CN115382514A - Preparation method and application of molecular imprinting MOFs material for selectively removing triazine herbicide pollution in water environment - Google Patents
Preparation method and application of molecular imprinting MOFs material for selectively removing triazine herbicide pollution in water environment Download PDFInfo
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Abstract
The invention discloses a preparation method and application of a molecular imprinting MOFs material for selectively removing triazine herbicide pollution in water environment, which is characterized by comprising the following steps: 1) Dissolving trimesic acid in a sodium hydroxide solution, dropwise adding a ferrous sulfate tetrahydrate solution, stirring, centrifuging to obtain a solid precipitate, washing the solid precipitate, and obtaining orange-yellow octahedral MIL100 in a drying oven; 2) Adding MIL100 into an acetonitrile solution, then adding triazine herbicide template molecules and methacrylic acid, ultrasonically mixing, sealing and prepolymerizing, adding trimethylolpropane trimethacrylate and azobisisobutyronitrile, ultrasonically mixing, introducing nitrogen, stirring, sequentially eluting with a methanol and acetic acid mixed solution and methanol, and vacuum drying to obtain the MIP @ MOFs material.
Description
Technical Field
The invention relates to the technical field of water treatment, in particular to a preparation method and application of a molecular imprinting MOFs material for selectively removing triazine herbicide pollution in a water environment.
Background
Triazine herbicides are high-efficiency broad-spectrum herbicides, are commonly used for controlling broadleaf weeds of field crops such as corn, sorghum and the like, and are one of the most widely used herbicides in the world. However, while promoting the development of agricultural modernization, due to its long-term and widespread use (about 160 ten thousand tons/year), in recent years, such pesticides have been frequently detected in the offshore marine fishery environment. Meanwhile, researches show that after the fishery environment in the offshore area is polluted by the herbicide, the primary productivity of algae, phytoplankton, aquatic plants and the like can show abnormal reproduction and growth inhibition phenomena, and the marine organism resources in the offshore area are seriously influenced. Meanwhile, as part of triazine herbicides have endocrine disrupting characteristics, high toxicity durability and biological accumulation, compound disrupting damage can be generated to endocrine systems of organisms and the like, teratogenic, carcinogenic and mutagenic effects can be generated, and the health of consumers can be influenced through a food net. Therefore, the problems of offshore area fishery environment pollution and aquatic product quality safety caused by the residue are increasingly prominent, and the healthy development of offshore area marine organism resources and aquaculture industry in China is seriously threatened. Especially, in view of the higher detection rate of the herbicide, the influence on the primary productivity of an ecosystem, the toxicity characteristics of endocrine disturbance and the like, the problem of residue of the herbicide in the offshore marine fishery environment and aquatic products is gradually paid high attention by governments and the public, the research on the pollution removal mechanism of the triazine herbicide in the offshore marine fishery environment is developed, and the herbicide has important significance for protecting the offshore marine fishery environment, the aquatic product safety and the human health.
At present, the researches on the removal technology of triazine herbicides mainly comprise biodegradation, chemical degradation, physical removal technology and the like, but all have some defects, and further researches are still needed for seeking a green and efficient method. For example, for microbial degradation, it is often difficult to obtain a stable and highly efficient degradation of microorganisms, and thus the degradation effect is poor in triazine herbicide-contaminated water environments. The biochar adsorption generally has better adsorption efficiency, but along with adsorption and use, the adsorption capacity of the biochar to triazine herbicides in water environment is reduced, and the biochar has the defects of difficult separation and the like. The MOFs material generally has the characteristics of ultra-large surface area, adjustable functions and structures and the like, has a good application prospect when being used as a high-efficiency adsorption material, and has the characteristics of similar bio-enzyme capable of catalyzing and degrading triazine herbicides, but the problems of adsorption selectivity, reusability and recovery are still important to solve.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method and application of a molecular imprinting MOFs material for selectively removing triazine herbicide pollution in a water environment, wherein the preparation method can be used for realizing the rapid and efficient removal of triazine herbicides in the water environment.
The technical scheme adopted by the invention for solving the technical problems is as follows: a preparation method of a molecular imprinting MOFs material for selectively removing triazine herbicide pollution in a water environment comprises the following steps:
(1) Preparation of octahedral MIL100
Mixing a certain mass of trimesic acid (H) 3 BTC) is dissolved in 1.0 mol/L sodium hydroxide solution, ferrous sulfate tetrahydrate solution with certain concentration is dripped while stirring, the mixture is continuously stirred for 20 hours at the constant temperature of 25 ℃, then the mixture is centrifuged to obtain solid precipitate, the solid precipitate is sequentially ultrasonically washed by deionized water and ethanol, the solid precipitate is repeatedly washed for three times, and then the solid precipitate is placed in a vacuum drying oven and dried for 12 hours at the constant temperature of 80 ℃ and 0.04 kPa to obtain orange octahedron MIL100;
(2) Preparation of MIP @ MOFs material
Adding 200 mg of MIL100 obtained in the step (1) into 45 mL of acetonitrile solution, then adding 1mmol of triazine herbicide template molecule and 4 mmol of functional monomer methacrylic acid (MAA), ultrasonically mixing for 5 min, sealing and placing at 4 ℃ for 30 min for prepolymerization, then adding 6 mmol of trimethylolpropane trimethacrylate and 80mg of azobisisobutyronitrile, ultrasonically mixing for 3 min, then introducing nitrogen, stirring at 65 ℃ and 150 rpm for 24 h, sequentially eluting with a solution formed by mixing methanol and acetic acid according to a volume ratio of 9.
Further, the step (1) is specifically as follows: 1.25 g FeCl was weighed 2 ·4H 2 O in 54.10 mL H 2 Stirring in O at 400 rpm for 30 min, and marking as a solution A; weighing 0.88 g of trimesic acid, dissolving in 12.62 mL of NaOH solution with the concentration of 1.0 mol/L, magnetically stirring and uniformly mixing at the speed of 400 rpm for 5 min, and marking as solution B; dropwise adding the solution A into the solution B while stirring, continuously stirring at a constant temperature of 25 ℃ for 20 hours, and centrifuging at the speed of 5000 rpm for 10 min to remove supernatant; washing the obtained solid precipitate with deionized water for 3 times, and then washing the solid precipitate with ethanol for 3 times; and after washing, drying in a vacuum drying oven at 80 ℃ and 0.04 kPa for 12 h to obtain orange yellow powder, namely the orange yellow octahedron MIL100.
Further, the step (2) is specifically as follows: adding 200 mg of MIL100 obtained in the step (1) into 45 mL of acetonitrile solution, then adding 1mmol of triazine herbicide and 4 mmol of functional monomer methacrylic acid, ultrasonically mixing for 5 min, sealing and placing in a 4 ℃ environment for prepolymerization for 30 min, waiting for the solution to return to room temperature after the prepolymerization is finished, then adding 6 mmol of trimethylolpropane trimethacrylate and 80mg of azodiisobutyronitrile, ultrasonically mixing for 3 min, introducing nitrogen to remove oxygen in the solution, sealing and placing in a 65 ℃ water bath, stirring at 150 rpm for 24 h, centrifuging at 8000 rpm for 10 min, and removing supernatant; wrapping the obtained solid product with filter paper, placing the wrapped solid product in a Soxhlet extractor, and eluting the wrapped solid product with an eluent formed by mixing methanol and acetic acid according to the volume ratio of 9; after the elution is finished, replacing the elution solvent with pure methanol for removing acetic acid in the eluent until the eluent is neutral; and after the elution is finished, putting the product in a vacuum drying oven, and performing vacuum drying for 12 h at the temperature of 40 ℃ under the environment of 0.04 kPa to obtain the MIP @ MOFs material.
The application of the molecular imprinting MOFs material obtained by the preparation method is characterized in that: adding the prepared MIP @ MOFs into a water environment polluted by triazine herbicides, adding a proper amount of catalyst sodium persulfate under the condition of pH5.0-9.0, and adsorbing and catalytically degrading for 30-120 min at the temperature of 5-45 ℃.
Further, the prepared MIP @ MOFs are added according to the proportion of 1-3.5 g/m 3 The addition amount of the sodium persulfate is added into a water environment polluted by triazine herbicides, the final concentration of the sodium persulfate catalyst is 1-10 mg/L, and the sodium persulfate catalyst is adsorbed and catalytically degraded for 80-140 min under the conditions of pH of 5.0-9.0 and temperature of 5-45 ℃.
Further, prepared MIP @ MOFs was expressed at 2 g/m 3 The addition amount of the sodium persulfate is added into a water environment polluted by triazine herbicides, the catalyst sodium persulfate is added to ensure that the final concentration is 1-5 mg/L, and the adsorption and catalytic degradation are carried out for 120 min under the conditions of pH6 and temperature of 25 ℃.
Compared with the prior art, the invention has the advantages that
(1) The raw materials for preparing MIL100 and MIP @ MOFs are ferrous sulfate tetrahydrate, so that the preparation cost is low;
(2) The invention utilizes the molecular imprinting technology to prepare MIP @ MOFs, has better selective adsorption performance and catalytic degradation performance, is easy to separate from the solution, is not easy to generate secondary pollution and has low use cost;
(3) The invention has a better application range, and can be directly used for removing triazine herbicide pollution in water environment.
Drawings
FIG. 1 is an SEM image of an MIL-100 material prepared according to the present invention;
FIG. 2 is an SEM image of MIP @ MOFs material prepared by the present invention;
FIG. 3 is an analysis of the influence of MIP @ MOFs prepared by the present invention on the adsorption capacity (Q) of triazine herbicides; (A) MIP @ MOFs amounts; (B) the pH of the system; (C) adsorption catalytic degradation time;
FIG. 4 is a graph showing the relationship between MIL100 and NIP @ MOF and MIP @ MOF in the total removal rate of triazine herbicides.
Detailed Description
The invention is described in further detail below with reference to the accompanying examples.
1. Detailed description of the preferred embodiments
Example 1
A preparation method of a molecular imprinting MOFs material for selectively removing triazine herbicide pollution in a water environment comprises the following steps:
(1) Preparation of octahedral MIL100
Mixing a certain mass of trimesic acid (H) 3 BTC) is dissolved in 1.0 mol/L sodium hydroxide solution, ferrous sulfate tetrahydrate solution with certain concentration is dripped while stirring, the mixture is continuously stirred for 20 hours at the constant temperature of 25 ℃, then the mixture is centrifuged to obtain solid precipitate, the solid precipitate is sequentially ultrasonically washed by deionized water and ethanol, the solid precipitate is repeatedly washed for three times, and then the solid precipitate is placed in a vacuum drying oven and dried for 12 hours at the constant temperature of 80 ℃ and 0.04 kPa to obtain orange octahedron MIL100;
(2) Preparation of MIP @ MOFs material
Adding 200 mg of MIL100 obtained in the step (1) into 45 mL of acetonitrile solution, then adding 1mmol of triazine herbicide template molecule and 4 mmol of functional monomer methacrylic acid (MAA), ultrasonically mixing for 5 min, sealing and placing at 4 ℃ for 30 min for prepolymerization, then adding 6 mmol of trimethylolpropane trimethacrylate and 80mg of azobisisobutyronitrile, ultrasonically mixing for 3 min, then introducing nitrogen, stirring at 65 ℃ and 150 rpm for 24 h, sequentially eluting with a solution formed by mixing methanol and acetic acid according to a volume ratio of 9.
Example 2
The difference from the above example 1 is that the step (1) is specifically: 1.25 g FeCl was weighed 2 ·4H 2 O in 54.10 mL H 2 O, placing the solution in a 100 mL round-bottom flask, stirring at 400 rpm for 30 min, and recording as a solution A; 0.88 g of H is weighed out 3 BTC was dissolved in 12.62 mL of a 1.0 mol/L NaOH solution, and the solution was placed in a 50 mL beaker at 400 rpmStirring and mixing uniformly for 5 min by magnetic force, and recording as a solution B; and uniformly adding the solution A into the solution B dropwise while stirring, and continuously stirring at a constant temperature of 25 ℃ for 20 hours to record the color change in the reaction process. After the reaction is finished, transferring the synthesized solution into a 50 mL centrifuge tube, centrifuging at 5000 rpm for 10 min, and removing the supernatant; subjecting the obtained solid precipitate to ultrasonic treatment with deionized water (100.0 mL water +1.0 g MIL100) for 10 min, shaking for 10 min, centrifuging at 5000 rpm for 10 min, removing supernatant, and repeating the step for 3 times; then subjecting the solid precipitate to ultrasonic treatment with ethanol (100.0 ml ethanol +1.0 g MIL100) for 10 min, shaking for 10 min, centrifuging at 10000 rpm for 10 min, removing supernatant, and repeating the step for washing 3 times; after the washing was completed, it was dried in a vacuum drying oven at 80 ℃ under 0.04 kPa for 12 hours to obtain orange yellow powder, which was collected and stored in a dry environment as MIL100 as shown in FIG. 1. As shown in fig. 1, the octahedral MIL100 prepared in this example was subjected to field emission Scanning Electron Microscope (SEM) characterization (fig. 1), and the material had a regular octahedral structure and a size of 0.8-1.2 μm.
Example 3
The difference from the above example 1 is that the step (2) is specifically: weighing 45.0 mL of acetonitrile, placing the acetonitrile in a double-neck round-bottom flask, adding 200.0 mg of MIL100, 1.0 mmol (217.6 mg) of triazine herbicide and 4.0 mmol (344.0 muL) of MAA into the acetonitrile, ultrasonically mixing for 5 min, sealing the joint of a bottle opening and a bottle stopper by using a sealing film, and placing the bottle opening and the bottle stopper in an environment at 4 ℃ for prepolymerization for 30 min. After the prepolymerization is finished, waiting for the solution to return to the room temperature, adding 6.0 mmol of trimethylolpropane trimethacrylate and 80.0 mg of azodiisobutyronitrile, ultrasonically mixing for 3 min, removing bubbles in the solution, introducing nitrogen to remove oxygen in the solution for 10 min, sealing, placing in a 65 ℃ water bath kettle, and stirring at the speed of 150 rpm for 24 h.
After the reaction is finished, transferring the synthesized solution into a 50 mL centrifuge tube, centrifuging at 8000 rpm for 10 min, and removing the supernatant; the solid product obtained was wrapped with filter paper, placed in a soxhlet extractor and extracted with the eluent methanol: acetic acid (v: v, 90); during the elution process, the elution solution is replaced every 8 h until atrazine cannot be detected by HPLC, which indicates that the elution process is finished; after the elution is finished, replacing the elution solvent with pure methanol for removing acetic acid in the eluent until the eluent is neutral; and after the elution is finished, placing the product in a vacuum drying oven, carrying out vacuum drying for 12 h at 40 ℃ in an environment of 0.04 kPa, and storing in a room temperature drying environment after the drying is finished to obtain the MIP @ MOFs material, wherein as shown in figure 2, a field emission Scanning Electron Microscope (SEM) shows that the material has a rough surface, the average particle size is 500 nm, and meanwhile, the material has a large specific surface area, provides rich imprinting sites for specific adsorption of triazine herbicides, and is the key for adsorbing and removing the triazine herbicides. The synthesis method of NIP @ MOFs in the control group was consistent with MIP @ MOFs except that no template molecule was added.
2. Application of MIP @ MOFs material
The application of MIP @ MOFs in selectively removing triazine herbicides in water environment. MIP @ MOFs prepared in the specific examples (0.5-2 g/m) 3 ) Adding the water into a water environment polluted by triazine herbicides, adding a proper amount of catalyst sodium persulfate (1 mM-5 mM), controlling the adsorption and catalytic degradation time to be 120 min at the temperature of 25 ℃, and controlling the pH of a system to be 6.0, wherein the adsorption and degradation efficiency of MIP @ MOFs to the triazine herbicides can reach more than 90%. FIG. 3 is an analysis of the influence of the prepared MIP @ MOFs on the adsorption capacity (Q) of triazine herbicides. FIG. 3 (A) shows that, as the amount of MIP @ MOFs increased, the efficiency of adsorption removal by MIP @ MOFs was increased and then decreased, and when the amount of MIP @ MOFs was 2.0 g/m 3 When the herbicide is used, the adsorption removal efficiency of MIP @ MOFs on triazine herbicides is highest; FIG. 3 (B) shows that the removal efficiency of the adsorption of MIP @ MOFs to triazine herbicides reaches 85% or more when the pH of the system is 6.0; FIG. 3 (C) shows that when the adsorption catalytic degradation time is 120 min, the adsorption removal efficiency of MIP @ MOFs on triazine herbicides reaches over 90%, which indicates that the removal efficiency of MIP @ MOFs on triazine herbicides reaches the optimum.
3. Comparative experiment
As shown in FIG. 4, the comparative analysis of the experimental data with the control group (without adding MIP @ MOFs material) and the treatment group shows that after 120 min, the total removal rate of triazine collected by the control group (without adding MIP @ MOFs material) is much lower than that of the treatment group. The total removal rate is the sum of the adsorption rate and the degradation rate, wherein the degradation rate is that MOFs and sodium persulfate generate sulfate radicals in a synergistic manner to accelerate the catalysis of the herbicide to degrade the herbicide. The treatment group is the MIP @ MOFs material prepared by the method, and the MIP @ MOFs material is used for repairing triazine herbicide pollution in water environment and can reach more than 90%. FIG. 4 shows that compared with the removal capacity of the three materials to triazine herbicides in water, MIP @ MOFs is higher than NIP @ MOFs and is higher than MIL100, which is probably because MIP @ MOF has sites for specifically recognizing and adsorbing triazine herbicides and a larger specific surface area, and simultaneously has MIL100 capable of catalytically degrading triazine herbicides, so that the three materials have excellent effect on removal of triazine herbicides.
The above description is not intended to limit the present invention, and the present invention is not limited to the above examples. Those skilled in the art should also realize that changes, modifications, additions and substitutions can be made without departing from the true spirit and scope of the invention.
Claims (6)
1. A preparation method of a molecular imprinting MOFs material for selectively removing triazine herbicide pollution in a water environment is characterized by comprising the following steps:
(1) Preparation of octahedral MIL100
Dissolving a certain mass of trimesic acid in 1.0 mol/L sodium hydroxide solution, dropwise adding ferrous sulfate tetrahydrate solution with a certain concentration while stirring, continuously stirring at a constant temperature of 25 ℃ for 20 hours, centrifuging to obtain solid precipitate, sequentially ultrasonically washing the solid precipitate with deionized water and ethanol, repeatedly washing for three times, placing in a vacuum drying oven, and drying at a constant temperature of 80 ℃ and 0.04 kPa for 12 hours to obtain orange octahedron MIL100;
(2) Preparation of MIP @ MOFs material
Adding 200 mg of MIL100 obtained in the step (1) into 45 mL of acetonitrile solution, then adding 1mmol of triazine herbicide template molecule and 4 mmol of functional monomer methacrylic acid, ultrasonically mixing for 5 min, sealing and placing at 4 ℃ for prepolymerization for 30 min, then adding 6 mmol of trimethylolpropane trimethacrylate and 80mg of azobisisobutyronitrile, ultrasonically mixing for 3 min, then introducing nitrogen, stirring at 65 ℃ and 150 rpm for 24 h, eluting with methanol to remove template molecules and residual impurities sequentially by using a solution prepared by mixing methanol and acetic acid according to a volume ratio of 9, and vacuum drying to obtain the MIP @ MOFs material.
2. The preparation method of the molecularly imprinted MOFs material for selectively removing triazine herbicide pollution in water environment according to claim 1, wherein the step (1) is specifically as follows: 1.25 g FeCl was weighed 2 ·4H 2 O in 54.10 mL H 2 Stirring the mixture in O at 400 rpm for 30 min, and marking the mixture as a solution A; weighing 0.88 g of trimesic acid, dissolving in 12.62 mL of NaOH solution with the concentration of 1.0 mol/L, magnetically stirring and uniformly mixing at the speed of 400 rpm for 5 min, and marking as solution B; dropwise adding the solution A into the solution B while stirring, continuously stirring at a constant temperature of 25 ℃ for 20 hours, and centrifuging at the speed of 5000 rpm for 10 min to remove supernatant; washing the obtained solid precipitate with deionized water for 3 times, and then washing the solid precipitate with ethanol for 3 times; and after washing, drying the mixture in a vacuum drying oven at the constant temperature of 80 ℃ and under the condition of 0.04 kPa for 12 hours to obtain orange yellow powder, namely the orange yellow octahedron MIL100.
3. The preparation method of the molecularly imprinted MOFs material for selectively removing triazine herbicide pollution in water environment according to claim 1, wherein the step (2) is specifically as follows: adding 200 mg of MIL100 obtained in the step (1) into 45 mL of acetonitrile solution, then adding 1mmol of triazine herbicide and 4 mmol of functional monomer methacrylic acid, ultrasonically mixing for 5 min, sealing and placing in a 4 ℃ environment for prepolymerization for 30 min, waiting for the solution to return to room temperature after the prepolymerization is finished, then adding 6 mmol of trimethylolpropane trimethacrylate and 80mg of azodiisobutyronitrile, ultrasonically mixing for 3 min, introducing nitrogen to remove oxygen in the solution, sealing and placing in a 65 ℃ water bath, stirring at 150 rpm for 24 h, centrifuging at 8000 rpm for 10 min, and removing supernatant; wrapping the obtained solid product with filter paper, placing the wrapped solid product in a Soxhlet extractor, and eluting the wrapped solid product with an eluent formed by mixing methanol and acetic acid according to the volume ratio of 9; after the elution is finished, replacing the elution solvent with pure methanol for removing acetic acid in the eluent until the eluent is neutral; and after the elution is finished, putting the product in a vacuum drying oven, and performing vacuum drying for 12 h at the temperature of 40 ℃ under the environment of 0.04 kPa to obtain the MIP @ MOFs material.
4. The application of the molecular imprinting MOFs material obtained by the preparation method of claim 1 is characterized in that: adding the prepared MIP @ MOFs into a water environment polluted by triazine herbicides, adding a proper amount of catalyst sodium persulfate under the condition of pH5.0-9.0, and adsorbing and catalytically degrading for 30-120 min at the temperature of 5-45 ℃.
5. The use of molecularly imprinted MOFs material according to claim 4, wherein: mixing the prepared MIP @ MOFs in a ratio of 1-3.5 g/m 3 The addition amount of the sodium persulfate is added into a water environment polluted by triazine herbicides, the final concentration of the sodium persulfate catalyst is 1-10 mg/L, and the sodium persulfate catalyst is adsorbed and catalytically degraded for 80-140 min under the conditions of pH of 5.0-9.0 and temperature of 5-45 ℃.
6. Use of molecularly imprinted MOFs materials according to claim 5, wherein: preparing MIP @ MOFs in 2 g/m 3 The addition amount of the sodium persulfate is added into a water environment polluted by triazine herbicides, the catalyst sodium persulfate is added to ensure that the final concentration is 1-5 mg/L, and the adsorption and catalytic degradation are carried out for 120 min under the conditions of pH6 and temperature of 25 ℃.
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