Coal transformation chemistry. Sixth quarterly progress report
Illinois No. 6 coal was methylated reductively in liquid ammonia and its tetrahydrofuran solubility and spectral properties were studied. The same coal sample was then subjected to a second selective methylation and its solubility and spectroscopic properties were examined. O-Alkylation did not proceed to completion during the first alkylation reaction. However, selective methylation using tetrabutylammonium hydroxide as a catalyst yielded virtually complete 0-alkylation. The carbon NMR spectra of the alkylation products have been obtained. The proton and carbon NMR spectra of the reductive methylation products prepared using methyl-/sup 13/C iodide suggest that carbon alkylation exceeds oxygen alkylation and that the alkylation of phenolic groups is the dominant 0-alkylation reaction. A /sup 13/C enriched reductively methylated Illinois bituminous No. 6 coal sample was selectively demethylated with lithium iodide in 2,4,6-collidine. The subsequent CMR analysis suggests that there is a preponderance of aryl methyl ethers and an absence of alkyl methyl ethers in the alkylation product. The influence of inorganic substances and organic sulfur compounds on the deuterium-hydrogen exchange reactions of diphenylmethane and tetralin-d/sub 12/ as well as the deuterium-hydrogen exchange reactions of diphenylmethane and naphthalene-d/sub 8/ were studied in the presence of oxygen and in inert atmospheres. The results indicate that most of the salts of alkaline earth metals, alkali metals and transition metals do not accelerate the reaction at 400/sup 0/ or 500/sup 0/C. Elemental sulfur does not enhance the coal dissolution at 400/sup 0/C. However, in the presence of oxygen, thiophenol enhanced the exchange reaction of diphenylmethane and tetralin-d/sub 12/.
- Research Organization:
- Chicago Univ., IL (USA)
- DOE Contract Number:
- AC22-80PC30088
- OSTI ID:
- 6164680
- Report Number(s):
- DOE/PC/30088-6; ON: DE82003315
- Country of Publication:
- United States
- Language:
- English
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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
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ALKALI METAL COMPOUNDS
AMMONIA
AROMATICS
BITUMINOUS COAL
BLACK COAL
CARBONACEOUS MATERIALS
CHEMICAL REACTIONS
CHEMISTRY
COAL
COAL LIQUEFACTION
CONDENSED AROMATICS
DEALKYLATION
DEUTERIUM
DEUTERIUM COMPOUNDS
ENERGY SOURCES
ETHERS
FOSSIL FUELS
FUELS
FURANS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
INORGANIC PHOSPHORS
IODIDES
IODINE COMPOUNDS
ISOTOPES
ISOTOPIC EXCHANGE
LIGHT NUCLEI
LIQUEFACTION
LITHIUM COMPOUNDS
LITHIUM HALIDES
LITHIUM IODIDES
MATERIALS
METHYLATION
NAPHTHALENE
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NMR SPECTRA
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHOSPHORS
RESEARCH PROGRAMS
SPECTRA
STABLE ISOTOPES
TETRAHYDROFURAN
THERMOCHEMICAL PROCESSES