留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码

[Amim]Cl/ZnCl2离子液体脱除燃料油中碱性氮化物

刘洁 周兆骞 李文深 宋世野 马波

刘洁, 周兆骞, 李文深, 宋世野, 马波. [Amim]Cl/ZnCl2离子液体脱除燃料油中碱性氮化物[J]. 燃料化学学报(中英文), 2016, 44(10): 1233-1239.
引用本文: 刘洁, 周兆骞, 李文深, 宋世野, 马波. [Amim]Cl/ZnCl2离子液体脱除燃料油中碱性氮化物[J]. 燃料化学学报(中英文), 2016, 44(10): 1233-1239.
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.
Citation: 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.

[Amim]Cl/ZnCl2离子液体脱除燃料油中碱性氮化物

详细信息
  • 中图分类号: TE622.1

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

More Information
  • 摘要: 合成了金属基离子液体[Amim]Cl/ZnCl2,采用红外光谱对其结构和酸性进行表征,并以碱性氮含量高达0.52%(质量分数)的抚顺页岩油柴油馏分为原料考察其脱氮性能。结果表明,在反应温度30℃、剂油质量比1:7、反应时间20 min、静置时间2 h的条件下,[Amim]Cl/ZnCl2对柴油馏分中碱性氮化物的脱除率可达83.78%,且该离子液体经回收重复使用四次后,碱氮脱除率仍能达到52%。
  • 图  1  [Amim]Cl的合成路线示意图

    Figure  1  Synthesis route of [Amim]Cl

    图  2  离子液体[Amim]Cl (a)和[Amim]Cl/ZnCl2 (b)的FT-IR谱图

    Figure  2  FT-IR spectra of [Amim]Cl (a) and [Amim]Cl/ZnCl2 (b)

    图  3  [Amim]Cl/ZnCl2离子液体氢核磁共振谱谱图

    Figure  3  1H NMR of [Amim]Cl/ZnCl2

    图  4  [Amim]Cl/ZnCl2离子液体的热重曲线

    Figure  4  TG curve of [Amim]Cl/ZnCl2

    图  5  吡啶探针法测定离子液体酸性的FT-IR谱图

    Figure  5  Investigation of the acidity of [Amim]Cl/ZnCl2 by FT-IR spectroscopy

    图  6  不同离子液体在不同时间下的碱氮脱除效果

    Figure  6  Basic-N-removal efficiency with different ionic liquids at different time

    图  7  不同反应温度对碱氮脱除效果的影响

    Figure  7  Effect of reaction temperature on basic-N-removal efficiency

    图  8  不同剂油质量比对碱氮脱除效果的影响

    Figure  8  Effect of mass ratio of IL/oil on basic-N-removal efficiency

    图  9  不同静置时间对碱氮脱除效果的影响

    Figure  9  Effect of settling time on basic-N-removal efficiency

    图  10  离子液体回收次数与碱氮脱除率的关系

    Figure  10  Relation of basic-N-extraction efficiency with recycle times

    表  1  抚顺页岩油柴油馏分基本性质

    Table  1  Properties of diesel fraction from Fushun shale oil

    ItemsDensity ρ/(g·mL-1)Basic nitrogen content w/(μg·g-1)v20 /(mm2·s-1)Freezing point t/℃
    Data0.865 55 2234.472
    下载: 导出CSV

    表  2  离子液体的元素分析

    Table  2  Elemental analysis of the ionic liquid

    ComplexContent w/%
    C (theoretical value)H (theoretical value)
    [Amim]Cl/ZnCl228.34 (28.51) 3.8.1(3.76)
    下载: 导出CSV
  • [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
  • 加载中
图(10) / 表(2)
计量
  • 文章访问数:  103
  • HTML全文浏览量:  61
  • PDF下载量:  9
  • 被引次数: 0
出版历程
  • 收稿日期:  2016-04-20
  • 修回日期:  2016-06-29
  • 网络出版日期:  2021-01-23
  • 刊出日期:  2016-10-10

目录

    /

    返回文章
    返回