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·396·                             精细化工   FINE CHEMICALS                                  第 37 卷

            脱除率分别为 73.4%和 65.6%。与离子液体脱除模                           Progresses  in the denitrogenation  of diesel oil  by complexation[J].
            拟油中氮化物相比,该离子液体对实际油品中氮化                                 Petrochemical Technology (石油化工), 2014, 43(7): 843-847.
                                                               [2]   Almarri M, Ma X L, Song C S. Selective adsorption for removal of
            物的脱除率偏低,这可能是由于在实际油品中除了
                                                                   nitrogen compounds from liquid hydrocarbon streams over carbon-
            含氮化合物,还含有较多的硫化物、氧化物及芳烃等,                               and alumina-based adsorbents[J]. Industrial & Engineering Chemistry
            而这些物质也可能溶解在离子液体中,从而降低了                                 Research, 2009, 48(2): 951-960.
            离子液体对氮化物的脱除性能。                                     [3]   Shao Zhicai (邵志才), Gao Xiaodong (高晓冬), Li Haoguang (李皓
                                                                   光),  et al. Effect  of nitrogen-containing compounds on deep and
            2.5   离子液体与甲苯-正十二烷溶液互溶度的测定
                                                                   ultradeep HDS for diesel oil[J]. Acta Petrolei Sinica (Petroleum
                 离子液体在油品中有一定溶解时,一方面会影                              Processing Section) (石油学报:  石油加工), 2006, 22(4): 12-17.
            响离子液体对氮化物的萃取效率,另一方面也可能                             [4]   Koltai T, Macaud M, Guevara A, et al. Comparative inhibiting effect
            会污染油品;同时油品在离子液体中有一定程度的                                 of polycondensed aromatics and  nitrogen compounds on  the
                                                                   hydrodesulfurization of alkyldibenzothiophenes[J]. Applied Catalysis, A:
            溶解会造成油品的损耗,因此,从工业应用角度研
                                                                   General, 2002, 231(1/2): 253-261.
            究离子液体与油品的互溶度是非常必要的。本文参                             [5]   Abro R, Abro M, Gao S R, et al. Extractive denitrogenation of fuel
            照文献[30]对离子液体 CH 3 CONH 2 -0.3ZnCl 2 和甲苯-               oils using ionic liquids:  A review[J]. RSC  Advance, 2016,  6:
            正十二烷溶液(质量比 20∶80)的互溶度进行了测                              93932-93946.
                                                               [6]   Zhang J, Xu J, Qian J, et al. Denitrogenation of straight-run diesel
            定。即在 50  ℃下,按照剂油质量比 1∶1 将离子液
                                                                   with complexing extraction[J]. Petroleum Science and Technology,
            体与甲苯-正十二烷溶液混合搅拌 60 min,静置 2 h,                         2013, 31(8): 777-782.
            取上层溶液,用硫氮测定仪测定有机相的总氮量,以                            [7]   Wang Yunfang (王云芳), Liu Wei (刘伟), Yuan Qian (袁倩), et al.
                                                                   Technology of oxidative denitrification combined with extraction for
            此计算离子液体在甲苯-正十二烷溶液中的溶解度;
                                                                   coking diesel[J]. Applied Chemical Industry (应用化工), 2011,
            碳氢化合物在离子液体中的溶解度则采用重量法测                                 40(8): 1430-1433, 1436.
            定。测定结果表明:甲苯-正十二烷在 CH 3 CONH 2 -                    [8]   Li Shaokai (李少凯), Li  Linlun (李琳潞), Shen Jian (沈健),  et al.
            0.3ZnCl 2 中的溶解度为 0.0206 g/g,低于文献[10]报                  Adsorption on removal of basic nitrogen in the shale diesel by USY
                                                                   molecular sieve[J]. Journal of Liaoning Shihua University (辽宁石油
            道的 [BMI][N(CN) 2 ] 离子液体的结果 。离子液体
                                                                   化工大学学报), 2013, 33(1): 22-24, 29.
            CH 3 CONH 2 -0.3ZnCl 2 在甲苯-正十二烷溶液的溶解               [9]   Eßer J, Wasserscheid P, Jess A. Deep desulfurization of oil refinery
            度为 41 mg/kg,即 0.0041%,说明离子液体在溶液                        streams by extraction with ionic liquids[J]. Green Chemistry, 2004,
            中的溶解度很小,对于将来的应用还需要对离子液                                 7: 316-322.
                                                               [10]  Asumana C, Yu G R, Guan Y W, et al. Extractive denitrogenation of
            体在油品中的溶解性能进一步优化。
                                                                   fuel oils with dicyanamide-based ionic liquids[J]. Green Chemistry,
                                                                   2011,11: 3300-3305.
            3   结论                                             [11]  Wang H, Xie C X, Yu S T, et al. Denitrification of simulated oil by
                                                                   extraction with H 2PO 4-based ionic liquids[J]. Chemical Engineering
                 按照不同的物质的量比合成配位离子液体                                Journal, 2014, 237: 286-290.
            CH 3 CONH 2 -xZnCl 2 (x=0.3、0.4、0.5),脱除模拟          [12]  Su Xiaolin (苏晓琳), Song Jun (宋军), Yang Jingyi (杨敬一),  et al.
            柴油中氮化物,CH 3 CONH 2 -0.3ZnCl 2 具有较好的脱                   Extractive denitrification of coal tar diesel fraction using  phosphate-
                                                                   based  alkylimidazolium ionic liquids[J].  Chemical Industry  and
            氮性能。在萃取时间 20 min、沉降时间 2 h、萃取温
                                                                   Engineering Progress (化工进展), 2016, 35(4): 1081-1086.
            度 50  ℃的条件下,当剂油质量比为 1∶3 时,喹啉和                      [13]  Zhang L Z, Xu D M, Gao J, et al. Extraction and mechanism for the
            吲哚脱除率分别为 96.8%、68.1%,继续增大剂油质                           separation of neutral N-compounds from coal tar by ionic liquids[J].
            量比至 1∶1,几乎检测不到喹啉模拟油的氮含量,而                              Fuel, 2017, 194: 27-35.
                                                               [14]  Xie L L, Alain F R, Wang X X, et al. Selective extraction of neutral
            吲哚模拟油氮含量由初始的 500 μg/g 降至 62.5 μg/g,
                                                                   nitrogen compounds found in  diesel feed by 1-butyl-3-methyl-
            该离子液体对碱性氮化物喹啉较高的脱除率可归因                                 imidazolium chloride[J]. Green Chemistry, 2008, 10(5): 524-531.
                                                 2+
            于其分子中含有的孤对电子与离子液体 Zn 的空轨道                          [15]  Huh E S, Zazybin A, Palgunadi J, et al. Zn-containing ionic liquids
            之间有较强的络合作用。配位离子液体 CH 3 CONH 2 -                        for the extractive  denitrogenation of  a  model oil: A mechanistic
                                                                   consideration[J]. Energy & Fuels, 2009, 23(6): 3032-3038.
            0.3ZnCl 2 在回收利用 5 次后,喹啉脱除率仍可达到
                                                               [16]  Chen X C, Yuan S, Abdeltawab A A, et al. Extractive desulfurization
            91.5%,具有较好的重复使用性能。                                     and denitrogenation of fuels using functional acidic ionic liquids[J].
                 与其他咪唑类离子液体相比,该配位离子液体                              Separation and Purification Technology, 2014, 133: 187-193.
            合成简单、成本低廉,可以作为加氢脱氮的补充方                             [17]  Liu Jie (刘洁), Zhou Zhaoqian (周兆骞), Li Wenshen (李文深), et al.
                                                                   Removal of basic nitrogen compounds from fuel oil with [Amim]Cl/
            法,具有较好的开发前景。
                                                                   ZnCl 2 ionic liquid[J]. Journal of Fuel Chemistry and Technology (燃
                                                                   料化学学报), 2016, 44(10): 1233-1239.
            参考文献:
            [1]   Tang Xiaodong (唐晓东), Hu Tao (胡涛), Li Jingjing (李晶晶), et al.                 (下转第 402 页)
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