Copyright (c) 2023 Jayaprakash Rajendran, Ezhilarasu .D, S. Rani
This work is licensed under a Creative Commons Attribution 4.0 International License.
Ultrasound and Two Active Site Phase-Transfer Catalyst Effect in Asymmetry Synthesis: A Kinetic Study
Corresponding Author(s) : S. Rani
Asian Journal of Chemistry,
Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024
Abstract
The phase transfer catalyst 1-benzyl-1,4-diazoniabicyclo[2.2.1]hepta-2,4(7)-dienedichloride (BDHDC) in organic chiral synthesis was used in this study. Kinetic parameters such as ultrasonication effect, phase transfer catalyst dose, solvents, butyl chloride volume, stirring speed and weight of KOH were examined for the phase transfer catalytic reactions. The reaction between phenyl acetonitrile and butyl chloride was carried out under basic conditions and ultrasonic irradiation (300 W, 40 kHz) using BDHDC as a phase transfer catalyst. The introduction of BDHDC catalyst significantly improved the overall reaction, resulting in a high yield of the chiral combination. The product formation has been optimized by modifying the kinetic parameters.
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- P.J. Lin and H.M. Yang, J. Mol. Catal. Chem., 235, 293 (2005); https://doi.org/10.1016/j.molcata.2005.04.009
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- M.L. Wang and V. Rajendran, Ultrason. Sonochem., 14, 46 (2007); https://doi.org/10.1016/j.ultsonch.2006.01.007
- V. Selvaraj, K. Harikumar, M. Sathiyaraj and V. Rajendran, J. Chem. Sci., 6, 104 (2015); https://doi.org/10.4172/2150-3494.1000104
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References
B.M. Abraham, K. Miyano and J.B. Ketterson, Ind. Eng. Chem. Prod. Res. Dev., 23, 245 (1984); https://doi.org/10.1021/i300014a014
A. Bhattacharya, Ind. Eng. Chem. Res., 35, 645 (1996); https://doi.org/10.1021/ie950483t
D.N. Sanjeev and L.K. Doraiswamy, AIChe J., 44, 612 (1998); https://doi.org/10.1002/aic.690440312
A. Akelah, A. Rehab, A. Selim and T. Agag, J. Mol. Catal., 94, 311 (1994); https://doi.org/10.1016/0304-5102(94)00146-4
S. Varathan and R. Venugopal, Ultrason. Sonochem., 21, 612 (2014); https://doi.org/10.1016/j.ultsonch.2013.09.013
P. Monsef-Mirzai and W.R. McWhinnie, Inorgan. Chim. Acta, 52, 211
(1981); https://doi.org/10.1016/S0020-1693(00)88598-9
A. Cornélis, P. Laszlo and W. Shaofang, Tetrahedron Lett., 34, 3849 (1993); https://doi.org/10.1016/S0040-4039(00)79244-6
S. Desikan and L.K. Doraiswamy, Chem. Eng. Sci., 55, 6119 (2000); https://doi.org/10.1016/S0009-2509(00)00221-9
G.P. Petrova, H.B. Li, K. Maruoka and K. Morokuma, J. Phys. Chem. B, 118, 5154 (2014); https://doi.org/10.1021/jp501520g
Y. Zhang, X. Zheng, K. Gai, Y. Li and D. Cheng, Asian J. Chem., 26, 455 (2014); https://doi.org/10.14233/ajchem.2014.15441
B. Lygo and B.I. Andrews, Acc. Chem. Res., 37, 518 (2004); https://doi.org/10.1021/ar030058t
B.A. Bhanu Prasad, A. Bisai and V.K. Singh, Tetrahedron Lett., 45, 9565 (2004); https://doi.org/10.1016/j.tetlet.2004.11.015
B. Gál, C. Bucher and N. Burns, Mar. Drugs, 14, 206 (2016); https://doi.org/10.3390/md14110206
B.S. Bhatkhande, M.V. Adhikari and S.D. Samant, Ultrason. Sonochem., 9, 31 (2002); https://doi.org/10.1016/S1350-4177(01)00097-9
D. Ezhilarasu and S. Rani, Asian J. Chem., 35, 929 (2023); https://doi.org/10.14233/ajchem.2023.27580
P.J. Lin and H.M. Yang, J. Mol. Catal. Chem., 235, 293 (2005); https://doi.org/10.1016/j.molcata.2005.04.009
N.S. Ahmed, K.O. AlFooty and S.S. Khalifah, J. Chem., 2014, 1 (2014); https://doi.org/10.1155/2014/126323
M. Tomoi and W.T. Ford, J. Am. Chem. Soc., 103, 3828 (1981); https://doi.org/10.1021/ja00403a033
M.L. Wang and V. Rajendran, Ultrason. Sonochem., 14, 46 (2007); https://doi.org/10.1016/j.ultsonch.2006.01.007
V. Selvaraj, K. Harikumar, M. Sathiyaraj and V. Rajendran, J. Chem. Sci., 6, 104 (2015); https://doi.org/10.4172/2150-3494.1000104
M.J. Bussemaker and D. Zhang, Ultrason. Sonochem., 21, 436 (2014); https://doi.org/10.1016/j.ultsonch.2013.07.002
V. Selvaraj and V. Rajendran, Ultrason. Sonochem., 20, 1236 (2013); https://doi.org/10.1016/j.ultsonch.2013.02.011