Chemical structures and reactivities of coal as an organic natural product

Conference · Mon Jan 01 00:00:00 EST 1979 · Am. Chem. Soc., Div. Fuel Chem., Prepr.; (United States)

OSTI ID:5954993

Collins, C J; Hombach, H P; Benjamin, B M; Roark, W H; Maxwell, B; Raaen, V F

Based on the results of experiments conducted with labelled model compounds, including tetralin, and with Illinois No. 6 coal, it was concluded that the role of tetralin during coal conversion is (1) to act as a dispersion vehicle; (2) to supply hydrogen radicals, when needed, to trap coal radicals; and (3) in a very minor way to undergo intermolecular reaction with the coal through making and breaking of C--C (and possibly other) bonds. Two chemical reactions for solubilizing coals which have received much attention in recent years are: (1) the Friedel Crafts reaction and reductions, either with lithium in suitable solvents, or electrolytically with lithium salts in ethylenediamine. Part of the interest in these reactions is undoubtedly due to the fact that they can be carried out at low temperatures. The chemical changes effected during coal reductions are usually considered to be breakage of ether and thioether linkages, as well as reduction of aromatic nuclei. Alkyl groups are not affected. The Birch--Hueckel reaction of aromatic rings to cyclic olefins is well known. It was recently reported that the use of NaK in mixed ethers as a coal reductant cleaves the alkyl linking groups between aromatic moieties, and results in an increase in the number of methyl groups in the reduced product. Oxidation studies have indicated a high frequency of ethylene connecting links in some bituminous coals. We therefore carried out the reduction of three model compounds using glycol ethers as the solvent. The compounds chosen were diphenyl-methane, bibenzyl, and 1,3-diphenylpropane. Of the three compounds, diphenylmethane exhibited some, and bibenzyl exhibited considerable C--C splitting in only 20 minutes, whereas 1,3-diphenylpropane was stable except for traces of toluene and ethylbenzene (when quenched with propanol-2).

• Research Organization: Oak Ridge National Lab., TN
• OSTI ID: 5954993
• Report Number(s): CONF-790415-P2
• Journal Information: Am. Chem. Soc., Div. Fuel Chem., Prepr.; (United States), Vol. 24:1; Conference: 177. national meeting of the American Chemical Society, Honolulu, HI, USA, 1 Apr 1979
• Country of Publication: United States
• Language: English

Related Subjects

01 COAL, LIGNITE, AND PEAT
COAL
CHEMICAL REACTIONS
STRUCTURAL CHEMICAL ANALYSIS
COAL LIQUEFACTION
CHEMICAL BONDS
CLEAVAGE
LABELLED COMPOUNDS
POTT-BROCHE PROCESS
RADICALS
REDUCTION
STRUCTURAL MODELS
TETRALIN
AROMATICS
CARBONACEOUS MATERIALS
CRYSTAL STRUCTURE
ENERGY SOURCES
FOSSIL FUELS
FUELS
HYDROCARBONS
LIQUEFACTION
MICROSTRUCTURE
ORGANIC COMPOUNDS
THERMOCHEMICAL PROCESSES
010600* - Coal
Lignite
& Peat- Properties & Composition
010405 - Coal
Lignite
& Peat- Hydrogenation & Liquefaction