Citation: CHEN Ying, ZHANG Qi, LIANG Hong-bao, TIAN Gong-wei, LI Jing. Preparation and properties of dibenzothiophene molecularly imprinted functionalized MOF199 adsorbent[J]. Journal of Fuel Chemistry and Technology, ;2018, 46(9): 1130-1136. shu

Preparation and properties of dibenzothiophene molecularly imprinted functionalized MOF199 adsorbent

Provincial Key Laboratory of Oil and Gas Chemical Technology, College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318, China

Corresponding author: CHEN Ying, chenying648617@163.com
Received Date: 4 May 2018
Revised Date: 13 July 2018

Fund Project: the National Natural Science Foundation of China 21463006The project was supported by the National Natural Science Foundation of China(21463006)

Figures(5)

Combined with molecular imprinting technology, a novel surface molecularly imprinted polymer material MOF@SMIP was prepared, using MOF199 used as matrix, dibenzothiophene (DBT) as template molecule and methacrylic acid (MAA) as functional monomer. The structure and morphology were characterized by SEM, BET, FT-IR, etc. The adsorption behavior was evaluated using a simulated oil sample. The adsorption equilibrium time was 1.5 h. The MOF@SMIP adsorption capacity for DBT (130.73 mg/g) was higher than that for the MOF199 (37.79 mg/g), while the MOF@SMIP adsorption capacity (57.13 mg/g) was comparable to the MOF@NIP adsorption capacity. The obvious advantage is that the imprint factor f_imp is 2.29. Adsorption behavior follows the pseudo-first-order kinetic model, indicating that the adsorption is primarily a physical process. The selective adsorption experiments showed that the MOF@SMIP exhibited a higher affinity for the target molecule DBT than the structural analog benzothiophene (BT) and biphenyl. The relative selection coefficient k' of the adsorbed DBT to the interferent BT and biphenyl was 2.55 and 2.14, respectively.
- MOFs,
- molecular imprinting,
- dibenzothiophene,
- functional monomer
1. [1]
  HU Ting-ping, ZHANG Yan-ming, ZHENG Li-hui, FAN Guo-zhi. Molecular recognition and adsorption properties of benzothiophene molecularly imprinted polymers on silica gel surface[J]. J Fuel Chem Technol, 2010,38(6):722-729. doi: 10.3969/j.issn.0253-2409.2010.06.016
2. [2]
  CHEN L, XU S, LI J. Recent advances in molecular imprinting technology:Current status, challenges and highlighted applications[J]. Chem Soc Rev, 2011,40(5):2922-2942. doi: 10.1039/c0cs00084a
3. [3]
  YANG Y Z, LIU X G, XU B S. Recent advances in molecular imprinting technology for the deep desulfurization of fuel oils[J]. New Carbon Mater, 2014,29(1):1-14. doi: 10.1016/S1872-5805(14)60121-9
4. [4]
  MEHRZAD-SAMARIN M, FARIDBOD F, DEZFULI A S, GANJALI M R. A novel metronidazole fluorescent nanosensor based on graphene quantum dots embedded silica molecularly imprinted polymer[J]. Biosens Bioelectron, 2017,92:618-623. doi: 10.1016/j.bios.2016.10.047
5. [5]
  CHANUT N, BOURRELLY S, KUCHTA B, SERRE C, CHANG J S, WRIGHT P A, LLEWELLYN P L. Screening the effect of water vapour on gas adsorption performance:Application to CO₂ capture from flue gas in metal-organic frameworks[J]. ChemSusChem, 2017,10(7):1543-1553. doi: 10.1002/cssc.v10.7
6. [6]
  CHOWDHUR Y, MOHAMMAD A. Metal-organic-frameworks for biomedical applications in drug delivery, and as MRI contrast agents[J]. J Biomed Mater Res A, 2017,105(4):1184-1194. doi: 10.1002/jbm.v105.4
7. [7]
  PAN H, ZHANG P, GAO D, ZHANG Y, LI P, LIU L, CAI L. Noninvasive visualization of respiratory viral infection usingbioorthogonal conjugated near-infrared-emitting quantum dots[J]. ACS Nano, 2014,8(6):5468-5477. doi: 10.1021/nn501028b
8. [8]
  ZHAO S N, SONG X Z, SONG S Y, ZHANG H J. Highly efficient heterogeneous catalytic materials derived from metal-organic framework supports/precursors[J]. Coordin Chem Rev, 2017,337:80-96. doi: 10.1016/j.ccr.2017.02.010
9. [9]
  XU Y, YIN X B, HE X W, ZHANG Y K. Electrochemistry and electrochemiluminescence from a redox-active metal-organic framework[J]. Biosens Bioelectron, 2015,68:197-203. doi: 10.1016/j.bios.2014.12.031
10. [10]
  BOUGRINI M, FLOREA A, CRISTEA C, SANDULESCU R, VOCANSON F, ERRACHID A, JAFFREZIC-RENAULT N. Development of a novel sensitive molecularly imprinted polymer sensor based on electropolymerization of a microporous-metal-organic framework for tetracycline detection in honey[J]. Food Control, 2016,59:424-429. doi: 10.1016/j.foodcont.2015.06.002
11. [11]
  GUO Z, FLOREA A, CRISTEA C, BESSUEILLE F, VOCANSON F, GOUTALAND F, JAFFREZIC-RENAULT N. 1, 3, 5-Trinitrotoluene detection by a molecularly imprinted polymer sensor based on electropolymerization of a microporous-metal-organic framework[J]. Sensor Actuat B:Chem, 2015,207:960-966. doi: 10.1016/j.snb.2014.06.137
12. [12]
  NGUYEN L T L, NGUYEN T T, NGUYEN K D, PHAN N T. Metal-organic framework MOF-199 as an efficient heterogeneous catalyst for the aza-Michael reaction[J]. Appl Catal A:Gen, 2012,425:44-52.
13. [13]
  WANG Xiao-jing, LIU Chao, DONG Yue, LI Fa-tang, ZHAO Jun, LI Yu-pei. Preparation of activated carbon modified by tetrafluoroboric acid and its adsorptive removal of dibenzothiophene[J]. J Fuel Chem Technol, 2015,43(5):607-613. doi: 10.3969/j.issn.0253-2409.2015.05.013
14. [14]
  YUAN Z, LIU Y, AN F. Preparation and phenol-recognizing ability of a poly (methacrylic acid) molecular imprint on the surface of a silica gel[J]. Microchim Acta, 2011,172(1/2):89-94.
15. [15]
  LI H, XU M, WANG S, LU C, LI Z. Preparation, characterization and selective recognition for vanillic acid imprinted mesoporous silica polymers[J]. Appl Surf Sci, 2015,328:649-657. doi: 10.1016/j.apsusc.2014.12.085
16. [16]
  LIU W, QIN L, SHI W, CHEN L, YANG Y, LIU X, XU B. Molecularly imprinted polymers on the surface of porous carbon microspheres for capturing dibenzothiophene[J]. Microchim Acta, 2016,183(3):1153-1160. doi: 10.1007/s00604-016-1746-2
17. [17]
  COLLET F, BART M, SERRES L, MIRIEL J. Porous structure and water vapour sorption of hemp-based materials[J]. Constr Build Mater, 2008,22(6):1271-1280. doi: 10.1016/j.conbuildmat.2007.01.018
18. [18]
  ZHANG L, YANG L, JELLE B P, WANG Y, GUSTAVSEN A. Hygrothermal properties of compressed earthen bricks[J]. Constr Build Mater, 2018,162:576-583. doi: 10.1016/j.conbuildmat.2017.11.163
19. [19]
  QIN L, SHI W, LIU W, YANG Y, LIU X, XU B. Surface molecularly imprinted polymers grafted on ordered mesoporous carbon nanospheres for fuel desulfurization[J]. RSC Adv, 2016,6(15):12504-12513. doi: 10.1039/C5RA23582K
20. [20]
  KHAN N A, JHUNG S H. Adsorptive removal and separation of chemicals with metal-organic frameworks:Contribution of π-complexation[J]. J Hazard Mater, 2017,325:198-213. doi: 10.1016/j.jhazmat.2016.11.070
21. [21]
  LEE K X, VALLA J A. Investigation of metal-exchanged mesoporous Y zeolites for the adsorptive desulfurization of liquid fuels[J]. Appl Catal B:Environ, 2017,201:359-369. doi: 10.1016/j.apcatb.2016.08.018
22. [22]
  YANG Y, LIU X, GUO M, LI S, LIU W, XU B. Molecularly imprinted polymer on carbon microsphere surfaces for adsorbing dibenzothiophene[J]. Colloid Surface A, 2011,377(1):379-385.
23. [23]
  XU W, ZHOU W, XU P P, PAN J M, WU X Y, YAN Y S. A molecularly imprinted polymer based on TiO₂ as a sacrificial support for selective recognition of dibenzothiophene[J]. Chem Eng J, 2011,172(1):191-198. doi: 10.1016/j.cej.2011.05.089
24. [24]
  YANG W, ZHOU W, XU W, LI H, HUANG W, JIANG B, YAN Y. Synthesis and characterization of a surface molecular imprinted polymer as a new adsorbent for the removal of dibenzothiophene[J]. J Chem Eng Data, 2012,57(6):1713-1720. doi: 10.1021/je201380m
25. [25]
  ZUHLKE C A, ANDERSON T P, ALEXANDER D R. Formation of multiscale surface structures on nickel via above surface growth and below surface growth mechanisms using femtosecond laser pulses[J]. Opt Express, 2013,21(7):8460-8473. doi: 10.1364/OE.21.008460
26. [26]
  YANG W, LIU L, ZHOU Z, LIU H, XIE B, XU W. Rational preparation of dibenzothiophene-imprinted polymers by surface imprinting technique combined with atom transfer radical polymerization[J]. Appl Surf Sci, 2013,282:809-819. doi: 10.1016/j.apsusc.2013.06.063
27. [27]
  LI Q, YANG K, LIANG Y, JIANG B, LIU J, ZHANG L, ZHANG Y. Surface protein imprinted core-shell particles for high selective lysozyme recognition prepared by reversible addition-fragmentation chain transfer strategy[J]. Acs Appl Mater Inter, 2014,6(24):21954-21960. doi: 10.1021/am5072783
28. [28]
  HUANG R, LIU Q, HUO J, YANG B. Adsorption of methyl orange onto protonated cross-linked chitosan[J]. Arab J Chem, 2017,10(1):24-32. doi: 10.1016/j.arabjc.2013.05.017
29. [29]
  LIU W, QIN L, YANG Y, LIU X, XU B. Synthesis and characterization of dibenzothiophene imprinted polymers on the surface of iniferter-modified carbon microspheres[J]. Mater Chem Phys, 2014,148(3):605-613. doi: 10.1016/j.matchemphys.2014.08.024
30. [30]
  ZHANG M, HUANG J, YU P, CHEN X. Preparation and characteristics of protein molecularly imprinted membranes on the surface of multiwalled carbon nanotubes[J]. Talanta, 2010,81(1):162-166.
31. [31]
  YU C, FAN X, YU L, BANDOSZ T J, ZHAO Z, QIU J. Adsorptive removal of thiophenic compounds from oils by activated carbon modified with concentrated nitric acid[J]. Energy Fuels, 2013,27(3):1499-1505. doi: 10.1021/ef400029b
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