Ceria-Based Mixed Oxide Supported Nano-Gold as an Efficient and Durable Heterogeneous Catalyst for Oxidative Dehydrogenation of Amines to Imines Using Molecular Oxygen

Bashir Ahmad Dar, Meena Sharma, Baldev Singh



Abstract


The present work is intended to determine the catalytic activity of Mixed Oxide supported gold for aerobic oxidative dehydrogenation of amines to imines using Ceria as a main constituent of the each support. The model catalysts Au/CeO2:TiO2 Au/CeO2:SiO2, Au/CeO2:ZrO2 and Au/CeO2:Al2Os were prepared by deposition co-precipitation method and deposition of gold was determined by EDEX analysis. The supported nano-gold catalyzes the dehydrogenation of secondary amines to imines without loss of activity. On recycling good amount of product yield is obtained. Oxidation of secondary amines to imines is carried at 100˚C and almost 90 % conversion was obtained with >99% selectivity. © 2012 BCREC UNDIP. All rights reserved

Received: 26th December 2011; Revised: 7th June 2012; Accepted: 13rd June 2012

[How to Cite: B.A. Dar, M. Sharma, B. Singh. (2012). Ceria-Based Mixed Oxide Supported Nano-Gold as an Efficient and Durable Heterogeneous Catalyst for Oxidative Dehydrogenation of Amines to Imines Using Molecular Oxygen. Bulletin of Chemical Reaction Engineering & Catalysis, 7(1): 79-84.  doi:10.9767/bcrec.7.1.1257.79-84]

[How to Link / DOI: http://dx.doi.org/10.9767/bcrec.7.1.1257.79-84 ]

| View in 


Graphical Abstract



Keywords


Heterogeneous Catalyst; Nano-Gold; Metal Oxides; Imines

Fulltext


Full Text: Fulltext PDF

References


  1. Li, X.D., Ying, R.L., Xue, L.H.,Yong, G.Z. (1999). Stereoselective reactions with imines, Pure Applied Chemistry. 71(6): 1033-1040.
  2. Gu, X.Q., Chen, W., Morales, D. M., Craig, M.J. (2002). Dehydrogenation of secondary amines to imines catalyzed by an iridium PCP pincer complex: initial aliphatic or direct amino dehydrogenation. Journal of Molecular Catalysis A: Chemical. 189: 119–124. CrossRef
  3. Friestad, G. K., Mathies, A.K., (2007). Recent developments in asymmetric catalytic addition to C=N bonds. Tetrahedron. 63 (12):2541-2569 CrossRef
  4. Amlan, R., Keming, Z., Kissin, Y.V., Cherian, A. E, Coates, G.W., Alan, S.G., (2005). Dehydrogenation of aliphatic polyolefins catalyzed by pincer-ligated iridium complexes. Chemical Communication. 3388–3390
  5. Liu, X., Zhang, Y., Wang, L., Fu, H., Jiang, Y., Zhao, Y. (2008). General and Efficient Copper-Catalyzed Amidation of Saturated C-H Bonds Using N-Halosuccinimides as the Oxidants. Journal of Organic Chemistry. (73): 6207–6212 CrossRef
  6. Zhang, S., Xu, L., Trudell, M. L. (2005) Selective Oxidation of Benzylic Alcohols and TBDMS Ethers to Carbonyl Compounds with CrO3-H5IO6. Synthesis 1757-1760. CrossRef
  7. Chae, S., Yi Lee, W.D. (2009) Efficient Dehydrogenation of Amines and Carbonyl Compounds Catalyzed by a Tetranuclear Ruthenium-μ-Oxo-μ-Hydroxo-Hydride Complex. Organometallics. 28(4): 947–949. CrossRef
  8. Wittstock, A., Zielasek, V., Biener, V., Friend, C., M., Bäumer, M. (2010). Nanoporous Gold Catalysts for Selective Gas-Phase Oxidative Coupling of Methanol at Low Temperature. Science 327 (5963): 319-322. CrossRef
  9. Corma, A., Garcia, H. (2008) Supported gold nanoparticles as catalysts for organic reactions Chemical Society Review, 37: 2096-2126. CrossRef
  10. Magureanu, M., Mandache, N.B., Hu, J., Richards, R., Florea, M., Parvulescu, V. I. (2007) Plasma-assisted catalysis total oxidation of trichloroethylene over gold nano-particles embedded in SBA 15 catalysts. Applied Catalysis B. Environmental 76: 275 –281. CrossRef
  11. Lopez-Sanchez, J.A., Dimitratos, N., Hammond, C., Brett, G.L., Kesavan, L., White, S., Miedziak, P., (...), Hutchings, G.J. (2011) Facile removal of stabilizer-ligands from supported gold nanoparticles. Nature Chemistry 3: 551-556. CrossRef
  12. Shaikhutdinov, S.K., Meyer, R., Naschitzki, M., Umer, M.B., Freund, H.J. (2003) Size and Support Effects for CO Adsorption on Gold Model Catalysts. Catalysis Letters 86 (4): 211-219. CrossRef
  13. Bhargava, S.K., Akolekar, D.B., Foran, G. (2007) Investigations on gold nanoparticles supported on rare earth oxide catalytic materials. Journal of Molecular Catalysis A: Chemical 267: 57–64. CrossRef
  14. Turner, M., Golovko, V.B., Vaughan, O.P.H., Abdulkin, P., Murcia, A.B., Tikhov, M.S., Johnson, B.F.G., Lambert, R.M. (2008) Selective oxidation with dioxygen by gold nanoparticle catalysts derived from 55-atom clusters. Nature 454: 981-983. CrossRef
  15. Ren, L., Pan, X. (2011) Catalysts used for microwave-assisted TCE decomposition by hydrogen. Catalysis Communications 12(14): 1366–1369. CrossRef
  16. Wang, L., Meng, X., Xiao, F. (2010) Au Nanoparticles Supported on a Layered Double Hydroxide with Excellent Catalytic Properties for the Aerobic Oxidation of Alcohols. Chinese Journal of Catalysis 31(8): 943–947.
  17. Sharma, V., Crozier, P.A., Sharma, R., Adams, J.B. (2012) Direct observation of hydrogen spillover in Ni-loaded Pr-doped ceria. Catalysis Today 180 (1, 17): 2–8 CrossRef
  18. Nikakhtari, H., Hill, G.H. (2005) Enhanced Oxygen Mass Transfer in an External Loop Airlift Bioreactor Using a Packed Bed. Industrial Engineering Chemistry Research. 44 (4): 1067–1072. CrossRef
  19. Reddy, E.L., Karuppiah, J., Biju, V.M., Subrahmanyam, C. (2012) Catalytic packed bed non-thermal plasma reactor for the extraction of hydrogen from hydrogen sulfide. International. Journal Energy Research. 37:2204-2209 CrossRef
  20. Bhalla, V., Carrara, S., Stagni, C. Samori, B. (2010) Chip cleaning and regeneration for electrochemical sensor arrays Thin solid Films 518: 3360–3366. CrossRef
  21. Iglesia, E. (1997) Fischer-tropsch synthesis on cobalt catalysts: Structural requirements and reaction pathways. Studies in Surface Science and Catalysis. 107: 153–162.
  22. Cassinelli, W.H., Feio, L.S.F., Araujo, J.C.S., Hori, C.E., Noronha, F.B., Marques, C.M.P., Bueno, J.M.C. (2008). Effect of CeO2 and La2O3 on the Activity of CeO2–La2O3/Al2O3-Supported Pd Catalysts for Steam Reforming of Methane. Catalysis Letters. 120 (1-2): 86-94. CrossRef
  23. Jia, M., Shen, Y., Li, C., Bao, Z., Sheng, S. (2005). Effect of Supports on the Gold Catalyst Activity for Catalytic Combustion of CO and HCHO. Catalysis Letters. 99 (3-4 ): 235-239. CrossRef
  24. Bashir, A., D., Mazahar, F. (2011) Supported nano gold a recyclable catalyst for green, solvent free, selective and efficient oxidation of alcohol using molecular oxygen. Orbital - Electronic Journal of Chemistry. 3(2): 89-93.
  25. Umpawan S., Apanee, L., Erdogan, G. (2012) Effect of Gold Loading on CeO2–Fe2O3 for Oxidative Steam Reforming of Methanol. World Academy of Science, Engineering and Technology 64: 461- 466.
  26. Wongkaew, A. (2008) Effect of Cerium Oxide and Zirconium Oxide to Activity of Catalysts. Chiang Mai Journal of Science. 35(1): 156-162. View at Publisher
  27. Miller, J.T., Kopf, A.J., Zha, Y., Regalbuto, J.R., Delannoy , L., Louis , C., Bus , E., van Bokhoven J.A. (2006) The effect of gold particle size on Au–Au bond length and reactivity toward oxygen in supported catalysts. Journal of Catalysis 240: 222–234. CrossRef
  28. Arcadi, A. (2008) Alternative Synthetic ethods through New Developments in Catalysis by Gold, Chemistry Review. 108: 3266–3325. CrossRef
  29. Liu, Y., Tsunoyama, H., Akita, T., Tsukuda, T. (2010) Size Effect of Silica-supported Gold Clusters in the Microwave-assisted Oxidation of Benzyl Alcohol with H2O2. Chemistry Letters. 39: 159 -161 CrossRef
  30. Vasant, R.C., Deepa, K.D. (2009) Supported Nano-Gold Catalysts for Epoxidation of Styrene and Oxidation of Benzyl Alcohol to Benzaldehyde. Topics in Catalysis 52(12): 1677-1687. CrossRef

Refbacks

  • There are currently no refbacks.





Creative Commons License
BCREC by http://ejournal.undip.ac.id/index.php/bcrec/ is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

View My Stats bcreccrossref