Abstract
Alkyl-substituted ammonium and lithium chlorides inhibit oxygen consumption in the oxidation of styrene epoxide in the presence of p-toluenesulfonic acid in a tert-butanol-chlorobenzene (9: 1, v/v) solution at 343 K. The inhibitory effect of chlorides is the same for tetramethylammonium, benzyltriethylammonium, and lithium chlorides, thus suggesting the inhibiting action of the anion. The oxidation inhibition effect of ammonium fluoride is ∼2.5 times as strong as that of the chlorides. The main finding of the study is the simultaneous retardation of oxidation and acid-catalyzed heterolytic epoxide consumption by the chloride and iodide anions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. V. Petrov and V. M. Solyanikov, Pet. Chem. 39, 89 (1999).
L. V. Petrov and V. M. Solyanikov, Pet. Chem. 45, 202 (2005).
L. V. Petrov and V. M. Solyanikov, Pet. Chem. 50, 154 (2010).
L. V. Petrov, B. L. Psikha, and V. M. Solyanikov, Pet. Chem. 49, 245 (2009).
A. L. Aleksandrov, T. I. Sapacheva, and E. T. Denisov, Neftekhimiya 10, 711 (1970).
J. Biggs, N. B. Chapman, A. F. Finch, and V. Wray, J. Chem. Soc. B 1, 55 (1971).
J. M. Coxon and D. Q. McDonald, Tetrahedron Lett. 29, 2576 (1988).
Y. Yamashita, K. Iwao, and K. Ito, Polym. Lett. Ed. 17, 1 (1979).
J. N. Brönsted, M. Kilpatrick, and M. Kilpatrick, J. Am. Chem. Soc. 51, 428 (1929).
J. G. Pritchard and F. A. Long, J. Am. Chem. Soc. 78, 2667 (1956).
Z. Jedlinski, J. Kasperczyk, and A. Dworak, Eur. Polym. J. 19, 899 (1983).
R. P. Hanzlik and R. B. Westkaemper, J. Am. Chem. Soc. 102, 2464 (1980).
T. Tsuj, Bull. Chem. Soc. Jpn. 62, 645 (1989).
S. R. Jacober and R. P. Hanzlik, J. Am. Chem. Soc. 108, 1594 (1986).
M. Korn, W. Gfrörer, J. G. Filser, and W. Kessler, Arch. Toxicol. 68, 524 (1994).
L. V. Petrov and V. M. Solyanikov, Pet. Chem. 43, 177 (2003).
A. Filippi and M. Speranza, Int. J. Mass. Spectrom. 185–187, 425 (1999).
W. M. Pasika, J. Polym. Sci. A: Polym Chem. 12, 4287 (1965).
C. O. Guss, H. R. Williams, and L. H. Jules, J. Am. Chem. Soc. 73, 1257 (1951).
T. M. Santusso and D. Swern, J. Org. Chem. 40, 2764 (1975).
J. Biggs, N. B. Chapman, and V. Wray, J. Chem. Soc. B 1, 63 (1971).
J. Biggs, N. B. Chapman, and V. Wray, J. Chem. Soc. B 1, 71 (1971).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © L.V. Petrov, V.M. Solyanikov, 2012, published in Neftekhimiya, 2012, Vol. 52, No. 5, pp. 362–370.
Rights and permissions
About this article
Cite this article
Petrov, L.V., Solyanikov, V.M. Inhibition of mild oxidation of styrene epoxide by oxygen in acidic alcohol solution by halide ions. Pet. Chem. 52, 327–334 (2012). https://doi.org/10.1134/S096554411205009X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S096554411205009X