CN110975831B - Preparation method of magnetic beta-cyclodextrin phospholipid membrane and experimental method for analyzing and degrading chlorobenzene compounds by using magnetic beta-cyclodextrin phospholipid membrane - Google Patents
Preparation method of magnetic beta-cyclodextrin phospholipid membrane and experimental method for analyzing and degrading chlorobenzene compounds by using magnetic beta-cyclodextrin phospholipid membrane Download PDFInfo
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- CN110975831B CN110975831B CN201911259169.8A CN201911259169A CN110975831B CN 110975831 B CN110975831 B CN 110975831B CN 201911259169 A CN201911259169 A CN 201911259169A CN 110975831 B CN110975831 B CN 110975831B
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- cyclodextrin
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- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
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Abstract
The invention discloses a preparation method of a magnetic beta-cyclodextrin phospholipid membrane and an experimental method for analyzing and degrading chlorobenzene compounds by using the magnetic beta-cyclodextrin phospholipid membrane, belonging to the field of application of water treatment technology. The invention aims to solve the problems that the existing pretreatment technology for the environmental water sample is long in time consumption and large in organic solvent dosage, a Fenton system is only suitable for a narrow pH range, and the common Fenton-like system has high toxicity, poor chemical stability and the like. The invention takes ferroferric oxide as a precursor, and adopts a hydrothermal synthesis method and a freeze-thaw method to prepare the magnetic beta-cyclodextrin phospholipid membrane, which is a material with adsorption and degradation functions. The invention provides an experimental method which has low toxicity, high efficiency, stability and sensitivity, can be used for quickly analyzing chlorobenzene compounds in an environmental water sample, and can realize the removal of the chlorobenzene compounds in water within a wide pH range.
Description
Technical Field
The invention relates to a preparation method of a magnetic beta-cyclodextrin phospholipid membrane and an experimental method for analyzing and degrading chlorobenzene compounds by using the magnetic beta-cyclodextrin phospholipid membrane, belonging to the field of application of water treatment technology.
Background
The chlorobenzene compounds are chemical raw materials widely applied to the industries of dye, medicine, chemical engineering and the like, and have stable chemical properties, poor biocompatibility and difficult degradation, so the chlorobenzene compounds have long detention time and large accumulation in the environment. Research shows that the chlorobenzene compounds in the environmental water body have low content, but are easy to accumulate in human and animal fat, inhibit nerve centers and reduce the immunity of human bodies. World health organization and international agency for research on cancer have recognized that p-dichlorobenzene is carcinogenic to animals and suspected carcinogenic to humans. In view of the potential hazards of chlorobenzene compounds to people's daily life and health, priority control of pollutants has been placed by many countries, including our country.
Liquid-liquid extraction is the most common water sample pretreatment technology at home and abroad, and is also a standard method for extracting chlorobenzene compounds in environmental water samples specified by the environmental protection department of China; but the dosage of the organic solvent is large, the emulsification phenomenon is easy to generate, and the secondary pollution is easy to cause. In view of the requirement of green chemistry, the use of organic solvents is reduced as much as possible, the number of analysis steps is reduced, the labor intensity is reduced, and the method is a development trend of sample pretreatment.
The advanced oxidation technology has the capability of completely mineralizing organic pollutants, and has the advantages of strong oxidation capability, wide application range, high reaction speed and the like, so that the advanced oxidation technology becomes one of effective methods for treating the organic wastewater difficult to degrade. In the advanced oxidation technology, the Fenton technology is relatively stable and simple, has application advantages, and is widely concerned. The core of the method is that the ferrous iron is used for catalyzing hydrogen peroxide to generate a strong oxidant OH (E) 0 1.8-2.7V) to remove organic pollutants. However, Fenton's reagent still has a series of disadvantages, such as the catalytic effect is greatly influenced by pH and is influenced by H 2 O 2 Has low utilization rate, and the effluent often contains a large amount of Fe 2+ The iron-containing sludge is easy to generate and is not easy to recover, secondary pollution is caused, and the like. Therefore, research and development not only have high specific surface area and guarantee the synergistic effect with hydrogen peroxide under neutral conditions, but also are easy to recover, activate and regenerate, and are the key problems of the application of the Fenton-like reagent in the treatment of the organic pollutants in the water environment.
Disclosure of Invention
The invention provides a material which is low in toxicity, high in efficiency, stable and sensitive, can be used for quickly analyzing chlorobenzene compounds in an environmental water sample, and can remove the chlorobenzene compounds in water within a wide pH range, in order to solve the problems that the existing pretreatment technology for the environmental water sample is long in time consumption and large in the using amount of an organic solvent, a Fenton system is only suitable for a narrow pH range, and a common Fenton-like system is high in toxicity, poor in chemical stability and the like.
The technical scheme of the invention is as follows:
a preparation method of a magnetic beta-cyclodextrin phospholipid membrane comprises the steps of taking ferric iron, ferrous iron, alkali liquor and beta-cyclodextrin as raw materials, synthesizing the magnetic beta-cyclodextrin by adopting a hydrothermal synthesis method, then adding the magnetic beta-cyclodextrin into chloroform in which soybean lecithin is dissolved, carrying out rotary evaporation at 37 ℃ after ultrasonic dispersion, carrying out hydration ultrasonic treatment for 30min, and obtaining the magnetic beta-cyclodextrin phospholipid membrane after twice freeze-thaw treatment, wherein the magnetic beta-cyclodextrin phospholipid membrane is a material with adsorption and degradation functions.
Further limiting, trivalent iron, divalent iron and OH in alkali liquor - And beta-cyclodextrin in a molar ratio of 2:1:8: 1.
Further limiting, the specific operation process for synthesizing the magnetic beta-cyclodextrin comprises the following steps: adding ferric iron and ferrous iron into deionized water for dissolving, introducing nitrogen for deoxidizing, adding alkali liquor for dissolving beta-cyclodextrin after heating in a water bath to 80 ℃, reacting for 1.5 hours under mechanical stirring, and synthesizing the magnetic beta-cyclodextrin.
Further, the alkali liquor is 2mol/L sodium hydroxide aqueous solution.
Further limiting, the mass ratio of the magnetic beta-cyclodextrin to the soybean lecithin to the trichloromethane is 2:1: 50.
further limiting, the freeze-thaw treatment process is as follows: freezing at-10 deg.C for 12h, and thawing at room temperature.
The experimental method for analyzing the content of chlorobenzene organic pollutants in an environmental water sample by using the magnetic beta-cyclodextrin phospholipid membrane prepared by the method comprises the following operation processes: adding the magnetic beta-cyclodextrin phospholipid membrane into an environmental water sample containing chlorobenzene organic pollutants, extracting, leaching, eluting and concentrating chlorobenzene compounds in the environmental water sample to obtain a sample liquid to be detected, detecting and analyzing the obtained sample liquid to be detected by using GC-QTOF MS, and calculating to obtain the actual content of the chlorobenzene compounds in the environmental water sample. The chlorobenzene compounds in the environmental water sample comprise one or a combination of more of chlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, dinitrochlorobenzene, pentachlorobenzene and hexachlorobenzene in any proportion.
And the specific operation process comprises the steps of adding the magnetic beta-cyclodextrin phospholipid membrane prepared by the method into an environmental water sample containing chlorobenzene organic pollutants, and extracting, purifying, enriching, eluting and concentrating chlorobenzene compounds in the environmental water sample to obtain a sample solution to be detected.
Wherein the specific operation process of extraction is as follows: adding an environmental water sample and a magnetic beta-cyclodextrin phospholipid membrane into a conical flask, and performing oscillation extraction for 20-30 min; wherein the mass ratio of the magnetic beta-cyclodextrin phospholipid membrane to the environmental water sample is 1g (3-5) L.
The specific operation process of leaching is as follows: after extraction is finished, separating out a magnetic beta-cyclodextrin phospholipid membrane by using a magnetic field, pouring out waste liquid, adding eluent ethanol, oscillating or ultrasonically treating for 30s, separating out the magnetic beta-cyclodextrin phospholipid membrane by using the magnetic field, and pouring out the waste liquid, wherein the volume ratio of the mass of the magnetic beta-cyclodextrin phospholipid membrane to the eluent ethanol is 1g (20-30) mL.
The specific operation process of elution is as follows: and after leaching, adding an eluent acetonitrile, eluting the trace substance to be detected adsorbed on the surface of the material, wherein the volume ratio of the mass of the magnetic beta-cyclodextrin phospholipid membrane to the eluent acetonitrile is 1g (60-80) mL, repeatedly eluting for 2-4 times, separating the magnetic beta-cyclodextrin phospholipid membrane by using a magnetic field, and collecting the eluent.
The specific operation process of the concentration is as follows: and drying the collected eluent by using nitrogen at the temperature of 40 ℃, and then re-dissolving by using normal hexane to obtain the sample liquid to be detected.
And then, detecting and analyzing the obtained sample liquid to be detected by adopting a gas chromatography-tandem high resolution mass spectrometry (GC-QTOF MS) analysis method, and qualitatively and quantitatively analyzing the chlorobenzene in the environmental water sample by combining a standard curve.
The standard curve refers to the standard curve which is obtained by respectively configuring gradient concentration standard solutions of chlorobenzene compounds, namely chlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, dinitrochlorobenzene, pentachlorobenzene and hexachlorobenzene standard products, contained in an environmental water sample by using an external standard method, performing qualitative detection and analysis by using GC-QTOF MS (gas chromatography-quantitative analysis) according to retention time, accurate molecular weight or isotopic peak abundance ratio, calculating peak areas of all components, taking 7-11 detection points, and performing linear regression on actual concentrations of all components in the standard solutions by using the peak areas of all the components.
Performing detection analysis on the sample liquid to be detected by using GC-QTOF, performing qualitative determination according to retention time, accurate molecular weight or isotope peak abundance ratio of each chlorobenzene compound standard, then calculating to obtain the peak area of each chlorobenzene compound, respectively substituting the peak area of each chlorobenzene compound into respective standard curve equation to obtain the actual concentration of each chlorobenzene compound in the sample liquid to be detected, calculating to obtain the actual concentration of each chlorobenzene compound in the sample liquid to be detected according to mass, concentration and volume, and further calculating to obtain the actual content of each chlorobenzene compound in an environmental water sample.
The method for degrading chlorobenzene organic pollutants in an environmental water sample by using the magnetic beta-cyclodextrin phospholipid membrane prepared by the method comprises the following specific operation processes: adding hydrogen peroxide into an environmental water sample containing chlorobenzene organic pollutants, adjusting the pH to 2-8, then adding a magnetic beta-cyclodextrin phospholipid membrane as a catalyst, stirring the water sample, irradiating the water sample with visible light for 10-210 min, detecting and analyzing the obtained sample liquid to be detected by using GC-QTOF MS, and calculating the degradation capability of the magnetic beta-cyclodextrin phospholipid membrane on chlorobenzene compounds in the environmental water sample.
Further limited, the addition amount of the magnetic beta-cyclodextrin phospholipid membrane is as follows: 0.5 g-2.0 g of water is added into 1L of environmental water sample.
Further limit of H 2 O 2 The addition amount is as follows: 10 mmol-60 mmol is added into 1L environmental water sample.
The invention has the following beneficial effects: the invention takes ferroferric oxide as a precursor, and adopts a hydrothermal synthesis method and a freeze-thaw method to prepare the material with the adsorption and degradation functions of the magnetic beta-cyclodextrin phospholipid membrane.
(1) The material has two functional adsorption groups of beta-cyclodextrin and a phospholipid double-layer membrane, can effectively adsorb chlorobenzene compounds in water, is used for quickly analyzing the content of the chlorobenzene compounds in an environmental water sample, and can naturally shield macromolecular interference groups in the water through a space effect. In addition, the magnetic beta-cyclodextrin phospholipid membrane is matched with hydrogen peroxide, and OH is generated by utilizing an oxide surface oxygen vacancy mechanism and a Haber-Weiss mechanism and is used for degrading chlorobenzene organic pollutants. Namely, the material can be used as an adsorbent and a catalyst.
(2) As an adsorbent, the material can extract chlorobenzene compounds in environmental water. It has excellent selectivity to target matter and natural anti-interference to humic acid in water. In addition, the adsorbent has excellent magnetism, and can be separated from the sample matrix in a short time after extraction is finished, so that the analysis time can be effectively saved.
(3) As a catalyst, the magnetic beta-cyclodextrin phospholipid membrane can be used together with hydrogen peroxide, has strong affinity to chlorobenzene compounds in environmental water, and has good catalytic degradation rate on organic pollutants under the condition of visible light. The conversion between Fe (II) and Fe (III) realizes the recycling of the catalyst, and compared with the traditional Fenton system, the method overcomes the defects that the traditional Fenton system is only suitable for a narrower pH range and the common Fenton-like system, such as Co 2+ PMS due to Co 2+ High toxicity, high price of PMS and relatively poor chemical stability, and limits the popularization and application of the PMS.
(4) The method for measuring chlorobenzene compounds by using the GC-QTOF MS method has high resolution and sensitivity, can accurately determine the target object and eliminate interferents with the mass-to-charge ratio similar to that of the target object.
(5) The material prepared by the invention has excellent degradation performance on chlorobenzene compounds within the pH range of 2-8, and has an obvious mineralization effect.
(6) In addition, the method has the advantages of lower price, more stable property, more contribution to industrial application and the like.
Drawings
FIG. 1 is a schematic representation of TEM characterization of a magnetic β -cyclodextrin phospholipid membrane prepared according to embodiment 1;
FIG. 2 is a graph showing the influence of extraction time on the adsorption effect of the magnetic β -cyclodextrin phospholipid membrane prepared in embodiment 1 on chlorobenzene compounds in an environmental water sample;
FIG. 3 is a GC-QTOF MS full-scan total ion flow graph of chlorobenzene compounds in a standard water sample;
FIG. 4 is a GC-QTOF MS extraction ion chromatogram of chlorobenzene compounds;
fig. 5 is a schematic diagram illustrating the degradation effect of the magnetic β -cyclodextrin phospholipid membrane prepared in embodiment 1 on chlorobenzene compounds.
Detailed Description
The experimental procedures used in the following examples are conventional unless otherwise specified.
Embodiment mode 1: preparation of magnetic beta-cyclodextrin phospholipid membranes
Ferric chloride and ferrous sulfate are used as raw materials, added into deionized water to be mixed and dissolved, nitrogen is introduced to remove oxygen, and the temperature is raised to 80 ℃ in a water bath. Dissolving beta-cyclodextrin in sodium hydroxide solution, adding the beta-cyclodextrin into the iron mixed solution, and mechanically stirring for reaction for 1.5h to synthesize the magnetic beta-cyclodextrin. After the reaction is finished, performing magnetic field separation, washing the magnetic material with deionized water until the magnetic material is neutral, adding the magnetic material into chloroform in which the soybean lecithin is dissolved, performing ultrasonic dispersion, and performing rotary evaporation at the temperature of 37 ℃ to obtain a uniform film; and (3) placing the rotary evaporation bottle in a vacuum drying oven for drying for 12h, adding deionized water, carrying out hydration ultrasound for 30min, freezing for 12h in an environment at the temperature of-10 ℃, then thawing in a room temperature environment, and freezing and thawing twice to obtain the magnetic beta-cyclodextrin phospholipid membrane. Wherein the molar ratio of the ferric chloride to the ferrous sulfate to the sodium hydroxide to the beta-cyclodextrin is 2:1:8: 1; the mass ratio of the magnetic beta-cyclodextrin to the soybean lecithin to the trichloromethane is 2:1: 50.
The TEM representation of the prepared magnetic beta-cyclodextrin phospholipid membrane is shown in figure 1. As can be seen from FIG. 1, the synthesized material has clear morphology, uniform particle size and diameter within the range of 15-20 nm.
Embodiment mode 2: experimental method for analyzing and detecting chlorobenzene compounds in environmental water sample by using magnetic beta-cyclodextrin phospholipid membrane prepared in specific embodiment 1
(1) Preparing a sample solution to be tested
a. And (3) extraction: measuring 500mL of surface water as an environmental water sample, adding the environmental water sample into a conical flask, mixing the environmental water sample with 100mg of magnetic beta-cyclodextrin phospholipid membrane, placing the mixture into a constant temperature oscillator, oscillating for 5-35 min under the condition of 100r/min, and adsorbing chlorobenzene compounds in the environmental water sample to a magnetic adsorbent phase from a water phase in the process. Wherein, the extraction time influences the adsorption effect of the magnetic beta-cyclodextrin phospholipid membrane on chlorobenzene compounds in an environmental water sample, as shown in fig. 2.
b. Leaching: after extraction is finished, placing a super-strong magnet at the bottom of the conical flask, adsorbing the magnetic beta-cyclodextrin phospholipid membrane at the bottom of the conical flask, and pouring off waste liquid; adding 2mL of ethanol, oscillating or ultrasonically treating for 30s, separating by a magnetic field, and pouring off waste liquid;
c. and (3) elution: washing the washed magnetic beta-cyclodextrin phospholipid membrane with acetonitrile, eluting the chlorobenzene compounds adsorbed on the membrane for 2 times, 3mL once, and performing ultrasonic treatment for 30s each time; magnetic field separation, and combining eluates;
d. concentration: and drying the collected eluent by using nitrogen at 40 ℃, and then re-dissolving by using 0.5mL of n-hexane to obtain a sample solution to be detected.
(2) GC-QTOF MS is used for analyzing and detecting sample liquid to be detected
And (3) carrying out gas chromatography separation and high-resolution mass spectrometry detection on the sample liquid to be detected obtained in the step (1).
Gas chromatographic separation: an Agilent 7890B system is adopted and is provided with elements such as an automatic sampler. The column was an Agilent HP-5M capillary column (length 30M. times.0.25 mm, 0.1 μ M). High-purity helium gas is used as carrier gas, and the flow rate is 1.2 mL/min. The initial temperature of the column box was maintained at 60 ℃ for 5 minutes, then the temperature was raised at a rate of 20 ℃/min to 140 ℃ and then at a rate of 10 ℃/min to 280 ℃. The temperature of a sample inlet is 250 ℃; injecting sample in a non-shunting mode; the sample injection volume is 2 mu L; high-purity helium is taken as carrier gas, and the flow rate is 1.2 mL/min; high purity nitrogen was used as the collision gas at a flow rate of 1.5 mL/min.
High-resolution mass spectrometry detection: an Agilent 7250 quadrupole series-connection time-of-flight mass spectrometer is adopted, and an EI ion source is matched, wherein the energy of the ion source is 70 eV; the full scanning range is 50-400 amu; mass Hunter software is adopted for data acquisition and analysis; the acquisition rate is 5 mass spectrograms/s; the acquisition time was 200 ms/mass spectrum.
The test results were as follows:
firstly, performing GC-QTOF MS detection on chlorobenzene compounds in a blank water sample (surface water without chlorobenzene compounds) and a standard water sample (surface water added with 7 chlorobenzene standard substances, chlorobenzene can not be detected in the sample liquid to be detected, and the standard is used for performing method verification) according to the experimental method, wherein the qualitative analysis result is shown in the following table.
The GC-QTOF MS full-scanning total ion flow graph of chlorobenzene compounds in the standard water sample is shown in figure 3. GC-QTOF MS extraction ion chromatogram of 7 chlorobenzene compounds is shown in figure 4.
And (3) carrying out gradient dilution sampling in a standard substance concentration range of 5-1000 ng/mL, taking the standard substance concentration as an abscissa, taking a corresponding peak area as an ordinate, and carrying out linear fitting by taking y as a + bx. The detection Limit (LOD) and lower quantification Limit (LOQ) of the target were determined at 3-fold and 10-fold signal-to-noise ratios, respectively. The standard adding concentration of the standard adding water sample is respectively LOQ, 5 times LOQ and 20 times LOQ, 3 samples are set for each concentration, the determination is carried out according to a proposed method, and the precision and the recovery rate in and during the day are calculated.
The experimental results show that: the standard recovery rate of the 7 chlorobenzene compounds obtained by the method is 80.5-99.1%, the intra-day precision is 4.4-5.7%, and the inter-day precision is 4.0-7.3%. Linear model R 2 The detection limit of 7 chlorobenzene compounds is 1.3-6.5ng/L, and the lower limit of quantification is 4.2-21.5 ng/L.
Specific example 3: experimental method for degrading and removing chlorobenzene compounds in environmental water sample by applying magnetic beta-cyclodextrin phospholipid membrane prepared in specific embodiment 1
Mixing 30% of H 2 O 2 (600 mu L) is added into a series of 200mL chlorobenzene compound aqueous solutions with the concentration of 10.0mg/L, the pH value is adjusted to be 4, then 100mg magnetic beta-cyclodextrin phospholipid membranes are added, the aqueous solutions are stirred to obtain suspended matters, visible light irradiation is carried out while stirring, the aqueous solutions are irradiated for 10-210 min, 5mL solutions are taken out at intervals during the illumination process to carry out magnetic field separation to obtain clear upper-layer solutions, n-hexane is used for carrying out liquid-liquid extraction (2mL multiplied by 3), the n-hexane is combined, and then GC-QTOF MS is used for measuring the concentration of the chlorobenzene compounds to examine the removal capacity of the chlorobenzene compounds, and the result is shown in figure 5.
Claims (6)
1. A preparation method of a magnetic beta-cyclodextrin phospholipid membrane is characterized in that ferric iron, ferrous iron, alkali liquor and beta-cyclodextrin are used as raw materials, a hydrothermal synthesis method is adopted to synthesize magnetic beta-cyclodextrin, then the magnetic beta-cyclodextrin is added into trichloromethane in which soybean lecithin is dissolved, rotary evaporation is carried out at 37 ℃ after ultrasonic dispersion, hydration and ultrasonic treatment are carried out for 30min, and after freeze thawing treatment is carried out twice, the magnetic beta-cyclodextrin phospholipid membrane is obtained, and is a material with adsorption and degradation functions;
OH in the ferric iron, the ferrous iron and the alkali liquor - And beta-cyclodextrin in a molar ratio of 2:1:8: 1;
the alkali liquor is 2mol/L sodium hydroxide aqueous solution;
the mass ratio of the magnetic beta-cyclodextrin to the soybean lecithin to the trichloromethane is 2:1: 50;
the freeze-thaw treatment process comprises the following steps: frozen at-10 ℃ for 12h and then thawed at room temperature.
2. The method for preparing the magnetic beta-cyclodextrin phospholipid membrane as claimed in claim 1, wherein the specific operation process for synthesizing the magnetic beta-cyclodextrin comprises the following steps: adding ferric iron and ferrous iron into deionized water for dissolving, introducing nitrogen for deoxidizing, heating in a water bath to 80 ℃, adding alkali liquor for dissolving beta-cyclodextrin, and reacting for 1.5 hours to obtain the magnetic beta-cyclodextrin.
3. An experimental method for analyzing the content of chlorobenzene organic pollutants in an environmental water sample by using the material prepared by the method as claimed in claim 1, which is characterized in that the operation process of the experimental method comprises the following steps: adding the magnetic beta-cyclodextrin phospholipid membrane into an environmental water sample containing chlorobenzene organic pollutants, extracting, leaching, eluting and concentrating chlorobenzene compounds in the environmental water sample to obtain a sample liquid to be detected, detecting and analyzing the obtained sample liquid to be detected by using GC-QTOF MS, and calculating to obtain the actual content of the chlorobenzene compounds in the environmental water sample.
4. An experimental method for degrading chlorobenzene organic pollutants in an environmental water sample by using the material prepared by the method as claimed in claim 1, is characterized in that the specific operation process of the experimental method is as follows: adding hydrogen peroxide into an environmental water sample containing chlorobenzene organic pollutants, adjusting the pH to 2-8, adding a material with adsorption and degradation functions as a catalyst, stirring the water sample, irradiating the water sample with visible light for 10-210 min, detecting and analyzing the obtained sample liquid to be detected by using GC-QTOF MS, and calculating the degradation capability of the magnetic beta-cyclodextrin phospholipid membrane on chlorobenzene compounds in the environmental water sample.
5. A degradation experimental method according to claim 4, wherein the magnetic β -cyclodextrin phospholipid membrane is added in an amount of: 0.5 g-2.0 g of water is added into 1L of environmental water sample.
6. A degradation assay method according to claim 4, wherein said H is 2 O 2 The addition amount is as follows: 10 mmol-60 mmol is added into 1L environmental water sample.
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