Issue

Vol. 34 No. 11 (2022): Vol 34 Issue 11, 2022

Copyright (c) 2022 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Effect of Reaction Conditions on the Conversion and Selectivity of MCM-41 and Al-20-MCM-41 Catalyzed Amine Coupling Reactions

https://doi.org/10.14233/ajchem.2022.23921
Nirav Bhavsar
Department of Chemical Engineering, Dharmsinh Desai University, Nadiad-387001, India
Vivaksha Patel
Department of Chemical Engineering, G.H. Patel College of Engineering & Technology, Vallabh Vidyanagar-388120, India
Manish Misra
Department of Chemistry, S.P. University, Vallabh Vidyanagar-388120, India

Corresponding Author(s) : Nirav Bhavsar

njbhavsar.ch@ddu.ac.in

Asian Journal of Chemistry, Vol. 34 No. 11 (2022): Vol 34 Issue 11, 2022

Abstract

The study has been performed to examine the effect of different reaction conditions (presence of a solvent, absence of solvent, presence of air and closed vessel with an absence of air) on the conversion and selectivity of oxidative coupling reactions of amines to imines using MCM-41 and Al-20-MCM-41 catalysts. Two types of coupling reactions were discussed viz. self-coupling and cross coupling. Self-coupling reaction was observed to be faster with Al-20-MCM-41 than MCM-41, while the cross-coupling reactions with Al-20-MCM-41 was slightly slower than MCM-41. The conversion and selectivity of self and cross coupling reactions in different reaction conditions were also investigated. The reaction was found to be of shifting order, initially first order when amine concentration was high and tending towards zero at lower amine concentration. It was evident that both catalysts Al-20-MCM-41 and MCM-41 showed a good catalytic activity on the oxidative coupling reactions of amine but somewhat higher conversion was obtained with Al-20-MCM-41 because of presence of acidic site.

Keywords

Oxidative coupling reaction Primary amines Imines MCM-41 Al-20-MCM-41
Bhavsar, N., Patel, V., & Misra, M. (2022). Effect of Reaction Conditions on the Conversion and Selectivity of MCM-41 and Al-20-MCM-41 Catalyzed Amine Coupling Reactions. Asian Journal of Chemistry, 34(11), 2929–2934. https://doi.org/10.14233/ajchem.2022.23921
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. E. Raczuk, B. Dmochowska, J. Samaszko-Fiertek and J. Madaj, Molecules, 27, 787 (2022); https://doi.org/10.3390/molecules27030787
  2. S.F. Martin, Pure Appl. Chem., 81, 195 (2009); https://doi.org/10.1351/PAC-CON-08-07-03
  3. J.P. Adams, J. Chem. Soc., Perkin Trans. I, 4, 125 (2000); https://doi.org/10.1039/a808142e
  4. A.E. Wendlandlt and S.S. Stahl, Org. Lett., 14, 2850 (2012); https://doi.org/10.1021/ol301095j
  5. H. Huang, J. Huang, Y.-M. Liu, H.-Y. He, Y. Cao and K.-N. Fan, Green Chem., 14, 930 (2012); https://doi.org/10.1039/c2gc16681j
  6. M.C. Law, T.W. Cheung, K.Y. Wong and T.H. Chan, J. Org. Chem., 72, 923 (2007); https://doi.org/10.1021/jo062198x
  7. M.A. Vazquez, M. Landa, L. Reyes, R. Miranda, J. Tamariz and F. Delgado, Synth. Commun., 34, 2705 (2009); https://doi.org/10.1081/SCC-200026190
  8. M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan and J. Thanusu, Res. Chem. Intermed., 33, 541 (2007); https://doi.org/10.1163/156856707782565822
  9. K.P. Guzen, A.S. Guarezemini, A.T.G. Orfao, R. Cella, C.N.P. Pereira and H.A. Stefani, Tetrahedron Lett., 48, 1845 (2007); https://doi.org/10.1016/j.tetlet.2007.01.014
  10. H. Naeimi, H. Sharghi, F. Salimi and K. Rabiei, Heteroatom Chem., 19, 43 (2008); https://doi.org/10.1002/hc.20383
  11. A.K. Chakraborti, S. Bhagat and S. Rudrawar, Tetrahedron Lett., 45, 7641 (2004); https://doi.org/10.1016/j.tetlet.2004.08.097
  12. H. Weingarten, J.P. Chupp and W.A. White, J. Org. Chem., 32, 3246 (1967); https://doi.org/10.1021/jo01285a088
  13. R.D. Patil and S. Adimurthy, RSC Adv., 2, 5119 (2012); https://doi.org/10.1039/c2ra20339a
  14. B. Zhu and R.J. Angelici, Chem. Commun., 21, 2157 (2007); https://doi.org/10.1039/b700555e
  15. B. Zhu, M. Lazar, B.J. Trewyn and R.J. Angelici, J. Catal., 260, 1 (2008); https://doi.org/10.1016/j.jcat.2008.08.012
  16. A. Grirrane, A. Corma and H. Garcia, J. Catal., 264, 138 (2009); https://doi.org/10.1016/j.jcat.2009.03.015
  17. K. Yamaguchi and N. Mizuno, Angew. Chem. Int. Ed., 42, 1480 (2003); https://doi.org/10.1002/anie.200250779
  18. B.K. Singh, Y. Kim, S. Kwon and K. Na, Catalysts, 11, 1541 (2021); https://doi.org/10.3390/catal11121541
  19. K.N. Tayade and M. Mishra, J. Mol. Catal. Chem., 382, 114 (2014); https://doi.org/10.1016/j.molcata.2013.11.001
  20. A.C. Carmo Jr., L.K.C. de Souza, C.E.F. da Costa, E. Longo, J.R. Zamian and G.N. da Rocha Filho, Fuel, 88, 461 (2009); https://doi.org/10.1016/j.fuel.2008.10.007
  21. B.R. Jermy and A. Pandurangan, Appl. Catal. A Gen., 288, 25 (2005); https://doi.org/10.1016/j.apcata.2005.03.047
  22. B. Rabindran Jermy and A. Pandurangan, J. Mol. Catal. Chem., 256, 184 (2006); https://doi.org/10.1016/j.molcata.2006.04.045
  23. M. Selvara, A. Pandurangan, K.S. Seshadri, P.K. Sinha, V. Krishnasamy and K.B. Lal, J. Mol. Catal. Chem., 186, 173 (2002); https://doi.org/10.1016/S1381-1169(02)00134-6
  24. K.G. Bhattacharyya, A.K. Talukdar, P. Das and S. Sivasanker, J. Mol. Catal. Chem., 197, 255 (2003); https://doi.org/10.1016/S1381-1169(02)00624-6
  25. V. Patel, N. Bhavsar and M. Mishra, J. Emerg. Technol. Innov. Res., 5, 777 (2018).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0