The hydrogenolysis reaction products derived from Muswellbrook coal were separated into dichloromethane insoluble (liquefaction residue CLR) and dichloromethane soluble (DS). Furthermore, DS was separated into basic (B), neutral (N) and acidic (A) fractions. Then, the hydrogenolysis reactions of mixture of CLR and any one of DS, B, N and A were investigated at 420°C for 1 h under the presence of H
2 (60 kg/cm
2), with red mud and sulfur catalysts. In the reaction of mixture of CLR and N, the decreases of hexane soluble (HS) and hexane insoluble-benzene soluble (HIBS) and the increase of dichloromethane insoluble (DI) were observed. The catalyst deactivation occurred by the adsorption on the catalyst surface of highly condensed aromatic compounds in CLR, the hydrogenolysis of aromatic compounds in N and the conversions of CLR to dichloromethane soluble were inhibited. In the reaction of mixture of CLR and A, since there were little interaction between CLR and phenols in A, the conversions of A to HS and CLR to dichloromethane soluble were inhibited by the catalyst deactivation described above. In the reaction of mixture of CLR and B, CLR was dissolved and dispersed into B composed of heterocyclic nitrogen compounds, and more donatable hydrogens were formed during the reaction of mixture of CLR and B. Therefore, the catalyst was not deactivated, the radicals derived from mixture of CLR and B were stabilized by hydrogen donation. As a result, the synergistic effects such as the increase of HS and the decrease of benzene insoluble, not predictable from the hydrogenolysis reaction of CLR or B alone, appeared.
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