Hydrogenolysis reactions of coal liquid related model compounds and coal liquefaction residue (CLR) from Muswellbrook coal were carried out using red mud and sulfur catalysts at 693K for 1 hour. In the hydrogenolysis reaction of 7, 8-benzoquinoline (7BQ) alone, amounts of 7BQ absorbed onto the catalyst surface were lesser than the reaction of 5, 6-benzoquinoline. Therefore, in the reaction of CLR and 7BQ, because 7BQ dissolved and dispersed CLR, the catalyst activity was maintained. Then, the synergistic effects such as the decrease of dichloromethane insoluble and the increase of n-hexane soluble in the products appeared.