A Probable Origin of Dibenzothiophenes in Coals and Oils

To probe the possibility of thiophenolate as an origin of dibenzothiophenes (DBTs) and establish the detailed chemical transformations from thiophenolate to DBTs, the thermal degradation of thiophenolate has been carried out at various temperatures. The characterizations of both gaseous products and solid residues indicate that DBTs together with benzene, diphenyl sulfide, and diphenyl disulfide are the major degradation products. The presence of benzene supports that the thermal degradation of thiophenolate begins with the homolysis of Ar‒H bonds. The subsequent hydroarylation followed by the elimination and cyclization reactions facilely generates DBTs. The transformation of thiophenolate to DBTs is chemically simple and highly geochemically feasible. It readily unifies the chemical pathways involved in the generation of DBTs from thiophenolate and that of dibenzofurans from phenolate in nature.Keywords:thiophenolate;dibenzothiophene;phenyldibenzothiophene;homolysis;hydroarylation;aromatic sulfur heterocyclics