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Remarkable Fractionation of the Hydrogen Isotope (δD) of Hydrocarbon during the Fast Aromatization Process: Insights from the Pyrolysis Experiments of n-Butylcyclohexane

Hydrocarbon aromatization involves the cleavage of multiple C–H bonds and the dehydrogenation of aliphatic rings, with a resultant fractionation of stable hydrogen between aromatic hydrocarbons and their counterpart precursors. Despite this understanding, there is still the paucity of studies on the hydrogen isotope (δD) fractionation of aromatic compounds and the δD fractionation characteristics during the aromatization process of hydrocarbons. In the present study, n-butylcyclohexane (BCH) was thermally pyrolyzed in a closed gold tube system at different time intervals to investigate the aromatization process of the monoaliphatic ring hydrocarbon. The δD evolutions of toluene (Tol) and methylcyclohexane (MCH) from the BCH pyrolysates were also examined, with the aim of studying the cleavage behavior of the C–H bond at the aliphatic ring. The results of the 24 h BCH pyrolysates showed that toluene was strongly enriched with 2H, whereas MCH was heavily depleted, with ΔδDTol–MCH (δDTol – δDMCH) being 162.3...