Page 137 - 《精细化工》2020年第4期
P. 137

第 4 期              孙林慧,等:  氯铝酸盐双阳离子液体催化合成乙氧基亚甲基丙二酸二乙酯                                    ·771·


            2.2.6    催化剂的循环使用性                                 [3]   PATEL N B,  PATEL J C,  MODI S H.  Synthesis  and  antimicrobial
                                                                   activity of carbonyl pyridoquinolones containing urea and piperazine
                 当反应完成后,有机相与离子液体分相,通过                              residue[J]. Journal of Saudi Chemical Society, 2011, 15(2): 167-176.
            倾析分离出目标产物。重复使用前,离子液体相用                             [4]   ALETANSKA-KOZAK  M,  KACZOR  A  A,  WRÓBEL  T  M,  et al.
                                                                   The       Pseudo-Michael    reaction    of
            环己烷洗涤除去残留有机物,分离得到的催化剂循                                 2-hydrazinylidene-1-arylimidazolidines   with   diethyl
            环使用,结果如图 5 所示。                                         ethoxymethylenemalonate[J].  Journal  of  Heterocyclic  Chemistry,
                                                                   2016, 53(2): 571-578.
                                                               [5]   MARRA R.Synthetic applications of diethyl ethoxymethylenemalonate[J].
                                                                   Synlett, 2010, 17: 2679-2680.
                                                               [6]   EGRI  G,  FOGASSY  E,  NOVAK  L, et  al.  Synthesis  and  lipase-
                                                                   catalyzed  asymmetric  acetylation  of  3-hydroxy-2-hydroxymethylpropanal
                                                                   acetals[J]. Tetrahedron: Asymmetry, 1997, 28(27): 547-558.
                                                               [7]   LI Aiju (李爱菊), LI Yushun (李玉顺), ZHANG Zhanchi (张展驰),
                                                                   et al.  Progress  in  synthesis  and  applications  of  diethyl
                                                                   ethoxymethylenemalonate[J]. Shandong Chemical Industry (山东化
                                                                   工), 2015, 44(3): 60-68.
                                                               [8]   ZHANG  Yan  ( 张彦 ), ZHENG Tucai ( 郑土才 ).  Progress  in
                                                                   application  of  diethyl  ethoxymethylenemalonate[J].  Chemical
                                                                   Production and Technology (化工生产与技术), 2013, 20(4): 41-43.
                                                               [9]   SATHISHKUMAR   S,   MAHASAMPATHGOWRI   S,

                                                                   BALASUBRAMANIAN  K  K, et al.  A  convenient  synthesis  of
                         图 5    离子液体的回收利用                          dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates
               Fig. 5    Reuse of chloroaluminatedicationionic liquids   by one carbon extension[J]. Tetrahedron Letters, 2015, 56(26): 4031-
                                                                   4035.
                                                               [10]  PARHAM  W  E,  REED  L  J.  Ethyl  ethoxymethylenemalonate[J].
                 在前 4 次重复使用中,离子液体在分离和纯化                            Organic Synthesis,1955, 3: 395.
            时产生轻微损失,平均每重复用一次收率降低约                              [11]  XUE  Teng  (薛腾),  DU  Huang  (杜煌),  ZHOU  Jian  (周剑),  et al.
                                                                   Synthesis of functional ionic liquid [N 4MIM]Cl and its coordination
            3%。当第 5 次使用催化剂时,MDE 的转化率为 73%。                         complexe  with  Cu   as  a  catalyst  for  ATRP  reaction[J].  Fine
                                                                               +
            适量添加 AlCl 3 可使离子液体恢复活性,EMME 的                          Chemicals (精细化工), 2017, 34(7): 804-809.
                                                               [12]  ZENG  S,  LIU  L,  SHANG  D,  et al.  Efficient  and  reversible
            收率可回到 89%。氯铝酸盐双阳离子液体重复使用                               absorption of ammonia by cobalt ionic liquids through Lewis acid-
            对产品纯度无影响,其既能提供铝盐活性中心,又                                 base  and  cooperative  hydrogen  bond  interactions[J].  Green  Chemistry,
                                                                   2018, 20(9): 2075-2083.
            不使催化剂失活,降低处理费用。                                    [13]  LIU T, ZHANG L X, SUN L Q, et al. Novel geminaldicationic ionic
                                                                   liquid  as  stationary  phase  for  capillary  gas  chromatography[J].
            3    结论                                                Advanced Materials Research, 2011, 382(2012): 477-480.
                                                               [14]  SHIROTA  H,  MANDAI  T,  FUKAZAWA  H,  et al.  Comparison
                                                                   between dicationic and monocationic ionic liquids:    Liquid density,
                 成功制备并表征了 7 种咪唑类氯铝酸盐双阳离                            thermal properties, surface tension, and shear viscosity[J]. Journal of
            子型离子液体,并用于 EMME 的制备反应中。采用                              Chemical & Engineering Data, 2011, 56(5): 2453-2459.
                                                               [15]  LÜ  X  Y,  WANG  W  C,  SUN  Y  Q, et  al.  Ionic  liquids  catalyzed
            IR 测定离子液体的酸度,并通过               27 AlNMR 检测反            Friedel-Crafts  alkylation  of  substituted  benzenes  with  CCl 4  toward
            应前后离子液体中铝的形态来验证推测的反应机                                  trichloromethylarenes[J]. Catalysis Letters, 2018, 149: 665-671.
                                                               [16]  LIU  S,  TAN  S,  BIAN  B, et  al.Isobutane/2-butene  alkylation
            理。优化工艺条件的结果显示:以 0.8%[C 6 (Mim) 2 ]                     catalyzed by Brønsted-Lewis acidic ionic liquids[J]. RSC Advances,
            Cl 2-4AlCl 3 作为催化剂,n(OFE)∶n(MDE)∶n(Ac 2O)=             2018, 8(35): 19551-19559.
                                                               [17]  GUO L, DENG L, JIN X, et al. Composite ionic liquids immobilized
            1.75∶1.00∶2.50 下,分别于 100 ℃反应 2 h,140 ℃                 on MCM-22 as efficient catalysts for the cycloaddition reaction with
            反应 6  h 后,反应转化率、选择性及收率可分别达                             CO 2 and propylene oxide[J]. Catalysis Letters, 2017, 147(9): 1-8.
                                                               [18]  KNIPPING E, AUCHER C, GUIRADO G, et al. Room temperature
            到 98%、98%和 97%。催化剂可套用 4 次,且催化                          ionic  liquids  versus  organic  solvents  as  lithium-oxygen  battery
            效率没有明显降低。氯铝酸盐双阳离子液体在此反                                 electrolytes[J]. New Journal of Chemistry, 2018, 42(6): 4693-4699.
                                                               [19]  QIN Q, ZHANG G, CHAI Z, et al. Ionic liquid-assisted synthesis of
            应中显示出较高的催化效率,大大缩短了反应时间。                                Cu 7Te 4 ultrathin nanosheets with enhanced electrocatalyticactivity for
            本研究对推动双阳离子液体的发展以及探索离子液                                 water oxidation[J]. Nano Energy, 2017, 41: 780-787.
                                                               [20]  ZHANG Baofang (张保芳), PU Min (蒲敏), CHEN Biaohua (陈标
            体在缩合反应中的应用具有一定的意义。                                     华),  et al.  New  environmental-friend  material  imidazolium-based
                                                                   ionic liquids[J]. Journal of Materials Science & Engineering (材料科
            参考文献:                                                  学与工程学报), 2006, 24(1): 165-168.
                                                               [21]  LI  M,  WESTOVER  A  S,  CARTER  R  E,  et al.  Noncovalent  Pi-Pi
            [1]   MA  Mingxia  (马明霞),  OUYANG  Guiping  (欧阳贵平), PEI Juanjuan   stacking  at  the  carbon-electrolyte  interface:  Controlling  the  voltage
                 (裴娟娟), et al. Synthesis and structural characterization of 8-aminobenzo   window  of  electrochemical  supercapacitors[J].  ACS  Applied
                 [4,5]  furo[3,2-d]pyrimidine  derivatives[J].  Fine  Chemicals  (精细化  Materials & Interfaces, 2016, 8(30): 19558-19566.
                 工), 2013, 30(4): 101-105.                     [22]  SWATLOSKI R P, SPEAR S K, HOLBREY J D, et al. Dissolution of
            [2]   PYATAKOV D A, ASTAKHOV A V, SOKOLOV A N, et al. Alkoxy   cellulose [correction of cellose] with ionic liquids[J]. Journal of the
                 base-mediated  selective  synthesis  and  new  rearrangements  of   American Chemical Society, 2002, 124(18): 4974-4975.
                 1,2,4-triazolodipyrimidinones[J].  Tetrahedron  Letters,  2017,  58(8):
                 748-754.                                                                     (下转第 778 页)
   132   133   134   135   136   137   138   139   140   141   142