Research progress in catalysts for selective hydrogenation of butadiene
MA Hao-wen1,2, YANG Chun-liang3, MA Ping1, CHEN Ming-lin1, FENG Hui-xia2, ZHAN Xue-cheng1, XIE Yuan1
1. Lanzhou Petrochemical Research Center, PetroChina Petrochemical Research Institute, Lanzhou 730060, China; 2. College of Petrochemical Technology, Lanzhou University of Technology, Lanzhou 730050, China; 3. Ningbo Kingfa New Material Co., Ltd., Ningbo 315000, China
Abstract: With the integration of refining and chemical industries and the rapid development of coal chemical industry, the amount of C4 by-product resources has grown substantially.Selective butadiene hydrogenation technology is the key to realize the appreciation and utilization of C4 fractions.However, the selective hydrogenation of butadiene to produce 1-butene will also accompany with the formation of by-products such as 2-butene and butane.Therefore, the development of catalysts with high activity and selectivity is the most important research content in this field.The design, preparation and application of the catalysts for selective butadiene hydrogenation in recent years are introduced.Several strategies for optimizing catalyst performance are summarized, and the application prospects of transition metal-based catalysts for selective butadiene hydrogenation are discussed.
马好文, 杨春亮, 马萍, 陈明林, 冯辉霞, 展学成, 谢元. 丁二烯选择性加氢催化剂研究进展[J]. 现代化工, 2021, 41(S1): 95-99.
MA Hao-wen, YANG Chun-liang, MA Ping, CHEN Ming-lin, FENG Hui-xia, ZHAN Xue-cheng, XIE Yuan. Research progress in catalysts for selective hydrogenation of butadiene. Modern Chemical Industry, 2021, 41(S1): 95-99.
[1] Wang Z,Wang G,Louis C,et al.Novel non-noble bimetallic Cu-Zn/TiO2 catalysts for selective hydrogenation of butadiene[J].Journal of Catalysis,2017,347:185-196. [2] Feng Y X,Zhou L S,Wan Q,et al.Selective hydrogenation of 1,3-butadiene catalyzed by a single Pd atom anchored on graphene:The importance of dynamics[J].Chemical Science,2018,9(27):5890-5896. [3] 郭振宇,詹小燕,陈浩.炼厂碳四资源利用方案的探讨[J].辽宁化工,2020,49(6):663-665. [4] Hou R J,Yu W T,Porosoff M D,et al.Selective hydrogenation of 1,3-butadiene on PdNi bimetallic catalyst:From model surfaces to supported catalysts[J].Journal of Catalysis,2014,316:1-10. [5] Lee D C,Kim J H,Kim W J,et al.Selective hydrogenation of 1,3-butadiene on TiO2-modified Pd/SiO2 catalysts[J].Applied Catalysis A:General,2003,244(1):83-91. [6] Pattamakomsan K,Ehret E,Morfin F,et al.Selective hydrogenation of 1,3-butadiene over Pd and Pd-Sn catalysts supported on different phases of alumina[J].Catalysis Today,2011,164(1):28-33. [7] Ardiaca N O,Bressa S P,Alves J A,et al.Experimental procedure for kinetic studies on egg-shell catalysts[J].Catalysis Today,2001,64(3/4):205-215. [8] 赵多.碳四选择性加氢催化剂结构与性能调控[D].上海:华东理工大学,2020. [9] Huang J L,Odoom-wubah T,Jing X L,et al.Plant-mediated synthesis of zinc oxide supported nickel-palladium alloy catalyst for the selective hydrogenation of 1,3-butadiene[J].Chem Cat Chem,2017,9(5):870-881. [10] 乐毅,杨栋,朱云仙,等.Pd-Ag/Al2O3催化剂上丁二烯的加氢反应性能[J].化工进展,2013,32(2):364-367,403. [11] 刘宪新,李斯琴.裂解汽油一段加氢Pd系和新型Ni系催化剂加氢性能对比及影响因素浅析[J].乙烯工业,2007,19(2):50-54,55. [12] Hou R J,Porosoff M D,Chen J G,et al.Effect of oxide supports on Pd-Ni bimetallic catalysts for 1,3-butadiene hydrogenation[J].Applied Catalysis A:General,2015,490:17-23. [13] 陈红娟,徐海升,王长发.丁二烯选择性加氢催化剂制备因素研究进展[J].西安石油学院学报(自然科学版),2002,17(3):41-45. [14] Lozano L,Brito J L,Olivera C,et al.Influence of toluene on the catalytic activity of NiPdCe catalyst for selective hydrogenation of 1,3-butadiene[J].Fuel,2013,110:76-82. [15] Piccolo L,Kibis L,Deweerd M,et al.Intermetallic compounds as potential alternatives to noble metals in heterogeneous catalysis:The partial hydrogenation of butadiene on γ-Al4Cu9(110)[J].ChemCatChem,2017,9(12):2292-2296. [16] Dror Y,Manassen J.Hydrogenation of olefins with rhodium-phosphine complexes,having substrate and catalyst in two different immiscible phases.An alternative method for the heterogenization of a homogeneous catalyst[J].Journal of Molecular Catalysis,1977,2(3):219-222. [17] Massard R,Uzio D,Thomazeau C,et al.Strained Pd overlayers on Ni nanoparticles supported on alumina and catalytic activity for buta-1,3-diene selective hydrogenation[J].Journal of Catalysis,2007,245(1):133-143. [18] Vigne F,Haubrich J,Loffreda D,et al.Highly selective hydrogenation of butadiene on Pt/Sn alloy elucidated by first-principles calculations[J].Journal of Catalysis,2010,275(1):129-139. [19] Piccolo L,Valcarcel A,Bausach M,et al.Tuning the shape of nanoparticles to control their catalytic properties:Selective hydrogenation of 1,3-butadiene on Pd/Al2O3[J].Physical Chemistry Chemical Physics,2008,10(36):5504-5506. [20] 马好文,展学成,郑云弟,等.烷基化原料预加氢催化剂LY-DBiso-03和PDB-02[J].石油科技论坛,2017,36(S1):191-193,212. [21] Bridier B,Karhanek D,Perez-ramirez J,et al.Molecular understanding of enyne hydrogenation over palladium and copper catalysts[J].ChemCatChem,2012,4(9):1420-1427. [22] Gomez G,Belelli P G,Cabeza G F,et al.A theoretical view of 1,3-butadiene selective hydrogenation toward cis-2-butene on PdNi layered catalyst[J].Applied Surface Science,2015,353:820-828. [23] Alves J A,Bressa S P,Martinez O M,et al.Kinetic evaluation of the set of reactions in the selective hydrogenation of 1-butyne and 1,3-butadiene in presence of n-butenes[J].Industrial & Engineering Chemistry Research,2013,52(17):5849-5861. [24] Cooper A,Bachiller-baeza B,Aanderson J A,et al.Design of surface sites for the selective hydrogenation of 1,3-butadiene on Pd nanoparticles:Cu bimetallic formation and sulfur poisoning[J].Catalysis Science & Technology,2014,4(5):1446-1455. [25] Furlong B K,Hightower J W,Chan Y L,et al.1,3-Butadiene selective hydrogenation over Pd/Alumina and CuPd/Alumina catalysts[J].Applied Catalysis A,2015,117(1):41-51. [26] 皇甫协立,李世伟,赵多.C4选择加氢催化剂SHB-01的工业应用[J].石油炼制与化工,2018,49(8):28-31. [27] Ma H W,Xu X P,Xu H X,et al.Understanding composition-dependent catalytic performance of PdAg for the hydrogenation of 1,3-butadiene to 1-butene[J].Catalysis Communications,2021,149:106255. [28] 任志鹏,杨智,张谦温.裂解汽油一段选择加氢Ni系催化剂的研究进展[J].石油化工,2009,38(1):98-102. [29] Spanjers C S,Sim R S,Sturgis N P,et al.In situ spectroscopic characterization of Ni1-xZnx/ZnO catalysts and their selectivity for acetylene semi-hydrogenation in excess ethylene[J].ACS Catalysis,2015,5(6):3304-3315. [30] Jeon J K,Park S K,Park Y K.Effects of phosphorous promoters on catalytic performance for oligomerization of butene over Ni-based catalysts[J].Catalysis Today,2004,93/95:467-470. [31] 刘建军,黄星亮.Ag助剂对C4烃选择加氢Ni基催化剂的影响[J].石油化工,2011,40(8):825-830. [32] Ding L N,Zheng M Y,Wang A Q,et al.A novel route to the preparation of carbon supported nickel phosphide catalysts by a microwave heating process[J].Catalysis Letters,2010,135(3-4):305-311. [33] 刘铁峰,郑卓.C4馏分中丁二烯选择性加氢镍基催化剂制备和应用[J].工业催化,2014,22(5):374-377. [34] Phillipson J J,Wells P B,Wilson G R.The hydrogenation of alkadienes.Part Ⅲ.The hydrogenation of buta-1,3-diene catalysed by iron,cobalt,nickel,and copper[J].Journal of the Chemical Society A Inorganic Physical Theoretical,1969,1351-1363. [35] Nudel J N,Umansky B S,Piagentini R O,et al.Selective hydrogenation of 1,3-butadiene over LaCoO3 perovskite[J].Journal of Catalysis,1984,89(2):362-370. [36] Yang Q C,Qiu R,Ma X X,et al.Surface reconstruction and the effect of Ni-modification on the selective hydrogenation of 1,3-butadiene over Mo2C-based catalysts[J].Catalysis Science & Technology,2020,10(11):3670-3680. [37] Zambelli T,Wintterlin J,Trost J,et al.Identification of the "active sites" of a surface-catalyzed reaction[J].Science,1996,273(5282):1688-1690. [38] Loffreda D,Michel C,Delbecq F,et al.Tuning catalytic reactivity on metal surfaces:Insights from DFT[J].Journal of Catalysis,2013,308:374-385. [39] Lu F F,Sun D H,Huang J L,et al.Plant-mediated synthesis of Ag-Pd alloy nanoparticles and their application as catalyst toward selective hydrogenation[J].ACS Sustainable Chemistry & Engineering,2014,2(5):1212-1218. [40] Liu D,Chen H Y,Zhang J Y,et al.Theoretical investigation of selective hydrogenation of 1,3-butadiene on Pt doping Cu nanoparticles[J].Applied Surface Science,2018,456:59-68. [41] Yang K R,Yang B.Identification of the active and selective sites over a single Pt atom-alloyed Cu catalyst for the hydrogenation of 1,3-butadiene:A combined DFT and microkinetic modeling study[J].The Journal of Physical Chemistry C,2018,122(20):10883-10891. [42] Feng Y,Zhou L,Wan Q,et al.Selective hydrogenation of 1,3-butadiene catalyzed by a single Pd atom anchored on graphene:The importance of dynamics[J].Chemical Science,2018,9(27):5890-5896. [43] Zhang X,Shi H,Xu B Q.Catalysis by gold:Isolated surface Au3+ ions are active sites for selective hydrogenation of 1,3-butadiene over Au/ZrO2 catalysts[J].Angewandte Chemie International Edition,2005,44(43):7132-7135. [44] Zhang Z C,Zhang X,Yu Q Y,et al.Pd cluster nanowires as highly efficient catalysts for selective hydrogenation reactions[J].Chemistry,2012,18(9):2639-2645.