Summary
-
1.
An investigation was made of the dehydrocyclization of 2-hexyl-and 2-(l-methylpentyl)-naphthalenes in presence of an alumina-chromia catalyst at 450° and of platinized charcoal at 350”.
-
2.
In presence of the alumina-chromia catalyst the dehydrocyclization proceeds mainly with the adjacent α-carbon atom and leads to the formation of phenanthrene hydrocarbons.
-
3.
In presence of platinized charcoal the dehydrocyclization proceeds mainly at the adjacent S -carbon atom (in the 3-position of the naphthalene) and leads to the formation of anthracene hydrocarbons.
-
4.
Under the given conditions there is observed the elimination of alkyl groups in the 4-position in phenanthrene and in the 1-and 4-positions in anthracene.
Similar content being viewed by others
Literature cited
N. I. Shuikin, L. A. Érivanskaya, and Yang Ai-hsi, Zh. obshch. khimii32, 823 (1962).
N. I. Shuikin, L. A. Érivanskaya, and Yang Ai-hsi, Dokl. AN SSSR133, 1125 (1960).
N. I. Shuikin, L. A. Érivanskaya, and Yang Ai-hsi, Trans. Conference in Honor of Centenary of Birth of N. D. Zelinskli [in Russian] (Izd. Odessk. gos. univ) (in press).
A. S. Bailey, G. B. Pickering, and J. C. Smith, J. Inst. Petrol.35, 103 (1949).
Yu. S. Zal'kind and S. A. Zonis, Zh. obshch. khimii6, 995 (1936).
Kh. M. Minachev, N. L Shuikin, and V. L. Vinogradov, Izv. AN SSSR, Otd. khim. n.1958, 866.
E. Clar, Aromatische Kohlenwasserstoffe (Berlin-Göttingen-Heidelberg, 1952).
M. S. Shvartsberg, M. I. Bardamova, and I. L. Koflyarevskii, Zh. obshch. khimii30, 436 (1960).
R. A. Friedel and M. Orchin, Ultraviolet Spectra of Aromatic Compounds (New York, 1951).
Collection: Application of Spectroscopy in Chemistry [Russian translation] (IL, Moscow, 1959).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Shuikin, N.I., Érivanskaya, L.A., Komissarova, N.L. et al. Catalytic dehydrocyclization of 2-hexyl- and 2-(1-methylpentyl)-naphthalenes. Russ Chem Bull 11, 304–308 (1962). https://doi.org/10.1007/BF00908041
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00908041