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Environmental Science and Pollution Research

, Volume 25, Issue 22, pp 21901–21914 | Cite as

Ternary cross-coupled nanohybrid for high-efficiency 1H-benzo[d]imidazole chemisorption

  • Tran Dinh Minh
  • Byeong-Kyu LeeEmail author
Research Article
  • 74 Downloads

Abstract

1H-Benzo[d]imidazole (BMA) has been considered as an emerging pharmaceutical organic contaminant, leading to the increasing BMA detection in wastewaters and need to be removed from ecosystem. This study investigated a highly synergistic BMA chemisorption using a novel ternary cross-coupled nanohybrid [γ-APTES]-Fe3O4@PAN@rGO. Magnetic nanoparticles (Fe3O4) were in situ core-shell co-precipitated with polyacrylonitrile polymer (PAN). Then, the prepared Fe3O4@PAN was decorated on hexagonal arrays of reduced graphene oxide (rGO) inside the framework of γ-aminopropyltriethoxysilane ([γ-APTES]). The final nanohybrid [γ-APTES]-Fe3O4@PAN@rGO produced adjacent inter-fringe distances of 0.2–0.4 nm corresponded well to (111), (220), and (311) parallel sub-lattices with two oblique intersections at 90° right angle and 60° triangle. The BMA adsorption was favorable in neutral pH 7, aroused temperature (50 °C), and controlled by endothermic process. The identified maximum adsorption capacity of 221.73 mg g−1 was 30% higher than the reported adsorbents. The adsorption mechanisms include ion exchange, hydrogen bond, dipole-dipole force, π-conjugation, electrostatic, and hydrophobic interaction.

Graphical abstract

The synthetic route of novel nanohybrid [γ-APTES]-Fe3O4@PAN@rGO was investigated. After BMA adsorption, the adsorbent surface was entirely changed, thus an efficiently facile magnetic separation within 8s. [γ-APTES]-Fe3O4@PAN@rGO formed different oblique intersections of 60° and 90° sub-lattices

Keywords

Emerging pharmaceutical organic contaminant (EPOCs) Cross-coupled Sub-lattices Fe3O4@PAN alloy Synergistic removal 

Notes

Acknowledgments

We would like to thank The Chemical Accident Prevention Technology Development Project and The Korea Environment Industry and Technology Institute, Korea Ministry of Environment, (ID Grant 2016001960002).

Compliance with ethical standards

Conflict of interest

The authors do not have any conflicts to declare.

Supplementary material

11356_2018_2297_MOESM1_ESM.docx (2.9 mb)
ESM 1 (DOCX 2929 kb)
11356_2018_2297_MOESM2_ESM.mp4 (2 mb)
Video 1 (MP4 2007 kb)

References

  1. Ahmada KS, Zahra T (2015) Comparative study of sorption-desorption behavior of benzimidazole based pesticides on selected soils. Eurasian J Anal Chem 10(1):19–33.  https://doi.org/10.12973/ejac.2015.103a CrossRefGoogle Scholar
  2. Alazmi A, Rasul S, Patole SP, Costa PM (2016) Comparative study of synthesis and reduction methods for graphene oxide. Polyhedron 116:153–161.  https://doi.org/10.1016/j.poly.2016.04.044 CrossRefGoogle Scholar
  3. Aly Z, Graulet A, Scales N, Hanley T (2014) Removal of aluminium from aqueous solutions using PAN-based adsorbents: characterisation, kinetics, equilibrium and thermodynamic studies. Environ Sci Pollut Res 21(5):3972–3986.  https://doi.org/10.1007/s11356-013-2305-6 CrossRefGoogle Scholar
  4. Arcos JC, Argus MF, Wolf G (2013) Chemical induction of cancer: structural bases and biological mechanisms. 1st edn. Elsevier, pp: 14–15Google Scholar
  5. Asimakopoulos AG, Wang L, Thomaidis NS, Kannan K (2013) Benzotriazoles and benzothiazoles in human urine from several countries: a perspective on occurrence, biotransformation, and human exposure. Environ Int 59:274–281.  https://doi.org/10.1016/j.envint.2013.06.007 CrossRefGoogle Scholar
  6. Bhatnagar A, Sharma P, Kumar N (2011) A review on “imidazoles”: their chemistry and pharmacological potentials. Int J PharmTech Res 3(1):268–282Google Scholar
  7. Błaszczak-Świątkiewicz K, Sikora J, Szymański J, Danilewicz M, Mikiciuk-Olasik E (2016) Biological evaluation of the toxicity and the cell cycle interruption by some benzimidazole derivatives. Tumor Biol 37(8):11135–11145.  https://doi.org/10.1007/s13277-016-4828-1 CrossRefGoogle Scholar
  8. Brown TN, Mora-Diez N (2006) Computational determination of aqueous pKa values of protonated benzimidazoles (part 1). J Phys Chem B 110(18):9270–9279.  https://doi.org/10.1021/jp055084i CrossRefGoogle Scholar
  9. Buzmakov V, Pshenichnikov A (1996) On the structure of microaggregates in magnetite colloids. J Colloid Interface Sci 182(1):63–70.  https://doi.org/10.1006/jcis.1996.0437 CrossRefGoogle Scholar
  10. Cao C, Xiao L, Chen C, Shi X, Cao Q, Gao L (2014) In situ preparation of magnetic Fe3O4/chitosan nanoparticles via a novel reduction-precipitation method and their application in adsorption of reactive azo dye. Powder Technol 260:90–97.  https://doi.org/10.1016/j.powtec.2014.03.025 CrossRefGoogle Scholar
  11. Čapkauskaitė E, Zakšauskas A, Ruibys V, Linkuvienė V, Paketurytė V, Gedgaudas M, Kairys V, Matulis D (2018) Benzimidazole design, synthesis, and docking to build selective carbonic anhydrase VA inhibitors. Bioorg Med Chem 26:675–687.  https://doi.org/10.1016/j.bmc.2017.12.035 CrossRefGoogle Scholar
  12. Chen B (2016) Zeolitic imidazolate frameworks (ZIFs) and their derivatives: synthesis and energy related applications. Doctoral Theses. University of Exeter ThesesGoogle Scholar
  13. Chen G-C, Shan X-Q, Zhou Y-Q, Shen X-e, Huang H-L, Khan SU (2009) Adsorption kinetics, isotherms and thermodynamics of atrazine on surface oxidized multiwalled carbon nanotubes. J Hazard Mater 169(1–3):912–918.  https://doi.org/10.1016/j.jhazmat.2009.04.034 CrossRefGoogle Scholar
  14. Dong Y-l, H-g Z, Rahman ZU, Su L, Chen X-j HJ, X-g C (2012) Graphene oxide-Fe3O4 magnetic nanocomposites with peroxidase-like activity for colorimetric detection of glucose. Nano 4(13):3969–3976.  https://doi.org/10.1039/C2NR12109C CrossRefGoogle Scholar
  15. Duan Z, Xing Y, Feng Z, Zhang H, Li C, Gong Z, Wang L, Sun H (2017) Hepatotoxicity of benzotriazole and its effect on the cadmium induced toxicity in zebrafish Danio rerio. Environ Pollut 224:706–713.  https://doi.org/10.1016/j.envpol.2017.02.055 CrossRefGoogle Scholar
  16. Ebele AJ, Abdallah MA-E, Harrad S (2017) Pharmaceuticals and personal care products (PPCPs) in the freshwater aquatic environment. Emerg Contam 3(1):1–16.  https://doi.org/10.1016/j.emcon.2016.12.004 CrossRefGoogle Scholar
  17. Feng H, Cheng R, Zhao X, Duan X, Li J (2013) A low-temperature method to produce highly reduced graphene oxide. Nat Commun 4:1539–1546.  https://doi.org/10.1038/ncomms2555 CrossRefGoogle Scholar
  18. Forte M, Mita L, Perrone R, Rossi S, Argirò M, Mita DG, Guida M, Portaccio M, Godievargova T, Ivanov Y (2017) Removal of methylparaben from synthetic aqueous solutions using polyacrylonitrile beads: kinetic and equilibrium studies. Environ Sci Pollut Res 24(2):1270–1282.  https://doi.org/10.1007/s11356-016-7846-z CrossRefGoogle Scholar
  19. Garrigues P, Aarab N, Champeau O, Mora P, Daubeze M, Narbonne J-F (2004) Scoring approach based on fish biomarkers applied to French river monitoring. Biomarkers 9(3):258–270.  https://doi.org/10.1080/13547500400015626 CrossRefGoogle Scholar
  20. Garrigues P, Devier M-H, Augagneur S, Budzinski H, Le Menach K, Mora P, Narbonne J-F (2005) One-year monitoring survey of organic compounds (PAHs, PCBs, TBT), heavy metals and biomarkers in blue mussels from the Arcachon Bay, France. J Environ Monit 7:224–240.  https://doi.org/10.1039/B409577D CrossRefGoogle Scholar
  21. Geffard O, Budzinski H, His E, Seaman MN, Garrigues P (2002) Relationships between contaminant levels in marine sediments and their biological effects on embryos of oysters, Crassostrea gigas. Environ Toxicol Chem 21(11):2310–2318.  https://doi.org/10.1002/etc.5620211108 CrossRefGoogle Scholar
  22. Golub AA, Zubenko AI, Zhmud BV (1996) γ-APTES modified silica gels: the structure of the surface layer. J Colloid Interface Sci 179(2):482–487.  https://doi.org/10.1006/jcis.1996.0241 CrossRefGoogle Scholar
  23. Gonçalves M, Molina-Sabio M, Rodriguez-Reinoso F (2010) Modification of activated carbon hydrophobicity by pyrolysis of propene. J Anal Appl Pyrolysis 89(1):17–21.  https://doi.org/10.1016/j.jaap.2010.04.009 CrossRefGoogle Scholar
  24. Gupta PK (2017) Herbicides and fungicides, reproductive and developmental toxicology. Chap. 37 (2nd edition). Elsevier, pp. 657–679. doi: https://doi.org/10.1016/B978-0-12-804239-7.00037-8
  25. Ho Y-S, McKay G (1999) Pseudo-second order model for sorption processes. Process Biochem 34(5):451–465.  https://doi.org/10.1016/S0032-9592(98)00112-5 CrossRefGoogle Scholar
  26. Huang Y-H, Hsueh C-L, Cheng H-P, Su L-C, Chen C-Y (2007) Thermodynamics and kinetics of adsorption of Cu (II) onto waste iron oxide. J Hazard Mater 144(1–2):406–411.  https://doi.org/10.1016/j.jhazmat.2006.10.061 CrossRefGoogle Scholar
  27. Jiang J-Q, Yang C-X, Yan X-P (2013) Zeolitic imidazolate framework-8 for fast adsorption and removal of benzotriazoles from aqueous solution. ACS Appl Mater Interfaces 5(19):9837–9842.  https://doi.org/10.1021/am403079n CrossRefGoogle Scholar
  28. Kawasaki K, Horikawa K, Sakai H (2017) Magnetic biomonitoring of roadside pollution in the restricted Midagahara area of Mt. Tateyama, Toyama, Japan. Environ Sci Pollut Res 24(11):10313–10325.  https://doi.org/10.1007/s11356-017-8702-5 CrossRefGoogle Scholar
  29. Khalil MI (2015) Co-precipitation in aqueous solution synthesis of magnetite nanoparticles using iron (III) salts as precursors. Arab J Chem 8(2):279–284.  https://doi.org/10.1016/j.arabjc.2015.02.008 CrossRefGoogle Scholar
  30. Koushkbaghi S, Jafari P, Rabiei J, Irani M, Aliabadi M (2016) Fabrication of PET/PAN/GO/Fe3O4 nanofibrous membrane for the removal of Pb (II) and Cr (VI) ions. Chem Eng J 301:42–50.  https://doi.org/10.1016/j.cej.2016.04.076 CrossRefGoogle Scholar
  31. Lamotte M, de Violet P, Garrigues P, Hardy M (2002) Evaluation of the possibility of detecting benzenic pollutants by direct spectrophotometry on PDMS solid sorbent. Anal Bioanal Chem 372(1):169–173.  https://doi.org/10.1007/s00216-001-1162-1 CrossRefGoogle Scholar
  32. Lamotte M, Belfutmi R, de Violet PF, Garrigues P, Lafontaine M, Dumas C (2003) Detection of 1-hydroxypyrene in urine by direct fluorometric analysis on a solid sorbing phase. Validation and application of the method to biological monitoring of PAH-exposed persons. Anal Bioanal Chem 376(6):816–821.  https://doi.org/10.1007/s00216-003-2002-2 CrossRefGoogle Scholar
  33. Lanchas M, Vallejo-Sanchez D, Beobide G, Castillo O, Aguayo AT, Luque A, Román P (2012) A direct reaction approach for the synthesis of zeolitic imidazolate frameworks: template and temperature mediated control on network topology and crystal size. Chem Commun 48(79):9930–9932.  https://doi.org/10.1039/C2CC34787C CrossRefGoogle Scholar
  34. Laurent S, Henoumont C, Stanicki D, Boutry S, Lipani E, Belaid S, Muller RN, Vander Elst L (2017) Magnetic properties, MRI contrast agents. Book Springer, pp:5–11Google Scholar
  35. Liang C, Huang S, Zhao W, Liu W, Chen J, Liu H, Tong Y (2015) Polyhedral Fe3O4 nanoparticles for lithium ion storage. New J Chem 39(4):2651–2656.  https://doi.org/10.1039/C4NJ02032D CrossRefGoogle Scholar
  36. Lin K-YA, Lee W-D (2016) Self-assembled magnetic graphene supported ZIF-67 as a recoverable and efficient adsorbent for benzotriazole. Chem Eng J 284:1017–1027.  https://doi.org/10.1016/j.cej.2015.09.075 CrossRefGoogle Scholar
  37. Liu C, Hsu P-C, Lee H-W, Ye M, Zheng G, Liu N, Li W, Cui Y (2015) Transparent air filter for high-efficiency PM2.5 capture. Nat Commun 6:6205–6212.  https://doi.org/10.1038/ncomms7205 CrossRefGoogle Scholar
  38. Ma J, Yang Q, Xu D, Zeng X, Wen Y, Liu W (2017) Efficient removal of antibiotics in a fluidized bed reactor by facile fabricated magnetic powdered activated carbon. Environ Sci Pollut Res 24(4):3820–3828.  https://doi.org/10.1007/s11356-016-8114-y CrossRefGoogle Scholar
  39. Magnet C, Lomenech C, Hurel C, Reilhac P, Giulieri F, Chaze A-M, Persello J, Kuzhir P (2017) Adsorption of nickel ions by oleate-modified magnetic iron oxide nanoparticles. Environ Sci Pollut Res 24(8):7423–7435.  https://doi.org/10.1007/s11356-017-8391-0 CrossRefGoogle Scholar
  40. Malik H, Qureshi UA, Muqeet M, Mahar RB, Ahmed F, Khatri Z (2018) Removal of lead from aqueous solution using polyacrylonitrile/magnetite nanofibers. Environ Sci Pollut Res 25(4):3557–3564.  https://doi.org/10.1007/s11356-017-0706-7 CrossRefGoogle Scholar
  41. Marcano DC, Kosynkin DV, Berlin JM, Sinitskii A, Sun Z, Slesarev A, Alemany LB, Lu W, Tour JM (2010) Improved synthesis of graphene oxide. ACS Nano 4(8):4806–4814.  https://doi.org/10.1021/nn1006368 CrossRefGoogle Scholar
  42. Matsuzawa S, Nasser-Ali L, Garrigues P (2001) Photolytic behavior of polycyclic aromatic hydrocarbons in diesel particulate matter deposited on the ground. Environ Sci Technol 35(15):3139–3143.  https://doi.org/10.1021/es001606q CrossRefGoogle Scholar
  43. Meroni D, Lo Presti L, Di Liberto G, Ceotto M, Acres RG, Prince KC, Bellani R, Soliveri G, Ardizzone S (2016) A close look at the structure of the TiO2-APTES interface in hybrid nanomaterials and its degradation pathway: an experimental and theoretical study. J Phys Chem C 121(1):430–440.  https://doi.org/10.1021/acs.jpcc.6b10720 CrossRefGoogle Scholar
  44. Minh TD, Lee B-K (2016) Effects of functionality and textural characteristics on the removal of Cd (II) by ammoniated and chlorinated nanoporous activated carbon. J Mater Cycles Waste Manage 19(3):1022–1035.  https://doi.org/10.1007/s10163-016-0570-4 CrossRefGoogle Scholar
  45. Nassar NN (2010) Rapid removal and recovery of Pb (II) from wastewater by magnetic nanoadsorbents. J Hazard Mater 184(1–3):538–546.  https://doi.org/10.1016/j.jhazmat.2010.08.069 CrossRefGoogle Scholar
  46. Neier R (2002) Science of synthesis: Houben-Weyl methods of molecular transformations. Category 2, Hetarenes and related ring systems: Vol. 12. Five-membered hetarenes with two nitrogen or phosphorus atoms. Thieme 12:800–810.  https://doi.org/10.1055/b-00000101
  47. Nguyen-Le M-T, Lee B-K, Tran D-M (2017) EDTA-Na2-assisted synthesis of rod-like titanate-TiO2 composite architectures with enhanced visible-light-driven properties. J Ind Eng Chem 56(25):225–233.  https://doi.org/10.1016/j.jiec.2017.07.015 CrossRefGoogle Scholar
  48. Niwas R, Gupta U, Khan A, Varshney K (2000) The adsorption of phosphamidon on the surface of styrene supported zirconium (IV) tungstophosphate: a thermodynamic study. Colloids Surf A Physicochem Eng Asp 164(2–3):115–119.  https://doi.org/10.1016/S0927-7757(99)00247-2 CrossRefGoogle Scholar
  49. Rabbani MG, El-Kaderi HM (2012) Synthesis and characterization of porous benzimidazole-linked polymers and their performance in small gas storage and selective uptake. Chem Mater 24(8):1511–1517.  https://doi.org/10.1021/cm300407h CrossRefGoogle Scholar
  50. Rajput S, Pittman CU, Mohan D (2016) Magnetic magnetite (Fe3O4) nanoparticle synthesis and applications for lead (Pb2+) and chromium (Cr6+) removal from water. J Colloid Interface Sci 468:334–346.  https://doi.org/10.1016/j.jcis.2015.12.008 CrossRefGoogle Scholar
  51. Regulation C (2008). Regulation (EC) No 1272:1340–1355Google Scholar
  52. Sada K, Kokado K, Furukawa Y (2015) Book chapter: polyacrylonitrile (PAN). Encyclopedia polymer. Nanomater, pp: 1745–1750. doi: https://doi.org/10.1007/978-3-642-29648-2_249
  53. Salazar-Camacho C, Villalobos M, de la Luz R-SM, Arenas-Alatorre J, Alcaraz-Cienfuegos J, Gutiérrez-Ruiz ME (2013) Characterization and surface reactivity of natural and synthetic magnetites. Chem Geol 347:233–245.  https://doi.org/10.1016/j.chemgeo.2013.03.017 CrossRefGoogle Scholar
  54. Sánchez RMT, Genet MJ, Gaigneaux EM, dos Santos AM, Yunes S (2011) Benzimidazole adsorption on the external and interlayer surfaces of raw and treated montmorillonite. Appl Clay Sci 53(3):366–373.  https://doi.org/10.1016/j.clay.2010.06.026 CrossRefGoogle Scholar
  55. Sarker M, Bhadra BN, Seo PW, Jhung SH (2017) Adsorption of benzotriazole and benzimidazole from water over a Co-based metal azolate framework MAF-5(Co). J Hazard Mater 324(part B):131–138.  https://doi.org/10.1016/j.jhazmat.2016.10.042 CrossRefGoogle Scholar
  56. Sharma A, Lee B-K (2014) Cd(II) removal and recovery enhancement by using acrylamide-titanium nanocomposite as an adsorbent. Appl Surf Sci 313:624–632.  https://doi.org/10.1016/j.apsusc.2014.06.034 CrossRefGoogle Scholar
  57. Sharma A, Lee B-K (2016a) Integrated ternary nanocomposite of TiO2/NiO/reduced graphene oxide as a visible light photocatalyst for efficient degradation of o-chlorophenol. J Environ Manag 181:563–573.  https://doi.org/10.1016/j.jenvman.2016.07.016 CrossRefGoogle Scholar
  58. Sharma A, Lee B-K (2016b) Structure and activity of TiO2/FeO co-doped carbon spheres for adsorptive-photocatalytic performance of complete toluene removal from aquatic environment. Appl Catal A 523:272–282.  https://doi.org/10.1016/j.apcata.2016.06.018 CrossRefGoogle Scholar
  59. Sharma AK, Lee B-K (2016c) Surfactant-aided sol-gel synthesis of TiO2-MgO nanocomposite and their photocatalytic azo dye degradation activity. J Compos Mater.  https://doi.org/10.1177/0021998316636464
  60. Sharma A, Lee B-K (2017) Growth of TiO2 nano-wall on activated carbon fibers for enhancing the photocatalytic oxidation of benzene in aqueous phase. Catal Today 287:113–121.  https://doi.org/10.1016/j.cattod.2016.11.019 CrossRefGoogle Scholar
  61. Spiridis N, Barbasz J, Łodziana Z, Korecki J (2006) Fe3O4 (001) films on Fe (001): termination and reconstruction of iron-rich surfaces. Phys Rev B 74:155423.  https://doi.org/10.1103/PhysRevB.74.155423 CrossRefGoogle Scholar
  62. Takagi K, Kusafuka K, Ito Y, Yamauchi K, Ito K, Fukuda R, Ehara M (2015) Synthesis and optical properties of imidazole-and benzimidazole-based fused π-conjugated compounds: influence of substituent, counteranion, and π-conjugated system. J Org Chem 80(14):7172–7183.  https://doi.org/10.1021/acs.joc.5b01028 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Civil and Environmental EngineeringUniversity of UlsanUlsanSouth Korea

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