Table I. Data from Routine Analysis of Prudhoe Bay, Alaska, Crude Oil0 Distillation, Bureau of Mines Routine Method Stage 1. Distillation at atmospheric pressure, 741 mm, first drop, 81°F Cut Fraction No.temp. °F

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Alkyl and aryl sulfides were separated from aromatic hydrocarbons by liquid chromatography on a copper-loaded carboxylic cation exchange resin. The sulfides were strongly absorbed from n-pentane solution while the hydrocarbons eluted relatively rapidly and in the order of the increasing number of aromatic rings in the compound. Sulfides were then recovered from the column by backwashing with a mixture of pentane and ethyl ether. All sulfides examined were recovered from the column without loss. The separation method is not limited by the molecular weight range of the sulfides and hydrocarbons tested and therefore may be used to Isolate sulfides from such materials as high-boiling petroleum fractions. Sulfides were isolated by this procedure from petroleum aromatic concentrates that had been prepared by alumina-silica gel chromatography. Mass spectral examination of these sulfide extracts showed the presence of cyclic and aryl sulfides as well as other materials.The problem of separating sulfur compounds from the hydrocarbons and other materials in petroleum has received much attention for many years. An extensive review of separation methods has been presented by Rall et al. (I), including valuations of the quality of the products and the types of materials for which the methods are useful. The purpose of this investigation was the development of a method for isolation of sulfides as a class that would be suitable for petroleum fractions.No separation method has been found to be completely satisfactory for the higher boiling fractions of crude oil. Formation of sulfonium halides by reaction of hydrogen halides with the sulfides has been the most satisfactory method for these materials (1 1. However, separations have been incomplete owing to occlusion of polycyclic aromatic hydrocarbons in the sulfonium halide fraction and excessive solubility of the sulfonium halides in the hydrocarbon fractions. Alkyl aryl sulfides and diary1 sulfides are not separated satisfactorily from aromatic hydrocarbons by the sulfonium halide method.Organic sulfides are known to form adducts with metal cations and many other substances (2-4), particularly those that may be classified as "soft" acids (5, 6). This characteristic has been used for separations by liquid extraction ( I , 7 ) and by liquid-liquid chromatography (8). The chromatographic procedure utilized an aqueous solution of mercury or zinc salts as the stationary phase and an aliphatic hydrocarbon as the mobile phase. Application of this method was limited to the lower molecular weight sulfides, presumably because of insolubility of higher sulfides in aqueous phases. In fact, the sulfides are eluted in the probable order of their solubility in water. This suggests that a chromatographic system that eliminates the water solubility effect may permit a class separation of sulfides without regard to the molecular weight range.Ligand exchange chromatography techniques have been developed to resolve mixtures that present somewhat similar problems (9, I O ) . Most often, this tech...

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Compositional data of coal liquid products derived from the H-Coal process were obtained. Two overhead products (one from the fuel oil mode of operation and the other from the syncrude mode of operation) were prepared by Hydrocarbon Research, Inc. from Illinois No. 6 coal. The compositional data of these products are tabulated, and characteristics of the materials are discussed. Separation and characterization methods, with slight modification, as developed by the Bureau of Mines-API Research Project 60 for characterizing heavy ends of petroleum were successfully used in analyzing coal liquid distillates within the boiling range 200° to 540° C. Distillates boiling below 200° C were separated and analyzed using chromatographic and spectral techniques. 1 Research chemist. 2 project leader.