The solubility and insolubility of heavy oils and their fractions in d
ilute mixtures with various solvents were used to characterize heavy o
il interactions. A two-dimensional solubility parameter, developed for
the selection of solvents for organic polymers, was found to group al
l the solvents for each heavy oil fraction in polygon areas when the c
omplexing solubility parameter component was plotted against the field
force solubility parameter component. All fractions of Cold Lake vacu
um residua, except for the saturate fraction, form concentric solubili
ty areas. Therefore, in going in the direction of decreasing aromatici
ty from coke to asphaltenes to resins to aromatics, all solvents for t
he previous fraction in the series are also solvents for all subsequen
t fractions in the series. As a result, asphaltenes can be precipitate
d, but not extracted, from heavy oils. This is attributed to the inter
action among polynuclear aromatics being the dominate interaction in p
etroleum that causes insolubility in hydrocarbon liquids. However, the
paraffinic chains on the same petroleum molecules limit their solubil
ity in highly complexing liquids. In contrast, even vacuum gas oils fr
om the Exxon Donor Solvent coal liquefaction process are insoluble in
aromatic liquids but soluble in moderately complexing liquids because
of hydrogen bonding, resulting from oxygen functionality. Hydrotreatin
g of these coal derived vacuum gas oils reduces their oxygen functiona
lity and increases their solubility areas so that they become compatib
le with petroleum liquids.