Citation: WANG Zhao-Yang, LI Gang, SUN Zhi-Guo. Denitrogenation through Adsorption to Sulfonated Metal-Organic Frameworks[J]. Acta Physico-Chimica Sinica, ;2013, 29(11): 2422-2428. doi: 10.3866/PKU.WHXB201309021 shu

Denitrogenation through Adsorption to Sulfonated Metal-Organic Frameworks

1.
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning Province, P. R. China

Received Date: 12 June 2013
Available Online: 2 September 2013
Fund Project: 国家重点基础研究发展计划项目(973)(2011CB201301)资助 (973)(2011CB201301)

Sulfonic acid functionalized MIL-101(Cr) (S-MIL-101(Cr)) are obtained by sulfonation of MIL-101(Cr) (Cr₃F(H₂O)₂O[(O₂C)-C₆H₄-(CO₂)]₃·nH₂O (n~25)) using triflic anhydride and sulfuric acid. The amount of sulfonic groups in the framework can be controlled by changing the molar ratio of MIL-101(Cr), triflic anhydride, and sulfuric acid. The sulfonated samples were characterized by X-ray diffraction (XRD), Fourier transform infrared (FTIR) spectroscopy, nitrogen physical adsorption/desorption, acid-base potentiometric titration, and thermogravimetric analysis (TGA). The results show that the sulfonated samples retain the general structure of MIL-101(Cr), but the specific areas and pore diameters decrease. The sulfonated samples formed with between 0.21 and 0.42 mmol·g^-1 of sulfonic acid groups. The adsorptive denitrogenation of a model fuel by different S-MIL-101(Cr) samples was investigated in batch adsorption experiments. Sulfonation can strengthen the interactions between nitrogen-containing compounds (NCCs) and the adsorbent. The sample obtained using a molar ratio of n(MIL-101(Cr)):n(H₂SO₄):n(Tf₂O)=1:3:4.5 had the largest adsorption capacity for quinoline and indole. Compared with the bare MIL-101(Cr), this sulfonated material showed enhancement of the maximum adsorption capacity by 12.2% and 6.3% for quinoline and indole, respectively. Regeneration of the used adsorbent was conducted by washing with ethanol, and the adsorptive capacity for NCCs from the model-fuel showed no obvious decrease after three cycles of use.
- Metal-organic framework,
- Sulfoacid functionalization,
- Adsorptive denitrogenation,
- Langmuir adsorption,
- Adsorption isothermal
1. [1]
  
  (1) Furimsky, E.; Massoth, F. E. Catal. Today 1999, 52 (4), 381.doi: 10.1016/S0920-5861(99)00096-6
2. [2]
  (2) Dong, D.; Jeong, S.; Massoth, F. E. Catal. Today 1997, 37 (3),267. doi: 10.1016/S0920-5861(97)00022-9
3. [3]
  (3) Xu, C. M.; Yang, Z. H. Petroleum Refining Engineering;Petroleum Industry Press: Beijing, 2009; pp 8-10 [徐春明, 杨朝合. 石油炼制工程. 北京: 石油工业出版社, 2009: 8-10]
4. [4]
  (4) Schlatter, J. C.; Oyama, S. T.; Metcalfe Iii, J. E.; Lambert, J. M.,Jr. Ind. Eng. Chem. Res. 1988, 27 (9), 1648. doi: 10.1021/ie00081a014
5. [5]
  (5) Choi, J.; Brenner, J. R.; Colling, C.W.; Demczyk, B. G.;Dunning, J. L.; Thompson, L. T. Catal. Today 1992, 15 (2),201. doi: 10.1016/0920-5861(92)80176-N
6. [6]
  (6) Song, H.; Guo, Y. T.; Li, F.; Yu, H. K. Acta Phys. -Chim. Sin.2010, 26, 2461. [宋华, 郭云涛, 李锋, 于洪坤. 物理化学学报, 2010, 26, 2461.] doi: 10.3866/PKU.WHXB20100937
7. [7]
  (7) Laredo, G. C.; Leyva, S.; Alvarez, R.; Mares, M. T.; Castillo, J.;Cano, J. L. Fuel 2002, 81 (10), 1341. doi: 10.1016/S0016-2361(02)00047-9
8. [8]
  (8) Almarri, M.; Ma, X.; Song, C. Energy Fuels 2009, 23 (8), 3940.doi: 10.1021/ef900051r
9. [9]
  (9) Sun, B.; Li, G.;Wang, X. J. Nat. Gas Chem. 2010, 19 (5), 471.doi: 10.1016/S1003-9953(09)60115-8
10. [10]
  (10) Kim, J. H.; Ma, X.; Zhou, A.; Song, C. Catal. Today 2006, 111 (1-2), 74.
11. [11]
  (11) Wu, J.; Li, X.; Du,W.; Dong, C.; Li, L. J. Mater. Chem. 2007,17 (21), 2233. doi: 10.1039/b612501h
12. [12]
  (12) Zhang, H.; Li, G.; Jia, Y.; Liu, H. J. Chem. Eng. Data 2009,55 (1), 173.
13. [13]
  (13) Laredo, G. C.; Vega-Merino, P. M.; Trejo-Zárraga, F.; Castillo,J. Fuel Proces. Technol. 2013, 106, 21. doi: 10.1016/j.fuproc.2012.09.057
14. [14]
  (14) Volkringer, C.; Loiseau, T.; Férey, G.; Morais, C. M.; Taulelle,F.; Montouillout, V.; Massiot, D. Microporous Mesoporous Mat. 2007, 105 (1-2), 111.
15. [15]
  (15) Cychosz, K. A.;Wong-Foy, A. G.; Matzger, A. J. J. Am. Chem. Soc. 2008, 130 (22), 6938. doi: 10.1021/ja802121u
16. [16]
  (16) Blanco-Brieva, G.; Campos-Martin, J. M.; Al-Zahrani, S. M.;Fierro, J. Fuel 2011, 90 (1), 190. doi: 10.1016/j.fuel.2010.08.008
17. [17]
  (17) Khan, N. A.; Jhung, S. H. Fuel Process. Technol. 2012, 100, 49.doi: 10.1016/j.fuproc.2012.03.006
18. [18]
  (18) Maes, M.; Trekels, M.; Boulhout, M.; Schouteden, S.;Vermoortele, F.; Alaerts, L.; Heurtaux, D.; Seo, Y.; Hwang, Y.K.; Chang, J.; Beurroies, I.; Denoyel, R.; Temst, K.; Vantomme,A.; Horcajada, P.; Serre, C.; De Vos, D. E. Angew. Chem. Int. Edit. 2011, 50 (18), 4210. doi: 10.1002/anie.v50.18
19. [19]
  (19) Ahmed, I.; Hasan, Z.; Khan, N. A.; Jhung, S. H. Appl. Catal. B 2013, 129, 123. doi: 10.1016/j.apcatb.2012.09.020
20. [20]
  (20) Wang, Z.; Cohen, S. M. Chem. Soc. Rev. 2009, 38 (5), 1315.doi: 10.1039/b802258p
21. [21]
  (21) Férey, G.; Mellot-Draznieks, C.; Serre, C.; Millange, F.; Dutour,J.; Surblé, S.; Margiolaki, I. Science 2005, 309, 2040. doi: 10.1126/science.1116275
22. [22]
  (22) esten, M. G.; Juan-Alcañiz, J.; Ramos-Fernandez, E. V.; SaiSankar Gupta, K. B.; Stavitski, E.; van Bekkum, H.; Gascon, J.;Kapteijn, F. J. Catal. 2011, 281 (1), 177. doi: 10.1016/j.jcat.2011.04.015
23. [23]
  (23) Akiyama, G.; Matsuda, R.; Sato, H.; Takata, M.; Kitagawa,S. Adv. Mater. 2011, 23 (29), 3294. doi: 10.1002/adma.201101356
24. [24]
  (24) Atorngitjawat, P.; Klein, R. J.; Runt, J. Macromolecules2006, 39 (5), 1815. doi: 10.1021/ma051717f
25. [25]
  (25) Warren, D. S.; Mcquillan, A. J. J. Phys. Chem. B 2008, 112 (34),10535. doi: 10.1021/jp801838n
26. [26]
  (26) Ostrowska-Gumkowska, B.; Ostrowska-Czubenko, J. Euro. Poly. J. 1994, 30 (8), 869. doi: 10.1016/0014-3057(94)90017-5
1. [1]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
2. [2]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
3. [3]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
4. [4]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
5. [5]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
6. [6]
  Shasha Ma , Zujin Yang , Jianyong Zhang . Facile Synthesis of FeBTC Metal-Organic Gel and Its Adsorption of Cr₂O₇²⁻: A Physical Chemistry Innovation Experiment. University Chemistry, 2024, 39(8): 314-323. doi: 10.3866/PKU.DXHX202401008
7. [7]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
8. [8]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
9. [9]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
10. [10]
  Qianqian Zhong , Yucui Hao , Guotao Yu , Lijuan Zhao , Jingfu Wang , Jian Liu , Xiaohua Ren . Comprehensive Experimental Design for the Preparation of the Magnetic Adsorbent Based on Enteromorpha Prolifera and Its Utilization in the Purification of Heavy Metal Ions Wastewater. University Chemistry, 2024, 39(8): 184-190. doi: 10.3866/PKU.DXHX202312013
11. [11]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
12. [12]
  Xiaosong PU , Hangkai WU , Taohong LI , Huijuan LI , Shouqing LIU , Yuanbo HUANG , Xuemei LI . Adsorption performance and removal mechanism of Cd(Ⅱ) in water by magnesium modified carbon foam. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1537-1548. doi: 10.11862/CJIC.20240030
13. [13]
  Jingke LIU , Jia CHEN , Yingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060
14. [14]
  Fang Niu , Rong Li , Qiaolan Zhang . Analysis of Gas-Solid Adsorption Behavior in Resistive Gas Sensing Process. University Chemistry, 2024, 39(8): 142-148. doi: 10.3866/PKU.DXHX202311102
15. [15]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
16. [16]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
17. [17]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
18. [18]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
19. [19]
  Jie ZHANG , Xin LIU , Zhixin LI , Yuting PEI , Yuqi YANG , Huimin LI , Zhiqiang LIU . Assembling a luminescence silencing system based on post-synthetic modification strategy: A highly sensitive and selective turn-on metal-organic framework probe for ascorbic acid detection. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 823-833. doi: 10.11862/CJIC.20230310
20. [20]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415

Get Citation

PDF

XML

Metrics

PDF Downloads(1120)
Abstract views(1914)
HTML views(204)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142