Elbistan-Afsin lignite, 64.2% C (daf), was reduced with lithium in THF
in the presence of purified naphthalene as an electron transfer agent
. The reduced lignite was then extracted with supercritical toluene. E
ven under comparatively mild conditions, 340 degrees C, relatively lar
ge yields of supercritical extract were obtained, almost all of which
dissolved in benzene. The n-pentane-soluble and benzene-soluble fracti
ons of the extract were eluted using column chromatography. Less than
half of the originally soluble material could be eluted with n-pentane
or benzene, the total methanol eluates amounting to 56.1% of the init
ial extract. The eluates were analysed by gas chromatography/mass spec
trometry. The amount of phenol was 23.6% of the original benzene solub
le fraction. It was concluded that bond cleavage had taken place durin
g the reduction of the lignite. The naphthalene used as an electron tr
ansfer agent participated in side reactions.