Acid-Catalyzed Depolymerization of Coal by Hydride Donors. Quarterly Report, November 1, 1983-January 31, 1984

摘要

The rate of reductive desulfuration of 1-naphthalenethiol by potassium iodide and trifluoromethane sulfonic acid in trichloroacetic acid increased with the addition of small amounts of water. Quantitative yields of naphthalene were obtained from 1-naphthalenethiol at 140 exp 0 C in trichloroacetic acid solutions containing from 2 to 8 wgt. % of water. The product was stable indefinitely under these reaction conditions. In contrast, the yield of naphthalene obtained using anhydrous conditions reached a maximum of ca. 60% and then decreased at longer reaction times, presumably due to the occurrence of electrophilic substitution and other side reactions. Similarly, reductive desulfuration of di-1-naphthyl sulfide in anhydrous trichloroacetic acid gave a maximum of ca. 1.5 moles of naphthalene per mole of sulfide, after which the yield of naphthalene began to decrease. In contrast, addition of ca. 4 wgt. % of water resulted in more rapid desulfuration and the formation of essentially quantitative yields of naphthalene. (ERA citation 09:015796)