Abstract
The occurrence of azaarenes and thiaarenes in coal and petroleum, and in products derived from them by pyrolysis and distillation, is reviewed, including their presence in the environment from accidental spillage and leakage from transport and process plant, in soil and water from abandoned process site, in products from biomass treatment, and in air from combustion, in food from grilling and in sewage. Methods for recovery and fractionation of azaarenes and thiaarenes are discussed including solvent extraction, column chromatography and planar chromatography. Techniques for their determination include gas chromatography with specific N and S detectors and mass spectrometry, high performance liquid and supercritical fluid chromatography with mass spectrometry, and planar chromatography. Evidence is cited for the occurrence of compounds with higher molecular weight than indicated by conventional GC-MS procedures used for PAH analysis. The application of field ionisation mass spectrometry and laser desorption mass spectrometric methods are reviewed. The persistence and toxicity of azaarenes and thiaarenes in the environment are briefly discussed.
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References
Aczel T (1972) Applications of high resolution mass spectrometry to the analysis of complex aromatic mixtures derived from petroleum and coal liquids. Reviews Anal Chem 1: 226
Aczel T, Lumpkin HE (1979) Mass spectrometric analysis of heterocompounds in coal extracts and coal liquefaction products. In: Refining of synthetic crudes. Adv Chem Series 179, American Chemical Society, p 13
Agblevor FA, Besler S, Wiselogel AE (1995) Fast pyrolysis of stored biomass feedstocks. Energy and Fuels 9: 635
Agency for Toxic Substances and Disease Registry, Atlanta, GA, USA (1993) Public health assessment for Newport Naval Education/Training Center Middletown, Newport County, Rhode Island, Region 1. CERCLIS No RI6 170 085 470, CA 123: 151 370
Agency for Toxic Substances and Disease Registry, Atlanta, GA, USA (1995) Public health assessment for Smeltertown/Koppers, Salida, Chaffee County, Colorado, Region 8. CERCLIS No COD983 769 738, CA 123: 348–482
Agency for Toxic Substances and Disease Registry, Atlanta, GA, USA (1993) Public health assessment for Geneva Industries/Fuhrmann Energy, Houston, Harris County, Texas, Region 6. CERCLIS No TXD980748453, CA 121: 17264
Agency for Toxic Substances and Disease Registry, Atlanta, GA, USA (1993) Public health assessment for Powell Road Landfill, Dayton, Montgomery County, Ohio, Region 5. CERCLIS No OHD000 382 663, CA 121: 16651
Agency for Toxic Substances and Disease Registry, Atlanta, GA, USA (1991) Health assessment for Doepke Disposal Holliday Site, Holliday, Johnson County, Kansas, Region 7. CERCLIS No KSD980632301, CA 118: 66083
Anabtawi JA, Alam K, Ali MA, Ali SA, Siddiqui MAB (1995) Performance evaluation of HDS catalysts by distribution of sulfur compounds in naphtha. Fuel 74: 1254
Andersson JT, Schmid B (1995) Polycyclic aromatic sulfur heterocycles: V. Determination of polycyclic aromatic compounds in a shale oil with the atomic emission detector. J Chromatogr A 693: 325
Antill JF (1991) Environmental improvements realized at United Kingdom coking plants measured by BCRA under the aegis of ECSC supported research study. In: The year book of the Coke Oven Managers Association. Mexborough, Yorks, p 148
Bai S, Pugmire RJ, Mayne CL, Grant DM (1995) “C NMR determination of protonated and nonprotonated carbons in model compounds, mixtures and coal derived liquid samples. Anal Chem 67: 3433
Ball JC, Young WC (1992) Evidence for a new class of mutagens in diesel oil. Environ Sci Technol 26: 2181
Barrio ME, Lliberia JL, Comellas L, Broto-Puig F (1996) Pyrolysis-gas chromatography applied to the study of organic matter evolution in sewage sludge-amended soils using nitrogen-phosphorus, flame ionisation and mass spectrometric detection. J Chromatogr A 719: 131
Baxter LL, Mitchell RE, Fletcher TH, Hurt RH (1996) Nitrogen release during coal combustion. Energy and Fuels 10: 188
Benner BA, Bryner NP, Wise SA, Mulholland GW, Lao RC, Fingas MF (1990) Polycyclic aromatic hydrocarbon emissions from the combustion of crude oil on water. Environ Sci Technol 24: 1418
Benson PA, Scheppele SE, Greenwood GJ, Aczel T, Grindstaff QG, Beier BF (1979) Characterisation of coal derived liquids and other fossil fuel related materials employing mass spectrometry; consequences of the mass spectrometric and infrared analysis of oils and asphaltenes for the chemistry of coal liquefaction. FE 2537–10 Report prepared for the United States Department of Energy under contract EX-76-S-01–2537
Bjergegaard C, Simonsen H, Sorensen H (1994) Determination of heterocyclic compounds by micellar electrokinetic capillary chromatography. J Chromatogr A 680: 561
Blazso M, Schulten H-R (1990) Pyrolysis field ionisation mass spectrometry of low rank coals. Org Geochem 15: 87
Blanco CG, Dominguez A, Iglesias MJ, Guillen MD (1994) Relation between solubility of coal tar pitches and composition of their volatile fraction. Fuel 73: 510
Boduszynski MM, Hurtubise RJ, Allen TW, Silver HF (1986) Changes in composition of solvent-refined coal with severity of hydrogenation. Fuel 65: 223
Boenigk W, Haenel MW, Zander M (1990) Structural features and mesophase formation of coal tar pitch fractions obtained by preparative size exclusion chromatography. Fuel 69: 1226
Bond M (1996) Dirty ships evade acid rain controls. New Scientist 2035: 4
Borra C, Wiesler D, Novotny M (1987) High-efficiency microcolumn liquid chromatography separation and spectral characterisation of nitrogen containing polycyclics from fossil fuels. Anal Chem 59: 339
Bradley D (1996) Tyre tracks trace runoff water. New Scientist 2035: 21
Brage C, Yu Q, Sjöström K (1995) Characteristics of evolution of tar from wood pyrolysis in a fixed bed reactor. Fuel 75: 213
Bragg JR, Prince RC, Harner EJ, Atlas RM (1994) Effectiveness of bioremediation for the Exxon Valdez oil spill. Nature 368: 413
Brumley WC, Jones WJ (1994) Comparison of micellar electrokinetic chromatography (MEKC) with capillary gas chromatography in the separation of phenols, anilines and polynuclear aromatics: potential field-screening applications of MEKC. J Chromatogr A 680: 163
Bublitz J, Dickenhausen M, Graetz M, Todt S, Schade W (1995) Fiber-optic laser-induced fluorescence probe for the detection of environmental pollutants. Appl Opt 34: 3223
Burchill P, Herod AA, James RG (1978) A comparison of some chromatographic methods for estimation of polynuclear aromatic hydrocarbons in pollutants. In: Jones PW, Freudenthal RI (eds) Carcinogenesis, vol 3. Raven Press, New York, p 35
Burchill P, Herod AA, Pritchard E (1982) Estimation of basic nitrogen compounds in some coal liquefaction products. J Chromatogr 246: 271
Burchill P, Herod AA, Pritchard E (1982) Determination of nitrogen-sulphur mixed heteroatomic compounds and sulphur heterocycles in an anthracene oil. J Chromatogr 242: 65
Burchill P, Herod AA, Mahon JP, Pritchard E (1983) Comparison of methods for the isolation of basic nitrogen compounds from coal tars. J Chromatogr 265: 223
Burchill P, Herod AA, Pritchard E (1983) Investigation of nitrogen compounds in coal tar products: 2. Basic fractions. Fuel 62: 20
Burchill P, Herod AA, Pritchard E (1983) Investigation of nitrogen compounds in coal tar products: 1. Unfractionated materials. Fuel 62: 11
Burchill P, Herod AA, Mahon JP, Pritchard E (1983) The class separation of nitrogen compounds in coal tars by liquid chromatography on a polar bonded-phase silica. J Chromatogr 281: 109
Burchill P, Herod AA, Mitchell CA (1986) The estimation of primary aromatic amines and other basic nitrogen compounds in some coal liquefaction products. Chromatographia 21: 67
Burchill P, Welch LS (1989) Variation of nitrogen content and functionality with rank for some UK bituminous coals. Fuel 68: 100
Burchill P (1993) A comparison of reductive and X-ray techniques for organic sulfur functionality in coal. Fuel 72: 1570
Calkins WH (1993) The chemistry of sulfur in coal - a historical perspective. Amer Chem Soc Div Fuel Chem 38 (2): 655
Calkins WH (1994) The chemical forms of sulfur in coal: a review. Fuel 73: 475
Caramao EB, Gomes LMF, de Oliveira MD, Lamas FM (1987) CGC-MS characterisation of tar bases from a Brazilian high ash coal. J High Res Chromatog 10: 579
Carlsson H, Össtman C (1995) Retention mechanisms of polycyclic aromatic nitrogen heterocyclics on bonded amino phases in normal-phase liquid chromatography. J Chromatogr A 715: 31
Carpenter GC (1992) Kress KIDC system solves coke oven emissions and coke side operating problems. Coke Making Int 4: 57
Chakhmakhchev A, Suzuki N (1995) Aromatic sulfur compounds as maturity indicators for petroleums from the Buzuluk depression, Russia. Org Geochem 23: 617
Chakhmakhchev A, Suzuki N (1995) Saturate biomarkers and aromatic sulfur compounds in oils and condensates from different source rock lithologies of Kazakhstan, Japan and Russia. Org Geochem 23: 289
Chen JC, Castagnoli C, Niksa S (1992) Coal devolatilisation during rapid transient heating: 2. Secondary pyrolysis. Energy and Fuels 6: 264
Chou MIM, Kruse CW, Lytle JM, Ho KK (1993) Organic volatile matter and its sulfur-containing compounds produced by coal pyrolysis. Amer Chem Soc Div Fuel Chem 38 (2): 655
Chou C-L, Hackley KC, Cao J (1993) Release of organic, pyritic, elemental and sulfate sulfur during temperature-programmed pyrolysis of Illinois Basin coals. In: Parekh BK, Groppo JG (eds) Processing and utilization of high-sulfur coals: V. Elsevier, Amsterdam, p 15
Christopher J, Sarpal AS, Kapur GS, Krishna A, Tyagi BR, Jain MC, Jain SK, Bhatnagar AK (1996) Chemical structures of bitumen-derived asphaltenes by nuclear magnetic resonance and X-ray diffractometry. Fuel 75: 899
Cohen CS, Stansberry PG, Stiller AH, Hobbs G, Vavro K, Miller MR (1995) Preliminary characterisation of bioreactivity of novel carbonaceous pitches extracted in N-methylpyrrolidone. Energy and Fuels 9: 1051
Connecticut Department of Public Health and Addiction Services, Hardford, CT, USA (1994). Public health assessment for Starr property, Enfield, Hardford County, Connecticut, Region 1. Report Order No PB95–154 795, CA 123: 320–854
Cooper HA, Hurtubise RJ, Silver HF (1986) Separation and characterization of hydroxyl aromatics in complex fractions from nondistillable coal-derived liquids. Anal Chem 58: 3011
Lide DR (1996) CRC handbook of chemistry and physics 77th edn. CRC Press, Boca Raton, sect 16
DeCanio SJ, Nero VP, DeTar MM, Storm DA (1990) Determination of the molecular weights of the Ratawi vacuum residue fractions - a comparison of mass spectrometric and vapour osmometry techniques. Fuel 69: 1233
Diez MA, Alvarez R, Gonzalez AI, Menendez R, Moinelo SR, Bermejo J (1994) Characterisation of coal tars produced under different carbonization conditions by FT-IR spectroscopy and extrography. Fuel 73: 139
Di Sanzo FP, Bray W, Chawla B (1994) Determination of the sulfur components of gasoline streams by capillary column gas chromatography with sulfur chemiluminescence detection. J High Res Chromatogr 17: 255
Doan B-T, Gillet B, Blondel B, Beloeil J-C (1995) Analysis of polyaromatics in crude gas oil mixtures: a new strategy using 2D NMR. Fuel 1995 74: 1806
Dong M, Schmeltz I, LaVoie E, Hoffmann D (1979) Aza-arenes in the respiratory environment: analysis and assays for mutagenicity. In: Jones PW, Freudenthal RI (eds) Carcinogenesis, vol 3. Raven Press, New York, p 97
Dzou LIP, Noble RA, Senftle JT (1995) Maturation effects on absolute biomarker concentration in a suite of coals and associated vitrinite concentrates. Org Geochem 23: 681
Eisenhut W, Nashan G, Schönau H (1992) Non-recovery coke plant - a challenge for cokemaking technology. Coke Making Int 4: 51
Eisenhut W, Friedrich F, Reinke M (1990) Coking plant environment in West Germany. Coke Making Int 2: 74
Ekinci E, Turkay S, Citiroglu M, Akar A (1994) Nitrogen compounds in pyrolysis produced liquids from two Turkish shales. Fuel Proc Technol 37: 175
Fetzer JC, Rechsteiner CE (1991) The analysis of large PAH in various pyrolytic products. In: Cooke M, Loening K, Merritt J (eds) 11th Meeting Polynucl Aromat Hydrocarbons: Meas, Means, Metab. Batelle Press, Columbus, p 259
Florida State Dept of Health and Rehabilitive Services, Tallahassee, FL, USA (1992) Public health assessment for American Creosote Works Inc.(Pensacola), Pensacola, Escambia County, Florida, Region 4. CERCLIS No. FLD008161994, CA 120: 13939
Gorbaty ML (1994) Prominent frontiers of coal science: past present and future. Fuel 73: 1819
Gray RH (1984) Chemical and toxicological aspects of coal liquefaction and other complex mixtures. Regul Toxicol Pharmacol 4: 380
Gray MR, Ayasse AR, Chan EW, Veljkovic M (1995) Kinetics of hydrodesulfurization of thiophenic and sulfide sulfur in Athabasca bitumen. Energy and Fuels 9: 500
Guan S, Marshall AG, Scheppele SE (1996) Resolution and chemical formula identification of aromatic hydrocarbons and aromatic compounds containing sulfur, nitrogen or oxygen in petroleum distillates and refinery streams. Anal Chem 68: 46
Guillen MD, Dominguez A, Iglesias MJ, Blanco CG (1995) Semiquantitative gas chromatographic analysis of the volatile fraction in several extracts obtained by treatment of coal tar pitches with different organic solvents. Fuel 74: 233
Gundel LA, Daisey JM, de Carvalho LRF, Kado NY, Scheutzle D (1993) Polar organic matter in airborne particles: chemical characterisation and mutagenic activity. Environ Sci Technol 27: 2112
Hagglund I, Blomberg LG, Janak K, Claude SG, Tabacchi R (1994) Silicone gum of OV225 type for open-tubular gas chromatography. J Chromatogr A 673: 93
Hall AJ, Watkins J, Hiby L (1996) The impact of the 1993 Braer oil spill on grey seals in Shetland. Sci Total Environ 186: 119
Hartgers WA, Sinninghe Damst, JS, de Leeuw JW, Ling Y, Dyrkacz GR (1994) Molecular characterisation of flash pyrolysates of two carboniferous coals and their constituting maceral fractions. Energy and Fuels 8: 1055
Haumaier L, Zech W (1995) Black carbon-possible source of highly aromatic components of soil humic acids. Org Geochem 23: 191
Hellyer A(1993) The Hellyer pocket guide. Hamlyn, London, p 29
Hemminki K, Grzybowska E, Chorazy M, Twardowska-Saucha K, Sroczynski JW, Putman KL, Randerath K, Phillips DH, Hewer A, Santella RM, Young TL, Perera FP (1990) DNA adducts in humans environmentally exposed to aromatic compounds in an industrial area of Poland. Carcinogenesis 11: 1229
Herod AA, Ladner WR, Stokes BJ, Berry AJ, Games DE, Hohn M (1987) Comparison of coal tars by LC-MS. Fuel 66: 935
Herod AA, Stokes BJ, Major HJ, Fairbrother AE (1988) Liquid chromatographic mass spectrometric analysis of coal tar fractions. Analyst 113: 797
Herod AA, Stokes BJ (1990) Separation schemes for coal tar analysis-a comparison of methods. Fuel Proc Technol 24: 45
Herod AA, Stokes BJ, Tye RE, Gaines AF, Li C-Z, Kandiyoti R (1993) Comparison of fast atom bombardment mass spectrometry and size exclusion chromatography in defining high molecular masses in coal-derived materials. Fuel 72: 1317
Herod AA, Stokes BJ, Schulten H-R (1993) Coal tar analysis by mass spectrometry - a comparison of methods. Fuel 72: 31
Herod A (1994) A review of the uses of planar chromatography in the coal and oil industries. J Planar Chromatogr 7: 180
Herod AA, Kandiyoti R (1995) Fractionation by planar chromatography of a coal tar pitch for characterisation by size-exclusion chromatography, UV fluorescence and direct-probe mass spectrometry. J Chromatogr A 708: 143
Herod AA, Johnson BR, Bartle KD, Carter DM, Cocksedge MJ, Domin M, Kandiyoti R (1995) A reconciliation of mass ranges from matrix-assisted laser desorption ionization mass spectrometry and size exclusion chromatography for coal-derived materials. Rapid Commun Mass Spectrom 9: 1446
Herod AA, Zhang S-F, Carter DM, Domin M, Cocksedge MJ, Parker JE, Johnson CAF, John P, Smith GP, Johnson BR, Bartle KD, Kandiyoti R (1996) Matrix assisted laser desorption/ionization mass spectrometry of pitch fractions separated by planar chromatography. Rapid Commun Mass Spectrom 10: 171
Herod AA, Kandiyoti R (1996) Fractionation of coal tar pitch by planar chromatoraphy for the characterisation of large molecular mass materials. J Planar Chromatogr 9: 16
Hewitt CN, Rashed MB (1990) An integrated budget for selected pollutants for a major rural highway. Sci Total Environ 93: 375
Hiatt MH (1995) Vacuum distillation coupled with gas chromatography/mass spectrometry for the analysis of environmental samples. Anal Chem 67: 4044
Holoubek I, Houskova L, Seda Z, Kalacek J, Stroufova Z, Vancura R (1991) Project TOCOEN: the fate of selected organic compounds in the environment: V. The model source of PAHs. Preliminary study. Toxicol Environ Chem 29: 251
Hsu CS, Qian K, Robbins WK (1994) Nitrogen speciation of polar petroleum compounds by compound class separation and on-line liquid chromatography-mass spectrometry ( LC-MS ). J High Res Chromatogr 17: 271
Huffman GP, Shah N, Huggins FE, Lu F, Zhao J (1993) Further sulfur speciation studies by sulfur K-edge XANES spectroscopy. In: Parekh BK, Groppo JG (eds) Processing and utilization of high-sulfur coals: V. Elsevier, p 1
Hughes WB, Holba A, Dzou LIP (1995) The ratios of dibenzothiophene to phenanthrene and pristane to phytane as indicators of depositional environment and lithology of petroleum source rocks. Geochim Cosmochim Acta 59: 3581
Hutte RS (1995) The sulfur chemiluminescence detector. In: Adlard ER (ed) Chromatography in the petroleum industry. Elsevier, Amsterdam, Chap 8
Ismail K, Mitchell SC, Brown SD, Snape CE, Buchanan III AC, Britt PF, Franco DV, Maes II, Yperman J (1995) Silica-immobilized sulfur compounds as solid calibrants for temperature programmed reduction and probes for the thermal behaviour of organic sulfur forms in fossil fuels. Energy and Fuels 9: 707
Jenssen BM (1996) An overview of exposure to, and effects of, petroleum oil and organochlorine pollution in Grey seals (Halichoerus grypus). Sci Total Environ 186: 109
Jones T, Bondoux G (1995) Capillary electrophoresis in the petroleum industry. In: Adlard ER (ed) Chromatography in the petroleum industry, Journal of Chromatography library series, vol 56. Elsevier, Amsterdam; p 401
Kalontarov L, Jing H, Amirav A, Cheskis S (1995) Mechanism of sulfur emission quenching in flame photometric detectors. J Chromatogr A 696: 245
Katritzky AR, Shipkova PA, Allin SM, Barcock RA, Siskin M, Olmstead WN (1995) Aqueous high-temperature chemistry: 22. Nitrogen heterocycles in supercritical water at 460 °C. Energy and Fuels 9: 580
Kelly GW, Bartle KD (1994) The use of combined LC-GC for the analysis of fuel products: a review. J High Res Chromatogr 17: 390
Kershaw JR, Black KJT (1993) Structural characterisation of coal tar and petroleum pitches. Energy and Fuels 7: 420
Kershaw JR, Smart PJ (1994) Supercritical fluid extraction of coal tar pitch: 2: extraction of the lower molecular weight species with aliphatic solvents. Fuel Proc Technol 38: 1
Kirton PJ, Ellis J, Crisp PT (1991) The analysis of organic matter in coke oven emissions. Fuel 70: 1383
Knobloch T, Engewald W (1993) Identification of some polar polycyclic compounds in emissions from brown-coal-fired residential stoves. J High Res Chromatog 16: 239.
Koopmans MP, Sinninghe Damst, JS, Lewan MD, De Leeuw JW (1995) Thermal stability of thiophene biomarkers as studied by hydrous pyrolysis. Org Geochem 23: 583
Kumata H, Takada H, Ogura N (1996) Determination of 2-(4-morpholinyl) benzothiazole in environmental samples by a gas chromatograph equipped with a flame photometric detector. Anal Chem 68: 1976
Lai W-C, Song C (1995) Temperature programmed retention indices for GC and GC-MS analysis of coal-and petroleum-derived liquid fuels. Fuel 74: 1436
Langenfeld JJ, Hawthorne SB, Miller DJ (1996) Quantitative analysis of fuel-related hydrocarbons in surface water and wastewater samples by solid-phase microextraction. Anal Chem 68: 144
Larsen JW, Lapucha AR, Wernett PC, Anderson WR (1994) Characterisation of coal liquefaction heavy products using 252Cf plasma desorption mass spectrometry. Energy and Fuels 8: 258
a. Larter SR, Bowler BFJ, Li M, Chen M, Brincat D, Bennett B, Noke K, Donohoe P, Simmons D, Kohnen M, Allan J, Telnaes N, Horstad I (1996) Molecular indicators of secondary oil migration distances. Nature 383: 593
Lee ML, Novotny M, Bartle KD (1981) Analytical chemistry of polycyclic aromatic compounds. Academic Press, NY
Lee LS, Suresh P, Roa C, Okuda I (1992) Equilibrium partitioning of polycyclic aromatic hydrocarbons from coal tar into water. Environ Sci Technol 26: 2110
Lee HK (1995) Recent applications of gas and high-performance liquid chromatographic techniques to the analysis of polycyclic aromatic hydrocarbons in airborne particulates. J Chromatogr A 710: 79
Leppälahti J, Koljonen T (1995) Nitrogen evolution from coal, peat and wood during gasification: literature review. Fuel Proc Technol 43: 1
LethbridgeG, Vits HJJ, Watkinson RJ (1994) Exxon Valdez and bioremediation. Nature 371: 97
Li M, Larter SR, Frolov YB, Bjoroy M (1994) Adsorptive interaction between nitrogen compounds and organic and/or mineral phases in subsurface rocks. Models for compositional fractionation of pyrrolic nitrogen compounds in petroleum during petroleum migration. J High Res Chromatogr 17: 230
Lin MS, Premuzic ET, Manowitz B, Jeon Y, Racaniello L (1993) Biodegradation of coals. Fuel 72: 1667
Lioy PJ, Greenberg A (1990) Factors associated with human exposures to polycyclic aromatic hydrocarbons. Toxicol Ind Health 6: 209
Llano JJ, Rosal R, Sastre H, Diez FV (1994) Catalytic hydrogenation of anthracene oil with red mud. Fuel 73: 688
Loads F (1980) Gardening tips of a lifetime. Hamlyn, London, p 38
Lopez-Avila V, Kraska S, Flanagan M (1988) Mass spectrometric analysis of azaarenes in a coal tar. Intern J Environ Anal Chem 33: 91
Lundanes E, Greibrokk T (1994) Separation of fuels, heavy fractions and crude oils into compound classes: a review. J High Res Chromatogr 17: 197
Ma X, Sakanishi K, Isoda T, Nagao S, Mochida I (1996) Structural characteristics and removal of visible-fluorescence species in hydrodesulfurized diesel oil. Energy and Fuels 10: 91
Malhotra R, McMillen DF, Watson EL, Huestis DL (1993) Characterisation of coal liquefaction resids by field ionization mass spectrometry: correlating spectral features with processing parameters. Energy and Fuels 7: 1079
Mao J, Pacheco CR, Traficante DD, Rosen W (1994) Analysis of neutral nitrogen compounds in diesel oil by direct injection high performance liquid chromatography-mass spectrometry-ultraviolet spectrometry methods. J Chromatogr A 684: 103
Mao J, Pacheco CR, Traficante DD, Rosen W(1995) Identification and characterisation of nitrogen compounds in Brazilian diesel oil by particle beam L.C.-M.S. Fuel 74: 880
Marzec A, Czajkowska S, Simmleit N, Schulten H-R (1990) Coal reactive sites involved in hydrogen transfer from an H-donor studied by field ionisation mass spectrometry. Fuel Proc Technol 26: 53
Marzec A, Czajowska S, Schulten H-R (1994) Mass spectrometric and chemometric studies of thermoplastic properties of coals: 3. Optical anisotropy and isotropy of carbonized coals. Energy and Fuels 8: 360
Masuda K, Okuma O, Nishizawa T, Kanaji M, Matsumura T (1995) High temperature N.M.R. analysis of aromatic units in asphaltenes and preasphaltenes derived from Victorian brown coal. Fuel 75: 295
Mauney T, Adams F, Sine MK (1984) Laser microprobe mass spectrometry of environmental soot particles. Sci Total Environ 36: 215
McElroy AE, Farrington JW, Teal JM (1989) Bioavailability of polycyclic aromatic hydrocarbons in the aquatic environment. In: Varanasi U (ed) Metabolism of poly-cyclic aromatic hydrocarbons in the aquatic environment. CRC Press, Boca Raton, pl
McKillop AG, Smith RM, Rowe RC, Wren SAC (1996) Optimisation of the separation of the dimethylpyridines by capillary electrophoresis. J Chromatogr A 730: 321
Milgrom LR (1994) Vitamin B12: the view from the summit. Chemistry in Britain 30: 923
Miller DJ, Hawthorne SB (1989) Identification of heteroatomic compounds in coal liquefaction and gasification products by deuterated reagent chemical ionization mass spectrometry. Fuel 68: 105
Mitchell SC, Ismail K, Garcia R, Moinelo SR (1995) Determination of organic forms in type I/II kerogens by high pressure temperature programmed reduction (TPR). In: Snape C (ed) Composition, geochemistry and conversion of oil shales. Kluwer, Dortrecht
Moliner R, Lazaro M, Fernandez A, Ibarra J (1993) Evidence obtained by gas chromatography-mass spectrometry of conversion of alkanes into aromatic compounds during coal pyrolysis. J Chromatogr A 655: 155
Moore MN, Livingstone DR, Widdows J (1989) Hydrocarbons in marine molluscs: biological effects and ecological consequences. In: Varanasi U (ed) Metabolism of poly-cyclic aromatic hydrocarbons in the aquatic environment. CRC Press, Boca Raton, pl
Motohashi N, Kamata K, Meyer R (1993) Chromatographic techniques used to determine benz[c]acridines in environmental samples. J Chromatogr A 643: 1
Motohashi N, Meyer R, Molnar J, Parkanyi C, Fang X (1995) Chromatographic determination of benz[c]acridines and related compounds in airborne carcinogens. J Chromatogr A 710: 117
Murphy AD, Carr JH (1991) High pressure water jet coke oven door cleaning and the mass flow charging of coke ovens. In: The year book of the Coke Oven Managers Association. Mexborough, Yorks, p 218
Nali M, Calemma V, Montanari L (1994) Pyrolysis/gas chromatography/mass spectrometry of asphaltene fractions. Org Mass Spectrom 29: 607
Neal AC (1995) HPLC and column liquid chromatography. In: Adlard ER (ED) Chromatography in the petroleum industry. Elsevier, Amsterdam, chap 12
Newborn JS, Preston JS (1991) Analytical field screening of soil by thin layer chromatography. Hazard Mater Control 4: 56
Niessen WMA, Tinke AP (1995) Liquid chromatography-mass spectrometry. General principles and instrumentation. J Chromatogr A 703: 37
Ogunsola OM, Berkowitz N (1995) Removal of heterocyclic S and N from oil precursors by supercritical water. Fuel 74: 1485
Palmer SR, Kruge MA, Hippo EJ, Crelling IC (1994) Speciation of heteroatoms in coal by sulfur-and nitrogen-selective techniques. Fuel 73: 1167
Payzant JD, Lown EM, Strausz OP (1991) Structural units of Athabasca asphaltene: the aromatics with a linear carbon framework. Energy and Fuels 5: 445
Peaden PA(1994) Simulated distillation of petroleum and its products by gas and supercritical fluid chromatography: a review. J High Res Chromatogr 17: 203
Pedersen-Bjergaard S, Griebrokk T (1994) N-, O- and P-selective on-column atomic emission detection in capillary gas chromatography. J Chromatogr A 686: 109
Pedley JF, Hiley RW, Hancock RA (1988) Storage stability of petroleum-derived diesel fuel: 3. Identification of compounds involved in sediment formation. Fuel 67: 1124
Pedley JF, Beranek LA, O’Connell MG, Solly RK (1990) The chemistry of sediment formation in Australian middle distillate fuels. Preprints Amer Chem Soc Div Fuel Chem 35 (4): 1100
Pelroy RA, Wilson BW (1981) Relative concentrations of polyaromatic amines and azaarenes in mutagenically active nitrogen fractions from a coal liquid. Mutat Res 90: 321
Pelroy RA, Stewart DL, Tominga Y, Iwao M, Castle RN, Lee ML (1983) Microbial mutagenicity of 3- and 4-ring polycyclic aromatic sulfur heterocycles. Mutat Res 117: 31
Philp RP (1994) High-temperature gas chromatography for the analysis of fossil fuels: a review. J High Res Chromatogr 17: 398
Pichini S, Altieri I, Passa AR, Rosa M, Zuccaro P, Pacifici R (1995) Use of solvent optimization software for rapid selection of conditions for reversed-phase high-performance liquid chromatography of nicotine and its metabolites. J Chromatogr A 697: 383
Pizzarello S, Feng X, Epstein S, Cronin JR (1994) Isotopic analyses of nitrogenous compounds from the Murchison meteorite ammonia, amines, amino acids and polar hydrocarbons. Geochim Cosmochim Acta 24: 5579
Ralston CY, Mitra-Kirtley S, Mullins OC (1996) Small population of one to three fused-aromatic ring moieties in asphaltenes. Energy and Fuels 10: 623
IEA Coal Research (1989) Reviews in coal science; the problems of sulphur. Butterworths, London
Rivera L, Curto MJC, Galceran MT, Puignou L (1996) Solid-phase extraction or the selective isolation of polycyclic aromatic hydrocarbons, azaarenes and heterocyclic aromatic amines in charcoal-grilled meat. J Chromatogr A 731: 85
Rogge WF, Hildemann LM, Mazurek MA, Cass GR, Simoneit BRT (1993) Sources of fine organic aerosol 5. Natural gas home appliances. Environ Sci Technol 27: 2736
Schobert HH (1995) Coal science and technology: 23. Lignites of North America, chap 3: the organic structure of lignites. Elsevier, Amsterdam, p 79
Sera N, Fukuhara K, Miyata N, Tokiwa H (1994) Detection of nitro-azabenzo(a)pyrene derivatives in the semi-volatile phase originating from airborne particulate matter, diesel and gasoline vehicles. Mutagenesis 9: 47
Shaw G (1995) PAHs in the environment. Chemistry in Australia June: 17
Shearer RL, Skelton RJ (1994) Supercritical fluid chromatography of petroleum products using flameless sulfur chemiluminescence detection. J High Res Chromatogr 17: 251
Shi H, Strode III JTB, Taylor LT, Fujinari EM (1996) Feasibility of supercritical fluid chromatography-chemiluminescent nitrogen detection with open tubular columns. J Chromatogr A 734: 303
Sinninghe Damst, JS, Rijpstra WIC, de Leeuw JW, Lijmbach WM (1994) Molecular characterisation of organically-bound sulfur in crude oils. J High Res Chromatogr 17: 489
Slooff W, Janus JA, Matthijsen AJCM, Montizaan GK, Ros JPM (1989) Integrated criteria document PAHs. Report RIVM-758474011, CA 115:14481, Bilthoven, Netherlands
Snape CE, Ismail K, Mitchell SC, Bartle KD (1995) Speciation of organic sulphur forms in solid fuels and heavy oils. In: Snape C (ed) Composition, geochemistry and conversion of oil shales. Kluwer, Dortrecht, p 125
Somsen GW, Morden W, Wilson ID (1995) Planar chromatography coupled with spectroscopic techniques, a review. J Chromatogr A 703: 613
Stewen W (1992) Environmental protection - a challenge for modern and innovatory cokemaking technology. Coke Making Int 4: 91
Stokes BJ (1992) Studies of coal derived material by chromatographic and mass spectrometric techniques. PhD Thesis, University of Wales, UK
Sung NJ, Johnson SJ, Parrott SL (1994) Determination of boiling point distribution of sulfur compounds in light cycle oil using a GC with flame photometric detector and pyrolyzer. J High Res Chromatogr 17: 457
Swannell RPJ, Head IM (1994) Bioremediation comes of age. Nature 368: 396
Szczeklik A, Szczeklik J, Galiszka Z, Musial J, Kolarzyk E, Targosz D (1994) Humoral immunosuppression in men exposed to polycyclic aromatic hydrocarbons and related carcinogens in polluted environments. Environ Health Perspect 102: 302
Szeja W, Wasilewski P, Swaryczewski Z (1995) Reduction of the environmental pollution resulting from coking industry. Karbo-Energochem-Ekol 40 (10): 255
Ternan M, Rahimi PM, Clugston DM, Dettman HD (1994) The + 525 °C residue before and after hydrocracking with bimodal catalysts of varying micropore volume. Energy and Fuels 8: 518
Texas State Dept. of Health, Austin, TX, USA (1992) Health assessment of Texarkana Wood Preserving Company, Texarkana, Bowie County, Texas, Region 6. CERCLIS No TXD008 056152, CA 119: 55 094
Thomas D, Crain SM, Sim PG, Benoit FM (1995) Use of immobilized copper ion chromatography and on-line mass spectrometry with atmospheric pressure chemical ionization for the profiling of complex mixtures of polycyclic aromatic compounds. J Chromatogr A 695: 1
Thompson JS, Green JB, McWilliams TB, Yu SK-T (1994) Analysis of amines in petroleum. J High Res Chromatogr 17: 415
Touchstone JC (1992) Practice of thin layer chromatography, 3rd edn. John Wiley, New York
Trauth DM, Stark SM, Petti TF, Neurock M, Klein MT (1994) Representation of molecular structure of petroleum resid through characterization and Monte Carlo modelling. Energy and Fuels 8: 576
Tyrpien K (1993) TLC identification of some nitrogen derivatives of PAH in airborne particular matter. J Planar Chromatogr 6: 413
Tyrpien K, Bodzek D, Janoszka B (1995) Application of TLC and GC-MS to the identification of azaarenes in sewage sludges. J Planar Chromatogr 8: 75
United States Environmental Protection Agency, Off. Emerg. Response, Washington, DC, USA (1990) Superfund Record of Decision (EPA Region 4): Dubose Oil Products site, Cantonment, Escambia County, FL (First remedial Action, March 1990. Report EPA/ROD/R04–90/071, CA 116: 262 050
Uthe JF (1991) Polycyclic aromatic hydrocarbons in the environment. Can Chem News Aug: 25
Van Berkel GJ, Quinones MA, Quirke JME (1993) Geoporphyrin analysis using electrospray ionization-mass spectrometry. Energy and Fuels 7: 411
Van Dyck MMC, Rollman B, De Meester C (1995) Quantitative estimation of heterocyclic aromatic amines by ion-exchange chromatography and electrochemical detection. J Chromatogr A 697: 377
Van Kaam-Peters HME, Köster J, De Leeuw JW, Sinninghe Damst, (1995) Occurrence of two novel benzothiophene hopanoid families in sediments. Org Geochem 23: 607
van Wijnen JH, Stijkel A (1988) Health risk assessment of residents living on harbour sludge. Int Arch Occup Environ Health 61: 77
Vignier V, Vandermeulen JH, Singh J, Mossman D (1996) Interannual mixed function oxidase (MFO) activity in winter flounder ( Pleuronectes americanus) from a coal tar contaminated estuary. Can J Fish Aquat Sci 51: 1368
Wang Z, Fingas M (1995) Differentiation of the source of spilled oil and monitoring of the oil weathering process using gas chromatography-mass spectrometry. J Chromatogr A 712: 321
Whittaker M, Pollard SJT (1994) Characterization of refractory wastes at hydrocarbon-contaminated sites: 1. Rapid column fractionation and thin layer chromatography of reference oils. J Planar Chromatogr 7: 354
Wiehe IA (1994) The pendant-core building block model of petroleum residua. Energy and Fuels 8: 536
Wild SR, Mitchell DJ, Yelland CM, Jones KC (1992) Arrested municipal solid waste incinerator fly ash as a source of polynuclear aromatic hydrocarbons ( PAH) to the environment. Waste Manage Res 10: 99
Wild S, Jones KC (1995) Polynuclear aromatic hydrocarbons in the United Kingdom environment: a preliminary source inventory and budget. Environ Pollut 88: 91
Willey C, Iwao M, Castle RN, Lee ML (1981) Determination of sulfur heterocycles in coal liquids and shale oils. Anal Chem 53: 400
Williams PT, Bottrill RP (1995) Sulfur-polycyclic aromatic hydrocarbons in tyre pyrolysis oil. Fuel 74: 736
Wilson BW, Peterson MR, Pelroy RA, Cresto JT (1981) In vitro assay for mutagenic activity and gas chromatographic-mass spectral analysis of coal liquefaction material and the products resulting from its hydrogenation. Fuel 60: 289
Wilson R(1993) The application of chemical ionisation mass spectrometry and linked scan techniques to the analysis of coal liquefaction products. PhD Thesis, Heriot-Watt University, Edinburgh
Winans RE, McBeth RL, Young JE (1990) The effects of acid demineralization on the sulfur-containing compounds found in an Illinois-Basin high-sulfur coal. In: Markuszewski R, Wheelock TD (eds) Processing and utilization of high sulfur coals: III. Elsevier, Amsterdam, p 53
Winans RE (1991) Pyrolysis fast atom bombardment tandem mass spectrometry characterisation of coals. J Anal Appl Pyrol 20: 1
Winans RE, Melnikov PE, Dyrkacz GR, Bloomquist CAA, Gorbaty ML, Keleman SR, George GN (1993). Determination of sulphur compounds in coal by mass spectrometry, correlated with xanes and xps. Amer Chem Soc Div Fuel Chem 38: 375
Winger PV, Schultz DP, Johnson WW (1990) Environmental contamination concentrations in biota from the Lower Savannah River, Georgia and South Carolina. Arch Environ Contam Toxicol 19: 101
Wisconsin Div of Health, Madison WI, USA (1991) Health assessment for MossAmerican Kerr-McGee Oil Company, Milwaukee, Milwaukee County, Wisconsin, Region 5. CERCLIS No. WID039 052 626, CA 118: 44776
Wojtowicz MA, Pels JR, Moulijn JA (1995) The fate of nitrogen functionalities in coal during pyrolysis and combustion. Fuel 74: 507
Wood KV, Schmidt CE, Cooks RG, Batts BD (1984) Identification of partially hydrogenated nitrogen-containing polycyclic aromatic hydrocarbons in coal liquids by tandem mass spectrometry. Anal Chem 56: 1335
Wornat MJ Sarofim AF, Longwell JP, Lafleur AL (1988) Effect of pyrolysis conditions on the composition of nitrogen-containing polycyclic aromatic compounds from a bituminous coal. Energy and Fuels 2: 775
Xu X, McDonald LM, McGowan CW, Glinski RJ (1995) Examination of sulfur forms in coal by direct pyrolysis and chemiluminescence detection. Fuel 74: 1499
Yperman J, Franco D, Mullens J, Van Poucke L.C, Gryglewicz G, Jasienko S (1995) Determination of sulfur groups in pyrolysed low-rank coal by atmospheric-pressure T.P.R. Fuel 74: 1261
Yperman J, Maes II, Franco D, Snape CE, Mitchell SC, Palmer SR, Mullens J, Van Poucke LC (1995) Determination of organic sulfur forms in some coals and kerogens by atmospheric pressure temperature programmed reduction (AP-TPR) Preprints, Amer Chem Soc Div Fuel Chem 40 (3): 95
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Herod, A.A. (1998). Azaarenes and Thiaarenes. In: Neilson, A.H. (eds) PAHs and Related Compounds. The Handbook of Environmental Chemistry, vol 3 / 3I. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49697-7_7
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