SOLVENT-INDUCED FREE RADICAL SCISSION OF STRONG BONDS IN COAL: AN EXPERIMENTAL AND THEORETICAL STUDY OF THE RADICAL HYDROGEN TRANSFER PATHWAY

Publisher Summary This chapter discusses the solvent-induced free radical scission of strong bonds in coal. In a study described in the chapter, degassed sealed ampules of a 1:1 mixture of anthracene and dihydroanthracene, containing 9,10-dimethylanthracene and 9-benzylanthracene, were pyrolyzed in a sand bath at 350–400°C. Products were analyzed by gas chromotography, and yields were determined using an internal standard. 2-ethylanthracene was substituted for anthracene in some experiments to determine the amount of alkyl radical addition to the solvent under the reaction conditions. All reactions were analyzed at less than 15% conversion of substrate. It was found that pyrolysis of a mixture of 9-benzylanthracene and 9,10-dimethylanthracene at 350°C in a 1:1 mixture of 9,10-dihydroanthracene (H 2 An) anthracene (An) in fused silica tubes leads to the selective scission of benzyl radical over scission of methyl radical. Product analysis of the yield of toluene and 9-methylanthracene gives a selectivity of 14:1 at 350°C after correction for the addition of Me· to the solvent.