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Bisphenol A (BPA) is one of the most widely used chemical products, which is discharged into rivers and oceans, posing great hazards to organisms such as reproductive toxicity, hormone imbalance and cardiopathy induction. With the expansion harm of BPA, people have paid more attention to the environmental effects. In this paper, the degradation of BPA from the synthetic wastewater using the immobilization of horseradish peroxidase membrane reactor (HPR) was investigated. The immobilized HRP microporous membrane was prepared by the porous calcium alginate method. In addition, the reuse of the immobilized HPR membrane and the measurement of membrane flux showed that the membrane has good activity and stability. Finally, the experimental parameters including reaction time, pH, the concentration of BPA and the dosage of H2O2 were optimized to remove the BPA, and about 78% degradation efficiency of BPA was achieved at the optimal condition as follows: H2O2 to BPA molar ratio of 1.50 with an initial BPA concentration of 0.1 mol/L, the HPR dosage of 3.84 u/mL, the initial solution pH of 7.0, a temperature of 20 °C and a contact time of 10 min.

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  • Horseradish peroxidase (HRP) can be effectively immobilized on the membrane.

  • The immobilized HRP can maintain high activity and be circulation utilization.

  • The optimum conditions for the mole rate of H2O2/BPA dosage and the pH value are 1.5 and 7, respectively.

Bisphenol A, enzymatic catalysis, horseradish peroxidase, microporous ultrafiltration membrane, water pollution remediation
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Water is an essential foundation for the environment and life, which has been seriously polluted by organic contaminants in recent years (Chen et al. 2021; Al-Qadri et al. 2022). Many organic pollutants in the water bodies cause serious environmental problems to ecosystems and human health due to their persistent, high solubility, and high toxic and carcinogenic properties (Wang et al. 2015a, 2015b; Ribeiro et al. 2017; Wu et al. 2023). For example, the animals’ long time exposure to the bisphenol A (BPA)-contained (≥ ng/L) water bodies could causes disrupt endocrine, symptoms of sexual maturation and alter their reproductive function (Moussavi et al. 2018). BPA is a typical environmental endocrine disruptor, belonging to environmental hormones. As a widely used plasticizer, it is widely used in the synthesis and decomposition process of materials in the plastic industry and the electronic industry (Yu et al. 2022). In addition, BPA can coexist with pollutants such as microplastics, heavy metals, pesticides, antibiotics and polyaromatic hydrocarbons in wastewater, and cannot be completely degraded in water or soil for decades (Adu-Gyamfi et al. 2022). Therefore, these have spurred intensive efforts to develop novel sustainable technologies for the cleanliness of these organic contaminants.

As an efficient and green biocatalyst, enzymes are widely used in wastewater treatment because of their good specificity, high catalytic efficiency and mild reaction conditions (Fernández-Fernández et al. 2013). Horseradish peroxidase (HRP) is a typical oxidoreductase and is a versatile enzyme used in the pharmaceutical, chemical, biotechnology and environmental industries (Chattopadhyay & Mazumdar 2000; Veitch 2004). When HRP is present, the oxidation of phenolic compound is catalyzed by the addition of H2O2 to form corresponding free radicals, and then, the free radicals spontaneously interact to quickly form insoluble polymers that can be easily removed from wastewater (Wang et al. 2015a, 2015b). However, in actual use, there are shortcomings such as poor operational stability, easy inactivation under extreme conditions, inability to reuse and recycle and high cost of use, which limit the further application of this technology (Sheldon 2007).

A large number of studies have found that the immobilization of enzymes by using carrier binding is one of the direct and effective methods to improve the catalytic efficiency of enzymes (Gasser et al. 2014; Mohamad et al. 2015). In order to obtain the ideal immobilization enzyme and improve the activity and stability of the immobilized enzyme, it is necessary to select an efficient immobilization method and a suitable immobilization vector (Kim et al. 2016; Patel et al. 2016, 2017). The membrane material is a good choice as a carrier for enzyme fixation, which combines the catalytic function of the enzyme with the separation function of the membrane (Vasconcelos et al. 2020). At the same time, with the selective transfer of membranes, reactants, reaction products and solvents can be separated, purified and enriched, so as to realize the two processes of enzyme-catalyzed reaction and separation in one system, which is an advantage that other carrier materials do not have (Girelli & Scuto 2021; Zhang et al. 2021). Escalona et al. (2014) used the enzyme-bound nanofiltration membrane to treat BPA to achieve a good removal effect, however, the production cost of nanofiltration membrane is relatively high, and the operating pressure of membrane filtration is large (Albergamo et al. 2019). In contrast, ultrafiltration is a low-pressure operation with the advantage of low cost and is more suitable for a wide range of applications in water treatment (Shi et al. 2014; Krahnstover et al. 2019; Ahmad et al. 2020).

In this study, HRP was fixed on the microporous ultrafiltration membrane by porous calcium alginate embedding (Aryal 2019; Meng et al. 2020), and the rich pore structure of the membrane provided an excellent matrix for the loading of HRP, and the small pore size of the membrane promoted the contact between BPA and the catalyst, which catalyzed the conversion of BPA into polymer precipitation and helped its removal. With this design, the ultrafiltration membrane can realize the immobilization and reuse of HRP, while removing the polymer precipitation during the filtration process to obtain purified water. Then, the influence of immobilization on the catalytic activity of HRP was explored. Finally, the optimal process parameters of HRP immobilized membranes for actual industrial wastewater treatment are investigated, including the amount of H2O2, the initial concentration of BPA, pH and reaction time. This work is expected to provide a novel approach for the further development of the catalysis membrane system.

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Materials and reagents

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HRP (lyophilized powder, 250 u/mg) was purchased from Shanghai Guchen Biotechnology Co., Ltd. BPA and Sodium alginate were purchased from Shanghai Aladdin Biochemical Technology Co., Ltd. Sodium dihydrogen phosphate and disodium hydrogen phosphate were obtained by Sinopharm Chemical Reagent Co., Ltd. Hydrogen peroxide 3% (w/w), hydrochloric acid, sodium hydroxide and calcium chloride were supplied from Shanghai Macklin Biochemical Co., Ltd. All the chemical reagents except hydrogen peroxide in experiment were analytically pure grade.

An electronic balance (ME204/02) was used to weigh the reagent. The concentration of BPA was analyzed by a UV–Vis spectrophotometer (UV, BlueStar A). A pipette gun (200 and 5,000 μL) was used to pick up the liquid. The HRP was loaded on an ultrafiltration filter (φ100 mm, membrane pore size 0.22 μm, PES). The ultrafiltration filter membrane was purchased from Tianjin Navigator Lab Instrument Institute.

The surface morphology and structure were characterized using a Supra55 Scanning Electron Microscope (SEM), and nitrogen gas purging was performed on the membrane section in advance. The acceleration voltage of the instrument was 20.00 kV, the working distance was 8.2 mm, the magnification was 7,940 times and the detector was SE2.

The configuration method of synthetic wastewater is as follows: a certain amount of BPA powder is weighed and dissolved in a beaker, and then, the volume is fixed with a volumetric flask to obtain a simulated synthetic wastewater containing a BPA concentration of 0.2 mmol/L.

The determination of BPA was as follows: it was determined at the characteristic absorption wavelength of 510 nm by a UV–Vis Spectrophotometer (R² = 0.9997). According to the following formula to calculate the removal rate of BPA: η = (A0 − At)/A0 × 100%, where η is the removal rate of BPA, A0 is the initial absorbance of BPA and At is the absorbance of BPA after the reaction.

Immobilization of HRP

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The HPR was immobilized on the microporous membrane through the porous calcium alginate method. The specific process of the immobilization method was as follows: 0.25 g of sodium alginate was dissolved into 100 mL of distilled water; meanwhile, 120 mg of HRP was dissolved in 10 mL phosphate buffer solution of pH 7.0, and after that 1.5 mL of sodium alginate solution and 1.5 mL of HRP solution were thoroughly mixed. Then, the whole mixture was evenly coated on the microporous membrane and allowed to stand for 10 min. Next, the microporous membrane was placed in 0.1 mol/L calcium chloride solution and allowed to stand for 20 min. Finally, the embedded membrane was placed indoors for 2.5 h, the prepared enzymatic membranes were stored in phosphate buffer solution for use (Figure 1).
Figure 1
Flowchart of the enzyme catalysis reaction.
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Flowchart of the enzyme catalysis reaction.

Figure 1
Flowchart of the enzyme catalysis reaction.
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Flowchart of the enzyme catalysis reaction.

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Experimental procedure

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The 100 mL of BPA was pumped into the reactor through the peristaltic pump. A portion of the solution, which is backwater, flowed through the surface of the microporous filter and reacted with the HPR on the surface of the membrane. The other part of the solution, which is the final water, passed through the microporous filter under pressure and reacted with HPR in the membrane pore. Finally, these two parts of the liquid were returned to the beaker. The flowchart of the reaction mechanism is shown in Figures 1 and 2. All experiments were conducted in two or more parallel experiments. The removal of BPA (%) was calculated according to the following formula:
Figure 2
Schematic diagram of the reaction mechanism of the HPR immobilized membrane.
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Schematic diagram of the reaction mechanism of the HPR immobilized membrane.

Figure 2
Schematic diagram of the reaction mechanism of the HPR immobilized membrane.
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Schematic diagram of the reaction mechanism of the HPR immobilized membrane.

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In the formula, C0 (mmol/L) is the initial concentration of BPA in wastewater and Ct (mmol/L) is the concentration of BPA in wastewater after a certain period of time.

The main factors of this study are the reuse effect of HRP; reaction time; the mole ratio of H2O2/BPA, including 1:1, 1.5:1, 2:1 and 2.5:1; the initial concentrations of BPA, including 0.025, 0.05, 0.1, 0.15 and 0.20 mmol/L and the initial pH of the solution includes 4, 6, 7, 8 and 10.

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Characterization of the HRP membrane

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The surface morphology and structure of the immobilized HRP membrane were characterized by SEM images. Figure 3(a)–3(c) shows the microporous membrane, the unreacted of HRP membrane and the reaction of HRP membrane with BPA. There was an uneven distribution aperture on the surface of microporous membrane; a small amount of filamentous reticular substance can be observed when HPR was immobilized on the microporous membrane. It was shown that HPR was attached to the three-dimensional void of the microporous membrane. After the reaction, the membrane still retained more three-dimensional pores, which indicated that most of the membrane pores were not blocked.
Figure 3
SEM image of microporous membrane (a), the unreacted of HRP membrane (b) and the reaction of HRP membrane (c).
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SEM image of microporous membrane (a), the unreacted of HRP membrane (b) and the reaction of HRP membrane (c).

Figure 3
SEM image of microporous membrane (a), the unreacted of HRP membrane (b) and the reaction of HRP membrane (c).
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SEM image of microporous membrane (a), the unreacted of HRP membrane (b) and the reaction of HRP membrane (c).

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Investigation on the activity of immobilized enzyme

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In the immobilized catalytic membrane system, a key problem that cannot be ignored is the reusability of the catalytic membrane. The catalyst on the membrane surface is easily inactivated during long-term filtration. Unfortunately, conventional catalyst regeneration methods, such as high-temperature calcination or washing with organic solvents, are not suitable for immobilized catalytic membrane systems (Li et al. 2019). Therefore, to investigate the stability of the immobilized HRP membrane, the membrane was recovered and reused after each experiment (Sri Kaja et al. 2018). The result in Figure 4 showed that the HRP membranes have considerable reusability for the degradation of BPA and the degradation rate decreased from 73.3 to 56.8% after being used for four recycles. The activity of immobilized HRP decreased with the increase of the times of reuses. The result showed that the immobilized HRP still maintained high activity after being used for four times. Therefore, the HPR membrane can be circulation utilization. Immobilized enzymes are prone to deformation and inactivation in harsh environments, and their stability is greatly affected in practical applications. Therefore, studies on the activity and recyclability of the immobilized enzyme are very necessary.
Figure 4
Stability of the catalytic activity of HRP membrane (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).
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Stability of the catalytic activity of HRP membrane (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).

Figure 4
Stability of the catalytic activity of HRP membrane (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).
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Stability of the catalytic activity of HRP membrane (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).

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Membrane flux is related to the ability of a membrane to remove contaminants. Ultrafiltration membranes can effectively remove insoluble polymers and water from wastewater. However, the permeation flux is reduced due to membrane contamination during filtration. The polymer deposited on the surface of the ultrafiltration membrane or the low polymer in the pores will lead to a decrease in the permeation flux of the membrane under the same pressure (Onishi & Kamimori 2013). Table 1 shows that the water flux of the membranes was used four times at 0.065 and 0.08 MPa. It could be seen that the higher the pressure, the greater the value of the water flux. And with the increase in the usage count of the HPR membrane, the value of water flux decreased slightly. The performance of the ultrafiltration membrane can be maintained by cleaning the membrane with air washing, reverse washing, chemical cleaning, etc., but it will eventually shorten the service life of the membrane (Akther et al. 2020).

Table 1

The pure water flux of the HPR membrane under different pressures

Test timeMembrane flux (L/(m2h))
Test 1 (Pressure: 0.08 MPa)Test 2 (Pressure: 0.065 MPa)
1st 301.3 222.0 
2nd 286.8 214.8 
3rd 288.0 216.0 
4th 260.4 205.2 
Test timeMembrane flux (L/(m2h))
Test 1 (Pressure: 0.08 MPa)Test 2 (Pressure: 0.065 MPa)
1st 301.3 222.0 
2nd 286.8 214.8 
3rd 288.0 216.0 
4th 260.4 205.2 

Membrane reactor system (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).

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Effect of reaction time on the degradation of BPA

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The degradation of BPA was conducted as shown in Figure 5. With the increase in reaction time, the removal rate of BPA rapidly increased in the initial 5 min and then slowly in 5–60 min. The removal rates of BPA were 71.5% in 5 min and 76.8% in 60 min, respectively. This result showed that the degradation of BPA rapidly increased with the increase in reaction time, and it tended to be steady. When the reaction reached equilibrium, no significant changes in removal rates were observed over time. It indicated that further increased reaction time (>5 min) had little effect on the BPA degradation. Therefore, the reaction time of the follow-up experiment was 10 min, and the optimum reaction time was 10 min.
Figure 5
Effect of the reaction time on the removal of BPA in immobilized enzymatic (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).
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Effect of the reaction time on the removal of BPA in immobilized enzymatic (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).

Figure 5
Effect of the reaction time on the removal of BPA in immobilized enzymatic (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).
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Effect of the reaction time on the removal of BPA in immobilized enzymatic (CBPA = 0.1 mmol/L, nH2O2:nBPA = 1.5:1, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).

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Effect of the dosage of H2O2 on the degradation of BPA

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In the absence of H2O2, it is difficult to perform biocatalytic reactions by immobilized HPR alone. Studies have shown that the removal efficiency of phenolic compounds can be improved by choosing the appropriate H2O2 concentration (Wu et al. 2022). As shown in Figure 6, the influences of H2O2 on the degradation of BPA were investigated. The removal rate of BPA was only 71.9% when the mole ratio of H2O2/BPA was 1:1. When the mole ratio of H2O2/BPA increased to 1.5, the removal rate of BPA reached 78.6%. When the mole ratio of H2O2/BPA was higher than 1.5, the degradation efficiency of BPA had a tendency to decrease. It was obviously observed that the excessive addition of H2O2 dosage could inhibit the degradation of BPA. That may be because the overdosage of H2O2 could result in the production of intermediate products that might inhibit the oxidation capacity of HRP (Wang et al. 2015a, 2015b). In addition, H2O2 could act as scavengers of active radicals through reduction reactions (Ai et al. 2017). Therefore, the optimum n(H2O2):n(BPA) was 1.5.
Figure 6
Effect of H2O2 dosage on the degradation of BPA in the immobilized enzymatic membrane reactor system. (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).
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Effect of H2O2 dosage on the degradation of BPA in the immobilized enzymatic membrane reactor system. (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).

Figure 6
Effect of H2O2 dosage on the degradation of BPA in the immobilized enzymatic membrane reactor system. (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).
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Effect of H2O2 dosage on the degradation of BPA in the immobilized enzymatic membrane reactor system. (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, pH = 7, T = 20 °C).

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In general, the amount of H2O2 added directly affects the efficiency of HRP in removing BPA; too low a concentration will not achieve the desired removal effect, and too high a concentration will inhibit the degradation of BPA, thus affecting the removal efficiency. Therefore, it is necessary to explore the effect of hydrogen peroxide concentration on BPA. At the same time, the cost of H2O2 is high in practical applications, so it is of great economic significance to choose the appropriate concentration of H2O2.

Effect of the initial concentration of BPA

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The degradation of phenolic compounds by HRP was closely related to the initial concentration of phenolic compounds (Moussavi et al. 2018). In the actual treatment of wastewater, the concentration of BPA in wastewater is variable, and different concentrations have different removal effects. The applicability of the immobilized HRP membrane system to changes in water quality was investigated by measuring the removal efficiency of BPA at different concentrations of BPA (Zhao et al. 2021).

The effect of the initial concentration of BPA on the removal rate is shown in Figure 7. When the initial concentration of BPA was 0.025, 0.05, 0.1 and 0.2 mmol/L, the removal rate of BPA in the immobilized HPR membrane process was 92.2, 75.4, 68.3 and 61.6%, respectively. It was observed that the degradation rate of BPA gradually decreased with the increase of the initial concentration of BPA. Obviously, the insufficiency of available HPR led to the decrease of degradation efficiency of BPA with the increase of BPA concentration.
Figure 7
Effect of the initial concentration of BPA on the degradation of BPA for the immobilized enzymatic membrane reactor system (reaction time of 10 min, nH2O2:nBPA = 1.5:1, pH = 7, T = 20 °C).
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Effect of the initial concentration of BPA on the degradation of BPA for the immobilized enzymatic membrane reactor system (reaction time of 10 min, nH2O2:nBPA = 1.5:1, pH = 7, T = 20 °C).

Figure 7
Effect of the initial concentration of BPA on the degradation of BPA for the immobilized enzymatic membrane reactor system (reaction time of 10 min, nH2O2:nBPA = 1.5:1, pH = 7, T = 20 °C).
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Effect of the initial concentration of BPA on the degradation of BPA for the immobilized enzymatic membrane reactor system (reaction time of 10 min, nH2O2:nBPA = 1.5:1, pH = 7, T = 20 °C).

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Effect of solution pH on the degradation of BPA

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For free/immobilized enzyme, pH was one of the most important influence factors on enzyme activity. In general, all enzymes have an optimum pH at which their activity is greatest, but not necessarily the same as their normal intracellular environment (Hu et al. 2018). It was necessary to investigate the degradation of BPA by the immobilized HRP membrane system in different solution pH values. The effect of pH on the degradation of BPA was investigated in the pH range of 4.0–10.0 and the obtained result is shown in Figure 8. When the initial pH increased from 4.0 to 7.0, the removal of BPA obviously increased from 69.2 to 77.6%. The removal rate of BPA was 72.7 and 68.9% at pH 8.0 and 10.0. As can be seen, the optimum pH was 7 and the removal of BPA was slightly inhibited in acid and alkaline conditions.
Figure 8
Effect of pH on the degradation of phenol in the immobilized enzymatic membrane reactor system (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, nH2O2:nBPA = 1.5:1).
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Effect of pH on the degradation of phenol in the immobilized enzymatic membrane reactor system (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, nH2O2:nBPA = 1.5:1).

Figure 8
Effect of pH on the degradation of phenol in the immobilized enzymatic membrane reactor system (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, nH2O2:nBPA = 1.5:1).
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Effect of pH on the degradation of phenol in the immobilized enzymatic membrane reactor system (CBPA = 0.1 mmol/L, reaction time of 10 min, the dosage of HRP = 3.84 u/mL, nH2O2:nBPA = 1.5:1).

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The results showed that immobilized HPR was able to oxidize BPA over the entire pH range studied, indicating that HRP was active over a wide pH range. The results are consistent with those reported previously in the literature, and the reason for the lower efficiency of BPA removal may be the increased instability of HRP under non-optimal pH conditions, leading to loss of enzyme activity (Zhang et al. 2022). At the same time, it may also be that the interaction between BPA and HPR is reduced (Yamada et al. 2010).

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In this paper, the application of the immobilized HPR microporous membrane reactor system for the degradation of BPA from aqueous solution was investigated. When HRP is present, BPA is catalyzed by the addition of H2O2 to form corresponding free radicals, and then, the free radicals spontaneously interact to quickly form insoluble polymers that can be easily removed from wastewater. The results showed that this strain had a high degradation efficiency for BPA. In addition, the reusability experiment showed that the immobilized HPR membrane can be used up to four times without serious deficiency in its activity and water flux of the membrane. The removal rate of BPA by the immobilized HPR membrane tended to be balanced after 10 min reaction. The removal rate of BPA increased initially and then decreased with the increase of H2O2 dosage and the solution pH value. The optimum conditions for the mole rate of H2O2/BPA dosage and the pH value are 1.5 and 7, respectively. In summary, under the conditions of HPR dosage of 3.84 u/mL, initial solution pH of 7.0, temperature of 20 °C, contact time of 10 min and molar ratio of H2O2 to BPA of 1.50, the optimal degradation efficiency of BPA was 78%. In conclusion, the immobilized HPR membrane reactor system was a considerable potential method for the efficient treatment of BPA effluents.

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This work was supported by the National Natural Science Foundation of China (52260022); Jiangxi Provincial Natural Science Foundation (20224BAB213031); Science and Technology Research Project of Jiangxi Provincial Department of Education (GJJ201416) and the Open Research Fund Program of Jiangxi Provincial Key Laboratory of Low-Carbon Solid Waste Recycling (20212BCD42015).

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All relevant data are included in the paper or its Supplementary Information.

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The authors declare there is no conflict.

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Author notes

†

Yingying Li, Linfeng Guo and Haitao Li were the first authors.

© 2023 The Authors
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