular to a 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative, a preparation method and application thereof. Background technique

[0002] As we all know, uranium is a radioactive element widely distributed in the earth's crust and oceans. It has a wide range of uses in industrial and agricultural production such as nuclear energy, military fields, and dyeing dyes. However, with the development of the uranium smelting industry, the uranium waste after mining enters the environment. Due to its strong radioactivity and chemical toxicity, if it is not handled properly, it will cause serious health problems to organisms. Studies have shown that long-term exposure to uranium can cause radiation damage to animals and humans or cause irreversible chemical pollution damage to target organs (mainly kidneys and bones).

[0003] Therefore, the detection and monitoring of uranium in the envi...

Examples

preparation example Construction

[0052] The present invention also provides a method for preparing the above-mentioned 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative, comprising the following steps:

[0053] A) mixing triphenylamine 4-boric acid, potassium carbonate, tetrakis(triphenylphosphine)palladium and solvent to obtain the first mixed solution;

[0054] B) reacting a solution of 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol with the first mixed solution at 80-110°C to obtain a second mixed solution;

[0055] C) quenching the second mixed solution with water to obtain a 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative having a structure shown in formula (I);

[0056] Said step A) and step B) are all carried out under the condition of protective gas.

[0057] In the present invention, 4-boric acid triphenylamine and 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol are main reaction raw materials, and described 4-boric acid triphenylamine and 2-(5- The mass ratio of bromo-2-pyridylazo)-5-...

Embodiment 1

[0114] Under nitrogen atmosphere, 4-triphenylamine borate, potassium carbonate solid, tetrakis (triphenylphosphine) palladium and solvent are mixed, obtain the first mixed solution, wherein, potassium carbonate solid and tetrakis (triphenylphosphine) palladium The mass ratio of 1,4-triphenylamine borate to tetrakis(triphenylphosphine)palladium is 1:1.5, and the solvent includes 1,4-dioxane and water with a volume ratio of 2:1 , the dosage ratio of the 4-triphenylamine borate to the solvent is 30mg:2mL.

[0115] Continue to raise the temperature of the first mixed solution to 90° C. under nitrogen atmosphere, and then add the solution of 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol dropwise into the warmed second mixed solution. A mixed solution was reacted at 90° C. for 6 h to obtain a second mixed solution. The mass ratio of the 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol to 4-triphenylamine borate is 1:0.8, and the 2-(5-bromo-2-pyridylazo The solvent in the solution of ...

Embodiment 2

[0119] Under nitrogen atmosphere, 4-triphenylamine borate, potassium carbonate solid, tetrakis (triphenylphosphine) palladium and solvent are mixed, obtain the first mixed solution, wherein, potassium carbonate solid and tetrakis (triphenylphosphine) palladium The mass ratio is 4:1.5, the mass ratio of 4-triphenylamine borate to tetrakis(triphenylphosphine)palladium is 1:1, and the solvent includes N,N-dimethylformamide and N,N-dimethylformamide with a volume ratio of 3:2 Water, the ratio of the amount of triphenylamine 4-borate to the solvent is 30mg: 1mL.

[0120] Continue to raise the temperature of the first mixed solution to 110° C. under nitrogen atmosphere, and then add the solution of 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol dropwise to the heated second mixed solution. The first mixed solution was reacted at 110° C. for 6 h to obtain the second mixed solution. The mass ratio of the 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol to 4-boric acid triphenylamine is 1...

technical field

[0001] The invention relates to the technical field of analysis, in particular to a 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative, a preparation method and application thereof. Background technique

[0002] As we all know, uranium is a radioactive element widely distributed in the earth's crust and oceans. It has a wide range of uses in industrial and agricultural production such as nuclear energy, military fields, and dyeing dyes. However, with the development of the uranium smelting industry, the uranium waste after mining enters the environment. Due to its strong radioactivity and chemical toxicity, if it is not handled properly, it will cause serious health problems to organisms. Studies have shown that long-term exposure to uranium can cause radiation damage to animals and humans or cause irreversible chemical pollution damage to target organs (mainly kidneys and bones).

[0003] Therefore, the detection and monitoring of uranium in the envi...

Examples

preparation example Construction

[0052] The present invention also provides a method for preparing the above-mentioned 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative, comprising the following steps:

[0053] A) mixing triphenylamine 4-boric acid, potassium carbonate, tetrakis(triphenylphosphine)palladium and solvent to obtain the first mixed solution;

[0054] B) reacting a solution of 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol with the first mixed solution at 80-110°C to obtain a second mixed solution;

[0055] C) quenching the second mixed solution with water to obtain a 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol derivative having a structure shown in formula (I);

[0056] Said step A) and step B) are all carried out under the condition of protective gas.

[0057] In the present invention, 4-boric acid triphenylamine and 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol are main reaction raw materials, and described 4-boric acid triphenylamine and 2-(5- The mass ratio of bromo-2-pyridylazo)-5-...

Embodiment 1

[0114] Under nitrogen atmosphere, 4-triphenylamine borate, potassium carbonate solid, tetrakis (triphenylphosphine) palladium and solvent are mixed, obtain the first mixed solution, wherein, potassium carbonate solid and tetrakis (triphenylphosphine) palladium The mass ratio of 1,4-triphenylamine borate to tetrakis(triphenylphosphine)palladium is 1:1.5, and the solvent includes 1,4-dioxane and water with a volume ratio of 2:1 , the dosage ratio of the 4-triphenylamine borate to the solvent is 30mg:2mL.

[0115] Continue to raise the temperature of the first mixed solution to 90° C. under nitrogen atmosphere, and then add the solution of 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol dropwise into the warmed second mixed solution. A mixed solution was reacted at 90° C. for 6 h to obtain a second mixed solution. The mass ratio of the 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol to 4-triphenylamine borate is 1:0.8, and the 2-(5-bromo-2-pyridylazo The solvent in the solution of ...

Embodiment 2

[0119] Under nitrogen atmosphere, 4-triphenylamine borate, potassium carbonate solid, tetrakis (triphenylphosphine) palladium and solvent are mixed, obtain the first mixed solution, wherein, potassium carbonate solid and tetrakis (triphenylphosphine) palladium The mass ratio is 4:1.5, the mass ratio of 4-triphenylamine borate to tetrakis(triphenylphosphine)palladium is 1:1, and the solvent includes N,N-dimethylformamide and N,N-dimethylformamide with a volume ratio of 3:2 Water, the ratio of the amount of triphenylamine 4-borate to the solvent is 30mg: 1mL.

[0120] Continue to raise the temperature of the first mixed solution to 110° C. under nitrogen atmosphere, and then add the solution of 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol dropwise to the heated second mixed solution. The first mixed solution was reacted at 110° C. for 6 h to obtain the second mixed solution. The mass ratio of the 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol to 4-boric acid triphenylamine is 1...

Images