Evidence for the involvement of quinone rings in reactions of some coals with tetralin

Model compounds representing a variety of hydrocarbon groups and most of the oxygen-containing functional groups have been tested for reactivity with tetralin at 400° C. Only the quinones were capable of oxidizing tetralin to naphthalene. Anthraquinone is completely deoxygenated to anthracene. Evidence for homolysis of carbon-carbon bonds was found only in the case of dibenzyl, and this was not accompanied by oxidation of tetralin. The extractability of subbituminous coals with the non-reducing solvent, diphenyl-diphenyl ether eutectic, is correlated with oxygen content and depth of burial. It is suggested that oxidized coals near the surface contain quinone rings, and that dissolution by tetralin is primarily then due to lowering of the solvent parameter as a consequence of deoxygenation.