Oil Shale, 2007, Vol. 24, No. 3, pp. 465–475

 

THE PRESENCE OF POLYCYCLIC AROMATIC HYDROCARBONS (PAH) IN OIL OBTAINED AT PYROLYSIS OF JORDAN OIL SHALE

(full text in pdf format)

 

J. M. NAZZAL

 

The presence of polycyclic aromatic hydrocarbons (PAH) in the oil obtained at pyrolysis of Jordan oil shale in a fluidised-bed reactor in the atmosphere of nitrogen and nitrogen/steam has been investigated. The final pyrolysis temperature was 520 °C, at which the maximum oil yield was established. The derived oils were fractionated into chemical classes using mini-column liquid chromatography followed by analysis using capillary column gas chromatography with mass spectrometry (GC/MS) for identification and quantification of PAH. The derived oils were found to contain significant amounts of PAH, mainly naphthalene, fluorene and phenanthrene and their alkylated derivatives, and lower amounts of fluoranthrene, pyrene and chrysene. Some of the PAH found in the derived oils are known to be carcinogenic and/or mutagenic, and consequently the oils may represent a significant environmental and health hazard. The PAH have probably formed via Diels-Alder type reactions or via gas-phase cracking of aliphatic compounds.

 

REFERENCES

 

1.        Ekstrom, A., Fookes, C. J. R., Loeh, H. J., Randall, C. H., Rovere, C., Ellis, J., Crisp, P. T. Chemical and pyrolysis characteristics of two types of oil shale from the Condor deposit in Queensland, Australia // Fuel. 1987. Vol. 66, No. 8. P. 1133–1138.

2.        Yanik, J., Yuksel, M., Saglam, M., Olukcu, N., Bartle, K., Frere, B. Charac­terization of the oil fractions of shale oil obtained by pyrolysis and supercritical water extraction // Fuel. 1995. Vol. 74, No. 1. P. 46–50.

3.        Carter, S. D., Taulbee, D. N. Fluidised bed steam retorting of Kentucky oil shale // Fuel Process. Technol. 1985. Vol. 11, No. 3. P. 251–272.
doi:10.1016/0378-3820(85)90004-9

4.        Tomingas, R. Remarks on the sampling procedures for polycyclic aromatic hydrocarbons from the atmosphere // Fresenius J. Anal. Chem. 1979. Vol. 297, No. 2–3. P. 97–101.

5.        Lee, M. L., Novotry, M., Bartle, K. D. Analytical Chemistry of Polycyclic Aromatic Hydrocarbons. – Academic Press, NY, 1981.

6.        Orr, W. L., Grady, J. R.  Perylene in basin sediments off Southern California // Geochem. Cosmochim. Acta. 1967. Vol. 31, No. 7. P. 1201–1209.

7.        Brown, F. S., Baedecker, M. J., Nissenbaum, A., Kaplan, I. R. Early diagenesis in a reducing fjord, Saanich Inlet, British Columbia – III. Changes in organic constituents of sediment // Geochim. Cosmochim. Acta. 1972. Vol. 36, No. 11. P. 1185–1203.
doi:10.1016/0016-7037(72)90045-2

8.        Fishbein, L. Atmospheric mutagens // Chemical Mutagens / A. Hollaender (ed.). Vol. 4, Plenum, NY, 1976. P. 219–319.

9.        Clar, E. Polycyclic Hydrocarbons. – Academic Press, NY, 1964.

10.     Doll, R. 7th Walter Hubert lecture. Pott and the prospects for prevention // Br. J. Cancer. 1975. Vol. 32, No. 2. P. 263–274.

11.     Yamagiwa, K., Ichikawa, K. Experimental study of the pathogenesis of carcinoma // J. Cancer Res. 1918. Vol. 3. P. 1–29.

12.     Kennaway, E. L. Further experiments on cancer-producing substances // Biochem. J. 1930. Vol. 24. P. 497–504.

13.     Cook, J. W., Hewett, C. L., Hieger, I. The isolation of cancer-producing hydrocarbon from coal tar. Parts I, II, and III // J. Chem. Soc. 1933. P. 395–405.
doi:10.1039/jr9330000395

14.     Hartwell, J. L. Survey of compounds which have been tested for carcinogenic activity // Public Health Services Publ. No. 149, 2nd Ed., 1951.

15.     Zedeck, M. S. Polycyclic aromatic hydrocarbons. A review // J. Envir. Pathol. Toxicol. 1980. Vol. 3. P. 537–545.

16.     Marquardt, H., Backer, S., Tierney, D., Greover, P. L., Sims, P. Comparison of mutagensis, and malignant transformation by dihydrodiols from benz[a]anthracene and 7,12-dimethylbenz[a]anthracene // Br. J. Cancer. 1979. Vol. 39, No. 5. P. 540–547.

17.     Oesche, F. Biochemistry of polycyclic aromatic hydrocarbons // Proc. Polycyclic Aromatic Hydrocarbons Conf., Hanover, 18-21 Sept., 1978.

18.     Zajdela, F., Buu-Hoi, N. P., Jacqumgnon, P., Dufour, M. The carcinogenicity of two diazadibenzopyrenes // Br. J. Cancer. 1972. Vol. 26, No. 4. P. 262–264.

19.     Rosenkranz, H. S., McCoy, E. C., Sanders, D. R., Butler, M., Kiriazides, D. K., Mermelstein, R. Nitropyrenes: isolation, identification, and reduction in mutagenic impurities in carbon black and toners // Science. 1980. Vol. 209, No. 4460. P. 1039–1043.

20.     Cypres, R. Aromatic hydrocarbons formation during coal pyrolysis // Fuel Process. Technol. 1987. Vol. 15. P. 1–15.
doi:10.1016/0378-3820(87)90030-0

21.     Fairburn, J. A., Behie, L. A., Svrcek, Y. Ultrapyrolysis of n-hexadecane in a novel micro-reactor // Fuel. 1990. Vol. 69, No. 12. P. 1537–1545.

22.     Depeyre, D., Flicoteaux, C., Chardaire, C. Pure n-hexadecane thermal steam cracking // Ind. Eng. Chem. Proc. Des. Dev. 1985. Vol. 24. P. 1251–1258.
doi:10.1021/i200031a059

23.     Williams, P. T., Taylor, J. Aromatization of tyre pyrolysis oil to yield poly­cyclic aromatic hydrocarbons // Fuel. 1993. Vol. 72, No. 11. P. 1469–1474.

24.     Williams, P. T., Besler, S. Polycyclic aromatic hydrocarbons in waste derived pyrolytic oils  // J. Anal. Appl. Pyrol. 1994. Vol. 30, No. 1. P. 17–33.
doi:10.1016/0165-2370(94)00802-7

25.     Williams, P. T., Nazzal, J. M. Polycyclic aromatic compounds in oils derived from the fluidised bed pyrolysis of oil shale // J. Anal. Appl. Pyrol. 1995. Vol. 35, No. 2. P. 181–197.
doi:10.1016/0165-2370(95)00908-9

26.     Burnham, A. K. Reaction kinetics between CO₂ and oil-shale residual carbon. 1. Effect of heating rate on reactivity // 1979. Fuel. Vol 58, No. 4. P. 285–292.