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Analytical Studies on Australian Oil Shales Jurgen Korth University of Wollongong

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Analytical Studies on Australian Oil Shales Jurgen Korth University of Wollongong University of Wollongong Research Online University of Wollongong Thesis Collection University of Wollongong Thesis Collections 1987 Analytical studies on Australian oil shales Jurgen Korth University of Wollongong Recommended Citation Korth, Jurgen, Analytical studies on Australian oil shales, Doctor of Philosophy thesis, Department of Chemistry, University of Wollongong, 1987. http://ro.uow.edu.au/theses/1110 Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] ANALYTICAL STUDIES ON AUSTRALIAN OIL SHALES. A thesis submitted in fulfilment of the requirements for the award of the degree of DOCTOR OF PHILOSOPHY from THE UNIVERSITY OF WOLLONGONG by JURGEN KORTH, B. Sc, M. Sc. DEPARTMENT OF CHEMISTRY 1987 ABSTRACT. Oil shale samples from the upper and lower units of the bipartite Duaringa oil shale deposit, Queensland Australia, have been analysed using a variety of fast characterisation procedures such as solvent extraction, pyrolysis-GC, isothermal pyrolysis and TGA. A CDS-150 pyroprobe was modified to simulate Fischer assay retort conditions on a micro scale basis and was used for the rapid assessment (pyrolysis-FID) of the hydrocarbon generating potential of these and other oil shale samples. Results obtained for Duaringa were extended to analytical studies on an extensive range of selected Australian and several overseas reference oil shales. An electronically-controlled tube-furnace retort was constructed to provide accurate control over heating rates and pyrolysis environments. The retort was used to produce shale oils for samples from both units of the Duaringa deposit, which were then compared with each other and with a Duaringa reference oil obtained using the conventional Fischer assay procedure. The retort was also used to study the composition of pyrolysate produced over narrow sequential temperature ranges to provide a better understanding of retort processes and pyrolysis mechanisms. Solvent extracts of the Duaringa lamosites contain a homologous series of linear alkanals not previously reported in Australian oil shales. Following their characterisation in the Duaringa bitumen (based on mass-spectral data and retention-index values) these aldehydes were subsequently detected in extracts from other Australian oil shale deposits. The possible origins and significance of these and other components found in oil shale bitumen are discussed in relation to the source, environment of deposition, maturation and bio-degradation of the kerogen comprising these deposits. Results obtained from the pyrolysis-FID procedures for Duaringa were used to characterise (type) the Australian and overseas oil shales on the basis of their relative abilities to generate (type-dependent) quantities of hydrocarbons (oil and gas) from the pyrolysis of their raw shale. For shales comprising type I and II organic matter, hydrocarbon oil and gas yields correlated positively with Fischer assay oil yields, petrographic data, kerogen content and elemental composition. The procedure provides a rapid and inexpensive screening method for the accurate first assessment of the relative oil -generating potential of a given deposit. Retort oils from the upper unit (resource seams) and lower unit (> 1000 m) were analysed by extraction and column chromatography, followed by detailed gas chromatography and mass spectrometry of each of the 19 fractions isolated. Hundreds of compounds were identified and their retention indices calculated where the components eluted as discrete peaks in respective gas chromatograms. Least-squares linear regression analysis of these data allowed retention-index equations to be calculated for a wide variety of different compound classes. Collectively this information provides reference data which should allow comprehensive chemical characterisation of shale oil to be achieved without the need for mass spectrometric analysis of each column fraction. Despite the substantial difference in the depth of burial, the chemical composition of the upper- and lower-seam Duaringa shale oils was very similar and found to resemble those from non-carbonaceous seams of other Tertiary Australian deposits (Condor and Rundle). The distribution and relative abundances of some of the isomeric structures encountered in each of them indicate that retort-product concentrations are influenced by relative variations in the thermocatalytic activity of the mineral matrix. Accurate and class-specific quantitative data obtained for Duaringa phenols, nitriles and ketones suggest that these volatile components constitute only a minor portion of the otherwise non-volatile column fractions in which they are found. This implies that gravimetric data published for these compound classes for Condor and Rundle shale oils overestimate their abundance. Data obtained from rapid characterisation techniques were interpreted in relation to the composition of the corresponding retort oils. Advantages and limitations of microscale screening techniques are discussed with reference to results obtained for Duaringa and other Australian oil shale deposits. i CONTENTS Abbreviations, iv CHAPTER ONE INTRODUCTION. 1 1.1 Oil Shales. 1 1.1.1 Definition. 1 1.1.2 Environment of deposition. 2 1.1.3 Mineralogy. 2 1.1.4 Kerogen accumulation and abundance. 4 1.1.5 Kerogen source material. 7 1.1.6 Kerogen evolution (maturation). 9 1.1.7 General classification of kerogens. 12 1.1.8 Organic petrography. 17 1.2 The shale oil industry. 20 1.3 Australian oil shale deposits. 21 1.4 Australian prospects for a shale oil industry. 24 1.5 The Duaringa Oil Shale Deposit. 27 1.5.1 Locality and setting. 27 1.5.2 History of the deposit. 27 1.5.3 Geology of the deposit. 29 1.5.4 Organic petrology. 31 1.5.5 Environment of deposition. 32 1.5.6 Resource potential and development status. 34 CHAPTER TWO CHEMICAL CHARACTERISATION OF OIL SHALE AND SHALE OIL. 36 2.1 Introduction. 36 2.2 Solvent extracts. 38 2.3 Elemental analysis (C H N O S). 40 2.4 Thermal Degradation Studies on Oil Shales. 42 2.4.1 Fischer Assay retort. 42 2.4.2 Commercial retorts (shale oil production). 44 2.4.3 Thermogravimetric analysis. 45 2.4.4 Isothermal pyrolysis. 49 2.4.5 Thermal distillation and pyrolysis-FID. 50 2.4.6 Pyrolysis gas chromatography. 52 ii 2.5 Chemical degradation of oil shales. 55 2.6 Chromatographic Procedures. 58 2.6.1 Adsorption chromatography. 58 2.6.2 Gas chromatography. 60 2.7 Mass spectrometry. 62 2.8 Modern infrared techniques. 66 CHAPTER THREE EXPERIMENTAL. 68 3.1 General procedures. 68 3.2 Solvent extraction. 68 3.3 The retorting of oil shale. 70 3.3.1 Retort construction and shale oil production. 70 3.4 Instrumentation. 73 3.4.1 Gas chromatography. 73 3.4.2 Mass spectrometry. 73 3.5 Pyrolysis Procedures. 74 3.5.1 Pyroprobe calibration. 74 3.5.2 Pyrolysis gas chromatography. 76 3.5.3 Pyrolysis-FID. 77 3.5.4 Thermogravimetric analysis. 79 3.6 Chemical Characterisation of Shale Oil. 79 3.6.1 Asphaltenes. 79 3.6.2 Acid-base extractions. 79 3.6.3 Column chromatography. 80 3.6.4 Gas chromatographic determination of phenol in shale oil. 83 3.7 Oxidation of prist-1-ene. 85 CHAPTER FOUR CHEMICAL CHARACTERISATION OF OIL SHALE AND SHALE OIL FROM THE DUARINGA DEPOSIT QUEENSLAND, AUSTRALIA. 86 4.1 Oil shale petrology. 86 4.2 Elemental composition of kerogen and shale oil. 88 4.3 Solvent extracts (bitumen analysis). 91 4.4 PyroIysis-GC-MS. 110 4.5 Oil shale hydrocarbon potential-(PyroIysis-FTD). 117 4.6 Total pyrolysate composition. 124 iii 4.7 Thermogravimetric analysis of raw shale and kerogen. 142 4.8 Shale Oil Characterisation. 152 4.8.1 Raw shale oil. 152 4.8.2 Shale oil asphaltenes. 155 4.8.3 Acid-base extractable compounds. 164 4.9 Open-Column Chromatography of Neutral Fractions from Duaringa Shale Oils. 180 CHAPTER FIVE COMPARATIVE ANALYTICAL STUDIES ON AUSTRALIAN OIL SHALES. 238 5.1 Thermal Characterisations. 238 5.1.1 Effects of temperature and time on the composition of oil shale retort products. 238 5.1.2 Rapid assessment of hydrocarbon generating potential and kerogen type of selected Australian oil shales using a modified CDS-150 pyroprobe. 258 5.2 Solvent Extracts. 287 Conclusion. 307 Acknowledgements. 313 Authors Publications. 314 Bibliography. 315 iv ABBREVIATIONS USED IN TEXT. NB. Unless otherwise stated, all aliphatic compounds are linear. BP -bonded phase. cn -n carbon atoms. org -total organic carbon. CI -chemical ionisation. CPI -carbon preference index. CP/MAS -cross polarisation magic angle spinning 13C NMR. DSC -differential scanning calorimetry. DTA -differential thermal analysis. EA -elemental analysis. EI -electron impact (ionisation). FAB -fast atom bombardment. FA -Fischer assay. FID -flame-ionisation detector. FTJR -fourier-transform infrared. GC -gas chromatography. GC-MS -gas chromatography-mass spectrometry. HPLC -high-performance liquid chromatography. IR -infrared. IS -internal standard. LC -liquid chromatography. LTOM -litres per tonne at zero % moisture. MFA -modified Fischer assay. MI -matrix isolation. MID -multiple-ion detection. MS -mass spectrometry. NMR -nuclear magnetic resonance. PAH -polycyclic aromatic hydrocarbon. R -correlation coefficient. RI -modified Kovats retention index. SIM -single-ion monitoring. TGA -thermogravimetric analysis. TLC -thin-layer chromatography. TSQ -triple-sector quadrupole. UV -ultraviolet. 1 CHAPTER ONE : INTRODUCTION . 1.1 OIL SHALES . 1.1.1 Definition. Oil shales from different sources vary widely in composition and no precise definition for them exists. In practice they continue to be described primarily in terms of their behaviour according to economic criteria. Gavin (cited by Yen and Chilingarian, 1976) defines them as compact laminated rocks of sedimentary origin, yielding over 33 % of ash and containing organic matter that yields oil when distilled at 500-600° C, but not appreciably when extracted with commonly used hydrocarbon solvents. Materials yielding less than 33 % of ash should be considered as coal. Many oil shales as defined are not shales in the restricted sense of their lithology, but have mineral and textural features which allow them to be classified as siltstone, impure limestone, black shale or impure coal.
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