Coal-transformation chemistry. Fourth quarterly progress report

Technical Report · Tue Jan 01 04:00:00 EST 1980

DOI:https://doi.org/10.2172/6573997· OSTI ID:6573997

Stock, Leon M.; Blain, D. A.; Handy, C. I.; Heimann, P.; Huang, C. B.; King, H. -H.; Landschulz, W.; Willis, R. S.

Pyrene, perylene, anthracene, 9,10-diphenylanthracene, naphthalene and biphenyl have been employed as electron transfer agents in the reduction of Illinois No. 6 coal with potassium in tetrahydrofuran. These electron transfer agents are about equally effective for the reduction of this coal at short reaction times (3 hours). We conclude that the anions of biphenyl and naphthalene achieve a greater degree of electron transfer to the coal molecules and that the use of these anions enhances the fragmentation reactions of the coal. Illinois No. 6 bituminous coal and Colorado subbituminous coal were reacted with potassium dissolved in a mixture of monoglyme and triglyme at -50/sup 0/C. The reduction reaction proceeded via solvated electrons rather than by an electron transfer reaction. The coals were then alkylated with methyl iodide and their solubilities in tetrahydrofuran were determined. The Illinois coal reductively alkylated via solvated electrons was considerably less soluble in tetrahydrofuran than the same coal reductively alkylated with potassium and naphthalene in tetrahydrofuran. A sample of Illinois No. 6 coal which had been reductively butylated with n-butyl-1-/sup 13/C iodide was hydrolyzed. Carbon nmr spectroscopy of the hydrolyzed coal revealed that the resonances previously assigned either to the presence of n-butyl carboxylates or to n-butyl tertiary ethers were removed. This observation provides definite evidence that only carboxylates were present in the original alkylated product. Selective alkylation of the acidic hydroxyl groups in Illinois No. 6 coal was carried out using tetrabutylammonium hydroxide as a phase transfer catalyst and iodomethane or 1-iodobutane as alkylating agent as described by Liotta. The tetrahydrofuran solubility of the product was significantly improved in a reaction where reductively butylated coal was subsequently coal was subsequently methylated using Liotta's procedure.

• Research Organization: Chicago Univ., IL (USA)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC22-80PC30088
• OSTI ID: 6573997
• Report Number(s): DOE/PC/30088-4
• Country of Publication: United States
• Language: English

Related Subjects

01 COAL, LIGNITE, AND PEAT
010405* -- Coal
Lignite
& Peat-- Hydrogenation & Liquefaction
ALKYLATION
CARBONACEOUS MATERIALS
CHEMICAL REACTIONS
CHEMISTRY
COAL
COAL LIQUEFACTION
ELECTRON TRANSFER
ENERGY SOURCES
FOSSIL FUELS
FUELS
INFRARED SPECTRA
LIQUEFACTION
MAGNETIC RESONANCE
MATERIALS
NUCLEAR MAGNETIC RESONANCE
REDUCTION
RESONANCE
SPECTRA
THERMOCHEMICAL PROCESSES