Efficient and Clean Catalytic Hydrogenolysis of Aromatic Ketones by Silica Supported Schiff Base Modify Chitosan-Palladium Catalyst

DOI: 10.4236/mrc.2013.21002   PDF   HTML   XML   4,895 Downloads   11,175 Views   Citations

Abstract

An silica supported chitosan-Schiff base Pd(II) catalyst was prepared in a simple way and characterized by XRD, FT-IR, SEM-EDS, XPS and TG, and the ability of this complex to catalyze hydrogenolysis of 1-tetralone into 1,2,3,4-tetrahydronaphthalene was also investigated in the presence of hydrogen. It has been revealed that the catalyst had high catalytic activity for hydrogenolysis of 1-tetralone at ambient temperature and normal pressure of hydrogen. Especially, the hydrogenolysis of 1-tetralone in ethanol solvent gave excellent results and the 100% conversion of 1-tetralone and the 100% selectivity for 1,2,3,4-tetrahydronaphthalene were obtained under optimized reaction conditions. The influences of reaction temperature, reaction time and solvent on the hydrogenolysis of 1-tetralone were also investigated. It has been also revealed that the catalyst was efficient and eco-friendly for the hydrogenolysis of carbonyl that connected with a benzene ring to give corresponding aromatic hydrocarbons.

Share and Cite:

T. Gu, L. Liu and C. Zhao, "Efficient and Clean Catalytic Hydrogenolysis of Aromatic Ketones by Silica Supported Schiff Base Modify Chitosan-Palladium Catalyst," Modern Research in Catalysis, Vol. 2 No. 1, 2013, pp. 9-17. doi: 10.4236/mrc.2013.21002.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] N. Desbois, A. Szollosi, A. Maisonial, V. Weber, E. Moreau, J. C. Teulade, O. Chavignon, Y. Blache and J. M. Chezal, “Simple and Convenient Conversion of Acridones into 9-Unsubstituted Acridines via Acridanes using Borane Tetrahydrofuran Complex,” Tetrahedron Letters, Vol. 50, No. 49, 2009, pp. 6894-6896. doi:10.1016/j.tetlet.2009.09.141
[2] W. P. Reeves, J. A. Murry, D. W. Willoughby and W. J. Friedrich, “Clemmensen Reductions Using Ultrasonic Irradiation,” Synthetic Communications, Vol. 18, No. 16-17, 1988, pp. 1961-1966.
[3] C. A. Marques, M. Selva and P. J. Tundo, “Facile Hydrodehalogenation with H2 and Pd/C Catalyst under Multiphase Conditions. 3. Selective Removal of Halogen from Functionalized Aryl Ketones. 4. Aryl Halide-Promoted Reduction of Benzyl Alcohols to Alkanes,” The Journal of Organic Chemistry, Vol. 60, 1995, pp. 2430-2435. doi:10.1021/jo00113a024
[4] L. S. Glebov, A. I. Mikaya, A. E. Yatsenko, V. G. Zaikin, G. A. Kliger and S. M. Loktev, “Effective Gas-phase Deoxygenation of Alcohols and Ketones on Iron Catalyst,” Tetrahedron Letters, Vol. 26, No. 28, 1985, pp. 3373-3376. doi:10.1016/S0040-4039(00)98301-1
[5] R. ?uláková, R. Hrdina and G. M. B. Soares, “Oxidation of Azo Textile Soluble Dyes with Hydrogen Peroxide in the Presence of Cu(II)-chitosan Heterogeneous Catalysts,” Dyes and Pigments, Vol. 73, No. 1, 2007, pp. 19-24. doi:10.1016/j.dyepig.2005.10.004
[6] A. Burkhardt, H. G?rls and W. Plass, “Nickel(II) Com- plexes with Schiff-base Ligands Derived from Epimeric Pyranose Backbones as 2,3-Chelators: Modeling the Coordination Chemistry of Chitosan,” Carbohydrate Re- search, Vol. 343, No. 7, 2008, pp. 1266-1277. doi:10.1016/j.carres.2008.01.039
[7] R. Abu-Reziq, D. Avnir and J. Blum, “Catalytic Hydro- genolysis of Aromatic Ketones by a Sol-Gel Entrapped Combined Pd-[Rh(cod)Cl]2 Catalyst,” Journal of Molecular Catalysis A: Chemical, Vol. 187, No. 2, 2002, pp. 277-281. doi:10.1016/S1381-1169(02)00235-2
[8] C. Van Doorslaer, J. Wahlen, P. G. N. Mertens, B. Thijs, P. Nockemann, K. Binnemans and D. E. De Vos, “Catalytic Hydrogenolysis of Aromatic Ketones in Mixed Choline-Betainium Ionic Liquids,” ChemSusChem, Vol. 1, No. 12, 2008, pp. 997-1005. doi:10.1002/cssc.200800140
[9] S. E. S. Leonhardt, A. Stolle, B. Ondruschka, G. Cravotto, C. De Leo, K. D. Jandt and T. F. Keller, “Chitosan as a Support for Heterogeneous Pd Catalysts in Liquid Phase Catalysis,” Applied Catalysis A: General, Vol. 379, No. 1-2, 2010, pp. 30-37. doi:10.1016/j.apcata.2010.02.029
[10] D. Wei, Y. Ye, X. Jia, C. Yuan and W. Qian, “Chitosan as an Active Support for Assembly of Metal Nanoparticles and Application of the Resultant Bioconjugates in Catalysis,” Carbohydrate Research, Vol. 345, No. 1, 2010, pp. 74-81. doi:10.1016/j.carres.2009.10.008
[11] N. Sudheesh, S. K. Sharma1 and R. S. Shukla, “Chitosan as an Eco-friendly Solid Base Catalyst for the Solvent-free Synthesis of Jasminaldehyde,” Journal of Molecular Catalysis A: Chemical, Vol. 321, No. 1-2, 2010, pp. 77- 82. doi:10.1016/j.molcata.2010.02.005
[12] A. B. Sorokin, F. Quignard, R. Valentin and S. Mangematin, “Chitosan Supported Phthalocyanine Complexes: Bifunctional Catalysts with Basic and Oxidation Active Sites,” Applied Catalysis A: General, Vol. 309, No. 2, 2006, pp. 162-168. doi:10.1016/j.apcata.2006.03.060
[13] J. W. Park, M. O. Park and K. K. Park, “Mechanism of Metal ion Binding to Chitosan in Solution. Cooperative Interand Intramolecular Chelations,” The Bulletin of the Korean Chemical Society, 1984, vol. 5, pp. 108-112.
[14] F. P. Blondet, T. Vincent and E. Guibal, “Hydrogenation of Nitrotoluene Using Palladium Supported on Chitosan Hollow Fiber: Catalyst Characterization and Influence of Operative Parameters Studied by Experimental Design Methodology,” International Journal of Biological Macromolecules, Vol. 43, No. 1, 2008, pp. 69-78. doi:10.1016/j.ijbiomac.2007.11.008
[15] F. Peirano, T. Vincent, F. Quignard, M. Robitzer and E. Guibal, “Palladium Supported on Chitosan Hollow Fiber for Nitrotoluene Hydrogenation,” Journal of Membrane Science, Vol. 329, No. 1-2, 2009, pp. 30-45. doi:10.1016/j.memsci.2008.12.022
[16] H. S. Han, S. N. Jiang, M. Y. Huang and Y. Y. Jiang, “Catalytic Hydrogenation of Aromatic Nitro Compounds by Non-Noble Metal Complexes of Chitosan,” Polymers for Advanced Technologies, Vol. 7, No. 8, 1996, pp. 704-706. doi:10.1002/(SICI)1099-1581(199608)7:8<704::AID-PAT567>3.0.CO;2-3
[17] M. Adlim, M. A. Bakar, K. Y. Liew and J. Ismail, “Syn- thesis of Chitosan-Stabilized Platinum and Palladium Na- noparticles and their Hydrogenation Activity,” Journal of Molecular Catalysis A: Chemical, Vol. 212, No. 1-2, 2004, pp. 141-149. doi:10.1016/j.molcata.2003.08.012
[18] T. Vincent, S. Spinelli and E. Guibal, “Chitosan-Supported Palladium Catalyst. II. Chlorophenol Dehalogena- tion,” Industrial & Engineering Chemistry Research, Vol. 42, No. 24, 2003, pp. 5968-5976. doi:10.1021/ie0301482
[19] M. Y. Yin, G. L. Yuan, Y. Q. Wu, M. Y. Huang and Y. Y. Jiang, “Asymmetric Hydrogenation of Ketones Catalyzed by a Silica-Supported Chitosan-Palladium Complex,” Journal of Molecular Catalysis A: Chemical, Vol. 147, No. 1-2, 1999, pp. 93-98. doi:10.1016/S1381-1169(99)00133-8
[20] Y. X. Sun, Y. Guo, Q. Z. Lu, X. L. Meng, X. H. Wu, Y. L. Guo, Y. S. Wang, X. H. Liu and Z. G. Zhang, “Highly Selective Asymmetry Transfer Hydrogenation of Pro- chiral Acetophenone Catalyzed by Palladium-Chitosan on Silica,” Catalsis Letter, Vol. 100, No. 3-4, 2005, pp. 213-217. doi:10.1007/s10562-004-3458-1
[21] J. E. dos Santos, E. R. Dockal and é. T. G. Cavalheiro, “Synthesis and Characterization of Schiff Bases from Chitosan and Salicylaldehyde Derivatives,” Carbohydrate Polymers, Vol. 60, No. 3, 2005, pp. 277-282. doi:10.1016/j.carbpol.2004.12.008
[22] G. K. Moore and G. A. F. Roberts, “A Compound Hy-drodynamic Shape Function Derived from Viscosity and Molecular Covolume Measurements,” International Journal of Biological Macromolecules, Vol. 3, No. 5, 1981, pp. 337-341. doi:10.1016/0141-8130(81)90053-2
[23] S. W. Gong, H. F. He, C. Q. Zhao, L. J. Liu and Q. X. Cui, “Convenient Deoxygenation of Aromatic Ketones by Silica Supported Chitosan Schiff-Base Palladium Catalyst,” Synthetic Communications, Vol. 42, No. 4, 2012, pp. 574- 581. doi:10.1080/00397911.2010.527423
[24] J. Tong, Z. Li and C. Xia, “Highly Efficient Catalysts of Chitosan-Schiff Base Co(II) and Pd(II) Complexes for Aerobic Oxidation of Cyclohexane in the Absence of Reductants and Solvents,” Journal of Molecular Catalysis A: Chemical, Vol. 231, No. 1-2, 2005, pp. 197-203. doi:10.1016/j.molcata.2005.01.011
[25] H. F. He, S. W. Gong, L. J. Liu and Q. X.Cui and H.D. Yin, “Hydrogenation of Aromatic Ketones to Aromatic Hydrocarbons over SiO2-Supported Chitosan Schiff-Base Palladium Catalyst,” Chinese Journal of Catalysis, Vol. 31, No. 7, 2010, pp. 846-850.

  
comments powered by Disqus

Copyright © 2020 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.