Pd/UiO-66 catalyst for one-pot synthesis of 2-butylcyclohexanone
XUE Wei-yang1,2, WU Hui-ling1,2, GU Bin1, LIU Meng-yang1,2, LI Jing-mei1, SUN Cheng-lin1
1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China; 2. University of Chinese Academy of Sciences, Beijing 100049, China
Abstract: Bifunctional Pd/UiO-66 catalyst is prepared and characterized by means of powder X-ray diffraction,scanning helium ion microscope,N2 physical adsorption,and transmission electron microscope.As the catalyst is employed in preparation of 2-butylcyclohexanone from N-butyraldehyde and cyclohexanone through one-pot method,the conversion of n-butanal can reach 100% and the selectivity of 2-butylcyclohexanone can achieve 62.6%.The effects of reaction temperature,Pd loading amount,catalyst dosage and ketone/aldehyde feeding ratio on the reaction are investigated.During the cycling test,the catalyst shows good stability with little weak of activity and product selectivity.After 3 cycles of reuse,the structure of catalyst remains unchanged.
[1] 邓智先,胡延雷,季棚,等.食用香料5(6)-癸烯酸的研究进展[J].化工中间体,2009,5(9):7-8. [2] Mino T,Masuda S,Nishio M,et al.Synthesis of lactones by baeyer-villiger oxidation with magnesium monoperphthalate hexahydrate[J].The Journal of Organic Chemistry,1997,62(8):2633-2635. [3] 刘树文.丁位烷基内酯及其合成方法的探讨[J].香料与香精,1982,(4):9-14. [4] 朱昌朋.5(6)-癸烯酸的合成[P].CN1266841A,2000-09-20. [5] Zou D,Liu D.Understanding the modifications and applications of highly stable porous frameworks via UiO-66[J].Materials Today Chemistry,2019,12:139-165. [6] Bi F,Zhang X,Chen J,et al.Excellent catalytic activity and water resistance of UiO-66-supported highly dispersed Pd nanoparticles for toluene catalytic oxidation[J].Applied Catalysis B:Environmental,2020,269:118767. [7] Chen D,Yang W,Jiao L,et al.Boosting catalysis of Pd nanoparticles in MOFs by pore wall engineering:The roles of electron transfer and adsorption energy[J].Adv Mater,2020,32(30):e2000041. [8] Chang Z,Li F,Qi X,et al.Selective and efficient adsorption of Au(Ⅲ) in aqueous solution by Zr-based metal-organic frameworks (MOFs):An unconventional way for gold recycling[J].J Hazard Mater,2020,391:122175. [9] 张雯,鲁金明,刘毅,等.混合配体合成金属有机骨架UiO-66吸附剂的研究[J].现代化工,2019,39(10):101-105. [10] Vikrant K,Deng Y X,Kim K H,et al.Application of Zr-cluster-based MOFs for the adsorptive removal of aliphatic aldehydes (C1 to C5) from an industrial solvent[J].ACS Appl Mater Interfaces,2019,11(47):44270-44281. [11] 韩易潼,刘民,李克艳,等.高稳定性金属有机骨架UiO-66的合成与应用[J].应用化学,2016,33(04):367-78. [12] Dhakshinamoorthy A,Santiago-portillo A,Asiri A M,et al.Engineering UiO-66 metal organic framework for heterogeneous catalysis[J].ChemCatChem,2019,11(3):899-923. [13] Jiang D,Fang G,Tong Y,et al.Multifunctional Pd@UiO-66 catalysts for continuous catalytic upgrading of ethanol to n-butanol[J].ACS Catalysis,2018,8(12):11973-11978. [14] Bakuru V R,Davis D,Kalidindi S B.Cooperative catalysis at the metal-MOF interface:Hydrodeoxygenation of vanillin over Pd nanoparticles covered with a UiO-66(Hf) MOF[J].Dalton Trans,2019,48(24):8573-8577. [15] Vermoortele F,Ameloot R,Vimont A,et al.An amino-modified Zr-terephthalate metal-organic framework as an acid-base catalyst for cross-aldol condensation[J].Chemical Communications,2011,47(5):1521-1523. [16] Hajek J,Vandichel M,Van De Voorde B,et al.Mechanistic studies of aldol condensations in UiO-66 and UiO-66-NH2 metal organic frameworks[J].Journal of Catalysis,2015,331:1-12. [17] 张艳梅,戴田霖,张帆,等.核壳结构Fe3O4@UiO-66-NH2磁性纳米复合材料的合成及其催化Knoevenagel缩合反应性能(英文)[J].催化学报,2016,37(12):2106-2113. [18] Li X,Guo Z,Xiao C,et al.Tandem catalysis by palladium nanoclusters encapsulated in metal-organic frameworks[J].ACS Catalysis,2014,4(10):3490-3497. [19] Herbst A,Janiak C.MOF catalysts in biomass upgrading towards value-added fine chemicals[J].CrystEngComm,2017,19(29):4092-4117. [20] Cavka J H,Jakobsen S,Olsbye U,et al.A new zirconium inorganic building brick forming metal organic frameworks with exceptional stability[J].Journal of the American Chemical Society,2008,130(42):13850-13851. [21] Ren J,Langmi H W,North B C,et al.Modulated synthesis of zirconium-metal organic framework (Zr-MOF) for hydrogen storage applications[J].International Journal of Hydrogen Energy,2014,39(2):890-895. [22] Sun R,Liu B,Li B G,et al.Palladium(II)@Zirconium-Based mixed-linker metal-organic frameworks as highly efficient and recyclable catalysts for suzuki and heck cross-coupling reactions[J].ChemCatChem,2016,8(20):3261-3271. [23] Schaate A,Roy P,Godt A,et al.Modulated synthesis of Zr-based metal-organic frameworks:From nano to single crystals[J].Chemistry,2011,17(24):6643-6651. [24] Gallezot P,Richard D.Selective hydrogenation of α,β-unsaturated aldehydes[J].Catalysis Reviews,1998,40(1-2):81-126.