A green chemical approach for nitration of aromatic compounds
DOI:
https://doi.org/10.20450/mjcce.2009.206Keywords:
photochemical nitration, aromatic, phenol, salicylic acid, ecofriendlyAbstract
Photochemical aromatic nitration of phenol and salicylic acid has been carried out in the presence of UV radiations and formation of products has been observed spectrophotometrically. The effect of various operating variables like pH, concentration of nitrite ion, formate ion, phenol and salicylic acid, etc. on the rate of the reaction has also been observed. A tentative mechanism involving NO2· radicals has been proposed for photochemical nitration of phenol and salicylic acid.References
W. H. Glaze, J. W. Kang, D. H. Chapin, The chemistry of water treatment processes involving ozone, H2O2 and ultraviolet radiation, Ozone: Sci. Engineering, 9, 335–352 (1987).
S. Selzer, F. Lam, L. Packer, Photonitration of phenols by tetranitromethane under visible light. J. Am. Chem. Soc., 104, 6470–6471 (1982).
D. Vione, V. Maurino, C. Minero, M. Vincenti, E. Pelizzeti, Aromatic photonitration in homogeneous and heterogeneous aqueous systems, Environ. Sci. Pollut. Res. Int., 10, 321–324 (2003).
S. Nelieu, L. Kerhoas, M. V. Shankar, J. Einhorn, Phototransformation of monuron induced by nitrate and nitrite ions in water: Contribution of photonitration, J. Photochem. Photobiol. A, 193, 1–9 (2008).
A. Lalitha, K. Sivakumar, Zeolite H-Y-supported copper( ii) nitrate: a simple and effective solid-supported reagent for nitration of phenols and their derivatives, Synthetic Commun., 38, 1745 – 1752 (2008).
N. Matykiewiczova, R. Kurkova, J. Klanova, P. Klan, Photochemically induced nitration and hydroxylation of organic aromatic compounds in the presence of nitrate or nitrite in ice, J. Photochem. Photobiol., 187A, 24–32 (2007).
M. A. Zolfigol, B. F. Mirjalili, A. Bamoniri, M. A. K. Zarchi, A. Zarei, L. Khazdooz, J. Noei, Nitration of aromatic compounds on silica sulphuric acid, Bull. Korean Chem. Soc., 25, 1414–1416 (2004).
S. Rajender Varma, P. Kannan Naicker, J. P. Liesen, Selective nitration of styrenes with clayfen and clayan: A solvent-free synthesis of β-nitrostyrenes, Tetrahedron Letters, 39, 3977–3980 (1998).
T. Beitz, W. Bechmann, R. Mitzner, Investigation on the photoreaction of nitrate and nitrite ions with selected azaarenes in water, Chemosphere, 38, 351–361 (1999).
V. M. Nagaev, G. A. Sorol Skii, S. S. Khokhhov, A. F. Eleev, Direct N-nitration of bis(trifluoromethyl)-containing 2-azanorbornanes, Russian Chem. Bulletin., 52, 2285–2286 (2003).
Y. Kono, T. Yamasaki, A. Ueda, H. Shibata, Catalase catalyzes of peroxynitrite-mediated phenolic nitration, Biosci. Biotechol. Biochem., 62, 448–452 (1998).
S. P. Degade, S. B. Waghmode, V. S. Kadam, M. K. Dongare, Vapor phase nitration of toluene using dilute nitric acid and molecular modeling studies over beta zeolite, Appl. Catal., 226, 49–61 (2002).
C. Desroches, S. Parola, F. Vocanson, M. Perrin, R. Lamartine, J. M. Letoffe, J. Bouix, Nitration of thiacalix-
arene using nitrosium nitrate complexes: synthesis and characterization of tetranitro-, and tetra(4-pyridylimino) tetrahydroxythiacalix
arene, New J. Chem., 26, 651– 655 (2002).
T. Yamato, K. Tsuchihashi, N. Nakamura, M. Hirahara, H. T. Suzuki, Medium-sized cyclophanes, part 59:1 Nitration of [3.3]- and [3.3.3]-metacyclophanes through space electronic interactions between two or three benzene rings, Can. J. Chem., 80, 207–215 (2002).
Y. Usui, S. Takebayashi, M. Takeuchi, Photochemical nitration of benzoic acid derivatives by irradiation to nitrate ions, Bull. Chem. Soc. Japan, 65, 3183–3185 (1992).
M. Fisher, P. Warneck, Photodecomposition of nitrite and undissociated nitrous acid in aqueous solution, J. Phys. Chem., 100, 18749–18756 (1996).
T. Arakaki, T. Migake, T. Hirakawa, H. Sakugawa, pH dependent photoformation of hydroxyl radical and absorbance of aqueous–phase N(III) (HNO2 and NO2–), Environ. Sci. Technol., 33, 2561–2565 (1999).
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