Coal-transformation chemistry. Ninth quarterly progress report. [1,2-di(1-naphthyl)ethane and 1,2-di(9-anthryl)ethane]
The effort on donor solvent coal chemistry during this quarter concerned the factors that govern the cleavage of ethylene linkages in several representative compounds. The behavior of the resulting radicals were also studied. Bibenzyl, 1,2-di(1-naphthyl)ethane and 1,2-di(9-anthryl)ethane were selected as the reaction substrates. The latter two compounds have been synthesized and the catalytic effect of these compounds on the exchange reaction of diphenylmethane with tetralin-d/sub 12/ at 400/sup 0/C was examined. The results showed that the catalytic effect was in the order: 1,2-di(1-naphthyl)ethane ..-->.. 1,2-di(9-anthryl)ethane ..-->.. bibenzyl. Nuclear Overhauser effect (NOE) suppression in carbon nmr spectra of reductively alkylated coals is discussed. Suppression of NOE in /sup 13/C-enriched alkylated coal samples does not result in a difference in carbon to oxygen alkylation ratios. However, for unenriched reductively alkylated coal samples, suppression of NOE is essential for accurate quantitative analysis. With NOE suppression, the carbon to oxygen alkylation ratios of reductively ethylated coal are consistent with previous results for reductively methylated and butylated Illinois No. 6 coal. The EPR spectra of Illinois No. 6 coal and several of its reductive alkylation products were studied. The EPR spectra of the hydrofuran soluble reaction products and the insoluble reaction products were each studied. There is a large decrease in the spin concentration in the reductive alkylation products in both the soluble and insoluble products. However, the insoluble materials which are, of course, relatively rich in inorganic compounds exhibit broad resonance bands extending to zero field. The substances responsible for these broad absorptions are readily removed by treatment with dilute hydrochloric acid. The materials treated in this way exhibit only a weak resonance at g = 2. 7 figures, 7 tables.
- Research Organization:
- Chicago Univ., IL (USA)
- DOE Contract Number:
- AC22-80PC30088
- OSTI ID:
- 5016785
- Report Number(s):
- DOE/PC/30088-9; ON: DE82021344
- Country of Publication:
- United States
- Language:
- English
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ALKYLATION
AROMATICS
BIBENZYL
CARBONACEOUS MATERIALS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMISTRY
COAL
COAL LIQUEFACTION
CONDENSED AROMATICS
DATA
DEUTERIUM
DEUTERIUM COMPOUNDS
ELECTRON SPIN RESONANCE
ENERGY SOURCES
EXPERIMENTAL DATA
FOSSIL FUELS
FUELS
HIGH TEMPERATURE
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
INFORMATION
ISOTOPES
ISOTOPIC EXCHANGE
LIGHT NUCLEI
LIQUEFACTION
MAGNETIC RESONANCE
MATERIALS
NMR SPECTRA
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
RESEARCH PROGRAMS
RESONANCE
SPECTRA
STABLE ISOTOPES
TETRALIN
THERMOCHEMICAL PROCESSES