Acid-Catalyzed Depolymerization of Coal by Hydride Donors. Quarterly Report, February 1-April 30, 1983 (1-Phenylthio-2-Naphthol).

摘要

To test the hypothesis that coal depolymerization resulting in low molecular weight products could result from acid catalyzed reaction of coal with phenols capable of alkylation only at a single site, samples of PSOC 1278 coal were reacted with 2,6-dimethylphenol, 2,4-dimethylphenol, and 2-naphthol, in the presence of p-toluenesulfonic acid at 182 to 212 exp 0 C, and the yields of solubilized materials compared with those obtained using phenol as the reagent. No significant reaction was observed with 2,6-dimethylphenol,but moderate solubilization was obtained with 2,4-dimethylphenol. Appreciable solubilization (compare to phenol) was obtained with 2-naphthol, but the results are ambiguous, since a very large increase in weight was obtained from the reaction. For use as a model compound in studies of coal desulfuration by formic acid solutions, 1-phenylthio-2-naphthol (1) was prepared by reaction of 2-naphthol with phenylsulfenyl bromide. Compound 1 was stable to formic acid solution at 100 exp 0 C, but cleavage of the naphthalene-sulfur bond to form 2-naphthol, thiophenol, and (with increasing time) phenyl disulfide proceeded smoothly on addition of potassium iodide. The reaction rates were inversely proportional to base concentration, and proportional to iodide ion and trifluoromethanesulfonic acid catalyst concentrations. (ERA citation 08:035058)