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1,2-Benzanthracene Derivatives in a Kuwait Mineral Oil

Nature volume 192, pages 256–257 (1961)Cite this article

Abstract

THE isolation of a number of polymethylanthracenes from fractions of a Kuwait crude oil has been reported by one of us1. The hydrocarbons were obtained by treatment of acetone extracts of the oil with maleic anhydride and chromatography of the material recovered from the acidic adducts by distillation from sodium hydroxide. We have now applied the same procedure to higher-boiling fractions of acetone and furfural extracts of the Kuwait oil (corrected boiling points in the range 390–440° C.) and have obtained crystalline fractions consisting essentially of alkyl derivatives of 1,2-benzanthracene. This is evident from their ultra-violet absorption spectra, which closely resemble those of typical alkylbenzanthracenes2. Vapour-phase chromatography of some of the fractions indicates, however, that they are mixtures containing varying proportions of benzanthracene and other components with retention times similar to those of mono- and dimethylbenzanthracenes. 1,2-Benzanthracene itself was isolated from several fractions by further chromatography on alumina as colourless plates, m.p. 154–156° undepressed, when mixed with an authentic specimen, m.p. 158–159°. The ultra-violet spectrum of the isolated material (λmax. 228, 256, 267, 277, 287; 299, 314, 327, 342, 358; 374, 384 mµ; log ɛ, 4.54, 4.51, 4.64, 4.89, 4.98; 3.95, 3.70, 3.80, 3.85, 3.69; 2.69, 2.86), and the infra-red spectrum3, were identical with those of 1,2-benzanthracene, and vapour-phase chromatography gave one peak with retention time similar to that of benzanthracene under the same conditions. The 2,4,7-trinitrofluorenone addition complex formed red needles, m.p. 217–221°, not depressed when mixed with an authentic specimen, m.p. 220–223° 4, and the identification was confirmed by preparation of the s-trinitrobenzene complex, orange needles, m.p. 161–163°, and comparison of this with an authentic specimen, m.p. 162–163° (found: C, 65.3; H, 3.6; C24H15N3O6 requires C, 65.3; H, 3.4 per cent).

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Authors and Affiliations

  1. Medical Research Council Carcinogenic Substances Research Unit, Washington Singer Laboratories, University of Exeter,

    W. CARRUTHERS & A. G. DOUGLAS

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  1. W. CARRUTHERS
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  2. A. G. DOUGLAS
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CARRUTHERS, W., DOUGLAS, A. 1,2-Benzanthracene Derivatives in a Kuwait Mineral Oil. Nature 192, 256–257 (1961). https://doi.org/10.1038/192256a0

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