CN115928110A - Hydrogenation dechlorination method of high-concentration chlorinated aromatic compound - Google Patents
Hydrogenation dechlorination method of high-concentration chlorinated aromatic compound Download PDFInfo
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Abstract
The invention discloses a hydrogenation dechlorination method of a high-concentration chlorinated aromatic compound, which is characterized in that the high-concentration chlorinated aromatic compound is added into an alkaline solution to obtain catholyte, the alkaline aqueous solution is used as anolyte, a palladium modified electrode is used as a cathode, stainless steel is used as an anode, an electrolytic reaction is carried out in an electrolytic tank separated by an ion exchange membrane, an electrolyte solution of the dechlorinated compound is obtained after the electrolytic reaction is finished, the electrolyte solution is separated and purified to obtain the dechlorinated compound, and the palladium modified electrode is prepared by adopting a cathode deposition method. The hydrogenation and dechlorination method of the high-concentration chlorinated aromatic compound provided by the invention can simultaneously realize high reactant concentration, high space-time yield, high selectivity, high current efficiency and high current density, not only can greatly reduce the consumption of catalyst palladium and reduce the energy consumption of electrolysis, but also can produce products with high added value in the treatment process of chlorinated organic compounds.
Description
Technical Field
The invention belongs to the field of water pollution treatment, and particularly relates to a hydrogenation dechlorination method of a high-concentration chlorinated aromatic compound.
Background
Chlorinated aromatic Compounds (CAPs) are an important class of persistent organic compounds, widely exist in industrial wastewater generated in the field of synthesis of pesticides, medicines, dyes and the like, and have very high toxicity to both organisms and the environment. The removal of chlorine atoms from CAPs to produce less toxic aromatic or paraffinic species is a common environmental remediation route. Palladium-catalyzed electrochemical hydrogenation processes are of particular interest because of the advantages of no need for the addition of expensive or hazardous reducing agents, mild reaction conditions, and high reaction selectivity. Various CAPs in the wastewater can be converted into the same substance through selective hydrogenation dechlorination reaction catalyzed by palladium (for example, chlorophenol can be dechlorinated into phenol, chlorophenoxyacetic acid can be dechlorinated into phenoxy acetic acid, and chloropicolinic acid can be dechlorinated into picolinic acid), and the hydrogenation dechlorination method with high chemical selectivity is expected to realize the change of the CAPs in the industrial wastewater into valuable.
Unfortunately, most of the current studies on palladium-catalyzed electrochemical hydrodechlorination are focused on the treatment of low concentrations (mg/L scale) of CAPs in water and require high amounts of palladium catalyst. For example, the invention patent application with the application number of 200910237763.7 discloses a palladium catalyst for treating chlorine-containing organic matters in water and a preparation method thereof, wherein the palladium catalyst takes an electrochemical reduction-oxidation coupling multifunctional supported palladium catalyst as an electrochemical cathode catalyst, has the functions of reduction dechlorination, and fully utilizes the reduction function of the cathode to improve the electrochemical treatment efficiency of the chlorine-containing organic matters in the water, but still has the defects. This leads to a series of problems such as high catalyst cost per CAPs throughput, low current efficiency, low current density, difficult recovery of dechlorinated products, etc., and difficult economic benefits. Therefore, the invention provides a hydrodechlorination method with low loading capacity and high conversion rate and selectivity for high-concentration CAPs, and has important application value.
Disclosure of Invention
In order to solve the technical problem, the invention provides a hydrogenation dechlorination method of a high-concentration chlorinated aromatic compound, which comprises the steps of adding various CAPs into an alkaline solution to obtain a high-concentration electrolytic reaction solution, and then carrying out electrolytic reaction in an electrolytic tank separated by an ion exchange membrane by taking a palladium modified conductive material as a cathode and a chemical inert conductive material as an anode, wherein the dechlorination with high current efficiency, high current density, high space-time yield and high selectivity can be realized by various CAPs. The method can effectively solve the problems of low reactant concentration, low palladium utilization rate, low current efficiency, low current density and the like in the existing palladium catalytic dechlorination technology.
The technical scheme adopted by the invention is as follows:
the invention provides a hydrogenation dechlorination method of a chlorinated aromatic compound, which comprises the following steps: adding the chlorinated aromatic compound shown in the formula (I) into an alkaline aqueous solution to obtain catholyte, taking the alkaline aqueous solution as anolyte, a palladium modified electrode as a cathode and stainless steel as an anode, carrying out an electrolytic reaction in an electrolytic tank separated by an ion exchange membrane, obtaining an electrolyte containing a dechlorinated compound shown in the formula (II) after the electrolytic reaction is finished, and separating and purifying the electrolyte to obtain the dechlorinated compound shown in the formula (II).
XRCln XRHn
(Ⅰ) (Ⅱ)
In the formula (I), R is a single benzene ring or a single pyridine ring; x is hydroxyl, carboxyl or methoxy acetate, and n is one of positive integers between 1 and 5; r, X and n in formula (II) are the same as formula (I).
The concentration of the chlorinated aromatic compound shown in the formula (I) in the catholyte is 5-300 g/L.
The chlorinated aromatic compound shown in the formula (I) is one or more of chloropicolinic acid, chlorophenol, chlorobenzoic acid and chlorophenoxyacetic acid.
The pH of the catholyte ranges from 10 to 14, preferably from 12 to 14, more preferably 14.
The pH of the anolyte is 13 to 14, preferably 12 to 14, more preferably 14.
The conditions of the electrolytic reaction are as follows: the current density is 1 to 20A/dm 2 Preferably 2 to 15A/dm 2 More preferably 2 to 12.5A/dm 2 The temperature is from 0 to 100 ℃, preferably from 10 to 80 ℃, more preferably from 20 to 70 ℃.
The alkaline aqueous solution is prepared by mixing water and supporting electrolyte; the supporting electrolyte is one or more of sodium hydroxide, potassium hydroxide, lithium hydroxide, ammonium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, tetramethylammonium hydroxide, tetraethylammonium hydroxide or tetrapropylammonium hydroxide, and preferably sodium hydroxide; the concentration of the supporting electrolyte in the electrolyte is 0.1 to 2.0mol/L, preferably 1 to 2.0mol/L.
The anode shape may be plate, rod, wire, mesh, net, foam, wool or sheet, preferably plate.
The electrolysis reaction according to the invention can be carried out batchwise or in a continuous or semi-continuous manner. The electrolysis cell may be a stirred cell containing electrodes or a flow cell of any conventional design. The electrolytic cell may be a diaphragm electrolytic cell or a non-diaphragm electrolytic cell, preferably a diaphragm electrolytic cell.
The anodic reaction described in the present invention may be an oxygen evolution reaction involving evolution of oxygen gas, but also an evolution involving chlorine and bromine molecules, a hydrogen oxidation reaction, the production of carbon dioxide by oxidation of protective substances such as formates or oxalates or the formation of valuable by-products by oxidation of organic reactants, preferably an oxygen evolution reaction.
The palladium modified electrode is prepared by adopting a cathode deposition method; further, the palladium modified electrode is specifically prepared by the following method:
(1) Preparing an electrode substrate: taking a conductive material as an electrode matrix, firstly cleaning grease on the surface of the matrix by using an organic solvent, and then etching an oxide layer on the surface of the matrix by using an acidic aqueous solution to obtain a treated electrode matrix;
(2) Cathode deposition: taking the treated electrode matrix obtained in the step (1) as a cathode, an inert material as an anode, an aqueous solution containing polyvinylpyrrolidone, sodium sulfate and palladium salt as a catholyte, an aqueous solution of sodium sulfate as an anolyte, and preparing the palladium loading capacity of 0.5-5 g/m by adopting a cathodic deposition method 2 The palladium-modified electrode of (1).
In the step (1), the electrode substrate is selected from metals of nickel, stainless steel, titanium and silver or carbon of graphite, carbon fiber, carbon felt and glassy carbon, the organic solvent is one or more of acetone, ethanol, methanol and ether, and the acidic aqueous solution is one or more of aqueous solutions of sulfuric acid, hydrochloric acid and nitric acid.
In the step (2), the inert material is one of graphite, platinum, titanium, silver, stainless steel and the like.
In the catholyte in the step (2), the concentration of the polyvinylpyrrolidone is 0.5-5 g/L, preferably 2-4 g/L, and more preferably 2.5g/L, the palladium salt is one or more of palladium chloride, sodium tetrachloropalladate, palladium acetate, palladium sulfate, and palladium nitrate, the concentration of the palladium salt is 5-50 mg/L, preferably 20-30 mg/L, and more preferably 25mg/L, and the concentration of the sodium sulfate is 5-50 g/L, preferably 10-20 g/L, and more preferably 14.2g/L. In the anolyte of the step (2), the concentration of the sodium sulfate is 5 to 50g/L, preferably 10 to 30g/L, and more preferably 14.2g/L.
The technological parameters of the cathode deposition method are as follows: the applied current density is 0.05-0.15A/dm 2 Preferably 0.06 to 0.10A/dm 2 More preferably 0.075A/dm 2 The deposition time is 20 to 60min, preferably 25 to 40min, more preferably 30min.
The present invention performs the required electrolytic reduction by techniques well known in the art. Generally, the starting chlorinated aromatic compound or mixture thereof is dissolved or partially dissolved in a solvent, a quantity of supporting electrolyte is added, sufficient current is passed through the cell until the desired degree of reduction is obtained, and after the electrolysis reaction is complete, the reaction solution is adjusted by further pH and the product is recovered by conventional techniques, such as acid precipitation filtration or chemical extraction.
The reaction involved in the electrochemical reduction of the high-concentration chloro-aromatic compound (taking chloro-picolinic acid as an example) is as follows:
(1) And (3) neutralization reaction:
(2) And (3) cathode reaction:
(3) And (3) anode reaction:
2n OH-→1/2n O 2 +2n e-
(4) And (3) total reaction:
the invention has the following beneficial effects: the hydrogenation dechlorination method of the high-concentration chlorinated aromatic compound provided by the invention can simultaneously realize high reactant concentration (200 g/L) and high current density (2-10A/dm) 2 ) Low electrolysis voltage (less than or equal to 3V), high conversion rate (more than or equal to 99 percent), high selectivity (more than or equal to 98 percent) and low energy consumption (SEEC less than or equal to 6kW h kg) of unit product of electrolysis production -1 ) The method not only can greatly reduce the consumption of catalyst palladium and reduce the electrolysis energy consumption, but also can produce products with high added value in the treatment process of chlorinated organic compounds.
Drawings
FIG. 1 is a scanning electron microscope comparison of palladium modified nickel foam prepared in example 1 and comparative example 1.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of protection of the invention is not limited thereto:
the inventionThe energy consumption per unit product of electrolytic production (SEEC) in an embodiment is calculated by the formula: SEEC = (I × t × U)/(1000 × Δ C × V) (kW h kg -1 )
Wherein: i is current (A), t is time (h), U is average electrolytic voltage (V), deltaC is mass concentration (kg/L) of the target product, and V is electrolyte volume (L).
EXAMPLE 1 preparation of Palladium modified foamed Nickel cathode (PdNPs/Ni)
Cutting 2cm multiplied by 2cm of foamed nickel to serve as an electrode matrix, firstly cleaning grease on the surface of the matrix by acetone, and then etching an oxide layer on the surface of the matrix by nitric acid aqueous solution to obtain the treated electrode matrix. The treated electrode matrix is used as a working electrode, graphite is used as a counter electrode, an aqueous solution containing 2.5g/L of polyvinylpyrrolidone, 25mg/L of sodium tetrachloropalladate with palladium concentration and 14.2g/L of sodium sulfate is used as a catholyte, an aqueous solution containing 14.2g/L of sodium sulfate is used as an anolyte, and 0.075A/dm of sodium sulfate is added 2 The deposition time was 30min.
Example 2 electrochemical hydrodechlorination of 3,6-dichloropicolinic acid (3,6-D) at a concentration of 0.1mol/L
In an ion exchange membrane-separated diaphragm cell, palladium modified nickel foam was used as the cathode (modification method according to example 1), stainless steel was used as the anode, and the distance between the cathode and the anode was 5cm.30mL 1.0mol/L NaOH +19.2 g/L3,6-D as catholyte; 30mL of 1.0mol/L NaOH was used as the anolyte. The temperature in the electrolysis process is controlled to be 25 ℃, and the current density is controlled to be 2.5A/dm 2 The electrolytic voltage is 1.8V-2.4V. After 5 hours of electrolysis, the catholyte was transferred to a beaker, adjusted to pH =4 by addition of sulfuric acid, and then analyzed by HPLC for a conversion of 3,6-D of 100%, a yield of picolinic acid of 95%, and a SEC of 6.08kW h kg -1 。
The high performance liquid phase analysis conditions are as follows: the chromatographic column (150 mm length × 4.6mm i.d.,5 μm particulate size) is a separation column, the volume ratio of mobile phase is acetonitrile/methanol/water =2/3/5 mixed solution (containing 30mmol/L phosphoric acid), the injection volume is 20 μ L, the injection temperature is 30 ℃, the flow rate is 1mL/min isocratic elution, the wavelength of the ultraviolet detector is 260nm, and the standard curve is determined by adopting an external standard method for the quantitative calculation of reactants and products.
Example 3 electrochemical hydrodechlorination of 3,6-dichloropicolinic acid (3,6-D) at a concentration of 1mol/L
In an ion exchange membrane-separated diaphragm cell, palladium modified nickel foam was used as the cathode (modification method according to example 1), stainless steel was used as the anode, and the distance between the cathode and the anode was 5cm.30mL 1.0mol/L NaOH +192 g/L3,6-D as catholyte; 30mL of 1.0mol/L NaOH was used as the anolyte. The temperature in the electrolytic process is controlled to be 25 ℃, different current densities are applied in sections according to the electrolytic time of 0 h-1 h, 1 h-3 h and 3 h-8 h, and the current densities are respectively 25A/dm 2 、12.5A/dm 2 And 2.5A/dm 2 The electrolytic voltage is respectively 6.7V-11.2V, 4.7V-5.5V and 2.9V-3.7V. After 8 hours of electrolysis, the catholyte was transferred to a beaker, adjusted to pH =4 by addition of sulfuric acid, and then analyzed by HPLC for a conversion of 3,6-D of 100%, a yield of picolinic acid of 95%, and a SEC of 8.94kW h kg -1 。
The high performance liquid phase analysis conditions are as follows: the chromatographic column (150 mm length × 4.6mm i.d.,5 μm particulate size) is a separation column, the volume ratio of mobile phase is acetonitrile/methanol/water =2/3/5 mixed solution (containing 30mmol/L phosphoric acid), the injection volume is 20 μ L, the injection temperature is 30 ℃, the flow rate is 1mL/min isocratic elution, the wavelength of the ultraviolet detector is 260nm, and the standard curve is determined by adopting an external standard method for the quantitative calculation of reactants and products.
Example 4 electrochemical hydrodechlorination of 4-amino-3,6-dichloropicolinic acid (4-N-3,6-D) at a concentration of 0.1mol/L
In an ion exchange membrane-separated diaphragm cell, palladium modified nickel foam was used as the cathode (modification method according to example 1), stainless steel was used as the anode, and the distance between the cathode and the anode was 5cm.30mL 1.0mol/L NaOH +20.7g/L4-N-3,6-D as catholyte; 30mL of 1.0mol/L NaOH was used as the anolyte. The temperature in the electrolysis process is controlled to be 25 ℃, and the current density is controlled to be 2.5A/dm 2 The electrolytic voltage is 1.9V-2.4V. After 8 hours of electrolysis, the catholyte was transferred to a beaker, adjusted to pH =4 by addition of sulfuric acid, and then analyzed by high performance liquid chromatography for a conversion of 4-N-3,6-D of 96%, a yield of 4-amino-picolinic acid of 95%, and a SECC of 8.87kW hkg -1 。
The high performance liquid phase analysis conditions were: the chromatographic column (150 mm length × 4.6mm i.d.,5 μm particle size) is a separation column, the volume ratio of mobile phase is acetonitrile/methanol/water =2/3/5 mixed solution (containing 30mmol/L phosphoric acid), the injection volume is 20 μ L, the injection temperature is 30 ℃, the flow rate is 1mL/min isocratic elution, the wavelength of the ultraviolet detector is 260nm, and a standard curve is determined by an external standard method for the quantitative calculation of reactants and products.
EXAMPLE 5 electrochemical hydrodechlorination of 2,4-dichlorophenol (2,4-DCP) at a concentration of 0.1mol/L
In an ion exchange membrane-separated diaphragm cell, palladium modified nickel foam was used as the cathode (modification method according to example 1), stainless steel was used as the anode, and the distance between the cathode and the anode was 5cm.30mL 1.0mol/L NaOH +16.3 g/L2,4-DCP as catholyte; 30mL of 1.0mol/L NaOH was used as the anolyte. The temperature in the electrolysis process is controlled to be 25 ℃, and the current density is controlled to be 2.5A/dm 2 The electrolytic voltage is 1.8V-2.4V. After 8 hours of electrolysis, the catholyte was transferred to a beaker, adjusted to pH =4 by addition of sulfuric acid, and then analyzed by HPLC for a conversion of 2,4-DCP of 98%, a yield of phenol of 96%, and a SEEC of 12.68kW h kg -1 。
The high performance liquid phase analysis conditions were: the chromatographic column (250 mm length × 4.6mm i.d.,5 μm particulate size) is a separation column, the volume ratio of mobile phase is a mixed solution (containing 30mmol/L phosphoric acid) of methanol/water =4/1, the injection volume is 20 μ L, the injection temperature is 20 ℃, the flow rate is 1mL/min isocratic elution, the wavelength of an ultraviolet detector is 280nm, and a standard curve is determined by adopting an external standard method for the quantitative calculation of reactants and products.
Examples 6 to 20
Examples 6 to 20 were carried out according to the experimental parameters of table 1, the rest being the same as example 2.3,6-dichloropicolinic acid, 4-chlorophenoxyacetic acid, 4-chloroformic acid, 4-chlorophenol, 2,4,6-trichlorophenol are represented by 3,6-D, 4-CPA, 4-CBA, 4-CP, 2,4,6-TCP, respectively.
Table 1 examples 6 to 20 experimental conditions and results
COMPARATIVE EXAMPLE 1 electrochemical hydrodechlorination of 3,6-dichloropicolinic acid (3,6-D) using a conventional palladium modified foamed nickel cathode (Pd/Ni) at a catalytic concentration of 0.1mol/L (compare with example 2)
Pd/Ni cathodes were prepared according to example 1, but without polyvinylpyrrolidone being added during the preparation.
In the diaphragm electrolytic cell separated by the ion exchange membrane, pd/Ni is used as a cathode, stainless steel is used as an anode, and the distance between the cathode and the anode is 5cm.30mL 1.0mol/L NaOH +19.2 g/L3,6-D as catholyte; 30mL of 1.0mol/L NaOH was used as the anolyte. The temperature in the electrolysis process is controlled at 25 ℃, and the current density is controlled at 2.5A/dm 2 The electrolytic voltage is 1.8V-2.4V. After 5 hours of electrolysis, the catholyte was transferred to a beaker, adjusted to pH =4 by adding sulfuric acid, and then analyzed by hplc for a conversion of 3,6-D of 95%, a yield of picolinic acid of 59%, and a SEEC of 10.86kW hr kg -1 。
Comparative example 1 illustrates that electrochemical dechlorination of 3,6-D by conventional Pd/Ni cathodic treatment does not yield desirable results (low yield, low current efficiency).
COMPARATIVE EXAMPLE 2 Low concentration 0.001 mol/L3,6-dichloropicolinic acid (3,6-D) electrochemical hydrodechlorination (compare with examples 2, 3)
In a membrane cell separated by an ion exchange membrane, palladium modified nickel foam was used as the cathode (modification method according to example 1), stainless steel was used as the anode, and the distance between the cathode and the anode was 5cm.30mL 1.0mol/L NaOH +192 mg/L3,6-D as catholyte; 30mL of 1.0mol/L NaOH was used as the anolyte. The temperature in the electrolysis process is controlled to be 25 ℃, and the current density is controlled to be 0.075A/dm 2 The electrolytic voltage is 1.9V-2.3V. After 5 hours of electrolysis, the catholyte was transferred to a beaker, addAdjusting pH =4 with sulfuric acid, and analyzing with HPLC for 3,6-D with 100% conversion, 99% yield of picolinic acid, and SEEC of 11.15kW h kg -1 。
Comparative example 2 illustrates that electrochemical dechlorination at low concentrations of 2,4-D does not give the desired results (low current density, low current efficiency, low space time yield).
Claims (10)
1. A process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations, said process comprising: adding a chlorinated aromatic compound shown in a formula (I) into an alkaline aqueous solution to obtain catholyte, taking the alkaline aqueous solution as anolyte, a palladium modified electrode as a cathode and stainless steel as an anode, carrying out an electrolytic reaction in an electrolytic tank separated by an ion exchange membrane, obtaining an electrolyte containing a dechlorinated compound shown in a formula (II) after the electrolytic reaction is finished, and separating and purifying the electrolyte to obtain the dechlorinated compound shown in the formula (II), wherein the chlorinated aromatic compound shown in the formula (I) is characterized in that: the palladium modified electrode is prepared by adopting a cathode deposition method;
XRCln XRHn
（Ⅰ） （Ⅱ）
in the formula (I), R is a single benzene ring or a single pyridine ring; x is hydroxyl, carboxyl or methoxy acetate, and n is one of positive integers between 1~5; r, X and n in formula (II) are the same as formula (I).
2. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 1, characterized in that: the palladium modified electrode is prepared by the following specific method:
(1) Taking a conductive material as an electrode matrix, firstly cleaning grease on the surface of the matrix by using an organic solvent, and then etching an oxide layer on the surface of the matrix by using an acidic aqueous solution to obtain a treated electrode matrix;
(2) And (2) taking the treated electrode matrix obtained in the step (1) as a cathode, taking an inert material as an anode, taking an aqueous solution containing polyvinylpyrrolidone, sodium sulfate and palladium salt as a catholyte, taking an aqueous solution of sodium sulfate as an anolyte, and preparing the palladium modified electrode by adopting a cathodic deposition method.
3. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 2, characterized in that: in the step (1), the electrode substrate is a metal selected from nickel, stainless steel, titanium and silver or carbon selected from graphite, carbon fiber, carbon felt and glassy carbon, the organic solvent is one or more of acetone, ethanol, methanol and ether, and the acidic aqueous solution is one or more of aqueous solutions of sulfuric acid, hydrochloric acid and nitric acid.
4. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 2, characterized in that: in the electrolyte in the step (2), the concentration of polyvinylpyrrolidone is 0.5 g-5 g/L, the palladium salt is one or more of palladium chloride, sodium tetrachloropalladate, palladium acetate, palladium sulfate and palladium nitrate, the concentration of palladium is 5-50mg/L, and the concentration of sodium sulfate is 5-50g/L.
5. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 2, characterized in that: the cathode deposition method comprises the following process parameters: the applied current density is 0.05 to 0.15A/dm 2 The deposition time is 20 to 60min.
6. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 2, characterized in that: the palladium loading capacity of the palladium modified electrode is 0.5 to 5g/m 2 。
7. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 1, characterized in that: the concentration of the chlorinated aromatic compound shown in the formula (I) in the catholyte is 5-300g/L.
8. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 1, characterized in that: the chlorinated aromatic compound shown in the formula (I) is one or more of chloropicolinic acid, chlorophenol, chlorobenzoic acid and chlorophenoxyacetic acid.
9. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 1, characterized in that: the conditions of the electrolytic reaction are as follows: the current density is 1 to 20A/dm 2 The temperature is 0 to 100 ℃.
10. The process for the hydrodechlorination of chlorinated aromatic compounds in high concentrations according to claim 1, characterized in that: the alkaline aqueous solution is prepared by mixing water and supporting electrolyte; the concentration of the supporting electrolyte in the electrolyte is 0.1 to 2.0mol/L.
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| CN115645814B (en) * | 2022-10-27 | 2024-04-05 | 浙江工业大学 | Ultralow-load palladium nanocrystal modified electrode, preparation method thereof and application thereof in electrochemical dechlorination |
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