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8685122 
Journal Article 
Reactions of cyclic hydrocarbons. Part III. The action of Oleum on cyclohexane, cyclohexene, and related hydrocarbons 
Sperling, R 
1949 
Yes 
Journal of the Chemical Society
ISSN: 0368-1769 
1932-1938 
English 
All the cycloalkanes examined (cyclohexane, dieyclohexyl, cyclohexyl-methyl-cyclopentane, and decahydronaphthalene) are attacked only slowly by oleum at moderately low temperatures. Oleum appears to dehydrogenate these hydrocarbons to unsaturated compounds which are then polymerised, the resulting unsaturated polymers being subsequently oxidised and sulphonated. Only a small proportion of the cycloalkane is completely dehydrogenated to the corresponding aromatic compound, cyclohexane giving a small yield of benzenesulphonic acid, and decahydronaphthalene a small proportion of naphthalene-2-sulphonic acid. Neither tetrahydronaphthalene nor its sulphonation products are formed as intermediate compounds during the latter reaction. Oleum and cyclohexene give rise to unsaturated polymers and their oxidation and sulphonation products, together with products resulting from the primary sulphonation of cyclohexene, modification by the excess of oleum present also occurring. In addition, cyclohexyl hydrogen sulphate is produced under mild conditions, and a little benzenesulphonic acid under severer conditions.