Catalytic activation of persulfate by nanoscale zero-valent iron-derived supported boron-doped porous carbon for bisphenol A degradation

doi:10.21203/rs.3.rs-3548672/v1

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Catalytic activation of persulfate by nanoscale zero-valent iron-derived supported boron-doped porous carbon for bisphenol A degradation

https://doi.org/10.21203/rs.3.rs-3548672/v1

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published 26 Mar, 2024

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In this study, boron modified carbon materials (BCs) with porous structures and high surface areas were firstly synthesized employing coffee grounds, sodium bicarbonate and boric acid as precursors, afterward, nanoscale zero-valent iron (nZVI) and BCs composites (denoted as nZVI@BCs) were synthesized through reduction of FeSO₄ by NaBH₄along with stirring. The catalytic performance of the nZVI@BCs was evaluated for the degradation of bisphenol A (BPA) via persulfate (PS) activation. In comparison with nZVI@Cs/PS, nZVI@BCs/PS could greatly promote the degradation and mineralization of BPA. Further analysis exhibited that our system existed radical pathway and non-radical pathway for BPA removal. On the one hand, electron spin resonance and radical quenching studies represented that ^•OH, SO₄^•− and O₂^•− were mainly produced in the nZVI@BCs/PS system, which were responsible for the degradation of BPA. On the other hand, the open circuit voltages of nZVI@BCs and nZVI@Cs in different systems indicated that non-radical pathway still existed in our system. PS could grab the unstable unpaired electron on nZVI@BCs to form a carbon materials surface-confined complex ([nZVI@BCs]*) with a high redox potential, then accelerate BPA removal efficiency via electron transfer. Furthermore, the performances and mechanisms for BPA degradation were examined by PS activation with nZVI@BCs composites at various conditions including dosages of nZVI@BCs, BPA and PS, initially pH value, temperature, common anions and humid acid. This study provides a novel insight for development of high-performance carbon catalysts toward environmental remediation.

boron

nZVI

persulfate

electron transfer

nonradical

radicals

Recently, generous researches have emerged that carbon materials have remarkable catalytic properties for persulfate due to its special sp2 hybrid structure and abundant oxygen-containing functional groups on the surface (Cheng et al. 2017, Duan et al. 2016, Ren et al. 2020, Tian et al. 2016). Carbon materials activate the persulfate system, which can degrade endocrine disruptor in the aqueous environment through adsorption and nonradical oxidation.

It is potentially more feasible to use nanoscale zero-valent iron (nZVI) as catalyst in wastewater treatment, now that it is environmentally friendly, cost-effective and high efficient material (Dong et al. 2017, Oh et al. 2009, Zhao et al. 2016). nZVI could be easily oxidized to produce Fe(II) under oxic/anoxic condition and/or oxidation by PS (Eqs. (1) to (3)). Nevertheless, it’s reported that nZVI was also prone to aggregation in solution due to magnetic interactions, which reduces its effectiveness (Gao et al. 2021). In order to solve this problem, porous materials such as biochar, resin, natural zeolite, and silica have been used as carriers for nZVI to improve dispersion (Ji et al. 2019, Xu et al. 2020). Carbon materials loading nZVI activate the persulfate system, which can remove endocrine disruptor in the aquatic environment with higher efficiency through adsorption, radical oxidation, and nonradical oxidation.

Fe⁰ + H₂O + 0.5O₂ → Fe²⁺ + 2OH⁻ (oxic conditions) (1)

Fe⁰ + 2H₂O → Fe²⁺ + 2OH⁻ + H₂ (anoxic conditions) (2)

Fe⁰ + S₂O₈²⁻ → Fe²⁺ + 2SO₄²⁻ (3)

In this work, first of all, BCs with porous structures and high surface areas were synthesized employing coffee grounds, sodium bicarbonate and boric acid as precursors, there is one more point, nZVI@BCs composites were synthesized through reduction of FeSO₄ by NaBH₄ along with stirring. The catalytic performance of the nZVI@BCs was evaluated for the degradation of BPA via PS activation, we explored nZVI@BCs /PS systems as follows: (i) nZVI@BCs/PS systems could greatly promote the degradation and mineralization of BPA; (ii) the properties of nZVI@BCs were characterized via SEM, EDS, XPS and XRD; (iii) the mechanism of the nZVI@BCs/PS systems were studied via EPR analysis, quenching tests and electrochemical technology (open circuit voltage); (Ⅳ) the effect of crucial parameters including dosage of nZVI@BCs, PS dosage, initial pH, different anions, humic acids, and water matrix was determined.

Materials and reagents

All reagents and chemicals were of analytical reagent grade and were used as received without further purification (Text S1).

Fabrication of nZVI@BCs

The preparation of BCs was demonstrated in Text S2. The preparation of nZVI@BCs composites was as follows. At first, 0.2 g BCs were dispersed into 100 mL deionized water under ultrasonic waves for ten-min. Furthermore, 1.0 g FeSO₄•7H₂O was dissolved and stirred for 30-min in the above solvent. Then, 50 mL of NaBH₄ solution (1.0 g/100 mL) was added at 2 drops s⁻¹ with continuous stirring under N₂ atmosphere. After another 30-min stirring, the black precipitates were washed with ethanol and deionized water several times and vacuum dried for 12 h at the temperature of -60 °C. For comparison, the nZVI@Cs particles were also synthesized following the same procedures.

Experimental procedures

The experiments were carried out in 500 mL beaker containing 250 mL BPA solution (0.04 mmol/L). Unless otherwise stated, the solution pH was controlled at 7.0 using 0.1 M H₂SO₄ or NaOH. A certain amount of catalyst was dispersed into the above solution to attain the adsorption–desorption equilibrium within 30 min. Subsequently, 0.50 mL of 0.5 M PS was added into the degradation reaction. 1.0 mL samples were taken at defined time intervals and quenched immediately by 20 μL of 0.5 M sodium thiosulfate solution. What’s more, the effects of PS dosage, the initially pH, carbon catalyst amount, water constituents (humic acid, Cl⁻ and HCO₃⁻) and actual water matrix on BPA degradation were assessed. The experiments were operated to the air. Control experiments were conducted and excluded the interaction between the filter and BPA. All the experiments were carried out in duplicate.

Analytical methods

The pH values of solutions were measured by the pH-meter (FiveEasy Plus, METTLER TOLEDO, Shanghai). The concentration of BPA in aqueous solution was analyzed by a HPLC chromatography (Waters, e2695) equipped with a 2489 UV-vis detector and the detection wavelength and binary phase composition were as follows: 276 nm and methanol/0.1% formic acid (70:30, v/v) for BPA. The flow rate of these binary phases was 1 mL/min and the temperature of liquid chromatographic column was 35 ^oC. The concentration of BPA was measured by Hitachi F-7000 fluorescence spectrometer (Hitachi High Technologies, Tokyo, Japan) with the excitation and emission wavelengths range set at 250-320 nm and 250-450 nm. After filtration with a cellulose ester membrane of 0.45 μm pore size and freeze vacuum drying in turn, the solid samples of residual BCs after reaction (reaction time 60 min) were prepared. The scanning electron microscopy (SEM, FEI Inspect F50(FSEM)) equipped with an energy dispersive X-ray spectrometer (EDX, FEI Inspect F50 (FSEM)), the transmission electron microscope (TEM, FEI G2 F20, America), the X-ray photoelectron spectroscopy (XPS, Escalab 250Xi) and the Fourier transform infrared spectroscopy (FT-IR, Nicolet iS 10). EPR analyses were carried out (Text S3). The concentrations of PS were measured spectrophotometrically (Text S4). The electrochemical analysis was performed with a CHI660E electrochemical workstation (Text S5).

Catalytic performances of nZVI@BCs catalysts

Fig. 1 exhibited the adsorption and degradation of BPA in various systems. As displayed in Fig. 1(a), BCs, nZVI@BCs and nZVI@Cs provided about 55.7%, 43.1% and 23.5% of BPA adsorption, respectively. Remarkably, when PS was introduced, the removal of BPA reached 100% in nZVI@BCs/PS and nZVI@Cs/PS systems, whereas only 61.1% of BPA removal was achieved in the BCs/PS system. TOC result further demonstrated that nZVI@BCs possessed outstanding mineralization ability, up to 63.2% after 90 min (Fig. 1(b)). Fig. 1(a) and Fig. 1(b) illustrated that nZVI@BCs possessed the best BPA removal performance and mineralization ability among all of the systems. And the fastest apparent rate constant (kobs) of BPA removal in various systems was shown in Fig. S2. Removal of BPA in our system could undergo two phases: a fast stage (first stage) and a subsequent slow phase (second stage). In the nZVI@BCs/PS system, approximately 24% of BPA is rapidly removal in the first min, and 76% of BPA is removed in the following 39 min.

3D EEM fluorescence spectroscopy was further employed to confirm efficient degradation of BPA. Fig 2(a) showed that a distinct fluorescence peak was identified from the initial samples. The peak centered at Ex/Em wavelengths of 275/305 nm may be ascribed to the BPA, because Lin et al. once reported that the fluorescence peak of phenol was located at Ex/Em wavelengths of 260–280/280–320 nm (Lin et al. 2019). As shown in Fig 2(b), the fluorescence intensity decreased to some extent after 30 min of adsorption. When PS was added, the fluorescence intensities of BPA gradually weakened as reaction proceeded and another fluorescence peak located at Ex/Em wavelengths of 285/395 nm rapidly strengthened and then weakened, which may be the intermediate products of the BPA (Fig 2(c) and Fig 2(d)). Further prolonging reaction time to 180 min, the fluorescence signals of both BPA and its intermediate products gradually weakened, which indicated that BPA was mostly destroyed or mineralized.

Characterization

As illustrated in Fig. 3, the SEM micrographs revealed that nZVI@BCs had a spherical porous structure and nZVI was dispersed on the surface of BCs with a relatively uniform distribution, which could be also confirmed by TEM (Fig. 4). Moreover, EDX elemental mapping images exhibited the uniform distribution of C, O, B and Fe elements within the carbon frameworks (Fig. 3 (c)) and the atoms contents of C, O, B and Fe were 81.83%, 6.85%, 9.69, and 1.62%, respectively (Fig. S4). Fig. S5 (a) showed XRD pattern for nZVI@BCs and the characteristic peaks of the pristine nZVI@BCs powder at 44.7º, 65.3º, and 82.5º matched well with the standard patterns of Fe⁰ (PDF#06-0696) (Li et al. 2015), which indicated that nZVI was doped into the framework of the BCs. FT-IR spectra of the nZVI@BCs was shown in Fig. S5 (b). The peaks at 3400 cm⁻¹, 1590 cm⁻¹, and 1103 cm⁻¹of the nZVI@BCs were assigned to the hydroxyl groups (–OH), carbonyl/carboxyl (C=O) and C–O–C stretching vibration modes. The peaks at 800–400 cm⁻¹ were associated with the Fe–O, which indicated that Fe was attached to the surface by bonding with oxygen-containing groups (Li et al. 2020, Liu et al. 2010).

XPS survey spectra of nZVI@BCs before and after reaction were shown in Fig. S6. There were four distinct peaks, which were assigned to C1s, O1s, B 1s and Fe 2p, respectively. It's worth noting that the oxygen content increased from 20.44% to 29.84%, indicating the surface oxidation of nZVI@BCs during catalytic reaction, which may because the surface of nZVI@BCs was surrounded with large amount of radicals during PS activation process, resulting in surface oxidation (Duan et al. 2015, Yang et al. 2019). Fig. 5 (a) and (e) indicated that C 1s atom was deconvoluted into five peaks at 283.11 eV (the sp2 carbon bonds), 284.15 eV (C-H), 285.15 eV (C-OH or C-O-C), 287.90 eV (C=O) and 290.40 eV (O-C=O) , respectively (Zhou et al. 2019). The corresponding O1s high resolution scans were also displayed in Fig. 5 (b) and (f), the nZVI@BCs mainly fit into three individual peaks located at around 530.42 eV, 531.81 eV and 535.63 eV, which were ascribed to C-O, C=O and Fe-O (Zhou et al. 2020). The increased propotion of Fe-O (from 7.5 to 36.75%) before and after reaction was attributed to the oxidization of the surface Fe⁰. The two predominant peaks at 188.13 eV and 192.30 eV are ascribed to the interfacial suboxide B and B₂O₃, respectively (Fig. 5 (c) and (g)). For the Fe 2p, as shown in Fig. 5 (d), the peak at 705.93 eV was assigned to Fe⁰ (Wu et al. 2020), which corroborated the impregnation and reduction of Fe²⁺ to nZVI on the porous surface of BCs. However, after reaction in the nZVI@BCs/PS system, the binding energy of Fe⁰almost disappeared (Fig. 5 (h)), which may also because the surface oxidation during catalytic reaction. The result was consistent with the Fig. 5 (f) results.

Mechanism investigation

BPA adsorption kinetics and isotherms

The adsorptive capacity of nZVI@BCs would notably affect the efficiency of BPA removal. As shown in Fig. 6, the adsorption kinetics experiments and adsorption isotherm experiments were carried out in this study. Through experiments, it was found that the adsorption of BPA by nZVI@BCs basically reached equilibrium within 30 min, therefore, the reaction time for the adsorption experiments were set at 30 min. The fitting of the kinetic model and its equilibrium data were shown in Fig. 6 and Table 1. As described in Fig. 6 and Table 1, the kinetics of BPA adsorption on nZVI@BCs might be simulated well using a pseudo-second-order kinetics model ( R² > 0.9999, which is closer to 1.0 compared to the first-order kinetic model and the intra particle diffusion model), indicating a chemisorption process. The adsorption isotherm model fitting and its data was shown in Fig. 6 and Table 2. The linear form R² of Langmuir model is closer to 1.0 than that of Freundlich model, indicating that the adsorption of BPA by nZVI@BCs occurs on a uniform surface with approximately equal energy in a single layer.

Table 1. Kinetic parameters for BPA adsorption onto nZVI@BCs.

Adsorption kinetics	Pseudo-first-order		Pseudo-second-order		Intra-particle diffusion
Adsorption kinetics	k₁ (g/mg min)	R²	k₂ (g/mg min)	R²	k_id (mg/g min^0.5)	C (mg/g)	R²
nZVI@BCs	0.0074	0.3584	0.5718	0.9999	0.0425	2.9513	0.6684

Table 2. Adsorption isotherm parameters for BPA adsorption onto nZVI@BCs.

Adsorption isotherm	Langmuir			Freundlich
Adsorption isotherm	q_m/(mg/g)	K_L/(L/mg)	R²	K_F/(mg/g)	n	R²
nZVI@BCs	19.685	0.927	0.9868	9.685	3.2755	0.9744

Identifying Main Active Species

EPR spectra in nZVI@BCs/PS system using DMPO for trapping ^•OH, SO₄^•− and O₂^•− were shown in Fig. 7(a). No signals were detected for sole PS in aqueous solution and in methanol solution. When nZVI@BCs was added, characteristic signals of DMPO-SO₄and DMPO-OH appeared in the aqueous solution (Zhou et al. 2019, Zhou et al. 2020) and six characteristic peaks of DMPO-HO₂was also obtained in the methanol solvent (Wu et al. 2020, Zhou et al. 2020), confirming the formation of ^•OH, SO₄^•− and O₂^•− during the reaction. Herein, different radical quenching reactions based on the radical scavengers (Ethanol, TBA and Chloroform) were conducted. Ethanol is a forceful quencher for both ^•OH and SO₄^•− (k(Ethanol/^•OH) = 1.2 ~ 2.8 × 10⁹ M^-1s^-1, k(Phenol/SO₄^•−) = 1.6 ~ 7.7 × 10⁷ M^-1s^-1), while TBA could only quench ^•OH in aqueous solutions (k(TBA/^•OH) = 3.8 ~ 7.6 × 10⁸ M^-1s^-1, k(TBA/SO₄^•−) < 4.0 ~ 9.1 × 10⁵ M^-1s^-1) (Liang &Su 2009). And trichloromethane is a powerful inhibitor for O₂^•− (k(CHCl3/O₂^•−) < 10⁶ M^-1s^-1) (Yang et al. 2019). As Fig. 7(b) showed, BPA removal obviously reduced when ethanol, TBA and chloroform were added. The BPA removal rates decreased 28.92%, 21.51% and 5.54% in the presence of 10 mM ethanol, TBA and chloroform, and 42.14%, 28.19% and 13.99% in the presence of 100 mM ethanol, TBA and chloroform, which demonstrated that all of SO₄^•−, ^•OH and O₂^•−existed in nZVI@BCs/PS system.

Electrochemical analysis

In the previous studies (Cheng et al. 2022, Yi et al. 2022), the electron transfer pathways were investigated on nonradical induced organic pollutants oxidation, and the equilibrium values of the open circuit voltage could reflect the potential of [carbon]*. As displayed in Fig. S8, the open circuit potentials of [nZVI@BCs]* and [nZVI@Cs]* were measured to evaluate the electron transfer process. Above all, the nZVI@BCs and nZVI@Cs were added into the reaction mixture, respectively. The nZVI@BCs had an open circuit voltage of approximately 0.25 V (vs. NHE), much greater than that of nZVI@Cs (averagely 0.02 V). In addition, when the PS was added into the reaction mixture the equilibrium potential raised further and the potential of [nZVI@BCs]* was raised to around 0.80 V (0.31 V for nZVI@Cs). The measures of open circuit voltages indicated that when PS was added into the reaction mixture, the potential of the [nZVI@BCs]* complexes was sharply elevated, then boosting the BPA removal rate via an electron transfer pathway.

As discussed above, the proposed radical and nonradical mechanism in our system was present in Fig. 8. On the one hand, nZVI@BCs as a reaction catalyst could react with PS to generate reactive species (SO₄^•−, ^•OH and O₂^•−)(Eqs. (1) to (7)) (Huo et al. 2019, Pulicharla et al. 2018, Yang et al. 2019), which could accelerate the reduction of BPA. On the other hand, PS could be bound onto the surface of nZVI@BCs to form metastable complexes ([nZVI@BCs]*) with a high oxidation potential toward BPA oxidation.

Fe⁰ + S₂O₈^2- → Fe²⁺ + SO₄²⁻ (1)

Fe⁰ + 2H⁺ + O₂ → Fe²⁺ + H₂O₂ (2)

Fe⁰ + 2H⁺ + H₂O₂ → Fe²⁺ + 2H₂O (3)

Fe²⁺ + S₂O₈^2- → Fe³⁺ + SO₄^•− + SO₄²⁻ (4)

SO₄^•− + H₂O → ^•OH + H⁺ + SO₄²⁻ (5)

^•OH + H₂O₂ → O₂^•− + H⁺ + H₂O (6)

Fe²⁺ + O₂ → Fe³⁺ + O₂^•− (7)

BPA removal in diﬀerent conditions

To study the practical application of the nZVI@BCs/PS system, the effect of nZVI@BCs dosage, PS dosage, initial pH, water common anions and various water matrix on the removal of BPA was studied, as shown in Fig. 9. The BPA removal ability with different nZVI@BCs dosages was shown in Fig. 9(a). With increasing nZVI@BCs dosage, both adsorption and degradation of BPA were enhanced. Similar phenomenon was observed that the enhanced BPA removal via increasing PS dosage (Fig. S9 and Table S5). Nevertheless, further increasing PS dosage did not result in a significant removal, which may because the available active sites on the nZVI@BCs surface were mostly occupied by PS (Chen et al. 2019). BPA removal in terms of initial pH was shown in Fig. 9(c) and it’s found that the initial pH could affect the adsorption and oxidation processes. Fig. S10 and Table S6 showed that when reaction solutions were adjusted to be more alkaline, the kobs were first decrease, and then increase apparently. It is because that the activation of PS can be facilitated in alkaline conditions (Duan et al. 2016). The related pH variation during the experiments was also recorded in the Fig. S11. The solution pH drastically decreased upon PS addition, which was attributable to the strong acidity of PS (Wu et al. 2018) and the formation of acid intermediates and H⁺ (Eqs. (8) and (9)) (Tang et al. 2018).

S₂O₈²⁻ + 2H₂O → 2SO₄²⁻ + HO₂⁻+ 3H⁺ (8)

S₂O₈²⁻ + HO₂⁻ → SO₄²⁻ + SO₄^•−+ O₂^•− + H⁺(9)

BPA removal with respect to diﬀerent anions (Cl⁻ and HCO₃⁻) in nZVI@BCs/PS system was shown in Fig. 9(c). As the Cl⁻levels were increased from 0 mM to 10 mM, distinct increases in the k were observed, the k of first stage were increased from 0.4508 to 2.7074 min^-1, which may because excessive Cl⁻ with negative charge could also donate electrons to PS, generating superabundant active chlorine species and sulfate radicals via Eqs. (10) to (13) participating in the BPA degradation process (Luo et al. 2019, Tang et al. 2018). However, BPA removal in the background of different levels of HCO₃⁻ showed the different phenomenon, a significantly inhibition effect of both adsorption and degradation of BPA were observed when dosing HCO₃⁻ (Fig. 9(c), Fig. S12 and Table S7), and the inhibition was enhanced with increasing HCO₃⁻ concentration. Previous studies (Ghauch &Tuqan 2012, Zhang et al. 2016) showed that HCO₃⁻ was an effective scavenger for SO₄^•−and ^•OH (Eqs. (14) to (18)), which could lead to an inhibitory effect on BPA removal. What’s more, humic acid is also common water component in the actual water, so the effect on BPA removal was investigated. Fig. 9(e) illustrated that in the presence of humic acid, only 5.8% of BPA removal decreased, which showed insignificant inhibition effect on BPA removal.

To evaluate the availability of nZVI@BCs as the catalyst in real applications, three kinds of water matrices, including tap water (RW), Jiangan river water (JAW) and Mingyuan laker water (MYW) were used as the reaction medium to perform the BPA removal experiment. Table S10 showed the characteristics of three real water samples, which indicated a near neutral pH and the dissolved organic matters and the inorganic species existing in three water samples. Fig. 9(d) illustrated that the removal efficiencies in RW, JAW and MYW samples were 85.47%, 74.40% and 76.95%, respectively, which demonstrated that the real water samples could affect the effectiveness of the oxidative process. But these also suggested the application potential of nZVI@BCs in practical water treatment.

SO₄^•− + Cl⁻ → SO₄²⁻ + Cl^•(10)

^•OH + Cl^• → ClOH^•−(11)

ClOH^•− + H⁺ → Cl^• + H₂O (12)

Cl^• + Cl⁻ → Cl₂^•− (13)

SO₄^•− + HCO₃⁻ → SO₄²⁻ + ^•HCO₃ (14)

SO₄^•− + CO₃²⁻ → SO₄²⁻ + ^•CO₃⁻ (15)

HCO₃⁻ + ^•OH → ^•CO₃⁻ + H₂O (16)

CO₃²⁻ + ^•OH → ^•CO₃⁻ + OH⁻ (17)

^•HCO₃ → H⁺ + ^•CO₃⁻ (18)

The nZVI@BCs composites were successfully fabricated based on coffee grounds, sodium bicarbonate, boric acid and FeSO₄. And the nZVI@BCs prepared exhibited an excellent activity and a higher mineralization efficiency in PS activation for BPA removal in aqueous solutions. Combining with radical scavenging tests, EPR signals and electrochemical analysis, radical and non-radical pathway can be accounted for the organic pollutant removal. In summary, both reactive species (SO₄^•−, ^•OH and O₂^•−) and electron transfer were validated to the BPA removal by nZVI@BCs/PS system. The effects of environmental factors (including dosages of nZVI@BCs, BPA and PS, initially pH value, temperature, common anions and humid acid) on the catalytic degradation process were analyzed. The results revealed the constructed nZVI@BCs/PS system can achieve considerable degradation efficiency for modeling organic compounds in complicated water matrices. This study will open up a new insight into the application of PS activation technology in environmental remediation.

Author contributions

Conceptualization, formal analysis, visualization, validation and writing – original draft: Xiaowei Huo; Conceptualization, validation and writing – original draft: Chao Xue; Formal analysis, visualization and writing – original draft: Chenggui Zhang; Data curation: Huichao Wang; Conceptualization, formal analysis, visualization and writing – original draft: Fuxiang Du; Data curation: Chao Dai; Writing – review & editing: Yang Yang; Writing – review & editing: Cheng Lai; Writing – review & editing: Junjun He. All authors read and approved the fnal manuscript.

Funding No funding was received.

Ethical approval Not applicable.

Consent to participate Not applicable.

Consent for publication Not applicable.

Competing interests The authors declare that they have no competing interests.

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Catalytic activation of persulfate by nanoscale zero-valent iron-derived supported boron-doped porous carbon for bisphenol A degradation

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