CN113913853A - Electrochemical deep degradation method of brominated phenolic compounds under synergistic adsorption of surfactant - Google Patents
Electrochemical deep degradation method of brominated phenolic compounds under synergistic adsorption of surfactant Download PDFInfo
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Abstract
The invention discloses an electrochemical deep degradation method of brominated phenolic compounds under synergistic adsorption of a surfactant. The method comprises the following steps in sequence: (1) preparing electrolyte and adding the electrolyte into an electrolytic cell; the solute of the electrolyte is brominated phenolic compounds, cationic surfactants and supporting electrolyte, and the solvent is water; the cationic surfactant is selected from at least one of dodecyl trimethyl ammonium bromide, hexadecyl trimethyl ammonium bromide, octadecyl trimethyl ammonium bromide and hexadecyl pyridine bromide; (2) and putting the cathode material and the anode material into an electrolytic cell, and connecting a voltage-stabilizing direct-current power supply to electrolyze so as to deeply degrade the brominated phenolic compounds. The invention utilizes the 'synergistic adsorption' action of the surfactant and the brominated phenolic compound on the surface of the electrode to promote the charge transfer process of the electrode reaction, thereby realizing the rapid deep debromination degradation of the brominated phenolic compound.
Description
(I) technical field
The invention belongs to the technical field of brominated flame retardant treatment applied to the aspect of environmental protection, and particularly relates to an electrochemical deep degradation method of brominated phenolic compounds.
(II) background of the invention
At present, brominated flame retardants are organic flame retardants with the greatest yield in China and throughout the world, mainly including tetrabromobisphenol A (TBBPA), polybrominated diphenyl ethers (PBDEs), polybrominated biphenyls (PBBs), 2,4, 6-Tribromophenol (TBP) and other novel brominated flame retardants, wherein TBBPA is widely applied to electronic and electrical equipment due to high flame retardant efficiency and strong heat resistance. According to statistics, the global annual output of TBBPA reaches 12 ten thousand tons, and the TBBPA accounts for 60 percent of the global brominated flame retardant market. These lipophilic additive organic flame retardants are easy to enter The Environment due to lack of chemical bonds with commercial products, such as TBBPA concentration of 41200ng/g (Science of The Total Environment,2019,646:58-67.) in The deposits near The electronic garbage dismantling field, and seriously threaten The environmental safety and human health.
At present, how to control deep reduction and debromination is a key step in the degradation technology of brominated phenolic compounds. The common degradation technical means at present mainly relate to biodegradation, photodegradation, zero-valent metal degradation, electrocatalytic degradation and the like. Among these degradation methods, Biodegradation methods are environmentally friendly, but require screening of appropriate species, strict control of culture conditions, and often require a period of up to several days or months to achieve deep degradation of TBBPA (International Biodegradation & Biodegradation,2018,129: 23-3.). Photodegradation is one of the major routes for the degradation and transformation of polyhalogenated compounds such as TBBPA in the natural environment, but the degradation rate is slow and easy to transform to produce more toxic by-products (Journal of Hazardous Materials,2012,241: 301-306.). Zero-valent iron and bimetallic systems doped with other metals are commonly used as reducing agents for debrominating and degrading TBBPA, but high-toxicity reagents such as sodium borohydride or lithium aluminum hydride (2012, 51(25): 8378-. Meanwhile, in the method, the TBBPA is degraded after being dissolved by using an organic solvent, which is not in line with the deep degradation of the TBBPA in water system pollutants in actual situations.
The selective dehalogenation can be realized by controlling the reduction potential and the hydrogen evolution potential of the solution by electrocatalytic reduction, and is currently a recognized simple electrocatalytic reduction method, for example, a Pd-Fe nanoparticle modified electrode material can show excellent debromination performance (Journal of Hazardous Materials,2018,343 (376-. The adoption of a three-dimensional biomembrane electrode reactor is a novel bioelectrochemical water treatment technology which has good water treatment effect, but cannot be applied to actual engineering on a large scale due to low electron transfer efficiency and high energy consumption on a membrane electrode (Environmental Research,2021,197 (111089)). Therefore, how to prepare cheap and easily-obtained cathode materials and design a proper electrolytic system are key problems to be solved for realizing efficient electrochemical dehalogenation and being capable of being implemented in a practical system.
Disclosure of the invention
Aiming at the defects in the prior art, the invention provides a method for deeply degrading brominated phenolic compounds electrochemically.
In order to avoid using an organic solvent, the method uses an alkaline solution to dissolve the brominated phenolic compound, and simultaneously adds the cationic surfactant to improve the electrochemical debromination degradation rate of the brominated phenolic compound. The positively charged part of the cationic surfactant is adsorbed onto the surface of the hydrophilic electrode, and the positively charged long-chain hydrophobic groups are arranged on the surface of the electrode to form a double-layer hydrophobic film, so that on one hand, the adsorption of solvent molecules on the surface of the electrode is blocked, and the hydrogen evolution potential of the system is shifted negatively, thereby being beneficial to the preferential occurrence of electrochemical degradation and debromination reaction. On the other hand, as the brominated phenolic compounds in the alkaline solution mainly exist in the form of anions, the positively charged part of the cationic surfactant adsorbed on the surface of the electrode induces and adsorbs the negatively charged reaction substrates, and the electrochemical debromination degradation reaction is further promoted to be smoothly carried out by utilizing the synergistic adsorption effect. Under the action, the deep degradation of the brominated phenolic compounds can be realized. The deep degradation of the invention refers to the complete removal of bromine in brominated phenolic compounds.
Specifically, the invention provides an electrochemical deep degradation method of brominated phenolic compounds, which sequentially comprises the following steps:
the method comprises the following steps: preparing electrolyte and adding the electrolyte into an electrolytic cell; the solute of the electrolyte is brominated phenolic compounds, cationic surfactants and supporting electrolyte, and the solvent is water; in the electrolyte, the concentration of the brominated phenolic compound is 0.1-20 mmol/L, the concentration of the cationic surfactant is 0.2-1 mmol/L, and the concentration of the supporting electrolyte is 0.2-0.4 mol/L; the cationic surfactant is selected from at least one of Dodecyl Trimethyl Ammonium Bromide (DTAB), hexadecyl trimethyl ammonium bromide (CTAB), octadecyl trimethyl ammonium bromide (STAB) and hexadecyl pyridine bromide (CPB);
step two: and putting the cathode material and the anode material into an electrolytic cell, and connecting a voltage-stabilizing direct-current power supply to electrolyze so as to deeply degrade the brominated phenolic compounds. During the electrolysis process, a proper amount of electrolyte can be taken regularly and detected by a high performance liquid chromatography instrument to monitor the degradation condition.
In the brominated phenolic compounds, the substitution position of bromine atom is one or more of ortho, meta and para, and the specific brominated phenolic compounds are monobromophenol, 2,4, 6-tribromophenol, 3',5,5' -tetrabromobisphenol A and the like. Preferably, the brominated phenolic compound is 3,3',5,5' -tetrabromobisphenol A (TBBPA).
Preferably, the supporting electrolyte is NaOH or KOH, most preferably NaOH. Further preferably, the concentration of the supporting electrolyte in the electrolytic solution is 0.4 mol/L.
Preferably, the cationic surfactant is cetyltrimethylammonium bromide (CTAB). Still more preferably, the concentration of the cationic surfactant in the electrolyte solution is 1 mmol/L.
Preferably, the anode material is a carbon rod, a titanium mesh, or a lead dioxide plate, and more preferably a carbon rod.
Preferably, the cathode material is a silver flake, a copper flake, a zinc flake or a galvanized iron flake, more preferably a zinc flake or a galvanized iron flake, and most preferably a galvanized iron flake.
Preferably, the electrolysis reaction in the second step is carried out at a temperature of 20 to 50 ℃, a rotation speed of 0 to 1000rpm, and a current density of 3mA/cm2～5mA/cm2Under the conditions of (1). The electrolysis reaction temperature is more preferably 25 ℃. More preferably, the current density is 3.5mA/cm2～4mA/cm2Most preferably 3.5mA/cm2. The rotation speed is more preferably 100rpm to 800rpm, and most preferably 600 rpm.
The invention utilizes the 'synergistic adsorption' action of the surfactant and the brominated phenolic compound on the surface of the electrode to promote the charge transfer process of the electrode reaction, thereby realizing the rapid deep debromination degradation of the brominated phenolic compound.
Compared with the prior art, the invention has the following advantages:
1. the method fully utilizes the characteristic that the brominated phenolic compound is easy to dissolve in alkaline solution, and does not need to add extra organic solvent.
2. The cathode material does not need special modification and pretreatment, and is cheap and easy to obtain.
3. The degradable bromophenol compound has wide concentration range and high degradation efficiency, and can be completely and deeply degraded into bisphenol A (BPA) in 5.5 hours for 10mmol/L TBBPA without generating other more toxic byproducts.
4. The surfactant is low in price, the degradation rate of the brominated phenolic compound can be obviously improved with a very small using amount, and the reaction time is short.
5. The invention has wide degradation conditions, and can completely and deeply degrade the brominated phenolic compounds under wide degradation conditions. And the deep degradation inhibition effect of humic acid on the brominated phenolic compounds is weaker, so that the possibility of implementing the deep degradation of the brominated phenolic compounds in an actual water system by the degradation method is effectively ensured.
(IV) description of the drawings
FIG. 1 is a cyclic voltammogram of TBBPA in different electrolysis systems.
FIG. 2 is a graph showing the variation of TBBPA and BPA concentrations on different cathode materials in examples 1-5.
FIG. 3 is a graph showing the change in TBBPA and BPA concentrations at different NaOH concentrations for examples 6-10.
FIG. 4 is a graph showing the variation of TBBPA and BPA concentrations at different CTAB concentrations in examples 11-17.
FIG. 5 is a graph showing the variation of TBBPA and BPA concentrations at different current densities for examples 18-22.
FIG. 6 is a graph showing the changes in TBBPA and BPA concentrations at different humic acid concentrations in examples 23-27.
(V) detailed description of the preferred embodiments
In order to make the objects, technical solutions and advantages of the present invention more clearly apparent to those skilled in the art, the present invention will be described in further detail below with reference to the accompanying drawings and examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 0:
to investigate the effect of the cationic surfactant CTAB on the TBBPA electrode process, cyclic voltammetry tests were performed and the results are shown in figure 1. The cyclic voltammetry test was performed in a standard three-electrode system with silver disk electrodes
As working electrode, a platinum plate (20X 0.2mm) was used as counter electrode and a standard mercury oxide electrode (Hg/HgO) was used as reference electrode. The scan rate was 50mV/s and the test temperature was 25 ℃. No redox peak was observed in the 0.4mol/L NaOH solution. When 1mmol/L CTAB is added into the blank NaOH solution, the hydrogen evolution potential of the system is negatively shifted, which shows that the CTAB is adsorbed on the surface of the electrode to form a layer of hydrophobic layerThe membrane prevents solvent molecules from accumulating on the surface of the electrode, thereby widening the electrochemical window. When 10mmol/L TBBPA is added into 0.4mol/L NaOH solution, the hydrogen evolution potential of the system is almost the same as that of the blank NaOH solution, but a small reduction peak appears around-1.13V, the peak current is only-0.04 mA, if 1mmol/L cationic surfactant CTAB is added into the solution, three obvious reduction peaks can be seen, and the peak potentials are respectively-1.17V, -1.24V and-1.32V. Since the cationic surfactant has no reduction peak in the potential interval, the series of peaks are generated by TBBPA debromination degradation, and the reduction peak current (Ip) of TBBPA is remarkably increased in the presence of CTAB, and the peak current reaches-0.48 mA. According to the magnitude of the peak current, the surfactant CTAB can be predicted to increase the enrichment amount of TBBPA by about 10 times.
Examples 1 to 5: the electrochemical deep degradation method of TBBPA in water comprises the following steps:
the method comprises the following steps: selecting a heatable single-chamber electrolytic bath with a clamping sleeve capable of containing 30mL of liquid, weighing CTAB (0.0054g, 1mmol/L,) and TBBPA (0.0815g, 10mmol/L,) to dissolve in 15mL of NaOH (0.12g, 0.2mol/L) aqueous solution, adding the obtained electrolyte into the electrolytic bath, selecting appropriate cathode materials and anode materials, and connecting a direct-current stabilized power supply with an electrode.
Step two: connecting with a constant temperature circulating water instrument, setting at 25 deg.C, adding 6mm × 10mm stirrer, setting magnetic stirring at 600rpm, starting a DC stabilized voltage supply to control current density at 4mA/cm2The following test was conducted on the obtained supernatant by measuring a predetermined amount of reaction solution at reaction times of 0h, 1h, 2h, 3h, 4h and 5h, respectively, and passing through a 0.22 μm microporous membrane.
Detection conditions are as follows: thermo U3000 high performance liquid chromatograph, C185 micron
(4.6X 250mm) as a separation column, mobile phase A as methanol, mobile phase B as 0.1 v/v% aqueous formic acid, mobile phase A: mobile phase B80: 20(v/v), detection wavelength 230nm, flow rate 1mL/min, temperature 25 ℃.
In order to better study the effect of cathode materials on the degradation of TBBPA, the following five experiments were carried out to study the degradation of TBBPA: in the first step, the cathode materials were silver flakes (example 1), copper flakes (example 2), iron flakes (example 3), zinc flakes (example 4) and galvanized iron flakes (example 5), respectively, the electrode size was 20 × 20 × 0.2mm, the anode material was a carbon rod with a diameter of 7 mm, and the results are shown in fig. 2. As can be seen from the figure, TBBPA does not react on the iron electrode, the degradation curves on silver, copper, zinc and galvanized iron electrodes are basically the same, and 94 percent of 10mmol/L TBBPA can be degraded within 3 hours. Compared with silver and copper electrodes, the deep degradation of TBBPA is more facilitated on zinc and galvanized iron electrodes, and 84 percent of 10mmol/L TBBPA is deeply degraded into BPA after 5 hours. The galvanized iron material can replace the conventional silver, copper and zinc electrode materials to be used for deeply degrading TBBPA in a water system by comprehensively considering the price of the electrode material and the degradation rate of TBBPA.
Examples 6 to 10: the electrochemical deep degradation method of TBBPA in water comprises the following steps:
the differences from examples 1 to 5 are: the cathode material in the first step was a 20X 0.2mm galvanized iron sheet, the NaOH concentrations in the first step were 0.1mol/L (example 6), 0.2mol/L (example 7), 0.3mol/L (example 8), 0.4mol/L (example 9), and 0.5mol/L (example 10), and the rest of the electrolysis conditions were unchanged, and the results are shown in FIG. 3. FIG. 3 shows that the NaOH concentration is between 0.2mol/L and 0.4mol/L, which basically has no influence on the TBBPA degradation rate, and the TBBPA degradation rate of 10mmol/L can reach 99 percent after 5 hours. The concentration of NaOH has certain influence on the deep degradation of TBBPA into BPA products, and 92 percent of 10mmol/L TBBPA is degraded into BPA under the condition of 0.4mol/L NaOH. The TBBPA degradation rate decreased when the NaOH concentration increased to 0.5mol/L, and only 78% of 10mmol/L of TBBPA degraded to BPA at 5 hours. From the comprehensive consideration of the actual situation and the TBBPA degradation rate, 0.2 mol/L-0.4 mol/L of NaOH can be selected for the deep degradation of TBBPA in a water system.
Examples 11 to 17: a method for electrochemically deeply degrading TBBPA in a water system comprises the following steps:
the differences from examples 6 to 10 are: in step one, the NaOH concentration was 0.4mol/L, the CTAB concentration was 0mmol/L (example 11), 0.2mmol/L (example 12), 0.4mmol/L (example 13), 0.6mmol/L (example 14), 0.8mmol/L (example 15), 1mmol/L (example 16) and 2mmol/L (example 17), and the results were shown in FIG. 4, except that the electrolysis conditions were unchanged. Figure 4 shows that CTAB and TBBPA "synergistic adsorption" on the electrode surface has a significant promoting effect on TBBPA degradation. Without CTAB, only 34% of 10mmol/L of TBBPA could be degraded within 5 hours. With CTAB, the degradation rate of TBBPA is obviously increased, when the CTAB is added in an amount of 0.2mmol/L, 97% of 10mmol/L TBBPA can be degraded in 3 hours, and 80% of 10mmol/L TBBPA can be deeply degraded into BPA in 5 hours. As CTAB concentration continues to increase, the degradation rate of TBBPA decreases, probably because as CTAB concentration continues to increase at the electrode surface, rapid charge transfer of TBBPA at the electrode surface is not favored. However, as the reaction time continued to increase, CTAB above 0.2mmol/L had little effect on the deep degradation of TBBPA to BPA, and even increased the rate of deep degradation, e.g., 93% of 10mmol/L of TBBPA was deeply degraded to BPA within 5 hours when the CTAB concentration exceeded the critical micelle concentration to 1 mmol/L. From the comprehensive consideration of actual conditions and TBBPA degradation rate, CTAB with the concentration of 0.2 mmol/L-1 mmol/L can be selected for deep degradation of TBBPA in a water system.
Examples 18 to 22: the electrochemical deep degradation method of TBBPA in water comprises the following steps:
the differences from examples 11 to 17 are: in the first step, the concentration of CTAB is 1mmol/L, and in order to study the influence of the current density on the TBBPA degradation rate, the following five experiments are carried out: before the power supply is started in the second step, the power supply is adjusted to a constant current mode, and the current density is respectively adjusted to be 3mA/cm2(example 18) 3.5mA/cm2Example 19, 4mA/cm2Example 20, 4.5mA/cm2(example 21) 5mA/cm2(example 22), the results are shown in FIG. 5, with the rest of the electrolysis conditions unchanged. FIG. 5 shows that when the current density was 3mA/cm2In this case, 90% of 10mM TBBPA was degraded within 3 hours, but only 55% of 10mmol/L TBBPA was deeply degraded into BPA. The TBBPA degradation rate increased with increasing current density. When the current density reaches 5mA/cm298% of 10mM TBBPA can be degraded within 3 hours, and 97% of 10mmol/L TBBPA can be degradedTBBPA of (A) is deeply degraded into BPA. The energy consumption and the TBBPA degradation rate are comprehensively considered, and 3.5mA/cm can be selected2～4mA/cm2The current density of (a) is used for deep degradation of TBBPA in water systems.
Examples 23 to 27: the electrochemical deep degradation method of TBBPA in water comprises the following steps:
the differences from examples 18 to 22 are: the fixed current density in the second step is 3.5mA/cm2Humic acid was further added to the electrolyte at concentrations of 0mg/L (example 23), 2mg/L (example 24), 4mg/L (example 25), 6mg/L (example 26) and 8mg/L (example 27), and the effect of humic acid on the debromination degradation performance of TBBPA in the system was investigated while keeping the remaining conditions constant, and the results are shown in FIG. 6. The results show that the degradation rate of TBBPA is hardly affected by humic acid. The existence of humic acid has certain influence on the deep degradation of TBBPA into BPA, but the deep degradation rate can still be kept above 80% as the degradation time is continuously increased to 5 hours, which effectively ensures the possibility of implementing the deep degradation of TBBPA in an actual water system by the degradation method.
Comparative examples 1 to 4: selecting different surfactants
The difference from example 16 is: the electrochemical degradation of TBBPA was studied by selecting anionic surfactant sodium dodecyl sulfate (SDS, 1mmol/L, comparative example 1), nonionic surfactant Triton X-100(Triton X-100, 1mmol/L, comparative example 2), dodecyl trimethyl ammonium bromide (DTAB, comparative example 3) and octadecyl trimethyl ammonium bromide (STAB, comparative example 4) respectively instead of cationic surfactant CTAB, and keeping the rest of the electrolysis conditions constant. The results show that only 29% of 10mmol/L TBBPA can be degraded in 5 hours by using SDS, and only 11% of 10mmol/L TBBPA can be degraded in 5 hours by using TritonX-100, and no deep degradation product BPA is generated. With DTAB, 70% of 10mmol/L of TBBPA was deeply degraded into BPA in 5 hours, and with STAB, 67.7% of 10mmol/L of TBBPA was deeply degraded into BPA in 5 hours.
It will be understood by those skilled in the art that the foregoing is only a preferred embodiment of the present invention, and is not intended to limit the invention, and that any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. An electrochemical deep degradation method of brominated phenolic compounds sequentially comprises the following steps:
the method comprises the following steps: preparing electrolyte and adding the electrolyte into an electrolytic cell; the solute of the electrolyte is brominated phenolic compounds, cationic surfactants and supporting electrolyte, and the solvent is water; in the electrolyte, the concentration of the brominated phenolic compound is 0.1-20 mmol/L, the concentration of the cationic surfactant is 0.2-1 mmol/L, and the concentration of the supporting electrolyte is 0.2-0.4 mol/L; the cationic surfactant is selected from at least one of dodecyl trimethyl ammonium bromide, hexadecyl trimethyl ammonium bromide, octadecyl trimethyl ammonium bromide and hexadecyl pyridine bromide;
step two: and putting the cathode material and the anode material into an electrolytic cell, and connecting a voltage-stabilizing direct-current power supply to electrolyze so as to deeply degrade the brominated phenolic compounds.
2. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 1, characterized in that: the brominated phenolic compound is monobromophenol, 2,4, 6-tribromophenol or 3,3',5,5' -tetrabromobisphenol A.
3. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 1, characterized in that: the supporting electrolyte is NaOH or KOH.
4. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 3, characterized in that: in the electrolyte, the concentration of the supporting electrolyte is 0.4 mol/L.
5. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 1, characterized in that: the cationic surfactant is cetyl trimethyl ammonium bromide.
6. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 1 or 5, characterized in that: in the electrolyte, the concentration of the cationic surfactant is 1 mmol/L.
7. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 1, characterized in that: the anode material is a carbon rod, a titanium mesh or a lead dioxide plate.
8. The method for electrochemical deep degradation of a bromophenol compound according to claim 1 or 7, characterized in that: the cathode material is a silver sheet, a copper sheet, a zinc sheet or a galvanized iron sheet.
9. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 8, characterized in that: the electrolytic reaction of the second step is carried out at the temperature of 20-50 ℃, the rotating speed of 0-1000 rpm and the current density of 3mA/cm2～5mA/cm2Under the conditions of (1).
10. The method for electrochemical deep degradation of brominated phenolic compounds according to claim 9, characterized in that: the current density is 3.5mA/cm2～4mA/cm2Most preferably 3.5mA/cm2(ii) a The rotating speed is 100 rpm-800 rpm.
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