Coal Liquefaction Model Studies: Free Radical Chain Decomposition of Diphenylpropane, Dibenzyl Ether, and Phenyl Ether via β-Scission Reactions

Article abstract of DOI:10.1021/jo00146a016

The termal decompositions of 1,3-diphenylpropane (1), dibenzyl ether (2), and phenethyl phenyl ether (3) have been found to proceed by free radical chain processes. 1 gave toluene and styrene with a reaction order of 1.55, E_A = 51.4 kcal/mol, and log A = 12.5.The reaction could be initiated by benzyl phenyl ether but not by 1,2-diphenylethane. 2 gave toluene and benzaldehyde with a reaction order of 1.43, E_A = 48 kcal/mol, and log A = 12.6.The reaction could be initiated with benzyl phenyl ether. 3 gave phenol and styrene with a reaction order of 1.21,E_A = 50.3 kcal/mol, and log A = 12.3.The reaction could be initiated by benzyl phenyl ether.All of the data are consistent with free radical chain processes with the reaction order determined by the termination reaction.No evidence for concerted reactions has been found.