Abstract
This work aims to highlight the promising adsorption capacity and kinetic of (poly)chlorobenzene pollutants in the hybrid MIL-101(Cr) type material for technological uses in industrial waste exhaust decontamination. The influence of the MIL-101(Cr) crystal size (nano- and microcrystals) on the adsorption behavior was studied in static and dynamic modes. For this purpose, crystals of MIL-101(Cr) in nano- and micrometric sizes were synthesized and fully characterized. Their sorption properties regarding 1,2-dichlorobenzene were examined using gravimetric method in dynamic (p/p° = 0.5) and static (p/p° = 1) modes at room temperature. 1,2,4-trichlorobenzene adsorption was only performed under static mode because of its too low vapor pressure. 1,2-dichlorobenzene and 1,2,4-trichlorobenzene were used to mimic 2,3-dichlorodibenzo-p-dioxin and 1,2,3,4-tetrachlorodibenzo-p-dioxin, respectively, and more largely dioxin compounds. Adsorptions of these probes were successfully carried out in nano- and microcrystals of MIL-101(Cr). Indeed, in static mode (p/p° = 1) and at room temperature, nanocrystals adsorb 2266 molecules of 1,2-dichlorobenzene and 2093 molecules of 1,2,4-trichlorobenzene per unit cell, whereas microcrystals adsorb 1871 molecules of 1,2-dichlorobenzene and 1631 molecules of 1,2,4-trichlorobenzene per unit cell. In dynamic mode, the 1,2-dichlorobenzene adsorbed amounts are substantially similar to those obtained in static mode. However, the adsorption kinetics are different because of a different scheme of diffusivity of the adsorbate between the two modes. To the best of our knowledge, these adsorption capacities of MIL-101(Cr) as adsorbent for polychlorobenzenes trapping have never been referenced. MIL-101(Cr) appears as a promising material for technological uses in industrial waste exhaust decontamination.
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References
Abad E, Adrados MA, Caixach J, Fabrellas B, Rivera J (2000) Dioxin mass balance in a municipal waste incinerator. Chemosphere 40:1143–1147. https://doi.org/10.1016/S0045-6535(99)00363-X
Aristizábal BH, Maya C, Correa CMD (2008) Ortho-dichlorobenzene oxidation over Pd/Co loaded sulfated zirconia and mordenite catalysts. Appl Catal A Gen 335:211–219. https://doi.org/10.1016/j.apcata.2007.11.026
Bell JG, Zhao X, Uygur Y, Thomas KM (2011) Adsorption of chloroaromatic models for dioxins on porous carbons: the influence of adsorbate structure and surface functional groups on surface interactions and adsorption kinetics. J Phys Chem C 115:2776–2789. https://doi.org/10.1021/jp1099893
Bertinchamps F, Grégoire C, Gaigneaux EM (2006) Systematic investigation of supported transition metal oxide based formulations for the catalytic oxidative elimination of (chloro)-aromatics: part II: influence of the nature and addition protocol of secondary phases to VOx/TiO2. Appl Catal B Environ 66:10–22. https://doi.org/10.1016/j.apcatb.2006.02.012
Bullot L, Ben Abda M, Simon-Masseron A, Daou TJ, Chaplais G, Nouali H, Schäf O, Zerega Y, Fiani E, Patarin J (2017) Dioxin and 1,2-dichlorobenzene adsorption in aluminosilicate zeolite beta. Adsorption 23:101–112. https://doi.org/10.1007/s10450-016-9828-3
Buragohain A, Couck S, Van Der Voort P, Denayer JPM, Biswas S (2016) Synthesis, characterization and sorption properties of functionalized Cr-MIL-101-X (X=−F, –Cl, –Br, –CH3, –C6H4, –F-2, –(CH3)(2)) materials. J Solid State Chem 238:195–202. https://doi.org/10.1016/j.jssc.2016.03.034
Cerius2, Molecular Simulations Inc (2000), Version 4.2 MatSci for SGI/IRIX machines edn, San Diego
Czuczwa JM, Hites RA (1986) Airborne dioxins and dibenzofurans: sources and fates. Environ Sci Technol 20:195–200. https://doi.org/10.1021/es00144a015
Daou TJ, Lauridant N, Arnold G, Josien L, Faye D, Patarin J (2013) Synthesis of MFI/EMT zeolite bi-layer films for molecular decontamination. Chem Eng J 234:66–73. https://doi.org/10.1016/j.cej.2013.08.103
Debecker DP, Bertinchamps F, Blangenois N, Eloy P, Gaigneaux EM (2007) On the impact of the choice of model VOC in the evaluation of V-based catalysts for the total oxidation of dioxins: furan vs. chlorobenzene. Appl Catal B Environ 74:223–232. https://doi.org/10.1016/j.apcatb.2007.02.016
Everaert K, Baeyens J (2004) Catalytic combustion of volatile organic compounds. J Hazard Mater 109:113–139. https://doi.org/10.1016/j.jhazmat.2004.03.019
Férey G, Mellot-Draznieks C, Serre C, Millange F, Dutour J, Surblé S, Margiolaki I (2005) A chromium terephthalate-based solid with unusually large pore volumes and surface area. Science 309:2040–2042. https://doi.org/10.1126/science.1116275
Ferreira AFP, Mittelmeijer-Hazeleger MC, vand der Bergh J, Aguado S, Jansen JC, Rothenberg G, Rodrigues AE, Kapteijn F (2013) Adsorption of hexane isomers on MFI type zeolites at ambient temperature: understanding the aluminium content effect. Microporous Mesoporous Mater 170:26–35. https://doi.org/10.1016/j.micromeso.2012.11.020
Gannoun C, Turki A, Kochkar H, Delaigle R, Eloy P, Ghorbel A, Gaigneaux EM (2014) Elaboration and characterization of sulfated and unsulfated V2O5/TiO2 nanotubes catalysts for chlorobenzene total oxidation. Appl Catal B Environ 147:58–64. https://doi.org/10.1016/j.apcatb.2013.08.009
Gibson LT (2014) Mesosilica materials and organic pollutant adsorption: part A removal from air. Chem Soc Rev 43:5163–5172. https://doi.org/10.1039/c3cs60096c
Gil A, Assis FCC, Albeniz S, Korili SA (2011) Removal of dyes from wastewaters by adsorption on pillared clays. Chem Eng J 168:1032–1040. https://doi.org/10.1016/j.cej.2011.01.078
Góralski P, Piekarski H (2007) Heat capacities and densities of some liquid chloro-, bromo-, and bromochloro-substituted benzenes. J Chem Eng Data 52:655–659. https://doi.org/10.1021/je600573w
Greenspan L (1977) Humidity fixed-points of binary saturated aqueous-solutions. J Res Natl Bur Stand Sect A Phys Chem 81:89–96. https://doi.org/10.6028/jres.081A.011
Gupta VK, Verma N (2002) Removal of volatile organic compounds by cryogenic condensation followed by adsorption. Chem Eng Sci 57:2679–2696. https://doi.org/10.1016/S0009-2509(02)00158-6
Höfler F, Schneider J, Möckel HJ (1986) Analytical investigations on the composition of gaseous effluents from a garbage dump. Fresenius’ Z Anal Chem 325:365–368. https://doi.org/10.1007/BF00505461
Hong D-Y, Hwang YK, Serre C, Férey G, Chang J-S (2009) Porous chromium terephthalate MIL-101 with coordinatively unsaturated sites: surface functionalization, encapsulation, sorption and catalysis. Adv Funct Mater 19:1537–1552. https://doi.org/10.1002/adfm.200801130
Huang Z, Lee HK (2015) Micro-solid-phase extraction of organochlorine pesticides using porous metal-organic framework MIL-101 as sorbent. J Chromatogr A 1401:9–16. https://doi.org/10.1016/j.chroma.2015.04.052
Jäger R, Schneider AM, Behrens P, Henkelmann B, Schramm K-W, Lenoir D (2004) Selective adsorption of polychlorinated dibenzo-p-dioxins and dibenzofurans by the zeosils UTD-1, SSZ-24, and ITQ-4. Chem Eur J 10:247–256. https://doi.org/10.1002/chem.200305474
Jain S, Bansiwal A, Biniwale RB, Milmille S, Das S, Tiwari S, Siluvai Antony P (2015) Enhancing adsorption of nitrate using metal impregnated alumina. J Environ Chem Eng 3:2342–2349. https://doi.org/10.1016/j.jece.2015.08.009
Jhung SH, Lee JH, Yoon JW, Serre C, Férey G, Chang JS (2007) Microwave synthesis of chromium terephthalate MIL-101 and its benzene sorption ability. Adv Mater 19:121–124. https://doi.org/10.1002/adma.200601604
Jiang D, Burrows AD, Edler KJ (2011) Size-controlled synthesis of MIL-101(Cr) nanoparticles with enhanced selectivity for CO2 over N2. CrystEngComm 13:6916–6919. https://doi.org/10.1039/C1CE06274C
Katsigiannis A, Noutsopoulos C, Mantziaras J, Gioldasi M (2015) Removal of emerging pollutants through granular activated carbon. Chem Eng J 280:49–57. https://doi.org/10.1016/j.cej.2015.05.109
Khan NA, Kang IJ, Seok HY, Jhung SH (2011) Facile synthesis of nano-sized metal-organic frameworks, chromium-benzenedicarboxylate, MIL-101. Chem Eng J 166:1152–1157. https://doi.org/10.1016/j.cej.2010.11.098
Kitagawa S (2006) Physical chemistry: gas in a straitjacket. Nature 441:584–585. https://doi.org/10.1038/441584a
Lebedev OI, Millange F, Serre C, Van Tendeloo G, Férey G (2005) First direct imaging of giant pores of the metal-organic framework MIL-101. Chem Mater 17:6525–6527. https://doi.org/10.1021/cm051870o
Lee CC, Chen HL, Su HJ, Guo YL, Liao PC (2005) Evaluation of PCDD/Fs patterns emitted from incinerator via direct ambient sampling and indirect serum levels assessment of Taiwanese. Chemosphere 59:1465–1474. https://doi.org/10.1016/j.chemosphere.2004.12.075
Leichsenring S, Lenoir D, May HG, Kettrup A (1996a) Catalytic oxidation of chloromatic trace contaminations adsorbed on Wessalith DAY by ozone. Chemosphere 33:343–352. https://doi.org/10.1016/0045-6535(96)00177-4
Leichsenring S, Lenoir D, May HG, Schramm K, Kettrup A (1996b) A new regenerative method for adsorption and oxidation of organic trace contaminants from flue gases. Chemosphere 32:1763–1770. https://doi.org/10.1016/0045-6535(96)00093-8
Lipovská M, Schmidt HG, Roháč V, Růžička V, Wolf G, Zábranský M (2002) Heat capacities of three isomeric chlorobenzenes and of three isomeric chlorophenols. J Therm Anal Calorim 68:753–766. https://doi.org/10.1023/A:1016157615186
Liu H, Kong S, Liu Y, Zeng H (2012) Pollution control technologies of dioxins in municipal solid waste incinerator. Procedia Environ Sci 16:661–668. https://doi.org/10.1016/j.proenv.2012.10.091
Martínez F, López-Muñoz MJ, Aguado J, Melero JA, Arsuaga J, Sotto A, Molina R, Segura Y, Pariente MI, Revilla A, Cerro L, Carenas G (2013) Coupling membrane separation and photocatalytic oxidation processes for the degradation of pharmaceutical pollutants. Water Res 47:5647–5658. https://doi.org/10.1016/j.watres.2013.06.045
Mercury M, Denoyel R, Simon-Masseron A, Carette M, Zerega Y, Patarin J, Soulard M, Reynard C, Janulyte A (2011) Selective adsorption of 2,3-DCDD and 1,2,3,4-TCDD on *BEA, EMT, FAU and MFI-type zeolites as alternative adsorbents for on-line dioxin monitoring. Adsorption 17:747–758. https://doi.org/10.1007/s10450-011-9349-z
Mercury M, Zouaoui N, Simon-Masseron A, Zerega Y, Reynard-Carette C, Denoyel R, Carette M, Soulard M, Janulyte A, Patarin J (2013) Adsorption of 2,3-DCDD on FAU and EMT-type zeolites: influence of the nature and the content of charge compensating cations. Microporous Mesoporous Mater 177:25–31. https://doi.org/10.1016/j.micromeso.2013.02.051
Neumann P, Schmidt KG (1999) Dioxin separation with natural zeolites. Organohalogen Compd 40:543–546
Nolan T, Srinivasan KR, Fogler HS (1989) Dioxon sorption by hydroxy-aluminum-treated clays. Clay Clay Miner 37:487–492. https://doi.org/10.1346/CCMN.1989.0370515
Pyartman AK, Keskinov VA, Lishchuk VV, Spiridonova IA (2006) Influence of temperature on phase separation in the ternary systems [Th(NO3)4(TBP)2]-decane-third organic component. Radiochemistry 48:272–278. https://doi.org/10.1134/s106636220603012x
Rioland G, Bullot L, Daou TJ, Simon-Masseron A, Chaplais G, Faye D, Fiani E, Patarin J (2016) Elaboration of FAU-type zeolite beads with good mechanical performances for molecular decontamination. RSC Adv 6:2470–2478. https://doi.org/10.1039/c5ra23258a
Roháč V, Růžička V, Růžička K, Poledníček M, Aim K, Jose J, Zábranský M (1999) Recommended vapour and sublimation pressures and related thermal data for chlorobenzenes. Fluid Phase Equilib 157:121–142. https://doi.org/10.1016/S0378-3812(99)00003-5
Saha D, Deng S (2010) Ammonia adsorption and its effects on framework stability of MOF-5 and MOF-177. J Colloid Interface Sci 348:615–620. https://doi.org/10.1016/j.jcis.2010.04.078
Shahidi D, Roy R, Azzouz A (2015) Advances in catalytic oxidation of organic pollutants—prospects for thorough mineralization by natural clay catalysts. Appl Catal B Environ 174-175:277–292. https://doi.org/10.1016/j.apcatb.2015.02.042
Taralunga M, Innocent B, Mijoin J, Magnoux P (2007) Catalytic combustion of benzofuran and of a benzofuran/1,2-dichlorobenzene binary mixture over zeolite catalysts. Appl Catal B Environ 75:139–146. https://doi.org/10.1016/j.apcatb.2007.03.014
Trens P, Belarbi H, Shepherd C, Gonzalez P, Ramsahye NA, Lee UH, Seo Y-K, Chang J-S (2012) Coadsorption of n-hexane and benzene vapors onto the chromium terephthalate-based porous material MIL-101(Cr) an experimental and computational study. J Phys Chem C 116:25824–25831. https://doi.org/10.1021/jp308258k
Trens P, Belarbi H, Shepherd C, Gonzalez P, Ramsahye NA, Lee UH, Seo Y-K, Chang J-S (2014) Adsorption and separation of xylene isomers vapors onto the chromium terephthalate-based porous material MIL-101(Cr): an experimental and computational study. Microporous Mesoporous Mater 183:17–22. https://doi.org/10.1016/j.micromeso.2013.08.040
Trung TK, Ramsahye NA, Trens P, Tanchoux N, Serre C, Fajula F, Férey G (2010) Adsorption of C5-C9 hydrocarbons in microporous MOFs MIL-100(Cr) and MIL-101(Cr): a manometric study. Microporous Mesoporous Mater 134:134–140. https://doi.org/10.1016/j.micromeso.2010.05.018
Verevkin SP, Emel’yanenko VN, Klamt A (2007) Thermochemistry of chlorobenzenes and chlorophenols: ambient temperature vapor pressures and enthalpies of phase transitions. J Chem Eng Data 52:499–510. https://doi.org/10.1021/je060429r
Walton KS, Snurr RQ (2007) Applicability of the BET method for determining surface areas of microporous metal-organic frameworks. J Am Chem Soc 129:8552–8556. https://doi.org/10.1021/ja071174k
Weber G, Benoit F, Bellat J-P, Paulin C, Mougin P, Thomas M (2008) Selective adsorption of ethyl mercaptan on NaX zeolite. Microporous Mesoporous Mater 109:184–192. https://doi.org/10.1016/j.micromeso.2007.04.044
Wei D, Wang L, Yan F, Zhang C (2010) Solid-liquid equilibria of acenaphthene with o-, m-, or p-dichlorobenzene. Fluid Phase Equilib 291:66–70. https://doi.org/10.1016/j.fluid.2009.12.013
Xian S, Yu Y, Xiao J, Zhang Z, Xia Q, Wang H, Li Z (2015) Competitive adsorption of water vapor with VOCs dichloroethane, ethyl acetate and benzene on MIL-101(Cr) in humid atmosphere. RSC Adv 5:1827–1834. https://doi.org/10.1039/c4ra10463c
Xu F, Xian S, Xia Q, Li Y, Li Z (2013) Effect of textural properties on the adsorption and desorption of toluene on the metal-organic frameworks HKUST-1 and MIL-101. Adsorpt Sci Technol 31:325–339. https://doi.org/10.1260/0263-6174.31.4.325
Yanagawa T, Hashimoto S, Nagai K (1958) Freezing point diagram of the ternary system of 1,2,3-, 1,2,4-, and 1,3,5-trichlorobenzene. Kagaku Ryoiki 12:63–66
Yang RT, Long RQ, Padin J, Takahashi A, Takahashi T (1999) Adsorbents for dioxins: a new technique for sorbent screening for low-volatile organics. Ind Eng Chem Res 38:2726–2731. https://doi.org/10.1021/ie990170o
Yang K, Sun Q, Xue F, Lin D (2011) Adsorption of volatile organic compounds by metal-organic frameworks MIL-101: influence of molecular size and shape. J Hazard Mater 195:124–131. https://doi.org/10.1016/j.jhazmat.2011.08.020
Yu Z, Peldszus S, Huck PM (2009) Adsorption of selected pharmaceuticals and an endocrine disrupting compound by granular activated carbon. 2. model prediction. Environ Sci Technol 43:1474–1479. https://doi.org/10.1021/es7032185
Zhao Z, Li X, Huang S, Xia Q, Li Z (2011a) Adsorption and diffusion of benzene on chromium-based metal organic framework MIL-101 synthesized by microwave irradiation. Ind Eng Chem Res 50:2254–2261. https://doi.org/10.1021/ie101414n
Zhao Z, Li X, Li Z (2011b) Adsorption equilibrium and kinetics of p-xylene on chromium-based metal organic framework MIL-101. Chem Eng J 173:150–157. https://doi.org/10.1016/j.cej.2011.07.051
Acknowledgements
We would like to thank Ludovic Josien, Laure Michelin, and Habiba Nouali for their assistance with the scanning electron microscopy, the X-ray fluorescence, and adsorption tests, respectively. We acknowledge the financial support from the French Agency for Environment and Energy Management (ADEME) and the Ecole Nationale Supérieure de Chimie de Mulhouse (ENSCMu) Foundation. This study is part of the Meterdiox + CORTEA funding program (Project METERDIOX+ - contract #1281C0038).
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Bullot, L., Vieira-Sellaï, L., Chaplais, G. et al. Adsorption of 1,2-dichlorobenzene and 1,2,4-trichlorobenzene in nano- and microsized crystals of MIL-101(Cr): static and dynamic gravimetric studies. Environ Sci Pollut Res 24, 26562–26573 (2017). https://doi.org/10.1007/s11356-017-0242-5
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DOI: https://doi.org/10.1007/s11356-017-0242-5