Citation: LIU Jie, MOU Hao-wen, LI Wen-shen. Theoretical study on the interaction between 1-butyl-3-methylimidazolium hydrosulphates ionic liquid and nitrogenous compounds[J]. Journal of Fuel Chemistry and Technology, ;2018, 46(11): 1386-1391. shu

Theoretical study on the interaction between 1-butyl-3-methylimidazolium hydrosulphates ionic liquid and nitrogenous compounds

College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun 113001, China

Corresponding author: LIU Jie, lj13898309829@163.com
Received Date: 23 March 2018
Revised Date: 21 August 2018

Figures(1)

The interaction between 1-butyl-3-methylimidazolium hydrosulphates ionic liquid ([Bmim]HSO₄) and nitrogenous compounds (quinoline and indole) were investigated by density functional theory, and analyzed by NBO and AIM methods. The most stable structure of [Bmim]HSO₄ ionic pair displays a strong hydrogen bond interaction between O atom in [HSO₄]^- anion and C14-H20 in imidazolium ring. NBO and AIM analysis at the molecular level proves that there is a strong interaction between quinoline or indole and the anion of [Bmim]HSO₄. The strong interaction between the active hydrogen of [HSO₄]^- and the N atom of quinoline molecule as well as the hydrogen bond formed between the H atom of N-H in indole molecule and the O atom of [HSO₄]^- are the main driving force for denitrogenation performance of [Bmim]HSO₄.
- ionic liquid,
- denitrogenation,
- density functional theory,
- quinoline,
- indole
1. [1]
  TANG Xiao-dong, HU Tao, LI Jing-jing, ZHANG Yong-fen, CHEN Lu. Progresses in the denitrogenation of diesel oil by complexation[J]. Petrochem Technol, 2014,43(7):843-847. doi: 10.3969/j.issn.1000-8144.2014.07.019
2. [2]
  NIE Y, GONG X, GAO H S, ZHANG X P, ZHANG S J. Simultaneous desulfurization and denitrogenation of liquid fuels using two functionalized group ionic liquids[J]. Sci Chin Chem, 2014,57(12):1766-1773. doi: 10.1007/s11426-014-5164-1
3. [3]
  ALMARRI M, MA X L, SONG C S. Selective adsorption for removal of nitrogen compounds from liquid hydrocarbon streams over carbon-and alumina-based adsorbents[J]. Ind Eng Chem Res, 2009,48(2):951-960. doi: 10.1021/ie801010w
4. [4]
  LI Guang-xin, HAN Dong-yun, CAO Zu-bin, MA Hai-yan, LI Dan-dong, SHI Wei-wei. Study on new processing technology of Fushun shale oil[J]. Modern Chem Ind, 2011,31(2):74-76.
5. [5]
  XU Ming, CHEN Deng-feng, XIAO Shuang-quan, XIE Min, HAO Lei. Experimental study on denitrogenation process of Daqing shale oil[J]. Acta Pet Sin (Pet Process Sect), 2012,28(1):55-59. doi: 10.3969/j.issn.1001-8719.2012.01.010
6. [6]
  WANG Yun-fang, LIU Wei, YUAN Qian, LI Qing-song. Technology of oxidative denitrification combined with extraction for coking diesel[J]. Appl Chem Ind, 2011,40(8):1430-1433. doi: 10.3969/j.issn.1671-3206.2011.08.037
7. [7]
  ZHANG J, XU J, QIAN J, LIU L. Denitrogenation of straight-run diesel with complexing extraction[J]. Pet Sci Technol, 2013,31(8):777-782. doi: 10.1080/10916466.2010.493911
8. [8]
  HUH E S, ZAZYBIN A, PALGUNADI J, AHN S, HONG J, KIM H S, CHEONG M, AHN B S. Zn-containing ionic liquids for the extractive denitrogenation of a model oil:A mechanistic consideration[J]. Energy Fuels, 2009,23:3032-3038. doi: 10.1021/ef900073a
9. [9]
  LAREDO G C, LIKHANOVA N V, LIJANOVA I V. Synthesis of ionic liquids and their use for extracting nitrogen compounds from gas oil feeds towards diesel fuel production[J]. Fuel Process Technol, 2015,130:38-45. doi: 10.1016/j.fuproc.2014.08.025
10. [10]
  LIN Sai-yan, LIU Dan, WANG Hong, GUI Jian-zhou, MENG Xiang-wei, XU Min, ZHANG Yan-jia. Removing basic nitrogen compounds from coker diesel by extraction with acidic ionic liquid[J]. J Petrochem Univ, 2012,25(1):8-12. doi: 10.3969/j.issn.1006-396X.2012.01.002
11. [11]
  SU Xiao-lin, SONG Jun, YANG Jing-yi, XU Xin-ru. Extractive denitrification of coal tar diesel fraction using phosphate-based alkylimidazolium ionic liquids[J]. Chem Ind Eng Prog, 2016,35(4):1081-1086.
12. [12]
  ASUMANA C, YU G R, GUAN Y W, YANG S D, ZHOU S Z, CHEN X C. Extractive denitrogenation of fuel oils with dicyanamide-based ionic liquids[J]. Green Chem, 2011,13:3300-3305. doi: 10.1039/c1gc15747g
13. [13]
  CHEN X C, YUAN S, ABDELTAWAB A A, ALDEYAB S S, ZHANG J W, YU L, YU G R. Extractive desulfurization and denitrogenation of fuels using functional acidic ionic liquids[J]. Sep Purif Technol, 2014,133:187-193. doi: 10.1016/j.seppur.2014.06.031
14. [14]
  WANG Hui, XIE Cong-xia, YU Shi-tao, LIU Fu-sheng. Removal of non-basic nitrogen in model oil with functionalized acidic ionic liquid[J]. J Fuel Chem Technol, 2014,42(1):55-60.
15. [15]
  WANG H, XIE C X, YU S T, LIU F S. Denitrification of simulated oil by extraction with H₂PO₄^- based ionic liquids[J]. Chem Eng J, 2014,237:286-290. doi: 10.1016/j.cej.2013.10.049
16. [16]
  LIU Jie, ZHOU Zhao-qian, LI Wen-shen, SONG Shi-ye, MA Bo. Removal of basic nitrogen compounds from fuel oil with[Amim]Cl/ZnCl₂ ionic liquid[J]. J Fuel Chem Technol, 2016,44(10):1233-1239. doi: 10.3969/j.issn.0253-2409.2016.10.011
17. [17]
  TUMER E A, PYE C C, SINGER R D. Use of an initio calculations toward the rational design of room temperature ionic liquids[J]. J Phys Chem A, 2003,107:2277-2288. doi: 10.1021/jp021694w
18. [18]
  DONG Kun, XU Chun-ming, GAO Jin-sen, WANG Da-xi. Quantum chemical study on structure property of ionic liquid of imidazolium[J]. Acta Pet Sin(Pet Process Sect), 2004,20(6):1-7. doi: 10.3969/j.issn.1001-8719.2004.06.001
19. [19]
  LÜ Ren-qing, LIN Jin, SONG Cai-cai, QU Zhan-qing. The density functional study of cation-anion interactions of 4, 5-dibromo-1-butyl-3-methylimidazolium trifluoromethane sulfonate[J]. Ludong Univ J(Nat Sci Ed), 2012,28(2):132-138. doi: 10.3969/j.issn.1673-8020.2012.02.012
20. [20]
  SONG Cai-cai, LIN Jin, QU Zhan-qing, LÜ Ren-qing. Density functional study on 4, 5-dibromo-1-propyl-3-methylimidazolyl and 1-propyl-3-methylimidazolyl hexafluorophosphate liquid[J]. J Jinggangshan Univ (Nat Sci), 2012,33(3):40-48. doi: 10.3969/j.issn.1674-8085.2012.03.009
21. [21]
  LÜ Ren-qing, LIN Jin, WANG Shu-tao. Theoretical study on interactions between pyridinium-based ionic liquids and thiophenic compounds[J]. Acta Pet Sin (Pet Process Sect), 2013,29(6):1015-1022.
22. [22]
  LIN Jin, LÜ Ren-qing. Theoretical study on interaction between imidazolyl ionic liquids and small molecules[J]. J Jinggangshan Univ (Nat Sci), 2013,34(1):39-46.
23. [23]
  DOU Rong-tan, WANG Da-xi, GAO Jin-sen, LIU Jing-jiang. Calculation of structure of alkylamine chloroaluminates molten salts by density function theory[J]. J China Univ Pet, 2007,31(5):104-108. doi: 10.3321/j.issn:1000-5870.2007.05.023
24. [24]
  ANANATHARAJ R, BANERJEE T. COSMO-RS-based screening of ionic liquids as green solvents in denitrification studies[J]. Ind Eng Chem Res, 2010,49:8705-8725. doi: 10.1021/ie901341k
25. [25]
  HIZADDIN H F, HADJ-KALI M K, RAMALINGAM A, HASHIM M. Extraction of nitrogen compounds from diesel fuel using imidazolium-and pyridinium-based ionic liquids:Experiments, COSMO-RS prediction and NRTL correlation[J]. Fluid Phase Equilib, 2015,405:55-67. doi: 10.1016/j.fluid.2015.07.021
26. [26]
  ANANATHARAJ R, JEGALAKSHIMI J. Simultaneous interaction between similar and dissimilar structures of aromatic sulfur and aromatic nitrogen compounds with imidazolium-based ionic liquid using quantum chemical method[J]. Asia-Pac J Chem Eng, 2015,10:904-922. doi: 10.1002/apj.1928
27. [27]
  ZHANG L Z, XU D M, GAO J, ZHOU S X, ZHAO L W, ZHANG Z S. Extraction and mechanism for the separation of neutral N-compounds from coal tar by ionic liquids[J]. Fuel, 2017,194:27-35. doi: 10.1016/j.fuel.2016.12.095
28. [28]
  ZHOU Z Q, LI W S, LIU J. Removal of nitrogen compounds from fuel oils using imidazolium-based ionic liquids[J]. Pet Sci Technol, 2017,35(1):45-50. doi: 10.1080/10916466.2016.1248771
29. [29]
  REED A E, CURTISS L A, WEINHOLD F. Intermolecular interactions from a natural bond orbital, donor-acceptor view point[J]. Chem Rev, 1988,88(6):899-926. doi: 10.1021/cr00088a005
30. [30]
  BIEGLER-KÖNIG F, SCHÖNBOHM J, BAYLES D. AIM2000-A program to analyze and visualize atoms in molecules[J]. J Comput Chem, 2001,22(5):545-559. doi: 10.1002/(ISSN)1096-987X
31. [31]
  BADER R F W. A quantum theory of molecular structure and its applications[J]. Chem Rev, 1991,91:893-928. doi: 10.1021/cr00005a013
32. [32]
  LÜ R Q, QU Z Q, YU H, WANG F, WANG S T. Comparative study on interactions between ionic liquids and pyridine/hexane[J]. Chem Phys Lett, 2012,532:13-18. doi: 10.1016/j.cplett.2012.02.051
1. [1]
  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
2. [2]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
3. [3]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
4. [4]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
5. [5]
  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
6. [6]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
7. [7]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
8. [8]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
9. [9]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
10. [10]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
11. [11]
  Zhengkun QIN , Zicong PAN , Hui TIAN , Wanyi ZHANG , Mingxing SONG . A series of iridium(Ⅲ) complexes with fluorophenyl isoquinoline ligand and low-efficiency roll-off properties: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1235-1244. doi: 10.11862/CJIC.20240429
12. [12]
  Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF模板法合成氮掺杂碳材料用于增强电化学钠离子储存和去除. Acta Physico-Chimica Sinica, 2025, 41(3): 2405002-. doi: 10.3866/PKU.WHXB202405002
13. [13]
  Ronghui LI . Photocatalysis performance of nitrogen-doped CeO₂ thin films via ion beam-assisted deposition. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1123-1130. doi: 10.11862/CJIC.20240440
14. [14]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
15. [15]
  Jun Huang , Pengfei Nie , Yongchao Lu , Jiayang Li , Yiwen Wang , Jianyun Liu . 丝光沸石负载自支撑氮掺杂多孔碳纳米纤维电容器及高效选择性去除硬度离子. Acta Physico-Chimica Sinica, 2025, 41(7): 100066-. doi: 10.1016/j.actphy.2025.100066
16. [16]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
17. [17]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
18. [18]
  Xuyang Wang , Jiapei Zhang , Lirui Zhao , Xiaowen Xu , Guizheng Zou , Bin Zhang . Theoretical Study on the Structure and Stability of Copper-Ammonia Coordination Ions. University Chemistry, 2024, 39(3): 384-389. doi: 10.3866/PKU.DXHX202309065
19. [19]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
20. [20]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(921)
HTML views(148)

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