An Efficient and Reusable Multifunctional Composite Magnetic Nanocatalyst for Knoevenagel Condensation

Nan Yao; Jin Tan; Yang Liu; Yu Lin Hu

doi:10.1055/s-0037-1612076

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(06): 699-702
DOI: 10.1055/s-0037-1612076

letter

An Efficient and Reusable Multifunctional Composite Magnetic Nanocatalyst for Knoevenagel Condensation

Authors

Nan Yao
Jin Tan
Yang Liu
Yu Lin Hu *

College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang 443002, P. R. of China eMail: huyulin@ctgu.edu.cn eMail: huyulin1982@163.com

Abstract

Alle Artikel dieser Rubrik

Abstract

A range of multifunctional magnetic metal–organic framework nanomaterials consisting of various mass ratios of the metal–organic framework MIL-53(Fe) and magnetic SiO₂@NiFe₂O₄ nanoparticles were designed, prepared, characterized, and evaluated as heterogeneous catalysts for the Knoevenagel condensation. The as-fabricated nanomaterials, especially the nanocatalyst MIL-53(Fe)@SiO₂@NiFe₂O₄(1.0), showed good catalytic performance in the Knoevenagel condensation at room temperature as a result of synergistic interaction between the Lewis acid iron sites of MIL-53(Fe) and the active sites of the magnetic SiO₂@NiFe₂O₄ nanoparticles. In addition, the heterogeneous catalyst was readily recovered and a recycling test showed that it could be reused for five times without significant loss of its catalytic activity, making it economical and environmentally friendly.

Key words

metal-organic frameworks - magnetic nanocatalyst - Knoevenagel condensation - cooperative catalysis - heterogeneous catalysis - iron catalysis

Volltext

Referenzen

References and Notes
1 Vekariya RH, Patel HD. Synth. Commun. 2014; 44: 2756
2 Krawczyk H, Albrecht Ł. Synthesis 2005; 2887
3 Raytchev PD, Roussi L, Dutasta JP, Martinez A, Dufaud V. Catal. Commun. 2012; 28: 1
4 Wang H, Wang C, Yang Y, Zhao M, Wang Y. Catal. Sci. Technol. 2017; 7: 405
5 Pullabhotla VS. R. R, Rahman A, Jonnalagadda SB. Catal. Commun. 2009; 10: 365
6 Sharma P, Sasson Y. RSC Adv. 2017; 7: 25589
7 Tuci G, Luconi L, Rossin A, Berretti E, Ba H, Innocenti M, Yakhvarov D, Caporali S, Pham-Huu C, Giambastiani G. ACS Appl. Mater. Interfaces 2016; 8: 30099
8 Li G, Xiao J, Zhang W. Green Chem. 2012; 14: 2234
9 Şen B, Akdere E.-H, Şavk A, Gültekin E, Paralı Ö, Göksu H, Şen F. Appl. Catal., B 2018; 225: 148
10 Shirotori M, Nishimura S, Ebitani K. J. Mater. Chem. A 2017; 5: 6947
11 del Hierro I, Pérez Y, Fajardo M. Mol. Catal. 2018; 450: 112
12 Boroujeni KP, Jafarinasab M. Chin. Chem. Lett. 2012; 23: 1067
13 Elhamifar D, Kazempoor S. J. Mol. Catal. A: Chem. 2016; 415: 74
14 Xu G, Wang L, Li M, Tao M, Zhang W. Green Chem. 2017; 19: 5818
15 Calvino-Casilda V, Olejniczak M, Martín-Aranda RM, Ziolek M. Microporous Mesoporous Mater. 2016; 224: 201
16 Varadwaj GB. B, Rana S, Parida KM. Dalton Trans. 2013; 42: 5122
17 Franconetti A, Domínguez-Rodríguez P, Lara-García D, Prado-Gotor R, Cabrera-Escribano F. Appl. Catal., A 2016; 517: 176
18 Li Q, Wang X, Yu Y, Chen Y, Dai L. Tetrahedron 2016; 72: 8358
19 Xu W, Thapa KB, Ju Q, Fang Z, Huang W. Coord. Chem. Rev. 2018; 373: 199
20 Schneemann A, Bon V, Schwedler I, Senkovska I, Kaskel S, Fischer RA. Chem. Soc. Rev. 2014; 43: 6062
21 Zhou W, Wu Y.-P, Wang X, Tian J.-W, Huang D.-D, Zhao J, Lan Y.-Q, Li D.-S. CrystEngComm 2018; 20: 4804
22 Zhang Y, Wang Y, Liu L, Wei N, Gao M.-L, Zhao D, Han Z.-B. Inorg. Chem. 2018; 57: 2193
23 Ezugwu CI, Mousavi B, Asraf MA, Luo Z, Verpoort F. J. Catal. 2016; 344: 445
24 Rambabu D, Ashraf M, Pooja, Gupta A, Dhir A. Tetrahedron Lett. 2017; 58: 4691
25 Opanasenko M, Dhakshinamoorthy A, Shamzhy M, Nachtigall P, Horáček M, Garcia H, Čejka J. Catal. Sci. Technol. 2013; 3: 500
26 Zhang L, He Y, Yang X, Yuan H, Du Z, Wu Y. Chem. Eng. J. (Amsterdam, Neth.) 2015; 278: 129
27 Baig RB. N, Nadagouda MN, Varma RS. Coord. Chem. Rev. 2015; 287: 137
28 Babazadeh M, Hosseinzadeh-Khanmiri R, Abolhasani J, Ghorbani-Kalhor E, Hassanpour A. RSC Adv. 2015; 5: 19884
29 Yang Q, Zhu Y, Luo B, Lan F, Wu Y, Gu Z. Nanoscale 2017; 9: 527
30 Wang H, Zhang W, Zhang F, Cao Y, Su W. J. Magn. Magn. Mater. 2008; 320: 1916
31 Liu Y, Cherkasov N, Gao P, Fernández J, Lees MR, Rebrov EV. J. Catal. 2017; 355: 120
32 Wang G.-H, Lei Y.-Q, Song H.-C. Anal. Methods 2014; 6: 7842
33 Yang Q, Wang J, Chen X, Yang W, Pei H, Hu N, Li Z, Suo Y, Li T, Wang J. J. Mater. Chem. A 2018; 6: 2184
34 Parmekar MV, Salker AV. RSC Adv. 2016; 6: 108458
35 Blanco-Gutierrez V, Virumbrales M, Saez-Puche R, Torralvo-Fernandez MJ. J. Phys. Chem. C 2013; 117: 20927
36 Shigematsu A, Yamada T, Kitagawa H. J. Am. Chem. Soc. 2011; 133: 2034
37 Dong W, Liu X, Shi W, Huang Y. RSC Adv. 2015; 5: 17451
38 2-Benzylidenemalononitrile; Typical ProcedureA mixture of PhCHO (5 mmol), malononitrile (5 mmol), EtOH (15 mL), and MIL-53(Fe)@SiO₂@NiFe₂O₄(1.0) (0.1 g) was magnetically stirred at r.t. until the reaction was complete (TLC). The catalyst that precipitated out from the mixture was collected by using an external magnet, washed with EtOH, and reused for consecutive cycles under the same reaction conditions. The product was crystallized from EtOH to give a white solid; yield: 755 mg (98%); mp 83.8–84.1 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.47–7.64 (m, 3 H, Ar-H), 7.78 (s, 1 H, CH), 7.85–7.94 (m, 2 H, Ar-H). MS: m/z [M + H]⁺ calcd for C₁₀H₇N₂: 155.1; found: 155.06; Anal. Calcd for C₁₀H₆N₂: C, 77.87; H, 3.90; N, 18.15. Found: C, 77.91; H, 3.92; N, 18.17.

Zusatzmaterial

Supporting Information (PDF)