CN111253388A - Preparation method of fluorescent probe test paper for detecting copper content in sewage - Google Patents
Preparation method of fluorescent probe test paper for detecting copper content in sewage Download PDFInfo
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- CN111253388A CN111253388A CN202010097521.9A CN202010097521A CN111253388A CN 111253388 A CN111253388 A CN 111253388A CN 202010097521 A CN202010097521 A CN 202010097521A CN 111253388 A CN111253388 A CN 111253388A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6443—Fluorimetric titration
Abstract
The invention relates to a preparation method of fluorescent probe test paper for detecting the copper content in sewage; the fluorescent probe test paper mainly comprises an organic small-molecule fluorescent material as shown in a formula (I) and potassium iodide; the fluorescent probe test paper is distinguished obviously under different heavy metal copper concentrations, can semi-quantitatively detect the copper ion concentration in the sewage generated by smelting, metal processing and electroplating, and has substantial significance; the fluorescent test paper for detecting the heavy metal copper ions has the advantages of simple preparation, low detection limit, sensitive reaction, high efficiency and the like.
Description
Technical Field
The invention relates to a preparation method of fluorescent probe test paper for detecting copper content in sewage, belonging to the field of sewage detection.
Background
Cu in water2+When the content is too high, not only aquatic organisms but also human health are threatened. Cu2+The content is the necessary index of sanitary standard of drinking water, Cu enriched in human body2+Too high a content can cause liver and kidney damage, gastrointestinal dysfunction, cognitive dysfunction and emotional disorder, and even death. Therefore, research and development can realize the search and development of Cu with low cost, easy operation, high sensitivity and good selectivity in aqueous solution2+The detection method has very important practical significance and use value.
The traditional detection of heavy metal ions mainly uses an electrochemical method, but the electrochemical method can only detect total heavy metal ions and cannot accurately measure single heavy metal copper ions. The test paper method is characterized in that certain specific color developing agents are attached to the test paper, and when the color developing agents are contacted with heavy metal ions, the color of the test paper is changed, so that the types and the content of the heavy metals can be analyzed. The test paper method has the advantages of convenience, low price, high analysis speed, simple operation, suitability for field detection and the like. The conventional common test paper method relies on visual observation, has high randomness, causes insufficient detection precision and high detection limit, and is mainly used for qualitative heavy metal detection at present; however, the research and development of the fluorescent probe test paper specially used for detecting heavy metal cadmium ions still basically belong to a blank state at present.
Disclosure of Invention
Aiming at the technical defects, the invention provides the preparation method of the fluorescent probe test paper for detecting the copper content in the sewage, which has the advantages of simple synthesis, low detection limit, sensitive reaction, high efficiency and the like, and solves the defects of insufficient detection precision and high detection limit of a test paper method on the market. The organic micromolecule fluorescent test paper also has the characteristic of wide application range, the heavy metal copper ions can be detected only by a small handheld fluorescent detector, and the content range of the heavy metal copper ions can be distinguished according to the fluorescence intensity detected by the handheld fluorescent detector. Compared with the traditional electrochemical qualitative detection of the content of heavy metals in the environment, the organic small-molecule fluorescent probe test paper has the advantages of lower price, more convenient and faster use, capability of greatly improving the working efficiency and wide application prospect.
The synthetic route of the organic micromolecule fluorescent probe for detecting the heavy metal copper ions is as follows:
the specific reaction steps are as follows:
(1) 4-chloro-8-hydroxy-2-methylquinoline and methyl iodide or dimethyl sulfate are put in n-butanol solution, the reaction is carried out under constant temperature and pressure magnetic stirring, the reaction time is about 4 hours, and the reaction temperature is 50-70 ℃. The system gradually changed from light yellow to purple with the precipitation of a tan solid. After the reaction is finished, adding twice equivalent of ethyl acetate, increasing solid precipitation, and washing a filter cake by using 3mL of ethanol to obtain a pure methylated intermediate a.
(2) The reaction of the intermediate b is carried out in a constant-temperature oil bath kettle, the reaction temperature is 60-80 ℃, condensation reflux is carried out, and the reactant 1, 3-dibromopropane is excessive. As the reaction proceeded, the color of the system gradually changed from clear to milky with the formation of solids. The solid is precipitated more by initial washing with ethyl acetate. D was obtained in the same manner.
(3) The molar ratio of ammonia to intermediate b was about 5: 1, the reaction solvent is glycerol or n-butanol, the reaction temperature is 80-100 ℃, and the reaction time is 2-5 h. The ammonia water can provide a stronger alkaline environment for the reaction, is beneficial to the condensation reaction of the amido and the intermediate b, and the condensation reaction is carried out to obtain c, and the e is obtained by the same method.
(4) And (3) performing equimolar mass of a and e in a constant-temperature oil bath kettle, heating for 3-5h at 50-70 ℃ by taking 5-10 times of n-butyl alcohol as a solvent and organic base as a catalyst, and primarily washing by using ethyl acetate to obtain a black solid f.
(5) And (3) reacting f and c with equivalent weight in an n-butanol system, adding an organic base as a condensation catalyst, heating the reaction to 130 ℃ from room temperature, and finally separating out black solids in the reaction system. After the reaction was complete, it was cooled to room temperature and an equal volume of ethyl acetate was added, more solid precipitated. The filter cake is washed with 0.5-1.5 times of methanol. The product was a reddish brown or black powder solid (I).
The invention aims to provide a preparation method of synthetic copper ion probe test paper.
The invention further aims to provide the application of the copper ion fluorescent probe test paper in semi-quantitative detection of copper ions in the sewage generated in smelting, metal processing and electroplating.
The preparation method of the fluorescent probe test paper of the invention specifically comprises the following operations:
soaking the blank filter paper in an acetone dispersion solution of the organic small-molecule fluorescent compound material and potassium iodide, taking out the filter paper after soaking for a period of time, placing the filter paper in a clean and ventilated place, and naturally drying the filter paper in the air to obtain the fluorescent test paper for detecting the heavy metal copper ions.
Further, the blank filter paper is soaked in an acetone dispersion solution of the organic small-molecule fluorescent compound for 10-15 minutes.
A method for detecting heavy metal copper ions by using the fluorescent test paper specifically comprises the following operations: taking a piece of fluorescent test paper, dissolving the solution of the heavy metal copper ions to be detected by using an acetone solution, immersing the test paper in the acetone solution, and taking out the test paper after 3-10 seconds; the test paper is placed under a fluorescent lamp for observation and comparison, and at the moment, the higher the content of heavy metal copper ions is, the stronger the fluorescence intensity is.
Has the advantages that: according to the heavy metal copper ion organic small molecule fluorescent probe test paper provided by the invention, the acetone solution of the organic small molecule fluorescent compound emits almost no fluorescence under a fluorometer, the acetone solution of the organic small molecule fluorescent compound is gradually dropped into the Tris-HCl solution containing heavy metal copper ions, so that the fluorescence spectrum is enhanced, and when the concentration of the organic small molecule fluorescent compound reaches 2 mu M, the intensity is about 42 times of the original intensity. Therefore, the fluorescent test paper provided by the invention has the advantages of obvious phenomenon and high sensitivity when being used for detecting heavy metal copper ions. The heavy metal copper ion organic small molecule fluorescent probe test paper and the detection method using the heavy metal copper ion organic small molecule fluorescent probe test paper have the advantages of simple preparation, easy operation, easy carrying and good anti-interference performance, can achieve the purposes of naked eye identification and field inspection implementation, and have better application prospects.
Drawings
FIG. 1 is a fluorescence curve of organic small molecule fluorescent compound (I).
FIG. 2 is a graph of titration of heavy metal copper ions of organic small molecule fluorescent compound (I) in Tris-HCl.
FIG. 3 is a graph of titration of heavy metal copper ions in acetone by organic small molecule fluorescent compound (I).
FIG. 4 is a comparison of fluorescent test paper at different concentrations of heavy metal copper ions.
FIG. 5 is a comparison of organic small molecule fluorescent compound (I) in cadmium ion fluorescent probe test paper for detecting sewage.
Detailed description of the preferred embodiments
EXAMPLE 1 Synthesis of organic fluorescent Small molecules
(1) The reaction is carried out under constant temperature and pressure magnetic stirring, the reaction time is about 4 hours, and the reaction temperature is 50-70 ℃. The system gradually changed from light yellow to purple with the precipitation of a tan solid. After the reaction is finished, adding twice equivalent of ethyl acetate, increasing solid precipitation, and washing a filter cake by using 3mL of ethanol to obtain a pure methylated intermediate a.
(2) The reaction of the intermediate b is carried out in a constant-temperature oil bath kettle, the reaction temperature is 60-80 ℃, condensation reflux is carried out, and the reactant 1, 3-dibromopropane is excessive. As the reaction proceeded, the color of the system gradually changed from clear to milky with the formation of solids. The solid is precipitated more by initial washing with ethyl acetate. D was obtained in the same manner.
(3) The molar ratio of ammonia to intermediate b was about 5: 1, the reaction solvent is glycerol or n-butanol, the reaction temperature is 80-100 ℃, and the reaction time is 2-5 h. The ammonia water can provide a stronger alkaline environment for the reaction, is beneficial to the condensation reaction of the amido and the intermediate b, and the condensation reaction is carried out to obtain c, and the e is obtained by the same method.
(4) And (3) performing equimolar mass of a and e in a constant-temperature oil bath kettle, heating for 3-5h at 50-70 ℃ by taking 5-10 times of n-butyl alcohol as a solvent and organic base as a catalyst, and primarily washing by using ethyl acetate to obtain a black solid f.
(5) And (3) reacting f and c with equivalent weight in an n-butanol system, adding an organic base as a condensation catalyst, heating the reaction to 130 ℃ from room temperature, and finally separating out black solids in the reaction system. After the reaction was complete, it was cooled to room temperature and an equal volume of ethyl acetate was added, more solid precipitated. The filter cake was washed with 0.9-fold amount of methanol. The product was a reddish brown or black powder solid (I).
Example 2 graph of titration of heavy metal copper ions in Tris-HCl by small organic molecule fluorescent compound
The organic small-molecule fluorescent compound stock solution of the present invention was diluted to a concentration of 5 μ M, heavy metal copper ions of different concentrations were added, and the fluorescence intensities thereof were measured with a spectrofluorometer (slit width 10, scanning speed 200nm, Ex 520nm), and the titration solution was Tris-HCl solution. After the organic small-molecule fluorescent compound is combined with the heavy metal copper ions, the fluorescence intensity is obviously enhanced along with the increase of the concentration of the metal ions, and the concentration is not enhanced when the concentration reaches saturation definitely, as shown in figure 2. While the fluorescence intensity of the organic small-molecule fluorescent compound is very weak when the organic small-molecule fluorescent compound is not combined with heavy metal copper ions, as shown in figure 1.
Example 3 graph of titration of heavy metal copper ions in acetone by organic small molecule fluorescent compound
The organic small-molecule fluorescent compound stock solution of the present invention was diluted to a concentration of 5 μ M, heavy metal copper ions of different concentrations were added, and the fluorescence intensities thereof were measured with a fluorescence spectrophotometer (slit width 10, scanning speed 200nm, Ex 520nm), and the titrated solution was acetone solution. After the organic small-molecule fluorescent compound is combined with the heavy metal copper ions, the fluorescence intensity is obviously enhanced along with the increase of the concentration of the metal, the concentration is not enhanced when the concentration reaches saturation, but the fluorescence intensity is lower than that in a Tris-HCl solution by about 30 percent, as shown in figure 3.
EXAMPLE 4 preparation of fluorescent test paper for organic Small molecule fluorescent Compound
Soaking the blank filter paper in an acetone dispersion solution of an organic small-molecule fluorescent compound material and potassium iodide, wherein the concentration of the organic small-molecule fluorescent compound material is 100 mu M, taking out the filter paper after soaking for a period of time, placing the filter paper in a clean and ventilated place, and naturally drying to finally obtain the fluorescent test paper for detecting the heavy metal copper. Further, the blank filter paper is soaked in an acetone dispersion solution of the organic small-molecule fluorescent compound for 10-15 minutes. Thus obtaining the organic micromolecule fluorescent compound fluorescent test paper.
Example 5 comparison of fluorescence of fluorescent test paper at different concentrations of heavy metal copper ion
5 parts of the fluorescent test paper prepared in example 4 were immersed in a 0.01. mu.M, 0.1. mu.M, 1. mu.M, 10. mu.M, 100. mu.M solution of heavy metal copper ions for 3 seconds, and the fluorescent intensity was observed under irradiation with a 15W 365nm portable ultraviolet lamp. The fluorescent probe can well distinguish heavy metal copper ion solutions with different concentrations. The results are shown in FIG. 4.
Example 6 application of fluorescent test paper to heavy metal copper ion content in sewage
Filtering 5ml of sewage with a 0.25 mu m filter membrane to remove other insoluble impurities in the medical wastewater, reducing experimental interference, averagely dividing the filtered wastewater into 5 parts, and diluting by 1 time, 10 times, 100 times, 1000 times and 10000 times respectively, wherein the serial numbers of the parts are 1-5. The heavy metal copper ion fluorescent test paper is respectively soaked in No. 1-5 solution for 3s, the test paper 1 '-5' is respectively marked corresponding to the serial number of sewage 1-5, and then the soaked fluorescent test paper is dried in the shade under natural conditions or is dried in an oven. The fluorescence intensity was observed by irradiating with a portable ultraviolet lamp of 15W and 365nm, respectively. The fluorescent test paper 1 '-5' shows different fluorescent intensities under the irradiation of an ultraviolet lamp. As shown in FIG. 5, the test paper is 1 '-5' fluorescence test paper from right to left. The detection limit of the detection reaches two exponential detection of the national heavy metal copper ion pollution discharge standard.
Claims (4)
1. A preparation method of fluorescent probe test paper for detecting the copper content of sewage is characterized by comprising the following steps: comprises an organic micromolecular fluorescent material and potassium iodide;
the structural formula of the organic micromolecule fluorescent material is shown as (I):
wherein n and m are 0 to 5;
(1) 4-chloro-8-hydroxy-2-methylquinoline and methyl iodide or dimethyl sulfate are put in n-butanol solution, the reaction is carried out under constant temperature and pressure magnetic stirring, the reaction time is about 4 hours, and the reaction temperature is 50-70 ℃; the system gradually changes from light yellow to purple with the separation of yellow brown solid; after the reaction is finished, adding twice equivalent of ethyl acetate, increasing solid precipitation, and washing a filter cake with 3mL of ethanol to obtain a pure methylated intermediate a;
(2) the reaction of the intermediate b is carried out in a constant-temperature oil bath kettle, the reaction temperature is 60-80 ℃, condensation reflux is carried out, and the reactant 1, 3-dibromopropane is excessive; as the reaction proceeds, the color of the system gradually changes from transparent to milky white with the generation of solid; the solid can be primarily washed by ethyl acetate, and the solid precipitation is increased; d is obtained in the same way;
(3) the molar ratio of ammonia to intermediate b was about 5: 1, a reaction solvent is glycerol or n-butyl alcohol, the reaction temperature is 80-100 ℃, and the reaction time is 2-5 hours; the ammonia water can provide a stronger alkaline environment for the reaction, is beneficial to the condensation reaction of the amido and the intermediate b, and is condensed to obtain c, and e is obtained by the same method;
(4) the method comprises the following steps of (1) performing equimolar mass of a and e in a constant-temperature oil bath kettle, heating for 3-5h at 50-70 ℃ by taking 5-10 times of n-butyl alcohol as a solvent and organic base as a catalyst, and primarily washing by using ethyl acetate to obtain a black solid f;
(5) reacting f and c with equivalent weight in a normal butanol system, adding organic base as a condensation catalyst, heating the reaction to 130 ℃ from room temperature, and finally separating out black solids in the reaction system; after the reaction is finished, cooling to room temperature, adding ethyl acetate with the same volume, and precipitating more solids; washing the filter cake with 0.5-1.5 times of methanol; the product is a reddish-brown or black powder solid (I);
the preparation method of the fluorescent probe test paper comprises the steps of soaking a blank test paper in an acetone dispersion solution of an organic small-molecule fluorescent material and potassium iodide for 3-10 min, taking out the filter paper, placing the filter paper in a clean and ventilated place, and naturally drying the filter paper to finally obtain the fluorescent test paper for detecting the heavy metal copper ions;
the concentration of the organic small-molecule fluorescent material is 0.05-1 mM.
2. The method for preparing the fluorescent probe test paper for detecting the copper content in the sewage according to claim 1, which is characterized in that: the use method of the fluorescent probe test paper comprises the following steps: the organic small molecular fluorescent material has no fluorescence or weak fluorescence; the fluorescent material is combined with heavy metal copper ions, fluorescence is displayed under an ultraviolet lamp, the higher the content of the heavy metal copper ions is, the stronger the fluorescence is, and the lower the content of the heavy metal copper ions is, the weaker the fluorescence is.
3. The fluorescent probe test paper for detecting the copper content in the sewage according to claim 1, which is characterized in that: the organic micromolecule fluorescent material can be used for detecting the content of heavy metal copper ions.
4. The fluorescent probe test paper for detecting the copper content in the sewage according to claim 1 or 3, which is characterized in that: the fluorescent probe test paper can be used for semi-quantitatively detecting the content of copper ions in smelting, metal processing and electroplating sewage.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111233856A (en) * | 2020-02-17 | 2020-06-05 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting chromium content in soil |
| CN111303143A (en) * | 2020-02-17 | 2020-06-19 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting cadmium content in soil |
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| CN108070275A (en) * | 2016-11-10 | 2018-05-25 | 中国科学院化学研究所 | Squaraine dye class compound, Preparation method and use |
| CN111233856A (en) * | 2020-02-17 | 2020-06-05 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting chromium content in soil |
| CN111303143A (en) * | 2020-02-17 | 2020-06-19 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting cadmium content in soil |
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| CN108070275A (en) * | 2016-11-10 | 2018-05-25 | 中国科学院化学研究所 | Squaraine dye class compound, Preparation method and use |
| CN111233856A (en) * | 2020-02-17 | 2020-06-05 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting chromium content in soil |
| CN111303143A (en) * | 2020-02-17 | 2020-06-19 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting cadmium content in soil |
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Cited By (2)
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| CN111233856A (en) * | 2020-02-17 | 2020-06-05 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting chromium content in soil |
| CN111303143A (en) * | 2020-02-17 | 2020-06-19 | 广州市尚信净化工程有限公司 | Preparation method of fluorescent probe test paper for detecting cadmium content in soil |
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