Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Oxidation of Cyclohexanol and Cyclohexanone by Monochromate Ions in Organic Solvents and on Solvent Free Microwave Irradiation under Phase Transfer Catalysis - A Comparative Study
Corresponding Author(s) : K. Bijudas
Asian Journal of Chemistry,
Vol. 33 No. 9 (2021): Vol 33 Issue 9, 2021
Abstract
Oxidation of cyclohexanol and cyclohexanone were carried out by acidified monochromate ions in ethyl acetate and toluene under phase transfer catalysis and also in solvent free condition under microwave irradiation. The extraction of monochromate ions from aqueous medium to organic phase was carried by employing various phase transfer catalysts in the presence of mineral acids. The effect of [catalyst] and [mineral acid] on extraction of monochromate from aqueous phase to organic phase was also studied. The product obtained, namely adipic acid obtained with both reactants was characterized by its melting point and infrared spectral technique. The reaction was over within 15 min with more than 85% yield at a temperature of 323 K under microwave irradiation where as it gave around 70% yield at 353 K within 150 min under phase transfer catalysis condition. The enhanced reaction rate and high yield of product substantiate the application of phase transfer catalytic technique under microwave irradiation for organic synthesis. A suitable mechanism for the oxidation of substrates by monochromate under phase transfer catalysis is also suggested.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- S. Valange and J.C. Védrine, Catalysts, 8, 483 (2018); https://doi.org/10.3390/catal8100483
- O.V. Kharissova, B.I. Kharisov, C.M. Oliva-González, Y. Peña-Méndez and I. López, R. Soc. Open Sci., 6, 191378 (2019); https://doi.org/10.1098/rsos.191378
- S. Dash, S. Patel and B.K. Mishra, Tetrahedron, 65, 707 (2009); https://doi.org/10.1016/j.tet.2008.10.038
- V.K. Ahluwalia, Oxidation in Organic Synthesis, CRC Press (2012).
- Z. Hu, L. Ma, J. Xie, H. Du, W.W.Y. Lam and T.-C. Lau, New J. Chem., 37, 1707 (2013); https://doi.org/10.1039/c3nj00102d
- L. Delaude and P. Laszlo, J. Org. Chem., 61, 6360 (1996); https://doi.org/10.1021/jo960633p
- P.D. Sharma, P. Panchariya, P. Purohit and P.K. Sharma, Eur. Chem. Bull., 2, 816 (2013).
- D. Dey and M.K. Mahanti, J. Org. Chem., 55, 5848 (1990); https://doi.org/10.1021/jo00310a015
- M.H. Heravi, M. Ghavidel and L. Mohammadkhani, RSC Adv., 8, 27832 (2018); https://doi.org/10.1039/C8RA04985H
- C.M. Starks and C.L. Liotta, Phase Transfer Catalysis, Principles and Techniques, Academic Press, New York (1978).
- E.V. Dehmlow and S.S. Dehmlow, Phase Transfer Catalysis, VCH Weinheim: Germany (1993).
- Y. Sasson and R. Neumann, Handbook of Phase Transfer Catalysis, Kluwer Academic Publishers, Dordrecht, Germany (1993).
- N.F. Carvalho and J.R. Pliego Jr., J. Org. Chem., 81, 8455 (2016); https://doi.org/10.1021/acs.joc.6b01624
- D. Landini, A. Maia, F. Montanari and F.M. Pirisi, J. Chem. Soc., Perkin Trans. 2, 46 (1980); https://doi.org/10.1039/P29800000046
- R.A. Jones, Quaternary Ammonium Salts, Their use in Phase-Transfer Catalyzed Reactions, Academic Press, New York, USA (2001).
- A. Brandstrom, Adv. Phys. Org. Chem., 15, 267 (1977); https://doi.org/10.1016/S0065-3160(08)60120-3
- K. Bijudas, Chem. Sci. Rev. Lett., 6, 2289 (2017).
- N.N. Dutta, S. Borthakur and G.S. Patil, Sep. Sci. Technol., 27, 1435 (1992); https://doi.org/10.1080/01496399208019435
- V.K. Ahluwalia and M. Kidwai, Phase Transfer Catalysis in Green Synthesis, Kluwer Academic Publishers, Dordrecht, Germany (2004).
- D.C.M. Albanese, F. Foschi and M. Penso, Org. Process Res. Dev., 20, 129 (2016); https://doi.org/10.1021/acs.oprd.5b00385
- M. Makosza, Pure Appl. Chem., 72, 1399 (2000); https://doi.org/10.1351/pac200072071399
- K.N. Rankin, Q. Liu, J. Hendry, H. Yee, N.A. Noureldin and D.G. Lee, Tetrahedron Lett., 39, 1095 (1998); https://doi.org/10.1016/S0040-4039(97)10788-2
- K. Bijudas, P. Bashpa, V.P. Bibin, L. Nair, A.P. Priya, M. Aswathy, C. Krishnendu and P. Lisha, Bull. Chem. React. Eng. Catal., 10, 38 (2015); https://doi.org/10.9767/bcrec.10.1.7189.38-42
- R.D. Patil, S. Bhadra, S. Adimurthy and B.C. Ranu, Synth. Commun., 40, 2922 (2010); https://doi.org/10.1080/00397910903340678
- B.E. Norcross, W.C. Lewis, H. Gai, N.A. Noureldin and D.G. Lee, Can. J. Chem., 75, 129 (1997); https://doi.org/10.1139/v97-017
- K. Bijudas and T.D. Radhakrishnan Nair, Indian J. Chem., 43A, 1216 (2004).
- D. Pletcher and S.J.D. Tait, J. Chem. Soc., Perkin Trans. 2, 788 (1979); https://doi.org/10.1039/p29790000788
- A.C. Ranveer, S.V. Ranade and C.K. Mistry, Iran. J. Chem. Chem. Eng., 37, 89 (2018); https://doi.org/10.30492/IJCCE.2018.36062
- K. Bijudas and T.D. Radhakrishnan Nair, Curr. Chem. Lett., 3, 109 (2014); https://doi.org/10.5267/j.ccl.2013.12.001
- C.M. Starks and C.L. Liotta, Phase Transfer Catalysis, Principles and Techniques, Academic Press: New York (1978).
- V. Palma, D. Barba, M. Cortese, M. Martino, S. Renda and E. Meloni, Catalysts, 10, 246 (2020); https://doi.org/10.3390/catal10020246
- A. Kokel, C. Schafer and B. Torok, Green Chem., 19, 3729 (2017); https://doi.org/10.1039/C7GC01393K
- Y.A. El-Badry, M.A. El-Hashash and K. Al-Ali, Acta Pharm., 70, 161 (2020); https://doi.org/10.2478/acph-2020-0001
- V. Polshettiwar and R.S. Varma, Acc. Chem. Res., 41, 629 (2008); https://doi.org/10.1021/ar700238s
- D.D. Perrin, W.L. Armarego and D.R. Perrin, Purification of Organic Compounds, Pergamon Press, Oxford (1966).
- A.I. Vogel, Text Book of Practical Organic Chemistry, Longman, London (1967).
References
S. Valange and J.C. Védrine, Catalysts, 8, 483 (2018); https://doi.org/10.3390/catal8100483
O.V. Kharissova, B.I. Kharisov, C.M. Oliva-González, Y. Peña-Méndez and I. López, R. Soc. Open Sci., 6, 191378 (2019); https://doi.org/10.1098/rsos.191378
S. Dash, S. Patel and B.K. Mishra, Tetrahedron, 65, 707 (2009); https://doi.org/10.1016/j.tet.2008.10.038
V.K. Ahluwalia, Oxidation in Organic Synthesis, CRC Press (2012).
Z. Hu, L. Ma, J. Xie, H. Du, W.W.Y. Lam and T.-C. Lau, New J. Chem., 37, 1707 (2013); https://doi.org/10.1039/c3nj00102d
L. Delaude and P. Laszlo, J. Org. Chem., 61, 6360 (1996); https://doi.org/10.1021/jo960633p
P.D. Sharma, P. Panchariya, P. Purohit and P.K. Sharma, Eur. Chem. Bull., 2, 816 (2013).
D. Dey and M.K. Mahanti, J. Org. Chem., 55, 5848 (1990); https://doi.org/10.1021/jo00310a015
M.H. Heravi, M. Ghavidel and L. Mohammadkhani, RSC Adv., 8, 27832 (2018); https://doi.org/10.1039/C8RA04985H
C.M. Starks and C.L. Liotta, Phase Transfer Catalysis, Principles and Techniques, Academic Press, New York (1978).
E.V. Dehmlow and S.S. Dehmlow, Phase Transfer Catalysis, VCH Weinheim: Germany (1993).
Y. Sasson and R. Neumann, Handbook of Phase Transfer Catalysis, Kluwer Academic Publishers, Dordrecht, Germany (1993).
N.F. Carvalho and J.R. Pliego Jr., J. Org. Chem., 81, 8455 (2016); https://doi.org/10.1021/acs.joc.6b01624
D. Landini, A. Maia, F. Montanari and F.M. Pirisi, J. Chem. Soc., Perkin Trans. 2, 46 (1980); https://doi.org/10.1039/P29800000046
R.A. Jones, Quaternary Ammonium Salts, Their use in Phase-Transfer Catalyzed Reactions, Academic Press, New York, USA (2001).
A. Brandstrom, Adv. Phys. Org. Chem., 15, 267 (1977); https://doi.org/10.1016/S0065-3160(08)60120-3
K. Bijudas, Chem. Sci. Rev. Lett., 6, 2289 (2017).
N.N. Dutta, S. Borthakur and G.S. Patil, Sep. Sci. Technol., 27, 1435 (1992); https://doi.org/10.1080/01496399208019435
V.K. Ahluwalia and M. Kidwai, Phase Transfer Catalysis in Green Synthesis, Kluwer Academic Publishers, Dordrecht, Germany (2004).
D.C.M. Albanese, F. Foschi and M. Penso, Org. Process Res. Dev., 20, 129 (2016); https://doi.org/10.1021/acs.oprd.5b00385
M. Makosza, Pure Appl. Chem., 72, 1399 (2000); https://doi.org/10.1351/pac200072071399
K.N. Rankin, Q. Liu, J. Hendry, H. Yee, N.A. Noureldin and D.G. Lee, Tetrahedron Lett., 39, 1095 (1998); https://doi.org/10.1016/S0040-4039(97)10788-2
K. Bijudas, P. Bashpa, V.P. Bibin, L. Nair, A.P. Priya, M. Aswathy, C. Krishnendu and P. Lisha, Bull. Chem. React. Eng. Catal., 10, 38 (2015); https://doi.org/10.9767/bcrec.10.1.7189.38-42
R.D. Patil, S. Bhadra, S. Adimurthy and B.C. Ranu, Synth. Commun., 40, 2922 (2010); https://doi.org/10.1080/00397910903340678
B.E. Norcross, W.C. Lewis, H. Gai, N.A. Noureldin and D.G. Lee, Can. J. Chem., 75, 129 (1997); https://doi.org/10.1139/v97-017
K. Bijudas and T.D. Radhakrishnan Nair, Indian J. Chem., 43A, 1216 (2004).
D. Pletcher and S.J.D. Tait, J. Chem. Soc., Perkin Trans. 2, 788 (1979); https://doi.org/10.1039/p29790000788
A.C. Ranveer, S.V. Ranade and C.K. Mistry, Iran. J. Chem. Chem. Eng., 37, 89 (2018); https://doi.org/10.30492/IJCCE.2018.36062
K. Bijudas and T.D. Radhakrishnan Nair, Curr. Chem. Lett., 3, 109 (2014); https://doi.org/10.5267/j.ccl.2013.12.001
C.M. Starks and C.L. Liotta, Phase Transfer Catalysis, Principles and Techniques, Academic Press: New York (1978).
V. Palma, D. Barba, M. Cortese, M. Martino, S. Renda and E. Meloni, Catalysts, 10, 246 (2020); https://doi.org/10.3390/catal10020246
A. Kokel, C. Schafer and B. Torok, Green Chem., 19, 3729 (2017); https://doi.org/10.1039/C7GC01393K
Y.A. El-Badry, M.A. El-Hashash and K. Al-Ali, Acta Pharm., 70, 161 (2020); https://doi.org/10.2478/acph-2020-0001
V. Polshettiwar and R.S. Varma, Acc. Chem. Res., 41, 629 (2008); https://doi.org/10.1021/ar700238s
D.D. Perrin, W.L. Armarego and D.R. Perrin, Purification of Organic Compounds, Pergamon Press, Oxford (1966).
A.I. Vogel, Text Book of Practical Organic Chemistry, Longman, London (1967).