CN111804287A - Fluorenone type chelate resin and preparation method and application thereof - Google Patents
Fluorenone type chelate resin and preparation method and application thereof Download PDFInfo
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- CN111804287A CN111804287A CN202010697959.0A CN202010697959A CN111804287A CN 111804287 A CN111804287 A CN 111804287A CN 202010697959 A CN202010697959 A CN 202010697959A CN 111804287 A CN111804287 A CN 111804287A
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28026—Particles within, immobilised, dispersed, entrapped in or on a matrix, e.g. a resin
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
Abstract
The invention relates to fluorenone type chelating resin, which is prepared by taking 4, 5-diazafluorene-9-ketone as a ligand through the reaction with a side group of chloromethylated polystyrene microspheres, and has the following structural formula:
Description
Technical Field
The invention relates to the field of chelate resin materials, in particular to fluorenone type chelate resin and a preparation method and application thereof.
Background
Heavy metal ion wastewater is one of the most serious industrial wastewater which pollutes the environment and has the greatest harm to human beings. Most metal ions and compounds thereof are easily adsorbed by suspended particles in water and precipitate in a settled layer at the bottom of the water, and pollute the water body for a long time. Some heavy metals can be enriched, accumulated and participate in biosphere circulation in fish and other aquatic organisms and crop tissues, so that the life health of human beings is threatened, and the wastewater containing the heavy metals can be discharged after being treated. The pollution problem of the water environment in the current society is increasingly serious, and how to efficiently remove heavy metal ions in wastewater is a research hotspot of people. Heavy metal wastewater is generally treated by chemical or physicochemical methods, such as neutralization, chemical precipitation, electrolysis, reverse osmosis, adsorption, redox, ion exchange, and the like. Adsorption is considered to be one of the most attractive techniques for treating heavy metal ions in wastewater due to its advantages of high efficiency, low cost, easy operation and no secondary pollution.
The chelating resin, i.e., a polymeric solid chelating agent, is a crosslinked polymer containing chelating groups and being insoluble in water and other solvents, and is capable of selectively chelating specific metal ions from an aqueous solution containing the metal ions to form a cyclic complex by ionic bonding and covalent bonding. Compared with the organic micromolecule chelating agent, the macromolecular chelating resin not only has the chelating effect of functional groups, but also can generate macromolecular effects, such as high adsorption property caused by the chelating group concentration effect and the properties of separability, reusability and the like in the solid phase extraction process. In addition, the chelate resin has the advantages of high selectivity, good physical and chemical stability, simple operation, and the like, and the treated wastewater reaches the national discharge standard, so the application is very wide. In recent years, polymer chemists at home and abroad have actively researched the aspects of development of new polymer chelate resin, heavy metal recovery, environmental protection and the like, and have made great contribution to the treatment of heavy metal ion wastewater.
The parent body of the chelating resin can be crosslinked polystyrene, crosslinked polyacrylonitrile or crosslinked polyacrylic acid, and the like, is prepared by conventional macromolecular suspension polymerization, and has the characteristics of mature preparation process, easy functionalization, high mechanical strength and good chemical stability. The disadvantage is that they all have a common feature, namely that essentially all divinylbenzene is used as a crosslinking agent, which has the disadvantage of poor hydrophilic properties.
Patent publication No. CN 104959130A discloses a chelate adsorption functional resin which uses macroporous chloromethylated crosslinked polystyrene microspheres as a matrix, methyl piperazine as a ligand and modifies benzyl on the microspheres, and the resin can remove heavy metal ions in sewage, is easy to separate and recycle and can be recycled. However, the bonding amount of the salicylhydroxamic acid on the chelating resin is 0.38-0.43 g/g, and the bonding amount is relative to Cu2+，Cd2+，Ni2+，Pd2+The adsorption effect of the plasma is not ideal, the adsorption capacity is low, the equilibrium static adsorption capacity for the metal ion solution of 60 mg/L is 8-30 mg/g, and the equilibrium static adsorption capacity for the metal ion solution of 1000 mg/L is 20-44 mg/g.
Disclosure of Invention
The invention aims to solve the technical problem of providing a fluorenone chelate resin with high adsorption capacity to heavy metals.
The invention also provides a preparation method of the fluorenone type chelating resin.
The third technical problem to be solved by the invention is to provide the application of the fluorenone type chelate resin.
In order to solve the above problems, the present invention provides a fluorenone type chelate resin, which is characterized in that: the chelating resin is prepared by taking 4, 5-diazafluorene-9-ketone as a ligand and reacting with a side group of chloromethylated polystyrene microspheres, and has the following structural formula:
the percentage of reaction of the fluorenone with the pendant groups of the chloromethylated polystyrene microspheres was 74%.
The preparation method of the fluorenone type chelate resin comprises the following steps:
adding a solvent into a container for placing vacuum-dried macroporous chlorine balls, and stirring and swelling for 12-15 hours to obtain a reaction liquid A; the mass volume ratio of the macroporous chlorine spheres to the solvent is 1 g: 40-50 mL;
heating the reaction liquid A to 60-90 ℃, adding triphenylphosphine, and reacting at the constant temperature of 60-90 ℃ for 16-19 h to obtain a quaternary phosphonium product; the mass ratio of the macroporous chlorine spheres to the triphenylphosphine is 1 g: 1.15-1.2 g;
washing the quaternary phosphonium product with absolute ethyl alcohol, drying in vacuum, and dissolving in the solvent again to obtain a reaction solution B; the mass-to-volume ratio of the quaternary phosphonium product to the solvent is 1 g: 40-50 mL;
adding 4, 5-diazafluorene-9-one into the reaction liquid B, stirring and reacting for 15-18 h at 60-90 ℃ to obtain a reaction product, washing the reaction product with absolute ethyl alcohol, and drying in vacuum to obtain fluorenone type chelate resin; the mass ratio of the macroporous chlorine spheres to the 4, 5-diazafluoren-9-one is 1 g: 1.05-1.1 g.
The process route is as follows:
the macroporous chlorine balls in the step are macroporous chloromethylated divinylbenzene crosslinked polystyrene beads (CPS), the crosslinking degree is 6%, the chlorine content is 18-20%, the chloromethyl grafting rate is 70-75%, the pore diameter of the chlorine balls is 25-30 nm, and the particle size is 0.4-1.0 mm.
The solvent in the step I and the step III refers to the solvent formed by mixing toluene and dioxane in a ratio of 1: 1 volume ratio of the mixture to the solution.
The vacuum drying conditions in the third step and the fourth step are that the temperature is 60 ℃, the pressure is 20KPa, and the time is 6 h.
The application of the fluorenone type chelating resin in treating wastewater containing heavy metal ions is characterized in that: after fluorenone type chelating resin is filled in an adsorption column, carrying out adsorption treatment on the wastewater containing heavy metal ions and having the concentration of 100 mg/L; the heavy metal ions in the wastewater refer to one or more of Cu (II), Ni (II) and Pb (II).
Compared with the prior art, the invention has the following advantages:
1. the invention takes macroporous chloromethylated polystyrene beads (chlorine spheres, CPS) as matrix resin and fluorenone as a ligand, because two N atoms in a pyridine ring on 4, 5-diazafluoren-9-one have very strong coordination capability and most importantly, the 4, 5-diazafluoren-9-one has active carbonyl at the 9-position, so that various derivatives can be brought, the derivatives can be easily bonded to the chlorine spheres to modify benzyl on the chlorine spheres, and the novel chelate resin taking pyridine as a functional group is obtained.
The infrared spectrums of the chloromethylated polystyrene microsphere, the quaternary phosphonium product and the fluorenone type chelating resin are shown in figure 1. As can be seen from the figure, in the spectrum of the chloromethylated polystyrene microsphere, 678 cm is observed except the characteristic absorption peak of the polystyrene-1Has a strong absorption peak of-CH2Stretching vibration of C-Cl bond in Cl; 1267 cm-1Is the 4-position of the benzene ring by-CH2In-plane bending vibration of C-H bond on 1, 4-disubstituted benzene ring strengthened after Cl substitution, 826 cm-1The absorption is out-of-plane bending vibration of the C-H bond on the benzene ring after binary substitution. In the spectrum of the fluorenone type chelate resin, two new peaks appear: 1635 cm-1The absorption at (a) is the C = C stretching vibration peak of the fluorenone-type chelate resin. 1045 cm-1The absorption is the in-plane bending vibration of the C-H bond on the 1, 4-disubstituted benzene ring strengthened after the 4-position on the benzene ring is substituted with C = C. Infrared spectroscopic analysis shows that 4, 5-diazafluoren-9-one is successfully bonded on the side group of chloromethyl polystyrene to prepare the fluorenone type chelating resin.
The chloromethylated polystyrene microspheres and the fluorenone type chelate resin are subjected to element analysis, and the element contents of the chloromethylated polystyrene microspheres and the fluorenone type chelate resin are shown in tables 1 and 2.
TABLE 1 Chloromethylated polystyrene elemental analysis
Elemental analysis of fluorenone-type chelate resin shown in Table 2
As can be seen from tables 1-2, the content of N in the fluorenone type chelate resin is about 74% of the theoretical value, which indicates that the reaction ratio of 4, 5-diazafluoren-9-one and chloromethyl polystyrene side group is about 74%.
2. The chelate resin of the present invention has the advantages of simple preparation process, easy control of the preparation process, easy synthesis, easy obtainment of raw materials, low cost and contribution to industrial production.
3. The chelating resin has better selective chelation on metal ions such as Cu (II), Ni (II), Pb (II) and the like, high chelating rate and large chelating amount, has high coordination and complexation capacity on heavy metal ions, and can reach 162 mg/g on Cu (II), so that the chelating resin prepared by the method can be filled in an adsorption column, can realize enrichment and recovery of various heavy metals, and effectively solves the problem of deep treatment of wastewater containing heavy metal ions.
[ adsorption Capacity test ]
1000 mg/L of Cu (II), Pb (II) and Ni (II) solutions are prepared and diluted to different concentrations. 50 mg of the fluorenone chelate resin obtained in example 1 of the present invention was added to 100 mL of solutions of Cu (II), Pb (II) and Ni (II) at different concentrations, and the mixture was placed in a constant temperature incubator shaker, and after shaking at room temperature for 24 hours, the change in absorbance of the solution was measured and the adsorption effect was observed. As shown in FIG. 2, the maximum adsorption amounts of the fluorenone-type chelate resin to Cu (II), Pb (II) and Ni (II) were 162 mg/g, 105 mg/g and 79 mg/g, respectively.
1g of fluorenone type chelate resin prepared in example 1 of the present invention was added to 100 mL of 200 mg/L Cu (II), Pb (II), and Ni (II) solutions, the initial pH of the solutions was adjusted to 1, 2, 3, 4,5, and 6 with hydrochloric acid, and the solutions were placed in a constant temperature incubator shaker at room temperature and shaken for 30-60 min, and then the absorbance change of the solutions was measured and the adsorption effect was observed. As shown in FIG. 3, since Cu (II), Pb (II) and Ni (II) form hydroxide precipitates under alkaline conditions, the effect of pH on adsorption was observed under a condition of pH < 7. As can be seen from fig. 3, when pH <4, the adsorption capacity increases with increasing pH, but when pH >5, the adsorption capacity of the adsorbent tends to level off. Therefore, as can be seen from FIG. 3, the optimum adsorption pH of the fluorenone-type chelate resin is 5.
[ column experiment ]
1g of the fluorenone-type chelate resin obtained in inventive example 1 was packed in a glass column having a height of 50 cm and a diameter of 1.0 cm. 500 mL of a solution of the monometallic ions of Cu (II), Ni (II) and Pb (II) at an initial concentration of 150 mg/L were allowed to flow down the column at 25 ℃ at a flow rate of 1.0 mL/min. The outlet metal ion concentration is measured by a microcomputer high-range copper (lead, nickel) ion concentration measuring instrument. After adsorption the loaded resin was eluted and regenerated with 0.2M HCl, and then the resin was washed carefully with distilled water until pH neutral, ready for reuse. The adsorption-desorption cycle of the metal ions was repeated 5 times. As shown in Table 3, the results of the concentration measurement of the outlet metal ions revealed that the fluorenone-type chelate resin obtained in example 1 of the present invention also exhibited a good effect of removing Cu (II), Ni (II) and Pb (II) during the adsorption on the fixed bed column. The adsorption data show that the final concentration of the Cu (II), Ni (II) and Pb (II) metal ion solutions is lower than 1.0 mg/L each time at the flow of 1.0mL/min and the temperature of 25 ℃, and the method meets the national heavy metal wastewater discharge standard (GB 8978-1996).
TABLE 3 exit of column experiment Metal ion concentration (mg/L)
4. The chelating resin is convenient to use, easy to separate and recover, easy to desorb, regenerate and reuse, can be recycled for 10 times, and has basically unchanged adsorption performance.
[ recovery experiment ]
50 mg of the fluorenone chelate resin prepared in the invention in example 1 was added to 20 mL of 50 mg/L Cu (II), Pb (II) and Ni (II) solution, and the mixture was placed in a constant temperature incubator shaker at room temperature and shaken for 30-60 min, and then the absorbance change of the solution was measured and the adsorption effect was observed. The saturated adsorbent with the target contaminant is loaded into a chromatography column, rinsed with 0.1M hydrochloric acid for 5 h, and then washed with deionized water for the next round of adsorption. The total time of the recycling is 5 times, and the experimental result is shown in figure 4. As is clear from FIG. 4, after repeated use 5 times, the adsorption capacity of the fluorenone-type chelate resin to Cu (II), Pb (II) and Ni (II) was slightly decreased. After 5 cycles, the adsorption capacity of the fluorenone type chelate resin to Cu (II), Pb (II) and Ni (II) can still reach 92%, 90% and 89% of the first adsorption respectively, which proves that the fluorenone type chelate resin has higher stability, is a durable resin for adsorbing single metal ions and can be reused.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 is an infrared spectrum of chloromethylated polystyrene microspheres, quaternary phosphonium products, fluorenone type chelate resin in the present invention.
FIG. 2 shows the maximum adsorption amounts of the fluorenone-type chelate resin of the present invention to Cu (II), Ni (II) and Pb (II).
FIG. 3 is a graph showing the effect of pH on the adsorption of Cu (II), Ni (II) and Pb (II) by the fluorenone-type chelate resin of the present invention.
FIG. 4 shows the reusability of fluorenone type chelate resin of the present invention for adsorbing Cu (II), Ni (II) and Pb (II).
Detailed Description
A fluorenone type chelating resin is prepared by taking 4, 5-diazafluorene-9-one as a ligand and reacting with a side group of chloromethylated polystyrene microspheres, and has the following structural formula:
wherein: the percent reaction of fluorenone with pendant groups of chloromethylated polystyrene microspheres was 74%.
Embodiment 1 a method for preparing fluorenone type chelate resin, comprising the steps of:
adding 40mL of solvent into a container for placing 1g of vacuum-dried macroporous chlorine balls, and stirring and swelling for 12 hours to obtain reaction liquid A;
heating the reaction solution A to 60 ℃, adding 1.15g of triphenylphosphine, and reacting at the constant temperature of 60 ℃ for 16 h to obtain a quaternary phosphonium product;
washing 1g of quaternary phosphonium product by absolute ethyl alcohol, drying in vacuum for 6 h at 60 ℃ under 20KPa, and dissolving in 40mL of solvent again to obtain reaction solution B;
and fourthly, adding 1.05 g of 4, 5-diazafluoren-9-one into the reaction liquid B, stirring and reacting for 15 hours at the temperature of 60 ℃ to obtain a reaction product, washing the reaction product by using absolute ethyl alcohol, and drying for 6 hours in vacuum at the temperature of 60 ℃ and under the pressure of 20KPa to obtain the fluorenone type chelate resin.
Embodiment 2 a method for preparing fluorenone type chelate resin, comprising the steps of:
adding 50 mL of solvent into a container for placing 1g of vacuum-dried macroporous chlorine balls, and stirring and swelling for 13 hours to obtain reaction liquid A;
heating the reaction solution A to 70 ℃, adding 1.2 g of triphenylphosphine, and reacting at the constant temperature of 70 ℃ for 17 h to obtain a quaternary phosphonium product;
washing 1g of quaternary phosphonium product by absolute ethyl alcohol, drying in vacuum for 6 h at 60 ℃ under 20KPa, and dissolving in 50 mL of solvent again to obtain reaction solution B;
and fourthly, adding 1.1 g of 4, 5-diazafluoren-9-one into the reaction liquid B, stirring and reacting for 16 hours at 70 ℃ to obtain a reaction product, washing the reaction product by using absolute ethyl alcohol, and drying for 6 hours in vacuum at 60 ℃ and 20KPa to obtain the fluorenone type chelate resin.
Embodiment 3 a method for preparing fluorenone type chelate resin, comprising the steps of:
adding 45 mL of solvent into a container for placing 1g of vacuum-dried macroporous chlorine balls, and stirring and swelling for 14 hours to obtain reaction liquid A;
heating the reaction solution A to 80 ℃, adding 1.18 g of triphenylphosphine, and reacting at the constant temperature of 80 ℃ for 18 h to obtain a quaternary phosphonium product;
washing 1g of quaternary phosphonium product by absolute ethyl alcohol, drying in vacuum for 6 h at 60 ℃ under 20KPa, and dissolving in 45 mL of solvent again to obtain reaction solution B;
and fourthly, adding 1.08 g of 4, 5-diazafluoren-9-one into the reaction liquid B, stirring and reacting for 17 hours at 80 ℃ to obtain a reaction product, washing the reaction product by using absolute ethyl alcohol, and drying for 6 hours in vacuum at 60 ℃ and 20KPa to obtain the fluorenone type chelate resin.
Embodiment 4 a method for preparing fluorenone type chelate resin, comprising the steps of:
adding 40mL of solvent into a container for placing 1g of vacuum-dried macroporous chlorine balls, and stirring and swelling for 15 hours to obtain reaction liquid A;
heating the reaction solution A to 90 ℃, adding 1.15g of triphenylphosphine, and reacting at the constant temperature of 90 ℃ for 19 h to obtain a quaternary phosphonium product;
washing 1g of quaternary phosphonium product by absolute ethyl alcohol, drying in vacuum for 6 h at 60 ℃ under 20KPa, and dissolving in 40mL of solvent again to obtain reaction solution B;
and fourthly, adding 1.05 g of 4, 5-diazafluoren-9-one into the reaction liquid B, stirring and reacting at 90 ℃ for 18 hours to obtain a reaction product, washing the reaction product with absolute ethyl alcohol, and drying in vacuum at 60 ℃ and 20KPa for 6 hours to obtain the fluorenone type chelate resin.
In the above examples 1 to 4, the macroporous chlorine spheres are macroporous chloromethylated divinylbenzene crosslinked polystyrene beads (CPS), the crosslinking degree is 6%, the chlorine content is 18 to 20%, the chloromethyl grafting rate is 70 to 75%, the pore diameter of the chlorine spheres is 25 to 30 nm, and the particle diameter is 0.4 to 1.0 mm.
The solvent is toluene and dioxane in a ratio of 1: 1 volume ratio of the mixture to the solution.
The container has an electric stirrer, a condenser tube and a charging opening.
The application of the fluorenone type chelating resin prepared in the above embodiments 1 to 4 in treating wastewater containing heavy metal ions: after fluorenone type chelating resin is filled in an adsorption column, carrying out adsorption treatment on the wastewater containing heavy metal ions and having the concentration of 100 mg/L; the heavy metal ions in the wastewater refer to one or more of Cu (II), Ni (II) and Pb (II).
Claims (7)
1. A fluorenone type chelate resin characterized in that: the chelating resin is prepared by taking 4, 5-diazafluorene-9-ketone as a ligand and reacting with a side group of chloromethylated polystyrene microspheres, and has the following structural formula:
2. the chelating resin of claim 1, wherein the fluorenone is: the percentage of reaction of the fluorenone with the pendant groups of the chloromethylated polystyrene microspheres was 74%.
3. The method for preparing the fluorenone-type chelate resin according to claim 1, comprising the steps of:
adding a solvent into a container for placing vacuum-dried macroporous chlorine balls, and stirring and swelling for 12-15 hours to obtain a reaction liquid A; the mass volume ratio of the macroporous chlorine spheres to the solvent is 1 g: 40-50 mL;
heating the reaction liquid A to 60-90 ℃, adding triphenylphosphine, and reacting at the constant temperature of 60-90 ℃ for 16-19 h to obtain a quaternary phosphonium product; the mass ratio of the macroporous chlorine spheres to the triphenylphosphine is 1 g: 1.15-1.2 g;
washing the quaternary phosphonium product with absolute ethyl alcohol, drying in vacuum, and dissolving in the solvent again to obtain a reaction solution B; the mass-to-volume ratio of the quaternary phosphonium product to the solvent is 1 g: 40-50 mL;
adding 4, 5-diazafluorene-9-one into the reaction liquid B, stirring and reacting for 15-18 h at 60-90 ℃ to obtain a reaction product, washing the reaction product with absolute ethyl alcohol, and drying in vacuum to obtain fluorenone type chelate resin; the mass ratio of the macroporous chlorine spheres to the 4, 5-diazafluoren-9-one is 1 g: 1.05-1.1 g.
4. The method for preparing a fluorenone-type chelate resin according to claim 3, wherein: the macroporous chlorine balls in the step are macroporous chloromethylated divinylbenzene crosslinked polystyrene beads, the crosslinking degree is 6%, the chlorine content is 18-20%, the chloromethyl grafting rate is 70-75%, the pore diameter of the chlorine balls is 25-30 nm, and the particle size is 0.4-1.0 mm.
5. The method for preparing a fluorenone-type chelate resin according to claim 3, wherein: the solvent in the step I and the step III refers to the solvent formed by mixing toluene and dioxane in a ratio of 1: 1 volume ratio of the mixture to the solution.
6. The method for preparing a fluorenone-type chelate resin according to claim 3, wherein: the vacuum drying conditions in the third step and the fourth step are that the temperature is 60 ℃, the pressure is 20KPa, and the time is 6 h.
7. The use of the fluorenone-type chelate resin of claim 1 for treating heavy metal ion-containing wastewater, wherein: after fluorenone type chelating resin is filled in an adsorption column, carrying out adsorption treatment on the wastewater containing heavy metal ions and having the concentration of 100 mg/L; the heavy metal ions in the wastewater refer to one or more of Cu (II), Ni (II) and Pb (II).
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Inventor after: Zhou Lincheng Inventor after: Zhang Shujiang Inventor after: Zhu Hao Inventor after: Zou Binze Inventor after: Zhang Wei Inventor before: Zhou Lincheng Inventor before: Zhang Shujiang Inventor before: Zou Binze Inventor before: Zhang Wei |