Summary
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1.
It has been found that cyclopentane, under a high pressure of hydrogen (20 atm), in presence of a platinum-alumina catalyst, and at 460°, undergoes far-reaching changes with formation not only of hydrogenolysis products (pentane, and isopentane formed by its isomerization), but also hydrogenosynthesis (methyl-cyclopentane, hexane and its isomers, benzene, toluene, xylene, polymethylbenzenes).
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2.
Under similar conditions (hydrogen pressure, 15 atm), methylcyclopentane is converted into a mixture of cyclopentane, pentane, 2-methylbutane, hexane and its isomers, benzene, toluene, xylene, and polymethylbenzenes.
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3.
In contact with the same catalyst at 460° under a pressure of hydrogen (15 atm), cyclohexane gives a mixture of benzene, methylcyclopentane, cyclopentane, hexanes, pentanes, toluene, xylenes, and polymethylbenzenes.
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4.
The synthesis reactions are in all cases to be explained by the alkylation of hydrocarbon molecules (cyclopentane, benzene, toluene) by means of methylene radicals arising under the given conditions as a result of the methane breakdown of cycloalkanes at the surface of the specific platinum-alumina catalyst.
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Shuikin, N.I., Berdnikova, N.G. & Novikov, S.S. Catalytic reactions of five- and six-membered cycloalkanes under a pressure of hydrogen at high temperature. Russ Chem Bull 2, 243–249 (1953). https://doi.org/10.1007/BF01170993
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DOI: https://doi.org/10.1007/BF01170993