Abstract
A new and direct procedure for the selective formation of para-iodotoluene from toluene is demonstrated for the first time using iodine monochloride (ICl) as the iodinating agent and zeolite H-beta as the catalyst. Zeolite H-beta and H.K-L are found to be more para-selective compared to other zeolite catalysts and the conventional catalysts, H2SO4 and SiO2. In the presence of a solvent (nitrobenzene) the conversion of ICl increases and the formation of side products (chlorotoluenes) decreases. The probable mechanism for the formation of iodotoluenes and some amount of chlorotoluenes involves the electrophilic attack of toluene by I+ and Cl+, respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
S. Rozen and D. Zamir, J. Org. Chem. 55 (1990) 3552.
H. Suzuki,Organic Synthesis Coll., Vol. VI (Wiley, New York, 1988) p. 700.
A.N. Noviko, Zh. Obshchei Khim. 24 (1954) 655.
B.V. Tronov and A.N. Novikov, Khim. Khim. Technol. 3 (1960) 872.
R. Boothe, C. Dial, R. Conaway, R.M. Pagni and G.W. Kabalka, Tetrahedron Lett. 27 (1986) 2207.
H. Suzuki and Y. Haruta, Bull. Chem. Soc. Jpn. 46 (1973) 589.
J.S. Pizey,Synthetic Reagents, Vol. 3 (Wiley, New York, 1977) p.227.
T. Sugita, M. Idei, Y. Ishibashi and Y. Takegami, Chem. Lett. (1982) 1481.
W.C. Baird Jr. and J.H. Surridge, J. Org. Chem. 35 (1970) 3436.
O. Yoshihiro and A. Keizo, J. Am. Chem. Soc. 90 (1968) 6187.
H.P. Braendlin and E.T. Mc Bee, in:Friedel-Crafts and Related Reactions, Vol. III, Part 2: Halogenation, ed. G.A. Olah (Wiley-Interscience, New York, 1964) p. 1531.
L.J. Lambourne and P.W. Robertson, J. Chem. Soc. (1947) 1167.
R.M. Keefer and L.J. Andrews, J. Am. Chem. Soc. 78 (1956) 5623.
L.J. Andrews and R.M. Keefer, J. Am. Chem. Soc. 86 (1964) 4159.
D.E. Turner, R.F. O'Malley, D.J. Sardella, L.S. Barinelli and P. Kaul, J. Org. Chem. 59 (1994) 7335.
P. Ratnasamy, A.P. Singh and S. Sharma, Appl. Catal., in press.
A.P. Singh, S. Sharma and S.R. Rojatkar, J. Chem. Res., in press.
A.P. Singh, S.B. Kumar, A. Paul and A. Raj, J. Catal. 147 (1994) 360.
S.B. Kumar and A.P. Singh, J. Catal. 150 (1994) 430.
A.P. Singh and S.B. Kumar, Catal. Lett. 27 (1994) 171.
A.P. Singh and S.B. Kumar, Appl. Catal. 126 (1995) 27.
A. Botta, H.J. Buysh and L. Puppe, Angew. Chem. Int. Ed. Engl. 30 (1991) 1689.
K. Smith, M. Butters and B. Nay, Synthesis (1985) 1157.
Th.M. Wortel, D. Oudijn, C.J. Vleugel, D.P. Roelfsen and H. van Bekkum, J. Catal. 60 (1973) 110.
F. de la Vega, Y. Sasson and K. Huddersman, Zeolites 13 (1993) 341.
R.J. Argauer and G.R. Landolt, US Patent 3,702,886 (1972).
M.A. Camblor and J. Pérez-Pariente, Zeolites 11 (1991) 202.
P.N. Joshi, A.N. Kotasthane and V.P. Shiralkar, Zeolites 10 (1990) 598.
A.P. Singh and K.R. Reddy, Zeolites 14 (1994) 290.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sharma, S., Deshmukh, A.R.A.S. & Singh, A.P. A novel and direct selective iodination of toluene to para-iodotoluene using zeolite catalysts. Catal Lett 40, 257–260 (1996). https://doi.org/10.1007/BF00815292
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00815292