Magnetically recyclable Cu-BTC@SiO2@Fe3O4 catalysts and their catalytic performance for the Pechmann reaction

Industrial and Engineering Chemistry Research

Volumn 53, Issue 39, 2014, Pages 14948-14955

  Li, Qingyuan ^a   Jiang, Sai ^a   Ji, Shengfu ^a   Shi, Da ^a   Yan, Junlei ^a   Huo, Yanxia ^a   Zhang, Qingmin ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; CATALYST SELECTIVITY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; IRON OXIDES; MAGNETITE; NANOMAGNETICS; NAPHTHOL; SCANNING ELECTRON MICROSCOPY; SILICA; SILICON; SIO2 NANOPARTICLES; SYNTHESIS (CHEMICAL);

CATALYTIC PERFORMANCE; ETHYLACETOACETATE; FE3O4 NANOPARTICLES; FOURIER TRANSFORM INFRA RED (FTIR) SPECTROSCOPY; PECHMANN REACTION; REACTION CONDITIONS; RECOVERY PROPERTIES; VIBRATION SAMPLE MAGNETOMETERS;

CATALYST ACTIVITY;

EID: 84907487858     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie502489q     Document Type: Article

References (40)

1. Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Coumarins in Polymers: From Light Harvesting to Photo-Cross-Linkable Tissue Scaffolds Chem. Rev. 2004, 104, 3059
2. Ahmed, A. I.; El-Hakam, S. A.; Khder, A. S.; Abo El-Yazeed, W. S. Nanostructure Sulphated Tin Oxide as an Efficient Catalyst for the Preparation of 7-Hydroxy-4-methyl Coumarin by Pechmann Condensation Reaction J. Mol. Catal. A: Chem. 2013, 366, 99
3. Bose, D. S.; Rudradas, A.; Babu, M. H. The Indium(III) Chloride-Catalyzed von Pechmann Reaction: A Simple and Effective Procedure for the Synthesis of 4-Substituted Coumarins Tetrahedron Lett. 2002, 43, 9195
4. Daru, J.; Stirling, A. Mechanism of the Pechmann Reaction: A Theoretical Study J. Org. Chem. 2011, 76, 8749
5. Laufer, M. C.; Hausmann, H.; Hclderich, W. F. Synthesis of 7-Hydroxycoumarins by Pechmann Reaction Using Nafion Resin/Silica Nanocomposites as Catalysts J. Catal. 2003, 218 (2) 315
6. Hinze, R.; Laufer, M. C.; Holderich, W. F.; Bonrath, W.; Netscher, T. The Use of Nafion/Silica Composite Catalysts for Synthesis of Fine Chemicals Catal. Today 2009, 140, 105
7. Gunnewegh, E. A.; Hoefnagel, A. J.; van Bekkum, H. Zeolite Catalysed Synthesis of Coumarin Derivatives J. Mol. Catal. A: Chem. 1995, 100, 87
8. Gu, Y.; Zhang, J.; Duan, Z.; Deng, Y. Pechmann Reaction in Non-Chloroaluminate Acidic Ionic Liquids under Solvent-Free Conditions Adv. Synth. Catal. 2005, 347, 512
9. Tyagi, B.; Mishra, M. K.; Jasra, R. V. Microwave-Assisted Solvent Free Synthesis of Hydroxy Derivatives of 4-Methyl Coumarin Using Nano-Crystalline Sulfated-Zirconia Catalyst J. Mol. Catal. A: Chem. 2008, 286, 41
10. Hoefnagel, A. J.; Gunnewegh, E. A.; Downing, R. S.; van Bekkum, H. Synthesis of 7-Hydroxycoumarins Catalysed by Solid Acid Catalysts J. Chem. Soc., Chem. Commun. 1995, 225
11. Selvakumar, S.; Chidambaram, M.; Singh, A. P. Benzylsulfonic Acid Functionalized Mesoporous Zr-TMS Catalysts: An Efficient and Recyclable Catalyst for the Preparation of Coumarin Derivatives by Pechmann Condensation Reaction Catal. Commun. 2007, 8, 777
12. Kalita, P.; Sathyaseelan, B.; Mano, A.; Javaid Zaidi, S. M.; Chari, M. A.; Vinu, A. Synthesis of Superacid-Functionalized Mesoporous Nanocages with Tunable Pore Diameters and Their Application in the Synthesis of Coumarins Chem.-Eur. J. 2010, 16, 2843
13. Kalita, P.; Kumar, R. Solvent-Free Coumarin Synthesis via Pechmann Reaction Using Solid Catalysts Microporous Mesoporous Mater. 2012, 149, 1
14. Yoon, M.; Srirambalaji, R.; Kim, K. Homochiral Metal-Organic Framework for Asymmetric Heterogeneous Catalysis Chem. Rev. 2012, 112, 1196
15. Tanabe, K. K.; Cohen, S. M. Postsynthetic Modification of Metal-Organic Frameworks-A Progress Report Chem. Soc. Rev. 2011, 40, 498
16. Jiang, H. L.; Xu, Q. Porous Metal-Organic Frameworks as Platforms for Functional Applications Chem. Commun. 2011, 47, 3351
17. Valveken, P.; Vermoortele, F.; De Vos, D. Metal-Organic Frameworks as Catalysts: The Role of Metal Active Sites Catal. Sci. Technol. 2013, 3, 1435
18. Dhakshinamoorthy, A.; Opanasenko, M.; Çejka, J.; Garcia, H. Metal Organic Frameworks as Solid Catalysts in Condensation Reactions of Carbonyl Groups Adv. Synth. Catal. 2013, 355, 247
19. Kurfirtova, L.; Seo, Y. K.; Hwang, Y. K.; Chang, J. S.; Cejka, J. High Activity of Iron Containing Metal-Organic-Framework in Acylation of p -Xylene with Benzoyl Chloride Catal. Today 2012, 179, 85
20. Serra-Crespo, P.; Ramos-Fernandez, E. V.; Gascon, J.; Kapteijn, F. Synthesis and Characterization of an Amino Functionalized MIL-101(Al): Separation and Catalytic Properties Chem. Mater. 2011, 23, 2565
21. Phan, N. T. S.; Nguyen, T. T.; Nguyen, C. V.; Nguyen, T. T. Ullmann-Type Coupling Reaction Using Metal-Organic Framework MOF-199 as an Eficient Recyclable Solid Catalyst Appl. Catal., A: Gen. 2013, 457, 69
22. Tran, U. P. N.; Le, K. K. A.; Phan, N. T. S. Expanding Applications of Metal-Organic Frameworks: Zeolite Imidazolate Framework ZIF-8 as an Efficient Heterogeneous Catalyst for the Knoevenagel Reaction ACS Catal. 2011, 1, 120
23. Opanasenko, M.; Shamzhy, M.; Cejka, J. Solid Acid Catalysts for Coumarin Synthesis by the Pechmann Reaction: MOFs versus Zeolites ChemCatChem 2013, 5, 1024
24. Sun, J.; Dong, Z. P.; Sun, X.; Li, P.; Zhang, F. W.; Hu, W. Q.; Yang, H. D.; Wang, H. B.; Li, R. Pd Nanoparticles in Hollow Magnetic Mesoporous Spheres: High Activity, and Magnetic Recyclability J. Mol. Catal. A: Chem. 2013, 367, 46
25. 2 Nanocomposite: Controlled Synthesis and Green Catalytic Application J. Mol. Catal. A: Chem. 2013, 378, 344
26. 2 Microsphere Catalysts Catal. Today 2010, 158, 305
27. 4 Magnetic Mirospheres and Their Properties of Photocatalytic Degradation Dyestuff Catal. Today 2011, 175, 293
28. 2 Shell for Removal of Microcystins J. Am. Chem. Soc. 2008, 130, 28
29. 2O)] Microporous Mesoporous Mater. 2010, 132, 121
30. 2 and Its Characterization by MAS NMR J. Phys. Chem. C 2009, 113, 13906
31. Zhang, Z.; Zhang, L.; Wojtas, L.; Eddaoudi, M.; Zaworotko, M. J. Template-Directed Synthesis of Nets Based upon Octahemioctahedral Cages that Encapsulate Catalytically Active Metalloporphyrins J. Am. Chem. Soc. 2012, 134, 928
32. Nguyen, L. T. L.; Nguyen, T. T.; Nguyen, K. D.; Phan, N. T. S. Metal-Organic Framework MOF-199 as an Efficient Heterogeneous Catalyst for the aza-Michael Reaction Appl. Catal., A: Gen. 2012, 425-426, 44
33. 2 Encapsulated Keggin Heteropolyacid Nanomaterial for Application in Catalysis Chem. Commun. 2010, 46, 8186
34. Sava, D. F.; Garino, T. J.; Nenoff, T. M. Iodine Confinement into Metal-Organic Frameworks (MOFs): Low-Temperature Sintering Glasses to Form Novel Glass Composite Material (GCM) Alternative Waste Forms Ind. Eng. Chem. Res. 2012, 51 (2) 614
35. 2-MIL-125 Catal. Today 2013, 204, 85
36. Pan, Y.; Yuan, B.; Li, Y.; He, D. Multifunctional Catalysis by Pd@MIL-101: One-Step Synthesis of Methyl Isobutyl Ketone over Palladium Nanoparticles Deposited on a Metal-Organic Framework Chem. Commun. 2010, 46, 2280
37. Sinhamahapatra, A.; Sutradhar, N.; Pahari, S.; Bajaj, H. C.; Panda, A. B. Mesoporous Zirconium Phosphate: An Efficient Catalyst for the Synthesis of Coumarin Derivatives through Pechmann Condensation Reaction Appl. Catal., A: Gen. 2011, 394, 93
38. DSouza, J.; Nagaraju, N. Clean and Efficient Synthesis of Coumarins over Modified Metal Oxides via Pechmann Reaction Indian J. Chem. Technol. 2008, 15, 244
39. Sudha, S.; Venkatachalam, K.; Priya, S. V.; Mabel, J. H.; Palanichamy, M.; Murugesan, V. Single Step Synthesis of Coumarin Derivatives over Al-MCM-41 and Its Supported Catalysts under Solvent-Free Condition J. Mol. Catal. A: Chem. 2008, 291, 22
40. Sabou, R.; Hoelderich, W. F.; Ramprasad, D.; Weinand, R. Synthesis of 7-Hydroxy-4-methylcoumarin via the Pechmann Reaction with Amberlyst Ion-Exchange Resins as Catalysts J. Catal. 2005, 232, 34