Citation: WANG Lei, ZHAO Xin-hua, XIONG Zhen-hu, ZHANG Jin-miao, LI Chen, WU Chun-sheng. Combination of amino functionalized metal organic framework with nitrogenous compounds in model fuel[J]. Journal of Fuel Chemistry and Technology, ;2016, 44(9): 1089-1098. shu

Combination of amino functionalized metal organic framework with nitrogenous compounds in model fuel

1.
School of Environmental Science and Engineering, Tianjin University, Tianjin 300072, China
2.
School of Environmental and Municipal Engineering, Tianjin Chengjian University, Tianjin 300384, China

Corresponding author: WANG Lei, zhenhu.xiong@126.com; wangl1026@tcu.edu.cn
Received Date: 16 March 2016
Revised Date: 12 May 2016

Fund Project: the National Natural Science Foundation of China 50878138

Figures(7)

The metal-organic frameworks, MIL-53 (Al)-NH₂ and MIL-53 (Al), were synthesized and used as the adsorbents for the removal of nitrogen-containing compounds (quinoline and pyrrole) from model fuel. The adsorbents were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), FT-IR spectroscopy, and thermogravimetric analysis. Compared with the adsorption capacity of MIL-53 (Al), MIL-53(Al)-NH₂ possesses a higher adsorption capacity for quinoline and pyrrole in the model fuel due to the hydrogen bonding interaction between MIL-53(Al)-NH₂ and the nitrogen-containing compounds. The factors affecting the adsorption capacity are the adsorptive time and temperature. Furthermore, the pseudo-first-order and pseudo-second-order adsorption kinetics models were tested. It is found that the pseudo-second-order kinetics model is preferable to characterize the adsorption process. The adsorption isotherms and adsorption thermodynamics of quinoline and pyrrole on the MIL-53(Al)-NH₂ were also evaluated. The calculation of separation factor R_L and thermodynamic parameters (ΔG⁰, ΔH⁰和ΔS⁰) show that the adsorption of quinoline/pyrrole on the MIL-53(Al)-NH₂ is a spontaneous and exothermic process. The used MIL-53 (Al)-NH₂ could be regenerated by simple solvent washing with ethanol and reused in the adsorption process.
- MIL-53(Al)-NH₂,
- nitrogen-containing compounds,
- adsorptive denitrogenation,
- model fuel,
- hydrogen bonding interaction
1. [1]
  WANG Z, SUN Z, KONG L, LI G. Adsorptive removal of nitrogen-containing compounds from fuel by metal-organic frameworks[J]. J Energy Chem, 2013,22(6):869-875. doi: 10.1016/S2095-4956(14)60266-7
2. [2]
  AHMED I, JHUNG S H. Adsorptive desulfurization and denitrogenation using metal-organic frameworks[J]. J Hazard Mater, 2016,301:259-276. doi: 10.1016/j.jhazmat.2015.08.045
3. [3]
  AHMED I, JHUNG S H. Adsorptive denitrogenation of model fuel with cucl-loaded metal-organic frameworks (MOFs)[J]. Chem Eng J, 2014,251:35-42. doi: 10.1016/j.cej.2014.04.044
4. [4]
  HONG Xin, TANG Ke, DING Shi-hong. Preparation and deep adsorption denitrification from diesel oil of heteroatoms mesoporous molecular sieve Co-MCM-41[J]. J Fuel Chem Technol, 2016,44(1):99-105.
5. [5]
  KHAN N A, JHUNG S H. Effect of central metal ions of analogous metal-organic frameworks on the adsorptive removal of benzothiophene from a model fuel[J]. J Hazard Mater, 2013,260:1050-1056. doi: 10.1016/j.jhazmat.2013.06.076
6. [6]
  GADDAFI I, DANMALIKI , SALEH T A. Influence of conversion parameters of waste tires to activated carbon on adsorption of dibenzothiophene from model fuels[J]. J Cleaner Prod, 2016,117:50-55. doi: 10.1016/j.jclepro.2016.01.026
7. [7]
  AHMED I, JHUNG S H. Remarkable improvement in adsorptive denitrogenation of model fossil fuels with cucl/activated carbon, prepared under ambient condition[J]. Chem Eng J, 2015,279:327-334. doi: 10.1016/j.cej.2015.05.035
8. [8]
  QIU M, CHEN C, LI W. Rapid controllable synthesis of Al-MIL-96 and its adsorption of nitrogenous vocs[J]. Catal Today, 2015,258:132-138. doi: 10.1016/j.cattod.2015.04.017
9. [9]
  HAN X, LIN H, ZHENG Y. The role of oxygen functional groups in the adsorption of heteroaromatic nitrogen compounds[J]. J Hazard Mater, 2015,297:217-223. doi: 10.1016/j.jhazmat.2015.04.056
10. [10]
  KHAN N A, HASAN Z, JHUNG S H. Adsorptive removal of hazardous materials using metal-organic frameworks (MOFs): A review[J]. J Hazard Mater, 2013,244-245:444-456. doi: 10.1016/j.jhazmat.2012.11.011
11. [11]
  LIN K Y A, CHANG H A. Ultra-high adsorption capacity of zeolitic imidazole framework-67(ZIF-67) for removal of malachite green from water[J]. Chemosphere, 2015,139:624-631. doi: 10.1016/j.chemosphere.2015.01.041
12. [12]
  BRITT D, TRANCHEMONTAGNE D, YAGHI O M. Metal-organic frameworks with high capacity and selectivity for harmful gases[J]. Proc Natl Acad Sci USA, 2008,105(33):11623-11627. doi: 10.1073/pnas.0804900105
13. [13]
  FALCARO P, RICCO R, YAZDI A, IMAZ I, FURUKAWA S, MASPOCH D, AMELOOT R, EVANS J D, DOONAN C J. Application of metal and metal oxide nanoparticles@Mofs[J]. Coord Chem Rev, 2016,307:237-254. doi: 10.1016/j.ccr.2015.08.002
14. [14]
  WU C. Zeolitic imidazolate metal organic framework ZIF-8 with ultra-high adsorption capacity bound tetracycline in aqueous solution[J]. Rsc Adv, 2015,5(100):82127-82137. doi: 10.1039/C5RA15497A
15. [15]
  CHEN Q, HE Q Q, LV M M, XU Y L, YANG H B, LIU X T, WEI F Y. Selective adsorption of cationic dyes by UiO-66-NH₂[J]. Appl Surf Sci, 2015,327:77-85. doi: 10.1016/j.apsusc.2014.11.103
16. [16]
  HASAN Z, JHUNG S H. Removal of hazardous organics from water using metal-organic frameworks (MOFs): Plausible mechanisms for selective adsorptions[J]. J Hazard Mater, 2014,283:329-339.
17. [17]
  AHMED I, JHUNG S H. Effective adsorptive removal of indole from model fuel using a metal-organic framework functionalized with amino groups[J]. J Hazard Mater, 2015,283:544-550. doi: 10.1016/j.jhazmat.2014.10.002
18. [18]
  QIAN X K, YADIAN B, WU R B, LONG Y, ZHOU K, ZHU B, HUANG Y Z. Structure stability of metal-organic framework MIL-53(Al) in aqueous solutions[J]. Int J Hydrogen Energy, 2013,38(36):16710-16715. doi: 10.1016/j.ijhydene.2013.07.054
19. [19]
  LI C, XIONG Z H, ZHANG J M, WU C S. The strengthening role of the amino group in metal-organic framework MIL-53(Al) for methylene blue and malachite green dye adsorption[J]. J Chem Eng Data, 2015,60(11):3414-3422. doi: 10.1021/acs.jced.5b00692
20. [20]
  JIAN M P, LIU B, ZHANG G S, LIU R P, ZHANG X W. Adsorptive removal of arsenic from aqueous solution by zeolitic imidazolate framework-8(ZIF-8) nanoparticles[J]. Colloid Surf A, 2014,465(1):67-76.
21. [21]
  XIE L T, LIU D H, HUANG H L, YANG Q Y, ZHONG C L. Efficient capture of nitrobenzene from waste water using metal-organic frameworks[J]. Chem Eng J, 2014,246:142-149. doi: 10.1016/j.cej.2014.02.070
22. [22]
  HO Y S, CHIANG T H, HSUEH Y M. Removal of basic dye from aqueous solution using tree fern as a biosorbent[J]. Process Biochem, 2005,40(1):119-124. doi: 10.1016/j.procbio.2003.11.035
23. [23]
  CHENG X, ZHANG A, HOU K, LIU M, WANG Y, SONG C, ZHANG G, GUO X. Size-and morphology-controlled NH₂-MIL-53(Al) prepared in DMF-water mixed solvents[J]. Dalton Trans, 2013,42(37):13698-13705. doi: 10.1039/c3dt51322j
24. [24]
  MORADI S E, DADFARNIA S, SHABANI A M H, EMAMI S. Removal of congo red from aqueous solution by its sorption onto the metal organic framework MIL-100(Fe): Equilibrium, kinetic and thermodynamic studies[J]. Desalin Water Treat, 2014,159(3):1-13.
25. [25]
  LIN S, SONG Z L, CHE G B, REN A, LI P, LIU C B, ZHANG J S. Adsorption behavior of metal-organic frameworks for methylene blue from aqueous solution[J]. Microporous Mesoporous Mater, 2014,193(2):27-34.
26. [26]
  HASAN Z, CHOI E J, JHUNG S H, HASAN Z, CHOI E J, JHUNG S H. Adsorption of naproxen and clofibric acid over a metal-organic framework MIL-101 functionalized with acidic and basic groups[J]. Chem Eng J, 2013,219(3):537-544.
27. [27]
  LIU H W, DONG Y H, WANG H Y, YUN L. Adsorption behavior of ammonium by a bioadsorbent-boston ivy leaf powder[J]. J Environ Sci, 2010,22(10):1513-1518. doi: 10.1016/S1001-0742(09)60282-5
28. [28]
  MCGUIRE C V, FORGAN R S. The surface chemistry of metal-organic frameworks[J]. Chem Commun, 2015,51(25):5199-5217. doi: 10.1039/C4CC04458D
29. [29]
  AHMED I, KHAN N A, HASAN Z, JHUNG S H. Adsorptive denitrogenation of model fuels with porous metal-organic framework (MOF) MIL-101 impregnated with phosphotungstic acid: Effect of acid site inclusion[J]. J Hazard Mater, 2013,250-251:37-44. doi: 10.1016/j.jhazmat.2013.01.024
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沈阳化工大学材料科学与工程学院沈阳 110142