Effective triclosan removal by using porous aromatic frameworks in continuous fixed-bed column studies

doi:10.21203/rs.3.rs-3132741/v1

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Effective triclosan removal by using porous aromatic frameworks in continuous fixed-bed column studies

https://doi.org/10.21203/rs.3.rs-3132741/v1

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published 10 Nov, 2023

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Triclosan (TCS) has been regarded as an emerging contaminant in aquatic systems, so its efficient removal holds great significance. In this study, NPVMo@iPAF-1, with specific surface area of 665 m²/g, prepared by incorporating (NH₄)₅H₆PV₈Mo₄O₄₀ into porous aromatic frameworks (PAF) was obtained. And fixed-bed columns packed with NPVMo@iPAF-1 were employed for TCS removal. The experiment data strongly correlated with the Thomas and Yoon-Nelson models under different operation conditions. The pore preservation, electrostatic effect and the synergistic effect of π-π interaction contributed to the effective adsorption of TCS onto NPVMo@iPAF-1. The NPVMo@iPAF-1 fixed-bed column could be effectively regenerated by in-situ ozonation for more than 10 regeneration cycles. NPVMo@iPAF-1 turned out to be a promising adsorbent for removing TCS not only from pure water but also from reclaimed water and surface water samples.

Porous aromatic frameworks

Triclosan

Adsorption

Fixed-bed column

Real water

In-situ regeneration

As a disinfectant and an antimicrobial agent, triclosan (TCS) has been widely applicated in personal care products (e.g., cosmetics, toothpaste, shampoos, liquid soap), household goods (e.g., toys, computer equipment, helmets) and medical supplies (e.g., catheters, ureteral stents) in the past decades (Wang and Yang, 2016; Yueh and Tukey, 2016). The pervasive application of TCS allows it to discharge into the environment through many pathways inevitably. The concentration of TCS in effluents from wastewater treatment plant and surface water can reach up to tens of µg/L (Chen et al., 2012; Dar et al., 2022; Li et al., 2020a; Price et al., 2019). Studies have revealed that the long-term residual in environment of TCS may easily degraded into more toxic byproducts (e.g., dioxins) upon ultraviolet light (Wang and Wang, 2019; Yueh and Tukey, 2016). Recent studies indicate that TCS, represented as a lyophobic compound by its high octanol-water partition coefficient (log K-ow) of 4.76, can be concentrated in the aquatic organisms even at ng/L level and causes endocrine disruption and interfere hormonal actions (Dar et al., 2022; Ma et al., 2019). Therefore, the removal of TCS from aquatic environments has received growing concern.

Typically, removal of contaminants from aquatic environments can be achieved by using coagulation-flocculation, biodegradation, advanced oxidation processes and adsorption process (Ji et al., 2021; Song and Jhung, 2017). Among them, adsorption has been presented as a promising technique owing to its relatively simple experimental conditions, straightforward operation, and cost efficiency.

Porous aromatic frameworks (PAFs) are a kind of cutting-edge porous material. They were constructed from various rigid aromatic building units via carbon-carbon coupling reactions (Li et al., 2020b; Song et al., 2019; Zhao et al., 2020). PAFs have been used as adsorbents in liquid because of their facile synthesis, large surface area, tunable porosity with well-defined pore size, ready functionality, and remarkable stability (Li et al., 2020b; Song et al., 2019; Tian et al., 2019). Studies have revealed that the application of PAFs owns exceptional capacities in the adsorptive removal of contaminants (e.g., iodine molecules (Yan et al., 2015), ethylene (Li et al., 2014)) from water and gas (Zhang et al., 2020).

In this study, PAF-modified NPVMo@iPAF-1 was prepared and evaluated for its effectiveness in removing TCS in laboratory-scale fixed-bed column systems. The aims of current paper were (1) to evaluate laboratory-scale fixed-bed column systems, in order to applicate it in practical water treatment processes preferably; (2) to predict the adsorption performance of NPVMo@iPAF-1 by breakthrough curves analysis (Thomas, Yoon-Nelson, Adams-Bohart, and BDST models); (3) to test in-situ regeneration and reusability of NPVMo@iPAF-1 column and its performance in real water.

Materials

Analytical reagent grade of reagents were used for all reaction. A stock solution of 1000 mg/L TCS was prepared in methanol and stored at 4°C. TCS solutions (i.e., 1, 2, 5, 10, 20, 50, 100, 200, 500, 1000 µg/L) were prepared for the standard curve. Reclaimed water and surface water were collected from a municipal wastewater treatment plant and South Lake in Changchun, China. Samples were filtered by glass fiber filters (0.45 µm) and stored at 4°C until use.

Preparation of NPVMo@iPAF-1

NPVMo@iPAF-1 was synthesized by (NH₄)₅H₆PV₈Mo₄O₄₀ (NPVMo) and iPAF-1. And iPAF-1 was obtained following the literature procedure (Song et al., 2019). 7.32 g of sodium metavanadate and 8.22 g of sodium molybdate were dissolved in ultrapure water (38 mL and 12 mL), respectively. The two solutions we prepared above were then mixed. Mixed solution was dripped with phosphoric acid (10 mL, 85%) under stirring conditions at 95°C for 60 min. After nature cooling, 150 mL of saturated ammonium chloride solution was mixed into the mixed solution. And resultant precipitate was collected and recrystallized twice with 0.25 M sulfuric acid. Then, NPVMo was obtained.

1 g of iPAF-1 and 3 g of NPVMo were dissolved in 100 mL of ultrapure water. After 2 days of stirring, the mixture was then filtrated, and the filter residues were collected and washed with ultrapure water for 8 times. NPVMo@iPAF-1 was obtained after freeze-drying for 24 h.

The Autosorb Station 1 automated gas sorption analyzer (Conta, USA) was used to determine the Brunauer-Emmett-Teller (BET) surface areas of NPVMo@iPAF-1. Nicolet 6700 (ThermoFisher, USA) was used to record the Fourier transform-infrared spectra (FT-IR) of NPVMo@iPAF-1, NPVMo and iPAF-1 within a range of 4000 − 500 cm^− 1. Sigma 300 microscope (Carl Zeiss, Germany) was used to obtain the scanning electron microscopy (SEM) images. The Nano ZS 90 zetasizer (Malvern, UK) was used to measure the zeta potential. D8 ADVANCE (Bruker, German) was used to record the X-ray diffraction (XRD) spectra. SDT Q600(TA, USA) was applied to measure the thermogravimetric analysis (TGA) curve from 30°C to 700°C at a scan rate of 10°C/min.

Continuous fixed-bed column studies

An SPE column with a bed depth of 6 cm and an internal diameter of 1.5 cm (Mai et al., 2022) was used to simulate the continuous fixed-bed reactor, and supporting layers of quartz sands were packed at both ends of the reactor to stabilize NPVMo@iPAF-1 inside the column reactor (Fig. 1). Quality Control (QC) were carried out with the above column that only packed with quartz sands. The influent flow was tuned by a standard digital peristaltic pump (BT100-2J, Longer pump, China) (Nag et al., 2015). 1 mL of the effluent was collected for gas chromatography analysis according to our previous work (Li et al., 2020a), and the details are shown in supplementary materials. Due to that concentration of TCS in environmental waters can reach up to tens of µg/L (Dar et al., 2022; Price et al., 2019), initial TCS concentration of 150, 500, 1000 µg/L were used in this experience. Bed depth of 0.16, 0.32, 0.44, 0.54, 0.70 mm were studied for their effects on TCS removal performance. And the flow rate is at 2 mL/min. 0.1 M HCl or NaOH was used to adjust the pH of the solutions. The adsorption processes were described using the Adams-Bohart, Yoon-Nelson, Thomas and BDST models (Eq. (SI-SⅣ)).

In-situ regeneration of NPVMo@iPAF-1 column

The NPVMo@iPAF-1 column was performed with the TCS solution with a concentration of 1000 µg/L, a bed depth of 0.16 mm, and a flow rate of 2 mL/min. After adsorption, the NPVMo@iPAF-1 fixed-bed was backwashed at a flow rate of 0.5 L/min for 120 s by using ozone gas and then dried with nitrogen.

Adsorption performance in real water

Static adsorption experiments were conducted under stirring conditions, 5 mg of NPVMo@iPAF-1 was added to 200 mL of TCS solution in reclaimed water, surface water and ultrapure water.

Characterization of NPVMo@iPAF-1

As shown in Fig. S1 and S2, NPVMo@iPAF-1 are micrometer-sized aggregations composed of nanoparticles. EDS analysis of NPVMo@iPAF-1 confirm the replacement of N, P, V and Mo.

The FT-IR spectrum presented in Fig. S3 shows that the NPVMo@iPAF-1 presented the characteristics of the imidazole skeleton region from 1618 cm^− 1 to 1153 cm^− 1 (Tian et al., 2019). The peaks at 1481, 1386 and 1153 cm^− 1 are C = N stretching vibration, C–H bond in the imidazolium ring (Wang et al., 2022)d stretching band, respectively, which indicates the presence of the imidazolium group after the cross-coupling reaction (Tian et al., 2019). The peaks at 2940 cm^− 1 and 2980 cm^− 1 can be ascribed to aliphatic C–H stretching vibrations. Moreover, peaks of P–O at 1052 cm^− 1, metal-oxygen terminal bonds (Song et al., 2019) at 941 cm^− 1 and vibration from the metals bridged by oxygen (M-O-M) (Song et al., 2019) ranging from 780 to 850 cm^− 1 are found (Song et al., 2019). The results primarily indicate the successful synthesis of NPVMo@iPAF-1. This conclusion is also showed in XRD patterns (Fig. S4). The diffraction peaks of crystalline NPVMo were disappeared in NPVMo@iPAF-1, indicating that the NPVMo anions with multiple negative charges are surrounded by several imidazolium cations through electrostatic interactions (Song et al., 2019).

Figure 2 and Table S1 shows the N₂ adsorption-desorption isotherms of NPVMo@iPAF-1 and the porosity and textural properties revealed in Table S1. Based on the IUPAC classification, the isotherms of NPVMo@iPAF-1 can be identified as type II with type H4 hysteresis loops (Li et al., 2020a; Srinivasakannan and Balasubramaniam, 2007). Calculated from the isotherms, the pore volume of NPVMo@iPAF-1 is 0.465 cc/g, and the BET surface area is 665 m²/g. Three kinds of pore diameter centered at 0.61, 1.18, and 3.41 nm distribute predominantly in the microporous (Eren, 2010). The specific large surface area provides more sufficient adsorption sites for TCS, resulting the huge adsorption capacity of NPVMo@iPAF-1. The results of TGA were shown in Fig. S5, iPAF-1 and NPVMo@iPAF-1 exhibited the lowest decomposition temperatures of 527°C and 501°C, respectively.

Continuous fixed-bed column studies

Figure 3a shows the breakthrough curves for various bed depths (0.16, 0.44, 0.70 mm). As the bed depth increases from 0.16 to 0.70 mm, the breakthrough curves move from left to right, and the slope of the breakthrough curve (Lim et al., 2022) becomes slower, indicating that breakthrough time and saturation time were increased (Jang and Lee, 2016). It is because that an increase in bed depth corresponded to an increase in the amount of adsorbent, meaning more adsorption binding sites for TCS removal and longer breakthrough and saturation time. Figure 3b shows how various initial TCS concentrations of environmental level (150, 500, 1000 µg/L) affected the breakthrough curves at the bed depth of 0.44 mm. As the initial TCS concentration increases from 150 to 1000 µg/L, the saturation time decreases quickly from 12 to 8 days. It is because that higher initial TCS concentration increases the concentration gradient of TCS between adsorbent and bulk solution, which leads to a stronger driving force. With a stronger driving force, the mass transfer resistance between TCS and NPVMo@iPAF-1 decreases, thus, the required saturation time is shorter. QC proved that the saturation time of column was less than 60 min, which indicated NPVMo@iPAF-1 plays a major role in the TCS removal.

Four classical mathematical models, including Adams-Bohart, BDST, Yoon-Nelson, and Thomas, models were used to analyze the column breakthrough curves of TCS versus time (Fig. 3). Parameters for the models are presented in Table 1.

Table 1

Calculated parameters of mathematical models for TCS adsorption by NPVMo@iPAF-1
C₀ (mg/L)	H (mm)	Thomas model			Yoon-Nelson model			Adams-Bohart model
C₀ (mg/L)	H (mm)	k_TH (mL/(mg·min))	q_e (mg/g)	R²	k_YN (min^− 1)	τ (d)	R²	k_AB (L/(min·g))	N₀ (mg/L)	R²
0.15	0.16	2.565	360.97	0.98	0.415	5.94	0.98	1.269	245.80	0.91
0.15	0.44	2.200	124.95	0.98	0.303	8.50	0.98	1.169	112.90	0.93
0.15	0.70	0.909	164.01	0.99	0.136	21.86	1.00	0.416	18.81	0.94
0.50	0.44	0.915	269.15	0.97	0.261	7.21	0.98	0.695	329.17	0.91
1.00	0.44	0.217	478.59	0.97	0.204	3.09	0.97	0.090	750.21	0.90

The correlation coefficients of the Thomas model are from 0.97 to 0.99, which shows the model can well portray the column experimental data. The Thomas model constants (k_TH) are 2.200, 0.915, 0.217 mL/(mg·min), and the adsorption capacity (q_e) are 124.95, 269.15, 478.59 mg/g as the initial TCS concentration increases. The reason for it is that a higher TCS concentration can cause a decrease in the resistance of mass transport (Lim et al., 2022) between TCS and sorbent. And increases in both bed depth and initial TCS concentration cause k_TH to decrease. As for the Yoon-Nelson model, correlation coefficients range from 0.97 to 1.00, indicating that the dynamic behavior in the fixed-bed column (Jang and Lee, 2019) can be described well. The Yoon-Nelson model constants (k_YN) are 0.415, 0.303, 0.136 min^− 1 and, the value of τ are 5.94, 8.50, 21.86 d with an increase of bed depth, because of the increase of axial dispersion and mass transport resistance (Li et al., 2020a). And an increase of initial TCS concentration causes both k_YN and τ to decrease. The R² values calculated from Adams-Bohart model are between 0.90 to 0.94 at various conditions, which is the worst fitting for experimental data obtained by fixed-bed column.

The BDST model was conducted to evaluate the required bed depth for a given service time (Singer et al., 2002) in the NPVMo@iPAF-1 column (Fig. 4 and Table S2). The R² values calculated from the BDST model is 0.98 at different bed depths in the range of 0.16–0.70 mm, which means that the column experimental data can be well portrayed by the BDST model (Calero et al., 2011). And the value of k_B and N₀ are 5.04 L/(min·g) and 137.15 mg/L.

NPVMo@iPAF-1 Adsorption mechanisms

The proposed mechanism of TCS adsorption by NPVMo@iPAF-1 was investigated, and three possible mechanisms, including π-π interaction, pore preservation and electrostatic effect are illustrated (Fig. 5). According to the results from adsorption kinetic and isotherm, the π-π interaction and electrostatic effect dominate the adsorption process (Jin et al., 2021). The π-π interaction occurs between the double benzene rings on TCS and the organic building units with carbon-carbon linkages (Li et al., 2020b; Song et al., 2019) on NPVMo@iPAF-1 (Fig. S3). Electrostatic effect is an important factor determining the adsorption efficiency for TCS onto NPVMo@iPAF-1. The TCS removal efficiency sharply decreases from 699.3 to 248.8 mg/g with an increase in pH from 3 to 7. The net charge of TCS, obtained from our previous work (Li et al., 2020a), and NPVMo@iPAF-1 decrease as the pH value rise (Table S3 and Fig. S6). It is due to the electrostatic repulsion between TCS and NPVMo@iPAF-1 may weaken the π-π interaction. In addition, pore presentation belongs to physical adsorption, and it is result of the huge surface area and abundant micropore structures of NPVMo@iPAF-1 (Fig. 2 and Table S1).

In-situ regeneration of NPVMo@iPAF-1 column

An in-situ regeneration method by ozone was established to evaluate the reusability of NPVMo@iPAF-1. The NPVMo@iPAF-1 column was reused for 10 adsorption cycles, displaying excellent removal efficiency (Fig. S7). After five cycles, a slight decline in removal efficiency (Jang and Lee, 2019) was observed, but the removal efficiencies of NPVMo@iPAF-1 column over ten consecutive processes were more than 88%. The results demonstrate that NPVMo@iPAF-1 column can be effectively regenerated for about ten cycles. And the chemical stability of NPVMo@iPAF-1 is attributed to the electrostatic assembly of polyoxometalates anions and imidazolium cations (Song et al., 2019).

Adsorption performance in real water

The practical application potential of NPVMo@iPAF-1 for TCS adsorption in real water was assessed (Fig. 6). And the real water’s water parameters samples are shown in Table S4. Compared to ultrapure water, the NPVMo@iPAF-1 adsorption amounts of TCS in the surface water are lower, and they reach the lowest in the case of the reclaimed water. It may result from the negative effect of the presented coexisting ions in real water. Although strong matrix interference occurs in reclaimed water, the adsorption capacity of TCS adsorbed onto NPVMo@iPAF-1 can reach 75.8 mg/g, which accounts for 84.0% of adsorption performance for ultrapure water. This phenomenon indicates that NPVMo@iPAF-1 can be a promising adsorbent for TCS removal in real aquatic environments.

The well-prepared NPVMo@iPAF-1 was identified with a rich pore structure, and the BET surface area was 665 m²/g. In laboratory-scale fixed-bed column systems, the maximum breakthrough time was observed for up to 30 days. The π-π interaction and electrostatic effect dominated the adsorption process, and the TCS removal efficiency decreased with an increasing pH. The Yoon-Nelson, BDST, Adams-Bohart and Thomas models all exhibited good fitting curves. The in-situ ozonation can regenerate the fixed column for more than 10 regeneration cycles. The adsorption capacity of TCS onto NPVMo@iPAF-1 in real reclaimed water samples can reach up to 75.8 mg/g, which accounts for 84.0% of adsorption performance for ultrapure water.

Author contribution

Ye Li: Investigation, Writing – Original Draft, Review & Editing, Validation, Funding acquisition. Fuxin Gong: Supervision, Review & Editing. Wu Yang: Formal analysis, Validation, Writing – Review & Editing. Bingxin Liu: Methodology, Conceptualization, Supervision, Writing – Review & Editing, Funding acquisition.

Funding

This work was supported by Fundamental Research Funds for the Central Universities (2412019FZ020) and Tianjin Research Innovation Project for Postgraduate Students (2021YJSB042)

Data availability Not applicable

Declaration of Competing Interest

Ethical approval There are no ethical issues.

Consent to participate The full consent of all authors is confirmed.

Consent for publication All authors agree to submit this paper for publication.

Competing interest The authors declare no competing interests.

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Effective triclosan removal by using porous aromatic frameworks in continuous fixed-bed column studies

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Abstract

Figures

Introduction

Materials and methods

Materials

Preparation of NPVMo@iPAF-1

Continuous fixed-bed column studies

In-situ regeneration of NPVMo@iPAF-1 column

Adsorption performance in real water

Results and discussion

Characterization of NPVMo@iPAF-1

Continuous fixed-bed column studies

NPVMo@iPAF-1 Adsorption mechanisms

In-situ regeneration of NPVMo@iPAF-1 column

Adsorption performance in real water

Conclusions

Declarations

References

Supplementary Files

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