Efficient and Reusable Pb(II) Metal-Organic Framework for Knoevenagel Condensation

被引:23
作者
Almasi, Miroslav [1 ]
Zelenak, Vladimir [1 ]
Opanasenko, Maksym V. [2 ]
Cejka, Jiri [2 ]
机构
[1] Safarik Univ, Fac Sci, Dept Inorgan Chem, Moyzesova 11, Kosice 04154, Slovakia
[2] ASCR Acad Sci Czech Republ, Vvi, J Heyrovsky Inst Phys Chem, Dept Synth & Catalysis, Dolejskova 2155-3, Prague 18223 8, Czech Republic
关键词
Lead(II); Methanetetrabenzoate; Metal-organic framework; Sorption properties; Knoevenagel condensation; GAS-ADSORPTION PROPERTIES; CATALYTIC-PROPERTIES; NATURAL-PRODUCTS; IONIC LIQUIDS; AQUEOUS-MEDIA; WATER; MOFS; NANOPARTICLES; SEPARATION; ACIDITIES;
D O I
10.1007/s10562-018-2471-8
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A microporous lead-organic framework {[Pb-4(A mu (8) -MTB)(2)(H2O)(4)]center dot 5DMF center dot H2O}(n) (MTB = methanetetrabenzoate, DMF = N,N'-dimethylformamide) was synthesized and studied as a catalyst in Knoevenagel condensation reactions. The framework is built from tetranuclear [Pb-4(A mu (3) -COO)(A mu (2) -COO)(6)(COO)(H2O)(4)] clusters and exhibits a 3D structure, with repeated 1D jar-like cavities with sizes about 14.98 x 7.88 and 14.98 x 13.17 (2) and BET specific surface area of 980 m(2) g(-1). To obtain open framework with unsaturated Pb(II) sites needed for catalysis, the thermal activation of the solvent exchanged sample was performed (DMF was exchanged by EtOH). The activated compound was tested in Knoevenagel condensation of bulky aldehydes and active methylene compounds at different temperatures. Excellent catalytic conversion and selectivity in condensation of small-sized aldehydes with malononitrile was observed, which indicates that the opened Pb(II) sites play a significant role in the heterogeneous catalytic process. Leaching test confirmed the stability of the catalyst in catalytic reactions. Moreover, the compound displayed good recyclability after several reuses without significant decrease in the original catalytic activity. Novel Pb(II) metal-organic framework was tested in Knoevenagel condensation. The catalyst showed excellent catalytic conversion, selectivity and recyclability. Aldehydes with lower kinetic diameter demonstrated high conversions and yields. Catalyst is less efficient for condensation of larger aromatic aldehydes. [GRAPHICS] .
引用
收藏
页码:2263 / 2273
页数:11
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共 54 条
[41]   Synthesis and Characterization of an Amino Functionalized MIL-101(Al): Separation and Catalytic Properties [J].
Serra-Crespo, Pablo ;
Ramos-Fernandez, Enrique V. ;
Gascon, Jorge ;
Kapteijn, Freek .
CHEMISTRY OF MATERIALS, 2011, 23 (10) :2565-2572
[42]   Effects of the Nitridation of Y and USY Zeolites on their Catalytic Activity for the Base Catalyzed Knoevenagel Condensation [J].
Srasra, Mondher ;
Delsarte, Stephanie ;
Gaigneaux, Eric M. .
TOPICS IN CATALYSIS, 2009, 52 (11) :1541-1548
[43]   Amino group immobilized on polyacrylamide: An efficient heterogeneous catalyst for the Knoevenagel reaction in solvent-free and aqueous media [J].
Tamami, B ;
Fadavi, A .
CATALYSIS COMMUNICATIONS, 2005, 6 (11) :747-751
[44]   Domino reactions in the synthesis of heterocyclic natural products and analogs [J].
Tietze, LF ;
Rackelmann, N .
PURE AND APPLIED CHEMISTRY, 2004, 76 (11) :1967-1983
[45]   Application of an amino-functionalised metal-organic framework: an approach to a one-pot acid-base reaction [J].
Toyao, Takashi ;
Fujiwaki, Mika ;
Horiuchi, Yu ;
Matsuoka, Masaya .
RSC ADVANCES, 2013, 3 (44) :21582-21587
[46]   Expanding Applications of Metal-Organic Frameworks: Zeolite Imidazolate Framework ZIF-8 as an Efficient Heterogeneous Catalyst for the Knoevenagel Reaction [J].
Tran, Uyen P. N. ;
Le, Ky K. A. ;
Phan, Nam T. S. .
ACS CATALYSIS, 2011, 1 (02) :120-127
[47]   Construction of 2D interwoven and 3D metal-organic frameworks (MOFs) of Cd(II): the effect of ancillary ligands on the structure and the catalytic performance for the Knoevenagel reaction [J].
Ugale, Bharat ;
Nagaraja, C. M. .
RSC ADVANCES, 2016, 6 (34) :28854-28864
[48]   Metal-dioxidoterephthalate MOFs of the MOF-74 type: Microporous basic catalysts with well-defined active sites [J].
Valvekens, Pieterjan ;
Vandichel, Matthias ;
Waroquier, Michel ;
Van Speybroeck, Veronique ;
De Vos, Dirk .
JOURNAL OF CATALYSIS, 2014, 317 :1-10
[49]   Development of a Scalable Synthesis of a GPR40 Receptor Agonist [J].
Walker, Shawn D. ;
Borths, Christopher J. ;
DiVirgilio, Evan ;
Huang, Liang ;
Liu, Pingli ;
Morrison, Henry ;
Sugi, Kiyoshi ;
Tanaka, Masahide ;
Woo, Jacqueline C. S. ;
Faul, Margaret M. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (03) :570-580
[50]   H3PW12O40/mpg-C3N4 as an efficient and reusable bifunctional catalyst in one-pot oxidation-Knoevenagel condensation tandem reaction [J].
Wang, Hefang ;
Wang, Cunyue ;
Yang, Yongfang ;
Zhao, Meng ;
Wang, Yanji .
CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (02) :405-417