Abstract
The occurrence and fate of antibiotic compounds in water can adversely affect human and animal health; hence, the removal of such substrates from soil and water is indispensable. Herein, we described the synthesis method of mesoporous carbon (MPC) via the pyrolysis route from a coordination polymer Fe-based MIL-53 (or MIL-53, shortly). The MPC structure was analyzed by several physical techniques such as SEM, TEM, BET, FT–IR, VSM, and XRD. The response surface methodology (RSM) was applied to find out the effects of initial concentration, MPC dosage, and pH on the removal efficiency of trimethoprim (TMP) and sulfamethoxazole (SMX) antibiotics in water. Under the optimized conditions, the removal efficiencies of TMP and SMX were found to be 87% and 99%, respectively. Moreover, the adsorption kinetic and isotherm studies showed that chemisorption and the monolayer adsorption controlled the adsorption process. The leaching test and recyclability studies indicated that the MPC structure was stable and can be reused for at least four times without any considerable change in the removal efficiency. Plausible adsorption mechanisms were also addressed in this study. Because of high maximum adsorption capacity (85.5 mg/g and 131.6 mg/g for TMP and SMX, respectively) and efficient reusability, MPC is recommended to be a potential adsorbent for TMP and SMX from water media.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abedini R, Omidkhah M, Dorosti F (2014) Highly permeable poly(4-methyl-1-pentyne)/NH2-MIL 53 (Al) mixed matrix membrane for CO2/CH4 separation. RSC Adv 4:36522–36537. https://doi.org/10.1039/C4RA07030E
Ahmed I, Jhung SH (2017) Applications of metal-organic frameworks in adsorption/separation processes via hydrogen bonding interactions. Chem Eng J 310:197–215
Ahmed MB, Zhou JL, Ngo HH, Guo W (2015) Adsorptive removal of antibiotics from water and wastewater: Progress and challenges. Sci Total Environ 532:112–126. https://doi.org/10.1016/j.scitotenv.2015.05.130
Ahmed I, Bhadra BN, Lee HJ, Jhung SH (2018) Metal-organic framework-derived carbons: Preparation from ZIF-8 and application in the adsorptive removal of sulfamethoxazole from water. Catal Today 301:90–97. https://doi.org/10.1016/j.cattod.2017.02.011
Alturki AA, Tadkaew N, McDonald JA et al (2010) Combining MBR and NF/RO membrane filtration for the removal of trace organics in indirect potable water reuse applications. J Membr Sci 365:206–215. https://doi.org/10.1016/j.memsci.2010.09.008
Amali AJ, Sun J-K, Xu Q (2014) From assembled metal-organic framework nanoparticles to hierarchically porous carbon for electrochemical energy storage. Chem Commun 50:1519–1522. https://doi.org/10.1039/C3CC48112C
An HJ, Bhadra BN, Khan NA, Jhung SH (2018) Adsorptive removal of wide range of pharmaceutical and personal care products from water by using metal azolate framework-6-derived porous carbon. Chem Eng J 343:447–454. https://doi.org/10.1016/j.cej.2018.03.025
Ay F, Kargi F (2010) Advanced oxidation of amoxicillin by Fenton’s reagent treatment. J Hazard Mater 179:622–627. https://doi.org/10.1016/j.jhazmat.2010.03.048
Bekçi Z, Seki Y, Kadir Yurdakoç M (2007) A study of equilibrium and FTIR, SEM/EDS analysis of trimethoprim adsorption onto K10. J Mol Struct 827:67–74. https://doi.org/10.1016/j.molstruc.2006.04.054
Calisto V, Ferreira CIA, Oliveira JABP et al (2015) Adsorptive removal of pharmaceuticals from water by commercial and waste-based carbons. J Environ Manag 152:83–90. https://doi.org/10.1016/j.jenvman.2015.01.019
Carabineiro SAC, Thavorn-amornsri T, Pereira MFR et al (2012) Comparison between activated carbon, carbon xerogel and carbon nanotubes for the adsorption of the antibiotic ciprofloxacin. Catal Today 186:29–34. https://doi.org/10.1016/j.cattod.2011.08.020
Chen H, Liu S, Xu X-R et al (2015) Antibiotics in typical marine aquaculture farms surrounding Hailing Island, South China: occurrence, bioaccumulation and human dietary exposure. Mar Pollut Bull 90:181–187. https://doi.org/10.1016/j.marpolbul.2014.10.053
Chen K-L, Liu L-C, Chen W-R (2017) Adsorption of sulfamethoxazole and sulfapyridine antibiotics in high organic content soils. Environ Pollut 231:1163–1171. https://doi.org/10.1016/j.envpol.2017.08.011
Chen Y-Z, Zhang R, Jiao L, Jiang H-L (2018) Metal–organic framework-derived porous materials for catalysis. Coord Chem Rev 362:1–23. https://doi.org/10.1016/j.ccr.2018.02.008
Cheng C, Zhang J, Zhang C et al (2014) Preparation and characterization of charcoal from feathers and its application in trimethoprim adsorption. Desalin Water Treat 52:5401–5412. https://doi.org/10.1080/19443994.2013.807477
Dias IN, Souza BS, Pereira JHOS et al (2014) Enhancement of the photo-Fenton reaction at near neutral pH through the use of ferrioxalate complexes: a case study on trimethoprim and sulfamethoxazole antibiotics removal from aqueous solutions. Chem Eng J 247:302–313. https://doi.org/10.1016/j.cej.2014.03.020
Dirany A, Sirés I, Oturan N et al (2012) Electrochemical treatment of the antibiotic sulfachloropyridazine: kinetics, reaction pathways, and toxicity evolution. Environ Sci Technol 46:4074–4082. https://doi.org/10.1021/es204621q
Domınguez-Vargas JR, Gonzalez T, Palo P, Cuerda-Correa EM (2013) Removal of carbamazepine, naproxen, and trimethoprim from water by amberlite XAD-7: a kinetic study. Clean Soil Air Water 41:1052–1061. https://doi.org/10.1002/clen.201200245
Enamul H, Nazmul Abedin K, Jung Hwa P, Hwa JS (2010) Synthesis of a metal–organic framework material, Iron terephthalate, by ultrasound, microwave, and conventional electric heating: a kinetic study. Chem – A Eur J 16:1046–1052. https://doi.org/10.1002/chem.200902382
Feng X, Chen H, Jiang F (2017) In-situ ethylenediamine-assisted synthesis of a magnetic iron-based metal-organic framework MIL-53(Fe) for visible light photocatalysis. J Colloid Interface Sci 494:32–37. https://doi.org/10.1016/j.jcis.2017.01.060
Fu C, He D, Wang Y, Zhao X (2018) Facile synthesis of porous Fe3O4@C core/shell nanorod/graphene for improving microwave absorption properties. RSC Adv 8:15358–15365. https://doi.org/10.1039/C8RA01838C
Guedidi H, Reinert L, Lévêque J-M et al (2013) The effects of the surface oxidation of activated carbon, the solution pH and the temperature on adsorption of ibuprofen. Carbon N Y 54:432–443. https://doi.org/10.1016/j.carbon.2012.11.059
Guo S-Z, Li Y, Jiang J-S, Xie H-Q (2010) Nanofluids containing γ-Fe2 O3 nanoparticles and their heat transfer enhancements. Nanoscale Res Lett 5:1222. https://doi.org/10.1007/s11671-010-9630-1
Ha PTM, Le BTT, To TC et al (2017) Synthesis of aryl-substituted pyridines via cyclization of N,N-dialkylanilines with ketoxime carboxylates under metal-organic framework catalysis. J Ind Eng Chem 54:151–161. https://doi.org/10.1016/j.jiec.2017.05.028
Han X, Liang C, Li T et al (2013) Simultaneous removal of cadmium and sulfamethoxazole from aqueous solution by rice straw biochar. J Zhejiang Univ Sci B 14:640–649. https://doi.org/10.1631/jzus.B1200353
Han F, Ma L, Sun Q et al (2014) Rationally designed carbon-coated Fe 3 O 4 coaxial nanotubes with hierarchical porosity as high-rate anodes for lithium ion batteries. Nano Res 7:1706–1717. https://doi.org/10.1007/s12274-014-0531-y
Ho PH, Lee S-Y, Lee D, Woo H-C (2014) Selective adsorption of tert-butylmercaptan and tetrahydrothiophene on modified activated carbons for fuel processing in fuel cell applications. Int J Hydrog Energy 39:6737–6745. https://doi.org/10.1016/j.ijhydene.2014.02.011
Ho HP, Kasinathan P, Kim J et al (2016) Deep desulfurization of fuel gas by adsorption on Cu-impregnated activated carbons in practical conditions. Korean J Chem Eng 33:1908–1916. https://doi.org/10.1007/s11814-016-0018-5
Homem V, Santos L (2011) Degradation and removal methods of antibiotics from aqueous matrices – a review. J Environ Manage 92:2304–2347. https://doi.org/10.1016/j.jenvman.2011.05.023
Hsu L-C, Liu Y-T, Syu C-H et al (2018) Adsorption of tetracycline on Fe (hydr)oxides: effects of pH and metal cation (Cu2+, Zn2+ and Al3+) addition in various molar ratios. R Soc Open Sci 5. https://doi.org/10.1098/rsos.171941
Jewell KS, Castronovo S, Wick A et al (2016) New insights into the transformation of trimethoprim during biological wastewater treatment. Water Res 88:550–557. https://doi.org/10.1016/j.watres.2015.10.026
Jiang H-L, Liu B, Lan Y-Q et al (2011) From metal–organic framework to Nanoporous carbon: toward a very high surface area and hydrogen uptake. J Am Chem Soc 133:11854–11857. https://doi.org/10.1021/ja203184k
Jin Y, Zhao C, Lin Y et al (2017) Fe-based metal-organic framework and its derivatives for reversible Lithium storage. J Mater Sci Technol 33:768–774. https://doi.org/10.1016/j.jmst.2016.11.021
Lai L, Yan J, Li J, Lai B (2018) Co/Al2O3-EPM as peroxymonosulfate activator for sulfamethoxazole removal: performance, biotoxicity, degradation pathways and mechanism. Chem Eng J 343:676–688. https://doi.org/10.1016/j.cej.2018.01.035
Le HTN, Tran TV, Phan NTS, Truong T (2015) Efficient and recyclable Cu2(BDC)2(BPY)-catalyzed oxidative amidation of terminal alkynes: role of bipyridine ligand. Catal Sci Technol 5:851–859. https://doi.org/10.1039/C4CY01074D
Li J, Zhou Q, Liu Y, Lei M (2017) Recyclable nanoscale zero-valent iron-based magnetic polydopamine coated nanomaterials for the adsorption and removal of phenanthrene and anthracene. Sci Technol Adv Mater 18:3–16. https://doi.org/10.1080/14686996.2016.1246941
Lim Y, Heo J-I, Madou M, Shin H (2013) Monolithic carbon structures including suspended single nanowires and nanomeshes as a sensor platform. Nanoscale Res Lett 8:492. https://doi.org/10.1186/1556-276X-8-492
Liu H, Zhang J, Bao N et al (2012) Textural properties and surface chemistry of lotus stalk-derived activated carbons prepared using different phosphorus oxyacids: adsorption of trimethoprim. J Hazard Mater 235–236:367–375. https://doi.org/10.1016/j.jhazmat.2012.08.015
Liu H, Zhang J, Ngo HH et al (2015) Effect on physical and chemical characteristics of activated carbon on adsorption of trimethoprim: mechanisms study. RSC Adv 5:85187–85195. https://doi.org/10.1039/C5RA17968H
Liu Q, Li M, Zhang F et al (2017a) The removal of trimethoprim and sulfamethoxazole by a high infiltration rate artificial composite soil treatment system. Front Environ Sci Eng 11:12. https://doi.org/10.1007/s11783-017-0920-z
Liu X, Lu S, Liu Y et al (2017b) Adsorption of sulfamethoxazole (SMZ) and ciprofloxacin (CIP) by humic acid (HA): characteristics and mechanism. RSC Adv 7:50449–50458. https://doi.org/10.1039/C7RA06231A
Luo S, Wang J (2018) MOF/graphene oxide composite as an efficient adsorbent for the removal of organic dyes from aqueous solution. Environ Sci Pollut Res 25:5521–5528. https://doi.org/10.1007/s11356-017-0932-z
Ma TY, Dai S, Jaroniec M, Qiao SZ (2014) Metal–organic framework derived hybrid Co3O4-carbon porous nanowire arrays as reversible oxygen evolution electrodes. J Am Chem Soc 136:13925–13931. https://doi.org/10.1021/ja5082553
Malekbala MR, Khan MA, Hosseini S et al (2015) Adsorption/desorption of cationic dye on surfactant modified mesoporous carbon coated monolith: equilibrium, kinetic and thermodynamic studies. J Ind Eng Chem 21:369–377. https://doi.org/10.1016/j.jiec.2014.02.047
Miao M, Ma S, Shu L et al (2017) Adsorption characteristics of antibiotics trimethoprim by activated carbon developed from low-cost alligator weed: kinetics, equilibrium and thermodynamic analyses. Desalin Water Treat 96:76–85. https://doi.org/10.5004/dwt.2017.21053
Molu ZB, Yurdakoç K (2010) Preparation and characterization of aluminum pillared K10 and KSF for adsorption of trimethoprim. Microporous Mesoporous Mater 127:50–60. https://doi.org/10.1016/j.micromeso.2009.06.027
Nanda S, Dalai AK, Berruti F, Kozinski JA (2016) Biochar as an exceptional bioresource for energy, agronomy, carbon sequestration, activated carbon and specialty materials. Waste Biomass Valoriz 7:201–235. https://doi.org/10.1007/s12649-015-9459-z
Nouar F, Devic T, Chevreau H et al (2012) Tuning the breathing behaviour of MIL-53 by cation mixing. Chem Commun 48:10237–10239. https://doi.org/10.1039/C2CC35348B
Pai R, Singh A, Simotwo S, Kalra V (2018) In situ grown Iron oxides on carbon nanofibers as freestanding anodes in aqueous supercapacitors. Adv Eng Mater 20:1701116. https://doi.org/10.1002/adem.201701116
Salunkhe RR, Kaneti YV, Yamauchi Y (2017) Metal–organic framework-derived nanoporous metal oxides toward supercapacitor applications: progress and prospects. ACS Nano 11:5293–5308. https://doi.org/10.1021/acsnano.7b02796
Sarker M, Song JY, Jhung SH (2018) Adsorptive removal of anti-inflammatory drugs from water using graphene oxide/metal-organic framework composites. Chem Eng J 335:74–81
Scherdel C, Reichenauer G, Wiener M (2010) Relationship between pore volumes and surface areas derived from the evaluation of N2-sorption data by DR-, BET- and t-plot. Microporous Mesoporous Mater 132:572–575. https://doi.org/10.1016/j.micromeso.2010.03.034
Serra-Crespo P, Gobechiya E, Ramos-Fernandez EV et al (2012) Interplay of metal node and amine functionality in NH2-MIL-53: modulating breathing behavior through intra-framework interactions. Langmuir 28:12916–12922. https://doi.org/10.1021/la302824j
Song JY, Bhadra BN, Jhung SH (2017) Contribution of H-bond in adsorptive removal of pharmaceutical and personal care products from water using oxidized activated carbon. Microporous Mesoporous Mater 243:221–228
Sreńscek-Nazzal J, Kamińska W, Michalkiewicz B, Koren ZC (2013) Production, characterization and methane storage potential of KOH-activated carbon from sugarcane molasses. Ind Crop Prod 47:153–159. https://doi.org/10.1016/j.indcrop.2013.03.004
Tang J, Wang J (2018) Metal organic framework with coordinatively unsaturated sites as efficient Fenton-like catalyst for enhanced degradation of sulfamethazine. Environ Sci Technol 52:5367–5377. https://doi.org/10.1021/acs.est.8b00092
Teixeira S, Delerue-Matos C, Santos L (2012) Removal of sulfamethoxazole from solution by raw and chemically treated walnut shells. Environ Sci Pollut Res 19:3096–3106. https://doi.org/10.1007/s11356-012-0853-9
Tonucci MC, Gurgel LVA, de Aquino SF (2015) Activated carbons from agricultural byproducts (pine tree and coconut shell), coal, and carbon nanotubes as adsorbents for removal of sulfamethoxazole from spiked aqueous solutions: kinetic and thermodynamic studies. Ind Crop Prod 74:111–121. https://doi.org/10.1016/j.indcrop.2015.05.003
Tran TV, Le HTN, Ha HQ et al (2017) A five coordination Cu(ii) cluster-based MOF and its application in the synthesis of pharmaceuticals via sp3 C-H/N-H oxidative coupling. Catal Sci Technol 7:3453–3458. https://doi.org/10.1039/C7CY00882A
Van Tran T, Bui QTP, Nguyen TD et al (2017) Application of response surface methodology to optimize the fabrication of ZnCl2-activated carbon from sugarcane bagasse for the removal of Cu2+. Water Sci Technol 75:2047 LP–2042055. https://doi.org/10.2166/wst.2017.066
Van Tran T, Nguyen DTC, Le HTN et al (2019a) Facile synthesis of manganese oxide-embedded mesoporous carbons and their adsorbability towards methylene blue. Chemosphere 227:455–461. https://doi.org/10.1016/j.chemosphere.2019.04.079
Van Tran T, Nguyen DTC, Le HTN et al (2019b) Combined minimum-run resolution IV and central composite design for optimized removal of tetracycline drug over metal–organic framework-templated porous carbon. Molecules 24:1887. https://doi.org/10.3390/molecules24101887
Van Tran T, Nguyen DTC, Le HTN et al (2019c) Tunable synthesis of mesoporous carbons from Fe3O (BDC) 3 for chloramphenicol antibiotic remediation. Nanomaterials 9:237. https://doi.org/10.3390/nano9020237
Van Tran T, Nguyen DTC, Le HTN et al (2019d) MIL-53 (Fe)-directed synthesis of hierarchically mesoporous carbon and its utilization for ciprofloxacin antibiotic remediation. J Environ Chem Eng 7:102881. https://doi.org/10.1016/j.jece.2019.102881
Van Tran T, Nguyen DTC, Le HTN et al (2019e) A hollow mesoporous carbon from metal-organic framework for robust adsorbability of ibuprofen drug in water. R Soc Open Sci 6:190058. https://doi.org/10.1098/rsos.190058
Van Tran T, Cao VD, Nguyen VH et al (2019f) MIL-53 (Fe) derived magnetic porous carbon as a robust adsorbent for the removal of phenolic compounds under the optimized conditions. J Environ Chem Eng 102902. https://doi.org/10.1016/j.jece.2019.102902
Vo YH, Le TV, Nguyen HD et al (2018) Synthesis of quinazolinones and benzazoles utilizing recyclable sulfated metal-organic framework-808 catalyst in glycerol as green solvent. J Ind Eng Chem 64:107–115. https://doi.org/10.1016/j.jiec.2018.03.006
Vuong G-T, Pham M-H, Do T-O (2013) Direct synthesis and mechanism of the formation of mixed metal Fe2Ni-MIL-88B. CrystEngComm 15:9694. https://doi.org/10.1039/C3CE41453A
Wang J, Wang S (2018) Activation of persulfate (PS) and peroxymonosulfate (PMS) and application for the degradation of emerging contaminants. Chem Eng J 334:1502–1517. https://doi.org/10.1016/j.cej.2017.11.059
Wang JL, Xu LJ (2012) Advanced oxidation processes for wastewater treatment: formation of hydroxyl radical and application. Crit Rev Environ Sci Technol 42:251–325. https://doi.org/10.1080/10643389.2010.507698
Wang X, Liu Y, Arandiyan H et al (2016) Uniform Fe3O4 microflowers hierarchical structures assembled with porous nanoplates as superior anode materials for lithium-ion batteries. Appl Surf Sci 389:240–246. https://doi.org/10.1016/j.apsusc.2016.07.105
Wang J, Zhuan R, Chu L (2019) The occurrence, distribution and degradation of antibiotics by ionizing radiation: an overview. Sci Total Environ 646:1385–1397. https://doi.org/10.1016/j.scitotenv.2018.07.415
Wei W, Yang S, Zhou H, Lieberwirth I, Feng X, Müllen K (2013) 3D graphene foams cross-linked with pre-encapsulated Fe3O4 nanospheres for enhanced lithium storage. Adv Mater 25:2909–2914. https://doi.org/10.1002/adma.201300445
Wu HB, Lou XW(D) (2017) Metal-organic frameworks and their derived materials for electrochemical energy storage and conversion: promises and challenges. Sci Adv 3. https://doi.org/10.1126/sciadv.aap9252
Xu M, Li J, Yan Y, Zhao X, Yan J, Zhang Y, Lai B, Chen X, Song L (2019) Catalytic degradation of sulfamethoxazole through peroxymonosulfate activated with expanded graphite loaded CoFe2O4 particles. Chem Eng J 369:403–413. https://doi.org/10.1016/j.cej.2019.03.075
Xue Z, Linh NTB, Noh SK, Lyoo WS (2008) Phosphorus-containing ligands for Iron(III)-catalyzed atom transfer radical polymerization. Angew Chem 120:6526–6529. https://doi.org/10.1002/ange.200801647
Xue G, Gao M, Gu Z et al (2013) The removal of p-nitrophenol from aqueous solutions by adsorption using gemini surfactants modified montmorillonites. Chem Eng J 218:223–231. https://doi.org/10.1016/j.cej.2012.12.045
Yan J, Li J, Peng J et al (2019) Efficient degradation of sulfamethoxazole by the CuO@ Al2O3 (EPC) coupled PMS system: optimization, degradation pathways and toxicity evaluation. Chem Eng J 359:1097–1110. https://doi.org/10.1016/j.cej.2018.11.074
Yang W, Lu Y, Zheng F et al (2012) Adsorption behavior and mechanisms of norfloxacin onto porous resins and carbon nanotube. Chem Eng J 179:112–118. https://doi.org/10.1016/j.cej.2011.10.068
Yao X, Bai C, Chen J, Li Y (2016) Efficient and selective green oxidation of alcohols by MOF-derived magnetic nanoparticles as a recoverable catalyst. RSC Adv 6:26921–26928. https://doi.org/10.1039/C6RA01617K
Zhang R, Zhang G, Zheng Q et al (2012) Occurrence and risks of antibiotics in the Laizhou Bay, China: impacts of river discharge. Ecotoxicol Environ Saf 80:208–215. https://doi.org/10.1016/j.ecoenv.2012.03.002
Zhang Y, Li G, Lu H et al (2014) Synthesis, characterization and photocatalytic properties of MIL-53(Fe)-graphene hybrid materials. RSC Adv 4:7594–7600. https://doi.org/10.1039/C3RA46706F
Zhang W, Li X, Zou R et al (2015) Multifunctional glucose biosensors from Fe 3 O 4 nanoparticles modified chitosan/graphene nanocomposites. Sci Rep 5:11129. https://doi.org/10.1038/srep11129
Zhao G, Li J, Wang X (2011) Kinetic and thermodynamic study of 1-naphthol adsorption from aqueous solution to sulfonated graphene nanosheets. Chem Eng J 173:185–190. https://doi.org/10.1016/j.cej.2011.07.072
Zhuang S, Cheng R, Wang J (2019) Adsorption of diclofenac from aqueous solution using UiO-66-type metal-organic frameworks. Chem Eng J 359:354–362. https://doi.org/10.1016/j.cej.2018.11.150
Zuorro A, Maffei G, Lavecchia R (2017) Kinetic modeling of azo dye adsorption on non-living cells of Nannochloropsis oceanica. J Environ Chem Eng 5:4121–4127. https://doi.org/10.1016/j.jece.2017.07.078
Funding
This research is funded by Vietnam National Foundation for Science and Technology Development (NAFOSTED) under grant number 104.05-2018.336.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Responsible editor: Bingcai Pan
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Van Tran, T., Nguyen, D.T.C., Nguyen, HT.T. et al. Application of Fe-based metal-organic framework and its pyrolysis products for sulfonamide treatment. Environ Sci Pollut Res 26, 28106–28126 (2019). https://doi.org/10.1007/s11356-019-06011-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-019-06011-2