Removal of basic nitrogen compounds from fuel oil with[Amim]Cl/ZnCl<sub>2</sub> ionic liquid

LIU Jie; ZHOU Zhao-qian; LI Wen-shen; SONG Shi-ye; MA Bo

Volume 44 Issue 10

Oct. 2016

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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]. Journal of Fuel Chemistry and Technology, 2016, 44(10): 1233-1239.

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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]. Journal of Fuel Chemistry and Technology, 2016, 44(10): 1233-1239.

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Removal of basic nitrogen compounds from fuel oil with[Amim]Cl/ZnCl₂ ionic liquid

LIU Jie^{1, 2
,
,},
ZHOU Zhao-qian¹,
LI Wen-shen¹,
SONG Shi-ye¹,
MA Bo^{1, 2}

1.
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun 113001, China
2.
College of Chemical Engineering, China University of Petroleum(East China), Qingdao 266580, China

More Information

Corresponding author: Tel: 13842352536, E-mail: lj13898309829@163.com
Received Date: 2016-04-20
Rev Recd Date: 2016-06-29

Available Online: 2021-01-23

Publish Date: 2016-10-10

Abstract

Abstract

Metal-based ionic liquid [Amim]Cl/ZnCl₂ was synthesized and its structure and acidity were characterized with FT-IR spectroscopy. The denitrogenation performance of the ionic liquid was investigated using Fushun shale diesel oil containing 0.52% basic nitrogen as feedstock. Experimental results showed that the ionic liquid exhibited good denitrogenation performance and 83.78% basic N-extraction efficiency was achieved under the optimized operation conditions, i.e., temperature of 30℃, 1:7 (mass ratio) IL:oil, reaction time of 20 min and settling time of 2 h. In addition, the basic N-removal efficiency of the ionic liquid can still remain 52% after four recycles.
- [Amim]Cl/ZnCl₂ ionic liquid,
- shale diesel oil,
- denitrogenation,
- basic nitrogen

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References(28)

References

[1]	唐晓东, 胡涛, 李晶晶, 张永汾, 陈露.柴油络合脱氮技术的研究进展[J].石油化工, 2014, 43(7):843-847. http://www.cnki.com.cn/Article/CJFDTOTAL-SYHG201407022.htm 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. http://www.cnki.com.cn/Article/CJFDTOTAL-SYHG201407022.htm
[2]	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
[3]	邵志才, 高晓冬, 李皓光, 聂红.氮化物对柴油深度和超深度加氢脱硫的影响I:氮化物含量的影响[J].石油学报(石油加工), 2006, 22(4):12-17. http://www.cnki.com.cn/Article/CJFDTOTAL-SXJG200604003.htm 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. http://www.cnki.com.cn/Article/CJFDTOTAL-SXJG200604003.htm
[4]	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.
[5]	李少凯, 李琳潞, 沈健, 阮本玺.USY吸附脱除页岩柴油中的碱性氮[J].辽宁石油化工大学学报, 2013, 33(1):22-24. http://www.cnki.com.cn/Article/CJFDTOTAL-FSSX201301007.htm LI Shao-kai, LI Lin-lun, SHEN Jian, RUAN Ben-xi.Adsorption on removal of basic nitrogen in the shale diesel by USY molecular sieve[J].J Liaoning Shihua University, 2013, 33(1):22-24. http://www.cnki.com.cn/Article/CJFDTOTAL-FSSX201301007.htm
[6]	李广欣, 韩冬云, 曹祖宾, 马海燕, 李丹东, 石薇薇.抚顺页岩油新型加工工艺研究[J].现代化工, 2011, 31(2):74-76. http://www.cnki.com.cn/Article/CJFDTOTAL-XDHG201102028.htm 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. http://www.cnki.com.cn/Article/CJFDTOTAL-XDHG201102028.htm
[7]	徐明, 陈登峰, 肖双全, 解民, 郝磊.大庆页岩油脱氮工艺实验研究[J].石油学报(石油加工), 2012, 28(1):55-59. http://www.cnki.com.cn/Article/CJFDTOTAL-SXJG201201011.htm 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. http://www.cnki.com.cn/Article/CJFDTOTAL-SXJG201201011.htm
[8]	王云芳, 刘伟, 袁倩, 李青松.焦化柴油氧化萃取脱氮技术研究[J].应用化工, 2011, 40(8):1430-1433. http://www.cnki.com.cn/Article/CJFDTOTAL-SXHG201108039.htm 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. http://www.cnki.com.cn/Article/CJFDTOTAL-SXHG201108039.htm
[9]	王辉, 张庆航.离子液体油品脱氮研究进展[J].化工科技, 2015, 23(6):88-93. http://www.cnki.com.cn/Article/CJFDTOTAL-JKGH201506021.htm WANG Hui, ZHANG Qing-hang.Research Progress in oil denitrification with ionic liquids[J].Sci Technol Chem Ind, 2015, 23(6):88-93. http://www.cnki.com.cn/Article/CJFDTOTAL-JKGH201506021.htm
[10]	胡玲玲, 李文深, 刘洁.离子液体脱除油品中氮化物的研究进展[J].应用化工, 2015, 44(10):1941-1945. http://www.cnki.com.cn/Article/CJFDTOTAL-SXHG201510039.htm HU Ling-ling, LI Wen-shen, LIU Jie.Research progress in removing nitride from fuel oil by the ionic liquids[J].Appl Chem Ind, 2015, 44(10):1941-1945. http://www.cnki.com.cn/Article/CJFDTOTAL-SXHG201510039.htm
[11]	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
[12]	HANSMEIER A R, MEINDERSMA G W, HANN A B.Desulfurization and denitrogenation of gasoline and diesel fuels by means of ionic liquids[J].Green Chem, 2011, 13:1907-1913. doi: 10.1039/c1gc15196g
[13]	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
[14]	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.
[15]	林赛燕, 刘丹, 王红, 桂建舟, 梦祥巍, 许敏, 张彦佳.酸性离子液体萃取脱除焦化柴油中碱性氮化物[J].石油化工高等学校学报, 2012, 25(1):8-12. http://www.cnki.com.cn/Article/CJFDTOTAL-SYHX201201002.htm 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. http://www.cnki.com.cn/Article/CJFDTOTAL-SYHX201201002.htm
[16]	金昌磊, 吕燕, 苑丽质, 刘华宾, 蔺东海.酸性离子液体脱除柴油中碱性氮的研究[J].唐山学院学报, 2010, 23(6):74-76. http://www.cnki.com.cn/Article/CJFDTOTAL-TSGD201006029.htm JIN Chang-lei, LV Yan, YUAN Li-zhi, LIU Hua-bin, LIN Dong-hai.Study of removing basic nitrogen compounds from diesel with acid ionic liquid[J].J Tangshan College, 2010, 23(6):74-76. http://www.cnki.com.cn/Article/CJFDTOTAL-TSGD201006029.htm
[17]	王辉, 解从霞, 于世涛, 刘福胜.功能化酸性离子液体脱除模拟油品中的非碱性氮[J].燃料化学学报, 2014, 42(1):55-60. http://rlhxxb.sxicc.ac.cn/CN/abstract/abstract18334.shtml 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. http://rlhxxb.sxicc.ac.cn/CN/abstract/abstract18334.shtml
[18]	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
[19]	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
[20]	ZHANG S G, ZHANG Q L, ZHANG Z C.Extraction desulfurization and denitrogenation of fuels using ionic liquids[J].Ind Eng Chem Res, 2004, (43):614-622.
[21]	谢莉莉, 陈旬, 王绪绪, 付贤智.氯化咪唑基离子液体对柴油中含氮化合物选择性脱除作用研究[J].无机化学学报, 2008, 24(6):919-925. http://www.cnki.com.cn/Article/CJFDTOTAL-WJHX200806015.htm XIE Li-li, CHEN Xun, WANG Xu-xu, FU Xian-zhi.Removal of N-compounds from diesel fuel by using chloridized imidazole based ionic liquids[J].Chin J Inorg Chem, 2008, 24(6):919-925. http://www.cnki.com.cn/Article/CJFDTOTAL-WJHX200806015.htm
[22]	XIE L L, ALAIN F R, STEPHANE T R, WANG X X, FU X Z, EATAGER J, VRINAT M, LEMAIRE M.Selective extraction and identification of neutral nitrogen compounds contained in straight-run diesel feed using chloride ionic liquid[J].Ind Eng Chem Res, 2008, 47(22):8801-8807. doi: 10.1021/ie701704q
[23]	XIE L L, ALAIN F R, WANG X X, FU X Z, STEPHANE T R, TOUSSAINT G, GEANTET C, VRINAT M, LEMAIRE M.Selective extraction of neutral nitrogen compounds found in diesel feed by 1-butyl-3-methyl-imidazolium chloride[J].Green Chem, 2008, 10:524-531. doi: 10.1039/b800789f
[24]	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
[25]	周雅文, 邓宇, 韩德新.氯代1-烯丙基-3-甲基咪唑离子液体的合成[J].化工科技, 2009, 17(3):9-12. http://www.cnki.com.cn/Article/CJFDTOTAL-JKGH200903004.htm ZHOU Ya-wen, DENG Yu, HAN De-xin.Synthesis of ionic liquid 1-allyl-3-methyl imidazole chloride[J].Sci Technol Chem Ind, 2009, 17(3):9-12. http://www.cnki.com.cn/Article/CJFDTOTAL-JKGH200903004.htm
[26]	王晓化, 陶国宏, 吴晓牧, 寇元.离子液体酸性的红外光谱探针法研究[J].物理化学学报, 2005, 21(5):528-533. http://www.cnki.com.cn/Article/CJFDTOTAL-WLHX200505014.htm WANG Xiao-hua, TAO Guo-hong, WU Xiao-mu, KOU Yuan.Investigation of the acidity of ionic liquids by IR spectroscopy[J].Acta Phys-Chim Sin (Wuli Huaxue Xuebao), 2005, 21(5):528-533. http://www.cnki.com.cn/Article/CJFDTOTAL-WLHX200505014.htm
[27]	徐海涛, 廖建华, 邢跃鹏.烯丙基功能化离子液体的制备及其分离CO₂性能[J].化工新型材料, 2014, 42(12):57-59. XU Hai-tao, LIAO Jian-hua, XING Yue-peng.Research on synthesis of allyl functionalized ionic liquids and its performance of CO₂ absorption[J].New Chem Mater, 2014, 42(12):57-59.
[28]	范明明, 王辉, 张萍波, 倪邦庆.1-丁基-3-甲基咪唑氯化锌离子液体的合成、表征及催化性能[J].无机化学学报, 2012, 28(7):1333-1337. http://www.cnki.com.cn/Article/CJFDTOTAL-WJHX201207006.htm FAN Ming-ming, WANG Hui, ZHANG Ping-bo, NI Bang-qing.Synthesis, characterization and catalysis performance of ionic liquid 1-butyl-3-methylimidazolium chlorozincate[J].Chin J Inorg Chem, 2012, 28(7):1333-1337. http://www.cnki.com.cn/Article/CJFDTOTAL-WJHX201207006.htm