Petroleum Hydrocarbons

Analyses data on the composition, structure and formation of various petroleum hydrocarbons: the alkanes, cycloalkanes and arenes. Attention is paid to biological markers, com- pounds that may have preserved the main structural features of the original biogenic molecules. Concepts of chemical classification of crude oils are reviewed with respect to the molecular mass distribution of biological markers, and the genesis and chemical evolution of petroleum hydrocarbons are discussed.

Contenu

1 General Characteristics of Petroleum Hydrocarbons Molecular and Group-Type Methods of Analysis and Classification.- Biological Markers and Transformed Hydrocarbons.- Homology of Biological Markers.- Chemical Classification of Crude Oils.- Group-Type Distribution of Naphthenic Hydrocarbons in Crudes (Naphthenic Fingerprint).- 2 C5-C40 Alkanes.- Gas Chromatography in the Analysis of Alkanes.- Quantitative Distribution of Alkanes in Petroleums Possible Ways of Alkane Formation.- Normal Alkanes.- Branched Alkanes. Relative Concentration of Isomers (C6-C10 Hydrocarbons).- Mono- and Dimethyl-Substituted C11-C15 Alkanes.- C16-C23 Methylalkanes (Iso- and Anteisoalkanes).- C24-C30 12- and 13-Methylalkanes.- Isoprenoid Alkanes (Isoprenanes).- Geochemical Significance of Isoprenoid Alkanes.- Retention Indices of Alkanes.- 3 Cycloalkanes (Naphthenes).- C7-C10 Monocyclic Naphthenes.- C12-C25 Monocyclic Naphthenes.- Trimethyl-Substituted Cyclohexanes with Isoprenoid Chains (Cyclohexanes of the Carotenoid Type).- Bicyclic Naphthenes.- C8-C10 Hydrocarbons.- C14-C16 Hydrocarbons. Sesquiterpane Hydrocarbons.- Tricyclic Naphthenes.- Hydrocarbons of the Adamantane Series.- Protoadamantane Tricyclanes.- Hydrocarbons with Perhydrophenanthrene Structure (C19-C26 Pentamethylalkylperhydrophen- anthrenes).- Tetracyclic Naphthenes.- Bridged Hydrocarbons. C12-C14 Adamantanoid Hydrocarbons.- Diterpenoids (Kauranes, Gibberellins).- Hydrocarbons with a Perhydrochrysene Structure.- Steranes.- Regular Steranes.- Rearranged Steranes.- Triterpenoid Hydrocarbons. Hopanes.- Structurally Modified Hopanes.- Geochemical Significance of Hopanes.- GC Analysis of Steranes and Hopanes.- Steranes, Hopanes and the Optical Activity of Crudes.- 4 Aromatic Hydrocarbons (Arenes).- Group-Type Distribution of Aromatic Hydrocarbons in Crude Oils (Aromatic Fingerprint).- Individual Aromatic Petroleum Hydrocarbons.- Monoaromatic Hydrocarbons.- Diaromatic Hydrocarbons.- Triaromatic Hydrocarbons.- Aromatic Steroid Hydrocarbons.- Aromatic Triterpenoids and Hopanes.- Other Polyaromatic Hydrocarbons.- Evaluation of the Quantitative Content of Various Hydrocarbons in Crudes.- 5 Sources and Reactions of Petroleum Hydrocarbon Formation.- Sources of Petroleum Hydrocarbons.- Transformations of Organic Molecules in Sediments (Dia- and Catagenesis).- Compositional Transformations of Coal Hydrocarbons at Various Stages of Catagenesis.- Laboratory Simulation of Petroleum Formation Reactions (Aluminosilicates as Catalysts).- Transformations of Fatty Acids.- Formation of Normal Alkanes.- Formation of Branched Alkanes.- Thermodynamically and Kinetically Controlled Mechanism of Hydrocarbon Formation.- Formation of Isoprenoid Alkanes.- Formation of Saturated and Monoaromatic Steroids.- 6 Transformations of Petroleum Hydrocarbons in Nature (Chemical and Biochemical Alteration of Crude Oils).- Alteration of Crude Oil under Thermal Stress (Thermolysis).- Compositional Analysis of Light Petroleum Fractions.- Compositional Changes in Medium Petroleum Fractions.- Alterations in the Chemical Composition of Crudes under Microbiological Influence (Petroleum Biodegradation).- Results of Experiments on Microbial Alteration of Crude Oils.- Compositional Alteration of Crudes in Nature (Comparison of Experimental Data).- Asphaltenes and the Geochemical History of Crudes.- Biological Markers and the Genetic Classification of Crudes.- Conclusion: Venues of Further Research on Petroleum Hydrocarbon Composition and Structure.- References.