PART I: THERMAL AND ACID-CATALYZED REACTIONS OF COAL AND COAL MODEL COMPOUNDS. PART II: ACID-CATALYZED REACTIONS OF AROMATIC CARBONYL COMPOUNDS

Part I. In an effort to elucidate structural characteristics of Texas lignite coal, transalkylations of the coal to diphenyl ether and m-xylene were performed in acidic medium and the reaction products were analyzed by capillary GC/MS. The pyridine solubility of the recovered coals was determined to assess any changes in coal structure.;Part II. Aromatic ketones with different electronic and steric characteristics were allowed to react with arenes of differing nucleophilicities in the presence of various acid catalysts. Analysis of the reaction products produced strong evidence for transacylation reactions. A mechanism is proposed that accounts for the observed products.;Attempts to expand the work to aromatic aldehydes demonstrated that transformylation does not occur under any of the experimental conditions examined. The aldehydes appeared to be more prone to give addition products and to decarbonylate. The addition products underwent secondary reactions to produce diarylmethanes and anthracenes. Mechanisms are proposed to account for all the observed products.;The thermal behavior of coal, coal extracts, and model compounds also was investigated to determine potential precursors to the n-alkanes and 1-alkenes often observed in the volatile matter from low temperature pyrolysis of coals. The model compounds included n-hydrocarbons as well as linear and branched alkyl-aromatics.