功能化酸性离子液体脱除模拟油品中的非碱性氮

王辉 解从霞 于世涛 刘福胜

引用本文: 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. shu
Citation:  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]. Journal of Fuel Chemistry and Technology, 2014, 42(1): 55-60. shu

功能化酸性离子液体脱除模拟油品中的非碱性氮

    通讯作者: 于世涛,Tel/Fax:0532-84022719,E-mail:yushitaoqust@126.com。
  • 基金项目:

    国家自然科学基金(21176129)。 (21176129)

摘要: 合成了一系列功能化酸性离子液体并用于模拟油品中非碱性氮-吲哚的脱除。结果表明,离子液体的阴离子对脱氮率有较大影响,离子液体的酸性越强,对吲哚的选择性脱除效果越好,不同阴离子的脱氮率顺序为:HSO4- > CF3COO- > H2PO4- > CH3COO-。以(CH3CH2)3N(CH2)3SO3HHSO4为例,考察了剂油比、剂水比、沉降时间、反应时间和温度对油品脱氮率的影响。结果表明,在优化的工艺路线下,(CH3CH2)3N(CH2)3SO3HHSO4对油品中的吲哚脱除率可达99.12%,重复使用六次后,脱氮活性未见明显降低,具有良好的稳定性,。

English

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    1. [1] BUSCA G. Bases and basic materials in industrial and environmental chemistry: A review of commercial processes[J]. Ind Eng Chem Res, 2009, 48(14): 6486-6511.[1] BUSCA G. Bases and basic materials in industrial and environmental chemistry: A review of commercial processes[J]. Ind Eng Chem Res, 2009, 48(14): 6486-6511.

    2. [2] 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.[2] 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.

    3. [3] SHI Q, HOU D J, CHUNG K H, XU C M, ZHAO S Q, ZHANG Y H. Characterization of heteroatom compounds in a crude oil and its saturates, aromatics, resins, and asphaltenes (SARA ) and non-basic nitrogen fractions analyzed by negative-ion electrospray ionization fourier transform ion cyclotron resonance mass spectrometry[J]. Energy Fuels, 2010, 24(4): 2545-2553.[3] SHI Q, HOU D J, CHUNG K H, XU C M, ZHAO S Q, ZHANG Y H. Characterization of heteroatom compounds in a crude oil and its saturates, aromatics, resins, and asphaltenes (SARA ) and non-basic nitrogen fractions analyzed by negative-ion electrospray ionization fourier transform ion cyclotron resonance mass spectrometry[J]. Energy Fuels, 2010, 24(4): 2545-2553.

    4. [4] REVELLIN N, DULOT H, GARCIA C L, BACO F. Specific nitrogen boiling point profiles of vacuum gasoils[J]. Energy Fuels, 2005, 19(6): 2438-2444.[4] REVELLIN N, DULOT H, GARCIA C L, BACO F. Specific nitrogen boiling point profiles of vacuum gasoils[J]. Energy Fuels, 2005, 19(6): 2438-2444.

    5. [5] LI N, MA X L, ZHA Q F, SONG C S. Analysis and comparison of nitrogen compounds in different liquid hydrocarbon streams derived from petroleum and coal[J]. Energy Fuels, 2010, 24(10): 5539-5547.[5] LI N, MA X L, ZHA Q F, SONG C S. Analysis and comparison of nitrogen compounds in different liquid hydrocarbon streams derived from petroleum and coal[J]. Energy Fuels, 2010, 24(10): 5539-5547.

    6. [6] 路蒙蒙, 孙守华, 丁保宏, 杨欣佳, 臧树良. 加氢脱氮反应研究进展[J]. 化工科技, 2011, 19(1): 65-71. (LU Meng-meng, SUN Shou-hua, DING Bao-hong, YANG Jia-xin, ZHANG Shu-liang. Advance in research on hydrodenitrogenation[J]. Science and Technology in Chemical Industry, 2011, 19(1): 65-71.)[6] 路蒙蒙, 孙守华, 丁保宏, 杨欣佳, 臧树良. 加氢脱氮反应研究进展[J]. 化工科技, 2011, 19(1): 65-71. (LU Meng-meng, SUN Shou-hua, DING Bao-hong, YANG Jia-xin, ZHANG Shu-liang. Advance in research on hydrodenitrogenation[J]. Science and Technology in Chemical Industry, 2011, 19(1): 65-71.)

    7. [7] HALLETT J P, WELTON T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. 2[J]. Chem Rev, 2011, 111(5): 3508-3576.[7] HALLETT J P, WELTON T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. 2[J]. Chem Rev, 2011, 111(5): 3508-3576.

    8. [8] XIE L L, REGUILLON A F, ROSTAING S P, WANG X X, FU X Z, ESTAGER J, VRINAT M, LEMAIRE M. Selective extraction and identification of neutral nitrogen compounds contained in straight-run diesel feed using chloride based ionic liquid[J]. Ind Eng Chem Res, 2008, 47(22): 8801-8807.[8] XIE L L, REGUILLON A F, ROSTAING S P, WANG X X, FU X Z, ESTAGER J, VRINAT M, LEMAIRE M. Selective extraction and identification of neutral nitrogen compounds contained in straight-run diesel feed using chloride based ionic liquid[J]. Ind Eng Chem Res, 2008, 47(22): 8801-8807.

    9. [9] ZHANG S G, ZHANG Q L, ZHANG Z C. Extractive desulfurization and denitrogenation of fuels using ionic liquids[J]. Ind Eng Chem Res, 2004, 43(2): 614-622.[9] ZHANG S G, ZHANG Q L, ZHANG Z C. Extractive desulfurization and denitrogenation of fuels using ionic liquids[J]. Ind Eng Chem Res, 2004, 43(2): 614-622.

    10. [10] 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.[10] 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.

    11. [11] 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(6): 3032-3038.[11] 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(6): 3032-3038.

    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.[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.

    13. [13] 侯明慧, 施力. 离子液体脱除柴油中碱性氮化物的研究[J]. 石油与天然气化工, 2008, 37(5): 383-385. (HOU Ming-hui, SHI Li. Removal of basic nitrogen compounds from the diesel oil by using ionic liquids[J]. Chemical Engineer of Gas and Oil, 2008, 37(5): 383-385.)[13] 侯明慧, 施力. 离子液体脱除柴油中碱性氮化物的研究[J]. 石油与天然气化工, 2008, 37(5): 383-385. (HOU Ming-hui, SHI Li. Removal of basic nitrogen compounds from the diesel oil by using ionic liquids[J]. Chemical Engineer of Gas and Oil, 2008, 37(5): 383-385.)

    14. [14] 金昌磊, 吕燕, 苑丽质, 刘华宾, 蔺东海. 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. (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]. Journal of Tangshan College, 2010, 23(6): 74-76.)[14] 金昌磊, 吕燕, 苑丽质, 刘华宾, 蔺东海. 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. (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]. Journal of Tangshan College, 2010, 23(6): 74-76.)

    15. [15] 冯锦锋, 袁军, 杨梅, 魏宇, 陈小霞. 液体脱除焦化柴油中碱性氮[J].武汉工程大学学报, 2011, 33(10): 17-21. (FEN Jing-feng, YUAN Jun, YANG Mei, WEI Yu, CHEN Xiao-xia. Removing basic nitrogen compounds from coker diesel with acid ionic liquid[J]. Journal of Wuhan Institute Technology, 2011, 33(10): 17-21.)[15] 冯锦锋, 袁军, 杨梅, 魏宇, 陈小霞. 液体脱除焦化柴油中碱性氮[J].武汉工程大学学报, 2011, 33(10): 17-21. (FEN Jing-feng, YUAN Jun, YANG Mei, WEI Yu, CHEN Xiao-xia. Removing basic nitrogen compounds from coker diesel with acid ionic liquid[J]. Journal of Wuhan Institute Technology, 2011, 33(10): 17-21.)

    16. [16] 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. (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]. Journal of Petrochemical Universities, 2012, 25(1): 8-12.)[16] 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. (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]. Journal of Petrochemical Universities, 2012, 25(1): 8-12.)

    17. [17] 刘晓飞, 陈静, 夏春谷. 吗啉基功能化酸性离子液体催化苯酚-叔丁醇选择性烷基化反应[J]. 分子催化, 2008, 22(5): 392-397. (LIU Xiao-fei, CHEN Jing, XIA Chun-gu. Selective alkylation of phenol with tertbutyl alcohol catalyzed by morpholine-based task specific acidic ionic liquids[J]. Journal of Molecular Catalysis(China), 2008, 22(5): 392-397.)[17] 刘晓飞, 陈静, 夏春谷. 吗啉基功能化酸性离子液体催化苯酚-叔丁醇选择性烷基化反应[J]. 分子催化, 2008, 22(5): 392-397. (LIU Xiao-fei, CHEN Jing, XIA Chun-gu. Selective alkylation of phenol with tertbutyl alcohol catalyzed by morpholine-based task specific acidic ionic liquids[J]. Journal of Molecular Catalysis(China), 2008, 22(5): 392-397.)

    18. [18] 刘鹰, 胡瑞生, 刘贵立, 徐春明. 酸性离子液体催化的异丁烷/丁烯烷基化反应研究[J]. 分子催化, 2010, 24(3): 217-221. (LIU Ying, HU Rui-sheng, LIU Gui-li, XU Chun-ming. Study on the alkylation of isobutane/butene in acidic ionic liquids[J]. Journal of Molecular Catalysis(China), 2010, 24(3): 217-221.)[18] 刘鹰, 胡瑞生, 刘贵立, 徐春明. 酸性离子液体催化的异丁烷/丁烯烷基化反应研究[J]. 分子催化, 2010, 24(3): 217-221. (LIU Ying, HU Rui-sheng, LIU Gui-li, XU Chun-ming. Study on the alkylation of isobutane/butene in acidic ionic liquids[J]. Journal of Molecular Catalysis(China), 2010, 24(3): 217-221.)

    19. [19] COLE A C, JENSEN J L, NTAI I, TRAN K L T, WEAVER K J, FORBES D C, DAVIS J H. Novel brnsted acidic ionic liquids and their use as dual solvent-catalysts[J]. J Am Chem Soc, 2002, 124(21): 5962-5963.[19] COLE A C, JENSEN J L, NTAI I, TRAN K L T, WEAVER K J, FORBES D C, DAVIS J H. Novel brnsted acidic ionic liquids and their use as dual solvent-catalysts[J]. J Am Chem Soc, 2002, 124(21): 5962-5963.

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  • 收稿日期:  2013-07-15
  • 网络出版日期:  2013-09-17
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