Citation: LI Wen-shen, GUO Xiao-wen, LIU Jin-bo, LIU Jie. Removal of nitrogen compounds from diesel oil with eutectic ionic liquid[J]. Journal of Fuel Chemistry and Technology, ;2018, 46(3): 305-310. shu

Removal of nitrogen compounds from diesel oil with eutectic ionic liquid

  • Corresponding author: LI Wen-shen, lj13898309829@163.com
  • Received Date: 23 October 2017
    Revised Date: 16 January 2018

Figures(9)

  • An eutectic ionic liquid (EIL), choline chloride/oxalic acid, was synthesized and its structure was characterized with FT-IR spectroscopy and 1H-NMR. The denitrogenation performance of the EIL was investigated in detail using model oil and coker diesel oil as feedstock. Experimental results show that the removal efficiencies of quinoline and indole are almost 100% and 88.05%, respectively at 30℃ with the EIL to oil ratio of 1:7 (mass ratio), extraction time of 30 min and settling time of 2 h. It is also found that the choline chloride/oxalic acid presents a better denitrogenation performance for coker diesel oil, and the basic and total N-extraction efficiency can reach 96.61% and 71.5%, respectively. In addition, the basic N-removal efficiency can still reach 87.2% after four recycles of the EIL.
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    1. [1]

      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

    2. [2]

      FAN Yin-shuai, LIU Shu-zhi, SUN Lan-lan, ZHANG Xue-jia, SI Wen-bin. New progress in denitrogenation of diesel oil[J]. Sci Technol Chem Ind, 2007,15(20):63-66.  

    3. [3]

      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 China Chem, 2014,57(12):1766-1773. doi: 10.1007/s11426-014-5164-1

    4. [4]

      SHAO Zhi-cai, GAO Xiao-dong, LI Hao-guang, NIE Hong. Effect of nitrogen-containing compounds on deep and ultradeep HDS for diesel oil[J]. Acta Pet Sin (Pet Process Sect), 2006,22(4):12-17.  

    5. [5]

      KOLTAI T, MACAUD M, GUEVARA A, SCHULZ E, LEMAIRE M, BACAUD R, VRINAT M. Comparative inhibiting effect of polycondensed aromatics and nitrogen compounds on the hydrodesulfurization of alkyldibenzothiophenes[J]. Appl Catal A:Gen, 2002,23:1253-1261.  

    6. [6]

      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.  

    7. [7]

      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.  

    8. [8]

      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

    9. [9]

      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

    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.  

    11. [11]

      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

    12. [12]

      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.  

    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]

      LIU J, MA B. Removal of nitrogen compounds from shale diesel fraction using ionic liquid[C4 mim]HSO4[J]. China Pet Process Petrochem Technol, 2016,18(3):15-21.  

    15. [15]

      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

    16. [16]

      WEI Lu, FAN You-jun. Progress of deep eutectic solvents and their applications[J]. Chem, 2011,74(4):333-339.  

    17. [17]

      ABBOTT A P, CAPPER G, DAVIES D L, RASHEED R K, TAMBYRAJAH V. Novel solvent properties of choline chloride/urea mixtures[J]. Chem Commun, 2003,1:70-71.  

    18. [18]

      LI Rui-qian, LIANG Jun, CHU Qing-wei. Electrodeposition of nanocrystalline Ni from choline chloride and ethylene glycol deep eutectic solvent[J]. Chin J Nonferrous Met, 2014,24(7):1839-1844.  

    19. [19]

      LIU Cheng-cheng, BU Lu-xia, ZHAO Shuang, MA Zhan-lin. Studies on preparation and properties of choline chloride and malonic acid ionic liquids[J]. J Tianjin Agr Univ, 2016,23(3):20-22.  

    20. [20]

      LI Xiao, WANG Xian-pei, LIU Wei-tao, LI Xiao-an. Synthesis of tributyl citrate catalyzed by ionic liquid of choline chloride[J]. Ind Catal, 2016,24(6):66-69.  

    21. [21]

      ZHANG Ying-ying, JI Xiao-yan, LU Xiao-hua. Properties and applications of choline chloride/urea and choline chloride/glycerol[J]. Scientia Sinica Chimica, 2014,44(6):927-941.  

    22. [22]

      JIANG W, ZHU W S, LI H M, CHAO Y H, XUN S H, CHANG Y H, LIU H, ZHAO Z. Mechanism and optimization for oxidative desulfurization of fuels catalyzed by Fenton-like catalysts in hydrophobic ionic liquid[J]. J Mol Catal A:Chem, 2014,382:8-14. doi: 10.1016/j.molcata.2013.10.017

    23. [23]

      LI Jia-hui, HU Jia, ZHAO Rong-xiang, QIAO Hai-yan, LI Xiu-ping. Oxidative desulfurization of model oil with choline chloride/oxalic acid as a eutectic solvent[J]. J Fuel Chem Technol, 2014,42(7):870-876.  

    24. [24]

      HOU Liang-pei, ZHAO Rong-xiang, LI Xiu-ping, SHI Wei-wei. Preparation of methylimidazole hydrochloride/oxalic acid type deep eutectic solvent and its application in oxidative desulfurization of model oil[J]. CIESC J, 2016,67(9):3972-3980.  

    25. [25]

      WANG Xiao-dan, WU Wen-yuan, TU Gan-feng, JIANG Kai-xi. Synthesis and physical chemistry properties of acidic 1-butyl-3-methylimidazolium hydrosulfate ionic liquids[J]. Acta Scientiarum Naturalium Universities Sunyatseni, 2009,48(6):69-72.  

    26. [26]

      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.  

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