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Title Acid-catalyzed depolymerization of coal by hydride donors. Quarterly report, November 1, 1983-January 31, 1984. [Naphthalenethiol; di-l-naphthyl sulfide]
Creator/Author Miller, B.
Publication Date1984 Jan 01
OSTI IdentifierOSTI ID: 5371532; Legacy ID: DE84007328
Report Number(s)DOE/PC/50805-T2
DOE Contract NumberFG22-82PC50805
Other Number(s)Other: ON: DE84007328
Resource TypeTechnical Report
Research OrgMassachusetts Univ., Amherst (USA). Dept. of Chemistry
Subject01 COAL, LIGNITE, AND PEAT; 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; COAL; DEPOLYMERIZATION; CONDENSED AROMATICS; REDUCTION; HYDRIODIC ACID; CHEMICAL REACTIONS; NAPHTHALENE; CHEMICAL REACTION YIELD; ORGANIC SULFUR COMPOUNDS; DESULFURIZATION; THIOLS; ACETIC ACID; CATALYTIC EFFECTS; CHEMICAL REACTION KINETICS; EXPERIMENTAL DATA; HIGH TEMPERATURE; ORGANIC CHLORINE COMPOUNDS; POTASSIUM IODIDES; RESEARCH PROGRAMS; STRUCTURAL MODELS; SULFONIC ACIDS; WATER; ALKALI METAL COMPOUNDS; AROMATICS; CARBONACEOUS MATERIALS; CARBOXYLIC ACIDS; DATA; DECOMPOSITION; ENERGY SOURCES; FOSSIL FUELS; FUELS; HALIDES; HALOGEN COMPOUNDS; HYDROCARBONS; HYDROGEN COMPOUNDS; INFORMATION; INORGANIC ACIDS; INORGANIC PHOSPHORS; IODIDES; IODINE COMPOUNDS; KINETICS; MATERIALS; MONOCARBOXYLIC ACIDS; NUMERICAL DATA; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; OXYGEN COMPOUNDS; PHOSPHORS; POTASSIUM COMPOUNDS; REACTION KINETICS; YIELDS
Description/Abstract 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/sup 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.
Country of PublicationUnited States
LanguageEnglish
FormatSize: Pages: 9
AvailabilityNTIS, PC A02/MF A01.
System Entry Date2007 Feb 06

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