Research Article pubs.acs.org/journal/ascecg
Environmentally Friendly β‑Cyclodextrin−Ionic Liquid PolyurethaneModified Magnetic Sorbent for the Removal of PFOA, PFOS, and Cr(VI) from Water Abu Zayed Md Badruddoza,*,† Bikash Bhattarai,‡ and Rominder P. S. Suri* NSF IUCRC Water and Environmental Technology (WET) Center, Civil and Environmental Engineering, Temple University, 1947 North 12th St., Philadelphia, Pennsylvania 19122, United States S Supporting Information *
ABSTRACT: Emerging contaminants such as perfluorinated compounds (PFCs) and heavy metals are of increasing concerns due to their detrimental effects on environment and human health. Their mixtures are often present at contaminated sites that pose a challenge in water remediation. Herein, we report a multifunctional magnetic sorbent (Fe3O4-CDI-IL MNPs) that was prepared by modifying the magnetic Fe3O4 nanoparticle with β-cyclodextrin−ionic liquid (β-CD-IL) polyurethanes for the removal of perfluorooctanesulfonate (PFOS), perfluorooctanoic acid (PFOA), and Cr(VI) from aqueous solution. The successful grafting of the β-CD-IL polymer on magnetic nanoparticles was confirmed by FTIR, ζ -potential, TGA, and VSM. The sorption behaviors of Fe3O4CDI-IL MNPs were investigated in terms of sorption kinetics, isotherms, simultaneous removal capability, and reusability. The kinetic results showed that the sorption of PFOS, PFOA, and Cr(VI) reached equilibrium within 4, 6, and 3 h, respectively, and the pseudo-second-order kinetic model best described the kinetic data. The solution pH had more obvious effects on the sorption of PFOA and Cr(VI) than that of PFOS. The coupling of ionic liquid with the β-CD polymer backbone could significantly enhance the removal efficiencies of both PFOS and PFOA. The sorption isotherms indicated that the heterogeneous sorption capacities of Fe3O4-CDI-IL MNPs were 13,200 and 2500 μg/g for PFOS and PFOA, respectively, and the monolayer sorption capacity was 2600 μg/g for Cr(VI) ions. The Cr(VI)-PFC binary sorption experiments exhibited a decrease in sorption capacities for PFCs, but the removal of Cr(VI) was unaffected with the introduction of PFCs as co-contaminants. The hydrophobic interactions and electrostatic attraction were mainly involved in the PFC sorption process, whereas the ion exchange and reduction was responsible for Cr(VI) sorption. In addition, Fe3O4-CDI-IL MNPs could be readily recovered with a permanent magnet, regenerated, and reused at least 10 times without any significant efficiency loss. This multifunctional sorbent thus shows potential in the removal of coexisting toxic contaminants from water or wastewater. KEYWORDS: Perfluorinated compounds, Emerging contaminants, Heavy metals, Adsorption, Cyclodextrin−ionic liquid, Multifunctional sorbent
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INTRODUCTION
utilized as an inhibitor of chromium (Cr) fog in order to reduce the chromium contaminant in the atmosphere.3 Eventually, the wastewater effluent discharged from electroplating plants contains a high concentration of PFOS mixed with hexavalent chromium. Hexavalent chromium [Cr(VI)] is also highly toxic and hazardous.4,5 This toxic and carcinogenic metal is usually released to the environment mainly by industrial activities, such as electroplating, metal finishing, leather tanning, chromate manufacture, and wood preservation. Exposure to Cr(VI) in drinking water, even at a trace level, increases the risk for human beings; it may trigger vomiting, skin irritation, lung
Environmental pollution by emerging contaminants (ECs) and heavy metals in different water sources and industrial effluents has aroused public concern over the past decade. In particular, perfluorinated compounds (PFCs) as ECs have attracted continuously increasing attention recently because of their extremely persistent nature in the environment, notable bioaccumulation, and potential toxicity to human beings and animals.1,2 The unique physical and chemical properties such as hydrophobicity and oleophobicity as well as high chemical stability have led to extensive use of PFCs in many applications. Perfluorooctanesulfonate (PFOS) and perfluorooctanoate (PFOA) are the most common PFCs used in many industries and are detected ubiquitously up to the μg L−1 level in aqueous environments.2 In an electroplating plant, PFOS is usually © 2017 American Chemical Society
Received: July 2, 2017 Revised: August 27, 2017 Published: August 28, 2017 9223
DOI: 10.1021/acssuschemeng.7b02186 ACS Sustainable Chem. Eng. 2017, 5, 9223−9232
Research Article
ACS Sustainable Chemistry & Engineering Scheme 1. Illustration of Synthesis Schemes for Preparation of Fe3O4-CDI-IL Sorbent
cancer, and kidney and liver damage.5 Therefore, due to their adverse impacts on environment and human health, an effective and simultaneous removal of such contaminants from various water sources is of significant importance. The sorption process is considered as an effective and economical approach for improving water quality and can be used to remove a wide variety of trace pollutants.6−11 To date, various sorbents such as boehmite,12 alumina,13 activated carbon,14 carbon nanotubes,15 chitosan polymers (MIPs),16,17 and clay minerals18 have been reported as sorbents for the removal of PFOS and PFOA from water. Similarly, activated carbon is widely used as a sorbent for the removal of Cr(VI) due to its high surface area and abundant micropores.19 However, further treatment is often needed to enhance its adsorption capacity and selectivity, such as oxidation, acidation, alkalization, and impregnation of foreign materials, and also to regenerate, thus increasing the cost and limiting its applications.20,21 Recently, magnetic nanoparticles (MNPs) such as iron oxide-nanostructured materials have been considered as potential sorbents in applications of environmental pollution cleanup.22−24 The advantages of MNPs are attributed to their high specific surface area, easy separation under external magnetic fields, and ease of surface functionalization. Magnetic cyclodextrin nanocomposites are of particular interest in environmental applications.25−29 β-Cyclodextrin (βCD) is a cyclic oligosaccharide composed of α-(1,4)-linked Dglucopyranoses, which have a hydrophobic inner cavity with a hydrophilic external surface.30 The introduction of cyclodextrin that is known to form host−guest inclusion complexes with various nonpolar species onto the surfaces of MNPs may render them water dispersible and capable of host−guest chemistry, thereby increasing the surface areas and improving their sorption capacities. Therefore, cyclodextrin complexation has become a promising choice of procedure for decontaminating techniques. In recent years, room temperature ionic liquids (ILs) that are known as salts of an organic cation are also of increasing interest due to their remarkable properties including excellent thermal and chemical stability, negligible vapor pressure, biocompatibility, and good extractabilities for different species.31 Various types of ionic liquids have been used for the liquid−liquid extraction, liquid phase microextraction, and separation of inorganic and organic substances from aqueous media.31−34 Recent studies on modification of cyclodextrin with several types of ILs showed enhanced molecular enantiose-
lectivity toward chiral analytes35 and also improved sorption capacity with organic pollutants.36 Both cyclodextrins and ILs are environmentally friendly and can improve the stability of functional materials.28,37−39 Modifying magnetic nanoparticles both with β-CD and IL allows new materials that possess an assortment of multiple properties, such as inclusion properties, ion-exchange capabilities, magnetic separation convenience, and high surface area. However, to the best of our knowledge, β-CD-IL polymerfunctionalized magnetic composites have not yet been used as sorbents. Further, no or very less work was focused on the simultaneous removal of ECs and heavy metals from water. The mixture of both organic and inorganic contaminants is often present at environmental sites that pose a challenge in remediating water. However, the conventional water treatment processes are unable to remove both classes of contaminants simultaneously to μg L−1 concentration levels. Due to the fundamentally different physiochemical properties of these contaminants, research is of utter importance focusing on remediating organic and inorganic contaminants concurrently rather than with a single and separate treatment. We report herein the development of a novel multifunctional magnetic sorbent based on cyclodextrin−IL polymers, namely, Fe3O4-CD-IL MNPs, where β-CD-IL molecules were covalently linked to the nanoparticle surface through cross-linking. This work was aimed at evaluating its performance as a sorbent for the effective and simultaneous removal of PFOA, PFOS, and Cr(VI) at environmentally relevant concentrations. The effects of solution pH, contact time, initial concentrations of the contaminants, and sorbent dosage on the sorption performance were investigated in this study. The reusability of Fe3O4-CD-IL MNPs was also explored using the repeated sorption− desorption regeneration tests in a multicomponent system. Furthermore, the underlying mechanisms and the possible interactions between the sorbent and sorbates are discussed.
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EXPERIMENTAL SECTION
Materials. Fe3O4 nanoparticles (10 mg/L), the removal of PFOA increased. Though this phenomenon was not clearly understood, one possible reason might be that at higher Cr(VI) concentrations more Cr(VI) ions were sorbed on the nanoparticles that underwent a reduction to Cr(III)) to a certain extent (SI-D4, Supporting Information), resulting in the creation of new sorption sites for PFCs sorption. The Fe3O4-CDI-IL sorbent was also tested for the simultaneous removal of PFOA, PFOS, and Cr(VI) ions in a tri-component system containing a mixture of 200 μg/L of each PFOA and PFOS and 1000 μg/L of Cr(VI) ions. The results for the removal efficiencies of the sorbent in a tri-component system are compared to those obtained for a single-component system (Figure 4B). Maximum removal of about 99% of both PFOA and PFOS and 96% of Cr(VI) ions was achieved with a dosage of 3.0 g/L in this tri-component system. The removal of PFOS and Cr(VI) was not affected by the introduction of other contaminants in the mixture. However, the removal rate of PFOA was slightly reduced at lower sorbent dosages. These results demonstrate that this multifunctional sorbent shows the potential in removing both organic contaminants and heavy metals from a water mixture present at environmentally relevant concentrations with higher removal efficiencies. Sorption Mechanism. Based on the above results and discussion, the possible sorption mechanisms for the simultaneous removal of PFOS, PFOA, and Cr(VI) are proposed and discussed in Figure 5. It appears that each component of our sorbent played a critical role in its functioning: the modified cavities of CDs are primarily responsible for the capture of the PFOS and PFOA molecules through host−guest inclusion. On the other hand, the ionic liquid (IL) component played roles not only for providing the sorption sites for metal ions (chemisorption) but also for contributing substantially in the sorption of both PFOS and PFOA. The imidazolium part in IL component imparted the electrostatic attractive forces for PFOS and PFOA, which might be the primary driving force to bind the anions onto the sorbent surface, thereby enhancing the sorption capacities of PFOS and PFOA. Previous studies suggest that the formation of micelles and hemimicelles of PFOA or PFOS in the solution and their subsequent accumulation on the sorbent surface may 9229
DOI: 10.1021/acssuschemeng.7b02186 ACS Sustainable Chem. Eng. 2017, 5, 9223−9232
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ACS Sustainable Chemistry & Engineering
bility of these magnetic nanocomposites make them excellent candidates as solid-phase extraction materials for water treatment of coexisting toxic pollutants.
ions in each cycle are shown in Figure 6. It shows that the Fe3O4-CDI-IL sorbent could be easily recovered from the
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ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.7b02186. Additional details regarding thermogravimetric analysis of cyclodextrin, Fe3O4 MNPs, and Fe3O4-CDI-IL MNPs; zeta potential measurement, VSM analysis, active groups quantitative analysis, and XPS analysis of Fe3O4-CDI-IL MNPs; sorption equilibrium and kinetic data; and desorption data for Cr(VI). (PDF)
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AUTHOR INFORMATION
Corresponding Authors
*E-mail:
[email protected]. *E-mail:
[email protected].
Figure 6. Regeneration study of Fe3O4-CDI-IL sorbent with PFOA, PFOS, and Cr(VI) ions in a ternary mixture. (For sorption study: initial concentration of each PFOA and PFOS, 200 μg/L; Cr(VI) ions, 1000 μg/L; sorbent dosage,3 g/L; sample volume, 10 mL; pH, 3.0; contact time, 24 h. For desorption study: 10 mL of 0.2 M NaOH+ 0.5 M NaCl solution used as a desorption buffer; contact time, 24 h).
ORCID
Abu Zayed Md Badruddoza: 0000-0002-7914-540X Present Addresses †
Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, E18-520, Cambridge, Massachusetts 02139, United States ‡ United Chemical Technologies, Inc., 2731 Bartram Road, Bristol, Pennsylvania 19007, United States
solution with a simple magnetic field, regenerated- and then reused at least 10 times without any significant loss of its removal efficiency. In addition, no leaching of iron ions from this magnetic sorbent was observed into the aqueous phase, which further implied the negligible dissolution of the magnetic core under the stated experimental conditions. Concluding Remarks. In summary, we developed a novel multifunctional sorbent, cyclodextrin−IL polymer-functionalized magnetic nanoparticles (Fe3O4-CDI-IL MNPs), and demonstrated the sorptive removal of PFOS, PFOA, and Cr(VI) at environmentally relevant concentrations from aqueous solutions. The sorption of PFOS, PFOA, and Cr(VI) on this magnetic sorbent reached equilibrium within 4, 6, and 3 h, respectively, and followed the pseudo-second-order kinetic model. The Sips model could best describe the sorption of PFCs, whereas the Langmuir model could describe well the Cr(VI) sorption. Our sorbent exhibited a greater sorption toward PFOS than PFOA, and this could be attributed to the hydrophobicity and functional groups of PFOS. The solution pH had more significant effects on the sorption of PFOA and Cr(VI) than that of PFOS. The simultaneous removal of both organic and inorganic pollutants was ascertained because of their dual sorption sites (host−guest inclusion and ionexchange capabilities) rendered by cyclodextrin moieties and IL components, respectively. The contaminants had negligible effects on each other in regard to the removal efficiencies within the lower concentration range. The hydrophobic interactions mainly played a dominant role in the sorption of PFCs on Fe3O4-CDI-IL MNPs. In contrast, the primary mechanisms for the removal of Cr(VI) were the electrostatic interactions and ion exchange. The magnetic iron oxide core rendered this sorbent magnetically responsive, thereby facilitating their separation and regeneration from the complex aqueous solutions. In addition, the synthesized sorbent maintained the high removal efficiency after 10 cycles of sorption−desorption regeneration tests. Overall, the chemical stability, efficient sorption performance, easy separability, and excellent recycla-
Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS The funding for this project was provided by the National Science Foundation (NSF) IUCRC - Water and Environmental Technology (WET) Center at Temple University and Temple University.
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