Coal Structure Cleavage Mechanisms: Scission of Methylene and Ether Linkages to Hydroxylated Rings.

Article abstract of DOI:10.1021/jo00329a034

The kinetics of the termolysis of the coal-model compounds (hydroxyphenyl)phenylmethanes and p-hydroxyphenyl phenyl ether in tetralin at 400 deg C are described.The observed rates for (hydroxyphenyl)phenylmethanes are shown to be quantitatively consistent with thermochemical data and an enol-keto tautomerization followed by rate-determining homolysis of the cyclohexadienone intermediate.For p-hydroxyphenyl phenyl ether the breakdown of this quantitative agreement and the effects of various additives indicate that the tautomerization is rate determining and most pro-bably involves electrophilic attack on the enolate ion.Implications for coal liquefaction and catalysis are briefly discussed.