Chemical Industry and Engineering Progress ›› 2018, Vol. 37 ›› Issue (12): 4669-4678.DOI: 10.16085/j.issn.1000-6613.2018-0200
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QI Yani, FENG Zhenlong, JI Haoke, WANG Hao, ZHU Qianwen, ZHANG Xuejie, ZHOU Yebin, LU Chunshan, LI Xiaonian
Received:
2018-01-23
Revised:
2018-05-28
Online:
2018-12-05
Published:
2018-12-05
齐亚妮, 冯振龙, 季豪克, 王昊, 朱倩文, 张雪洁, 周烨彬, 卢春山, 李小年
通讯作者:
卢春山,副教授,硕士生导师,研究方向为工业催化。
作者简介:
齐亚妮(1993-),女,硕士研究生,研究方向为工业催化。E-mail:qiyani12@163.com。
基金资助:
CLC Number:
QI Yani, FENG Zhenlong, JI Haoke, WANG Hao, ZHU Qianwen, ZHANG Xuejie, ZHOU Yebin, LU Chunshan, LI Xiaonian. Latest progress on synthesis of chloroaniline by selective catalytic hydrogenation[J]. Chemical Industry and Engineering Progress, 2018, 37(12): 4669-4678.
齐亚妮, 冯振龙, 季豪克, 王昊, 朱倩文, 张雪洁, 周烨彬, 卢春山, 李小年. 选择性催化加氢合成氯代苯胺最新进展[J]. 化工进展, 2018, 37(12): 4669-4678.
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[1] CÁRDENAS-LIZANA F, HAO Y F, CRESPO-QUESADA M, et al. Selective gas phase hydrogenation of p-chloronitrobenzene over Pd[J]. ACS Catalysis, 2013, 3:1386-1396. [2] MA L, WANG J G, ZHANG H B, et al.High halogenated nitrobenzene hydrogenation selectivity over nano Ir particles[J]. Chinese Journal of Chemical Engineering, 2018, 25(3):306-312. [3] LI H, XU C F, MU X-L, et al.Acetylene-mediated synthesis of supported Pt nanocatalyst for selective hydrogenation of halonitrobenzene[J]. ChemNanoMat, 2018, 4(5):518-523. [4] DONGIL A B, PASTOR-PEREZ L, FIERRO J L G, et al.Synthesis of palladium nanoparticles on carbon nanotubes and graphene for the chemoselective hydrogenation of para-chloronitrobenzene[J]. Catalysis Communications, 2016, 75:55-59. [5] DONGIL A B, PASTOR-PEREZ L, FIERRO J L G, et al.Synthesis of palladium nanoparticles over graphite oxide and carbon nanotubes by reduction in ethylene glycol and their catalytic performance on the chemoselective hydrogenation of para-chloronitrobenzene[J]. Applied Catalysis A:General, 2016, 513:89-97. [6] WANG Y, RONG Z M, WANG Y, et al.Ruthenium nanoparticles loaded on multiwalled carbon nanotubes for liquid-phase hydrogenation of fine chemicals:an exploration of confinement effect[J]. Journal of Catalysis, 2015, 329:95-106. [7] OUBENALI M, VANUCCI G, MACHADO B, et al.Hydrogenation of p-chloronitrobenzene over nanostructured-carbon-supported ruthenium catalysts[J]. ChemSusChem, 2011, 4(7):950-956. [8] BESWICK O, LAMEY D, MURISET F, et al.Ni-based structured catalyst for selective 3-phase hydrogenation of nitroaromatics[J]. Catalysis Today, 2016, 273:244-251. [9] LI X, ZHAO S, ZHANG W, et al.Ru nanoparticles supported on nitrogen-doped porous carbon derived from ZIF-8 as an efficient catalyst for the selective hydrogenation of p-chloronitrobenzene and p-bromonitrobenzene[J]. Dalton Trans, 2016, 45(39):15595-15602. [10] WANG X, LI Y W.Chemoselective hydrogenation of functionalized nitroarenes using MOF-derived Co-based catalysts[J]. Journal of Molecular Catalysis A:Chemical, 2016, 420:56-65. [11] XIE Y L, XIAO N, YU C, et al. Magnetically recyclable Pt/C(Ni) nanocatalysts with improved selectivity for hydrogenation of o-chloronitrobenzene[J]. Catalysis Communications, 2012, 28:69-72. [12] XU X S, LI X Q, GU H Z, et al. A highly active and chemoselective assembled Pt/C(Fe) catalyst for hydrogenation of o-chloronitrobenzene[J]. Applied Catalysis A:General, 2012, 429/430:17-23. [13] TSU Y T, CHEN Y W.Hydrogenation of p-chloronitrobenzene on Au nano-clusters:effect of support[J]. Journal of Nanoscience and Nanotechnology, 2018, 18(1):301-308. [14] ZHANG Q F, MA L, LU C S, et al.Solvent-free selective hydrogenation of o-chloronitrobenzene over large palladium particles on oxygen-poor activated carbon[J]. Reaction Kinetics, Mechanisms and Catalysis, 2015, 114(2):629-638. [15] EVAGELISTI C, ARONICA L A, BOTAVINA M, et al. Chemoselective hydrogenation of halonitroaromatics over γ-Fe2O3-supported platinum nanoparticles:the role of the support on their catalytic activity and selectivity[J]. Journal of Molecular Catalysis A:Chemical, 2013, 366:288-293. [16] LIU H Q, LIANG M H, XIAO C, et al.An excellent Pd-based nanocomposite catalyst for the selective hydrogenation of para-chloronitrobenzene[J]. Jourmal of Molecular Catalysis A:Chemical, 2009, 308:79-86. [17] 宋华, 汪淑影, 李锋, 等.微乳液法制备Pt/Al2O3催化剂及其催化氯代硝基苯选择加氢活性[J]. 化工进展, 2011, 30(3):771-776. SONG H, WANG S Y, LI F, et al.Preparation of Pt/Al2O3 catalyst by microemulsion and its activity in selective hydrogenation of chloronitrobenzene[J]. Chemical Industry and Engineering Progress, 2011, 30(3):771-776. [18] LI F, CAO B, MA R, et al.Preparation of Pt/Al2O3 catalyst in CTAB microemulsion and kinetics of m-chloronitrobenzene hydrogenation[J]. Russian Journal of Physical Chemistry A, 2016, 90(2):276-281. [19] LI Y Z, YU J Y, LI W, et al.The promotional effect of surface defects on the catalytic performance of supported nickel-based catalysts[J]. Physical Chemistry Chemical Physics, 2016, 18(9):6548-6558. [20] PIETROWSKI M, WOJCIECHOWSKA M.The origin of increased chemoselectivity of platinum supported on magnesium fluoride in the hydrogenation of chloronitrobenzene[J]. Catalysis Today, 2011, 169(1):217-222. [21] PIETROWSKI M, ZIELINSKI M, WOJCIECHOWSKA M. Nanocolloidal Ru/MgF2 catalyst for hydrogenation of chloronitrobenzene and toluene[J]. Polish Journal of Chemical Technology, 2014, 16(2):63-68. [22] HAN X X, ZHOU R X, LAI G H, et al.Influence of rare earth (Ce, Sm, Nd, La, and Pr) on the hydrogenation properties of chloronitrobenzene over Pt/ZrO2 catalyst[J]. Catalysis Letters, 2003, 89(3/4):255-259 [23] XIE Y L, XIAO N, LING Z, et al.Flower-like Co-Ni/C bimetallic catalysts for the selective hydrogenation of o-chloronitrobenzene[J]. Chinese Journal of Catalysis, 2012, 33(11/12):1883-1888. [24] MAHATA N, SOARES O S G P, RODRIGUEZ-RAMOS I, et al. Promotional effect of Cu on the structure and chloronitrobenzene hydrogenation performance of carbon nanotube and activated carbon supported Pt catalysts[J].Applied Catalysis A:General, 2013, 464/465:28-34. [25] MISTRI R, LLORCA J, RAY B C, et al.Pd0.01Ru0.01Ce0.98O2-δ:a highly active and selective catalyst for the liquid phase hydrogenation of p-chloronitrobenzene under ambient conditions[J]. Journal of Molecular Catalysis A:Chemical, 2013, 376:111-119. [26] LIU M H, BAI Q, XIAO H L, et al.Selective hydrogenation of o-chloronitrobenzene over tin dioxide supported platinum-ruthenium bimetallic nanocatalysts without solvent[J]. Chemical Engineering Journal, 2013, 232:89-95. [27] LIHAMA S, FURUKAWA S, KOMATSU T. Efficient catalytic system for chemoselective hydrogenation of halonitrobenzene to haloaniline using PtZn intermetallic compound[J]. ACS Catalysis, 2016, 6(2):742-746. [28] WU M, XU Y, JU J X, et al.Preparation of Pd-B/palygorskite amorphous catalyst for the selective hydrogenation of o-chloronitrobenzene to o-chloroaniline[J]. Micro & Nano Letters, 2016, 11(6):315-318. [29] LI F, MA R, CAO B, et al.Effect of Co-B supporting methods on the hydrogenation of m-chloronitrobenzene over Co-B/CNTs amorphous alloy catalysts[J].Applied Catalysis A, 2016, 14:248-252. [30] LI F, CAO B, MA R, et al.Preparation of Pt-B/Al2O3 amorphous alloy catalysts via microemulsion methods and application into hydrogenation of m-chloronitrobenzene[J]. The Canadian Journal of Chemical Engineering, 2016, 94(1):89-93. [31] LIU H, DENG J, LI W.Synthesis of nickel nanoparticles supported on boehmite for selective hydrogenation of p-nitrophenol and p-chloronitrobenzene[J]. Catalysis Letters, 2010, 137(3/4):261-266. [32] CHEN Y W, LEE D S.Hydrogenation of p-chloronitrobenzene on nanosized modified NiMoB catalysts[J]. Catalysis Surveys from Asia, 2012, 16(4):198-209. [33] ZHAO B, CHEN Y W.The effect of poly-N-vinylpyrrolidone modification on NiCoB catalysts for hydrogenation of p-chloronitrobenzene[J]. Materials Chemistry and Physics, 2011, 125(3):763-768. [34] LIU M H, ZHANG J, LIU J Q, et al.Synthesis of PVP-stabilized Pt/Ru colloidal nanoparticles by ethanol reduction and their catalytic properties for selective hydrogenation of ortho-chloronitrobenzene[J]. Journal of Catalysis, 2011, 278(1):1-7. [35] LI F, CAO B, MA R, et al.Polyvinylpyrrolidone-stabilized Pt colloidal catalysts in chloronitrobenzene hydrogenation and modification with rare earth ions[J]. Reaction Kinetics, Mechanisms and Catalysis, 2015, 116(2):479-489. [36] LI F, MA R, SONG H L, et al.Selective hydrogenation of m-chloronitrobenzene to m-chloroaniline over polyvinyl-pyrrolidone-stabilized Pt and Pt/Sn catalysts[J].Russian Journal of Physical Chemistry A, 2015, 89(5):766-770. [37] DANI A, CROCELLA V, MADDALENA L, et al.Spectroscopic study on the surface properties and catalytic performances of palladium nanoparticles in poly(ionic liquid)s[J].The Journal of Physical Chemistry C, 2016, 120(3):1683-1692. [38] LU C S, WANG M J, FENG Z L, et al.A phosphorus-carbon framework over activated carbon supported palladium nanoparticles for the chemoselective hydrogenation of para-chloronitrobenzene[J]. Catalysis Science & Technology, 2017, 7(7):1581-1589. [39] SHI W, ZHANG B S, LIN Y M, et al.Enhanced chemoselective hydrogenation through tuning the interaction between pt nanoparticles and carbon supports:insights from identical location transmission electron microscopy and X-ray photoelectron spectroscopy[J].ACS Catalysis, 2016, 6(11):7844-7854. [40] ZHANG Q F, SU C, CEN J, et al.The modification of diphenyl sulfide to Pd/C catalyst and its application in selective hydrogenation of p-chloronitrobenzene[J].Chinese Journal of Chemical Engineering, 2014, 22(10):1111-1116. [41] WEI Q, SHI Y S, SUN K Q, et al. Pd-on-Si catalysts prepared via galvanic displacement for the selective hydrogenation of para-chloronitrobenzene[J].Chemical Communications, 2016, 52(14):3026-3029. [42] HU Z, TAN S Q, MI R L, et al.Solvent-controlled reactivity of Au/CeO2 towards hydrogenation of p-chloronitrobenzene[J]. Catalysis Letters, 2018, 148(5):1490-1498. [43] 卢春山.氯代苯胺合成中金属催化剂性能与溶剂效应研究[D].杭州:浙江工业大学, 2011. LU C S.Solvent effects and the catalytic performance of metallic catalysis in the highly selective hydrogenation of chloronitrobenzenes to chloroanilines[D]. Hangzhou:Zhejiang University of Technology, 2011. [44] NING J B, XU J, LIU J, et al.A remarkable promoting effect of water addition on selective hydrogenation of p-chloronitrobenzene in ethanol[J]. Catalysis Communications, 2007, 8(11):1763-1766. [45] XIAO C, WANG H, MU X, et al.Ionic-liquid-like copolymer stabilized nanocatalysts in ionic liquids Ⅰ. Platinum catalyzed selective hydrogenation of o-chloronitrobenzene[J]. Journal of Catalysis, 2007, 250(1):25-32. [46] XI C Y, CHENG H Y, HAO J M, et al.Hydrogenation of o-chloronitrobenzene to o-chloroaniline over Pd/C in supercritical carbon dioxide[J]. Journal of Molecular Catalysis A:Chemical, 2008, 282(1/2):80-84. [47] ICHIKAWA S, TADA M, IWASAWA Y, et al.The role of carbon dioxide in chemoselective hydrogenation of halonitroaromatics over supported noble metal catalysts in supercritical carbon dioxide[J]. Chem Commun (Camb), 2005(7):924-926. [48] WANG X D, PERRET N, KEANE M A.The role of hydrogen partial pressure in the gas phase hydrogenation of p-chloronitrobenzene over alumina supported Au and Pd:a consideration of reaction thermodynamics and kinetics[J].Chemical Engineering Journal, 2012, 210:103-113. [49] PERRET N, CARDENAS-LIZANA F, LAMEY D, et al.Effect of crystallographic phase (beta vs. gamma) and surface area on gas phase nitroarene hydrogenation over Mo2N and Au/Mo2N[J].Topics in Catalysis, 2012, 55(14/15):955-968. [50] YU W, LIN H W, TAN C S, et al.Direct synthesis of Pd incorporated in mesoporous silica for solvent-free selective hydrogenation of chloronitrobenzenes[J]. Chemical Engineering Journal, 2017, 325:124-133. [51] 李小年, 卢春山, 吕井辉, 等.一种无溶剂条件下高选择性液相加氢合成卤代芳胺的方法:CN201010153731.1[P]. 2010-08-25. LI X N, LU C S, LÜ J H, et al. A highly selective hydrogenation of halogenated aromatic amines under solvent-free conditions in liquid phase:CN201010153731.1[P]. 2010-08-25. [52] LIAN C, LIU H Q, XIAO C, et al. Solvent-free selective hydrogenation of chloronitrobenzene to chloroaniline over a robust Pt/Fe3O4 catalyst[J]. Chemical Communications, 2012, 48(25):3124-3126. [53] WANG Y A, YANG Y X, LI Y W, et al.A green synthesis route of ortho-chloroaniline:solvent-free selective hydrogenation of ortho-chloronitrobenzene over Pt-Ru/Fe3O4/C catalyst[J].Catalysis Communications, 2012, 19:110-114. [54] LIU M H, BAI Q, XIAO H L, et al.Selective hydrogenation of o-chloronitrobenzene over tin dioxide supported platinum-ruthenium bimetallic nanocatalysts without solvent[J].Chemical Engineering Journal, 2013, 232:89-95. [55] YU W, LIN H W, TAN C S.Direct synthesis of Pd incorporated in mesoporous silica for solvent-free selective hydrogenation of chloronitrobenzenes[J]. Chemical Engineering Journal, 2017, 325:124-133. |
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