At 400 °C in 20 min runs, coal was converted by methanol/KOH systems to a product which was extractable by pyridine fully, and 15-25% by methanol. The methanol-sotuble fraction is significantly enriched in hydrogen relative to the starting coal, reduced in both N and organic S, and was fluid at room temperature. It was established that this liquid product was derived from the coal, and not the methanol. The liquid was distillable at 300 °C/133 Pa (1 torr), and an analysis of the liquid by gas chromatography/mass spectrometry techniques shows it to consist of significant quantities of butyrolactone, polymethyl phenols, and some unidentified compounds having major C4H7O and C4H7O2 MS fragments. The methanol-insoluble products were hydrogen-enriched also, but to a lesser degree. The suggested conversion scheme is similar to that proposed for isopropyl alcohol, where alkoxide ion donates hydride to the coal, followed by proton abstraction by the anionic intermediate from the alcohol medium. In model-compound studies at 400 °C with the system, it was found that phenyl ether was converted in 33% yield to a collection of polymethyl phenols, similar to those found in the coal distillate. Anthracene was converted in about 80% yield to 9,10-dihydroanthracene. Biphenyl, phenanthrene and bibenzyl were found to be unreactive in our system. © 1979.
