Chromatographic Separation and Atmospheric Pressure Ionization/Mass Spectrometric Analysis of Nitrogen, Sulfur and Oxygen Containing Compounds in Crude Oils

  • Walter E. Rudzinski
Chapter
Part of the Modern Analytical Chemistry book series (MOAC)

Abstract

Crude oil is a naturally occurring, flammable liquid whose chemical composition varies depending upon the source. Crude oil and products in refinery streams primarily consist of hydrocarbons (50-90%) with the remainder composed of compounds containing N, S, 0, and trace amounts of organometallics. Oxygen containing compounds usually are alcohols, phenols, furans and acids. The acids include alkanoic, naphthenic and aromatic species. Sulfur containing compounds include thiols, sulfides, disulfides and thiophene type compounds as well as inorganic sulfur. The nitrogen containing compounds usually are anilines, pyrroles, pyridines, indoles, quinolines and carbazoles. In addition to compounds which contain only one functional group based on NSO, recent results indicate that up to 50% of the compounds in crude contain two or more functional groups per molecule.1,3 These multifunctional compounds have yet to be elucidated.

Keywords

PAHs Pyridine Diesel Fractionation Thiol 

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References

  1. 1.
    Tomczyk, N.A., Winans, R.E., Shinn, J.H., and Robinson, R.C., Energy Fuels, 2001, 151498–1504.CrossRefGoogle Scholar
  2. 2.
    Qian, K., Robbins, W.K., Hughey, C.A., Cooper, H.J.; Rodgers, R.P.; Marshall, A.G., Energy Fuels, 2001, 15. 1505–1511.CrossRefGoogle Scholar
  3. 3.
    Lai, J.W.S., Pinto, L.J., Kiehlmann, E., BendellYoung, L.I., Moore, M.M., Environ. Toxicol. Chem. 1996, 15, 1482–1491.CrossRefGoogle Scholar
  4. 4.
    Guisnet, M., Magnoux, P., Appl. Catal. 1989, 54, 1–27.CrossRefGoogle Scholar
  5. 5.
    Qian, K., Tomczak, D.C., Rakiewicz, E.F., Harding, R.H., Yaluris, G. , Cheng, W.-C., Zhao, X., Peters, A.W., Energy & Fuels 1997, 11, 596–601.CrossRefGoogle Scholar
  6. 6.
    Harding, R.H., Zhao, X., Qian, K., Rajagopalan, K., Cheng, W.-C. Ind. Eng. Chem. Res. 1996, 35, 2561–2569.CrossRefGoogle Scholar
  7. 7.
    Speight, J.G. Fuel Science and Technology Handbook, Marcel Dekker, New York, 1990.Google Scholar
  8. 8.
    ASTM D1319–95a. Annual Book of ASTM Standards; American Society for Testing and Materials; Philadelphia, PA, 1998; Vol 5.01, pp. 465–470.Google Scholar
  9. 9.
    ASTM D2549–91. Annual Book of ASTM Standards; American Society for Testing and Materials; Philadelphia, PA, 1998; Vol 5.01, pp. 892–897.Google Scholar
  10. 10.
    ASTM D2007–93. Annual Book of ASTM Standards; American Society for Testing and Materials; Philadelphia, PA, 1998; Vol 5.01, pp. 655–661.Google Scholar
  11. 11.
    Corbett, L.W., Anal. Chem. 1969, 41, 576–579.CrossRefGoogle Scholar
  12. 12.
    Campbell, R.M.; Lee, M.L. Anal.Chem. 1986, 58, 2247–2251.CrossRefGoogle Scholar
  13. 13.
    Later, D.W.; Lee, M.L.; Bartle, K.D.; Kong, R.C.; Vassilaros, D.L. Anal. Chem. 1981, 53, 1612–1620.CrossRefGoogle Scholar
  14. 14.
    Fan, T.P., Energy & Fuels, 1991, 5, 371–375.CrossRefGoogle Scholar
  15. 15.
    Nali, M.; Fabbi, M.; Scilingo, A. Petroleum Science and Technology 1997, 75, 307–322.CrossRefGoogle Scholar
  16. 16.
    Altgelt, K.H., Jewell, D.M. Latham, D.L., Selucky, M.L., in Chromatography in Petroleum Analysis, K.H. Altgelt and T.H. Gouw, Eds; Chromatogr. Sci. Vol 11; Marcel Dekker: New York, 1979; pp. 185–214.Google Scholar
  17. 17.
    Altgelt, K.H., Boduszynski, M.M., Composition and Analysis of Heavy Petroleum Fractions Marcel Dekker: New York, 1994; pp. 203–255.Google Scholar
  18. 18.
    Leontaritis, K.J., Proc. Int. Symp. Oilfield Chem. 1997, 421–440.Google Scholar
  19. 19.
    Mansfield, C.T.; Barman, B.N.; Thomas, J.V.; Mehrotra, A.K.; McCann, J.M., Anal. Chem. 1999, 71, 81R–107R.CrossRefGoogle Scholar
  20. 20.
    Barman, B.N., Cebolla, V.L., Membrado, L., Crit. Rev. Anal. Chem., 2000, 30, 75–120.CrossRefGoogle Scholar
  21. 21.
    Ali, M.F.; Bukhari, A.; Hassan, M. Fuel Sci. Technol. 1989, 7, 1179–1208.CrossRefGoogle Scholar
  22. 22.
    Akhlaq, M.S. J. Chromatogr. 1993, 644, 253–258.CrossRefGoogle Scholar
  23. 23.
    Fetzer, J.C., in Chemical Analysis of Polycyclic Aromatic Compounds, T.Vo-Dinh, Ed; Wiley: New York, 1989; Chap. 3, pp. 59–109.Google Scholar
  24. 24.
    McKerrell, E.H., Fuel, 1993, 72, 1403–1409.CrossRefGoogle Scholar
  25. 25.
    Matsunaga, A., Anal. Chem., 1983, 55, 1375–1379.CrossRefGoogle Scholar
  26. 26.
    Hayes, P.C., Jr., Anderson, S.D., Anal. Chem. 1985, 57, 2094–2098.CrossRefGoogle Scholar
  27. 27.
    Hayes, P.C., Jr., Anderson, S.D., Anal. Chem. 1986, 58, 2384–2388.CrossRefGoogle Scholar
  28. 28.
    Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. 1987, 387, 333–344.CrossRefGoogle Scholar
  29. 29.
    Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. Sci, 1988, 26, 210–217.Google Scholar
  30. 30.
    Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. Sci., 1988, 26, 250–257.Google Scholar
  31. 31.
    Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. 1988, 437, 365–377.CrossRefGoogle Scholar
  32. 32.
    Robbins, W.K., J. Chromatogr. Sci., 1998, 36, 457–466.Google Scholar
  33. 33.
    Heine, CE., Geddes, M.M., Org. Mass Spectrom. 1994, 29, 277–282.CrossRefGoogle Scholar
  34. 34.
    Pfeifer, S., Beckey, H.D., Schulten, H.R., Fresenius Z. Anal. Chem. 1977, 284,193–195.CrossRefGoogle Scholar
  35. 35.
    Malhotra, R. , McMillen, D.F., Tse, D.S. , St. John, G.A., Coggiola, M.J., Matsui, H.P., Prepr.-Am. Chem. Soc., Div. Petr. Chem. 1989, 34, 330–338.Google Scholar
  36. 36.
    Rahimi, P.M., Fouda, S.A., Kelly, J.F., Malhotra, R., McMillen, D.F., Fuel, 1989, 68, 422–429.CrossRefGoogle Scholar
  37. 37.
    Boduszynski, M.M., Energy & Fuels, 1987, 2, 697.Google Scholar
  38. 38.
    Hsu, C.S., Qian, K., Energy & Fuels, 1993, 7, 268–272.CrossRefGoogle Scholar
  39. 39.
    Cole, R.B., Electrospray Ionization Mass Spectrometry, John Wiley & Sons, New York, 1997.Google Scholar
  40. 40.
    Zhan, D., Fenn, J.B., Int. J. Mass Spec. 2000, 194, 197–208.CrossRefGoogle Scholar
  41. 41.
    Lambert, J.B., Shurvell, H.F., Lightner, D.A., Cooks, R.G., Organic Structural Spectroscopy, Prentice Hall, Upper Saddle River NJ, 1998, p.375.Google Scholar
  42. 42.
    Tomczyk, N.A., Winans, R.E. Shinn, J.H., Robinson, R.C. Prepr. -Am. Chem. Soc. Div. Pet. Chem. 1998, 43, 123–125Google Scholar
  43. 43.
    McCarthy, R., Duthie, A., J. Lipid Res. 1962, 3, 117–119.Google Scholar
  44. 44.
    Green, J.B., Hoff, R.J., Woodward, P.W., Stevens, L.L., Fuel 1984, 63, 1290–1301.CrossRefGoogle Scholar
  45. 45.
    Green, B.J., J. Chromatogr. 1986, 358, 65–75.Google Scholar
  46. 46.
    Robbins, W.K. Prepr.-Am. Chem. Soc., Div. Pet. Chem. 1998 43 137–140.Google Scholar
  47. 47.
    Hertz, H.S.; Brown, J.M.; Chesler, S.N.; Guenther, F.R.; Hilpert, L.R.; May, W.E.; Parris, R.M.; Wise, S.A. Anal. Chem. 1980, 52, 1650–1657.CrossRefGoogle Scholar
  48. 48.
    Schmeltz, I. Phytochemistry 1967, 6, 33–38.CrossRefGoogle Scholar
  49. 49.
    Willsch, H.; Clegg, H.; Horsfield, B.; Radke, M.; Wilkes, H. Anal. Chem. 1997, 69, 4203–4209.CrossRefGoogle Scholar
  50. 50.
    Miller, J.T.; Fisher, R.B.; Thiyagarajan, P.; Winans, R.E.; Hunt, J.E. Energy Fuels, 1998, 12, 1290–1298.18. McCarthy,R; Duthie, A. J. Lipid Res. 1962, 3, 117–119.Google Scholar
  51. Yepez, O., Lorenzo, R. Callaroti, R, Vera J, Prepr. -Am. Chem. Soc. Div. Pet. Chem. 1998, 43, 114–122.Google Scholar
  52. 52.
    Jones, D.M. Watson, J.S., Meredith, W., Chen, M., Bennett, B. Anal. Chem., 2001, 73, 703–707.CrossRefGoogle Scholar
  53. 53.
    Green, J.B., Yu, S. K-T; Vrana, R.P., J. High Res. Chromatogr. 1994, 17, 427–438.CrossRefGoogle Scholar
  54. 54.
    Hsu, C.S., Dechert, G.J., Robbins, W.K., Fukuda, E., Roussis, S.G., Prepr.--Am. Chem. Soc. Div. Petrol. Chem. 1998, 43, 127–130.Google Scholar
  55. 55.
    Hsu, C.S.; Dechert, G.J.; Robbins, W.K.; Fukuda E.K., Energy Fuels 2000,14, 217–223.CrossRefGoogle Scholar
  56. 56.
    Seifert, W., Teeter, R., Howells, W., Cantow, M., Anal. Chem., 1969, 47,1639–1646.Google Scholar
  57. 57.
    Seifert, W., Fortzchr. Chem. Org. Naturst., 1975, 32, 1–49CrossRefGoogle Scholar
  58. 58.
    Headley, J.V., Peru, K.M., McMartin, D.W., Winkler, M., J. AOAC, 2002, 85, 182–187.Google Scholar
  59. 59.
    Rudzinski, W.E., Oehlers, L., Zhang, Y., Najera, B., Energy & Fuels, 2002 (submitted for publication).Google Scholar
  60. 60.
    Sassman, S., Fractionation and Analysis of Maya Crude Oil, M.S. Thesis, 1999, Southwest Texas State U., San Marcos, TX, p.51.Google Scholar
  61. 61.
    Snyder, L.R., Buell, B.E., Anal. Chem. 1968, 40, 1295–1302.CrossRefGoogle Scholar
  62. 62.
    Snyder, L.R., Buell, B.E., Howard, H.E., Anal. Chem. 1968, 40, 1303–1317.CrossRefGoogle Scholar
  63. 63.
    Yoshida, T., Chantai, P.D., Sawatzky, H., Energy & Fuels, 1991, 5, 299–303.CrossRefGoogle Scholar
  64. 64.
    Hsu, C.S., Qian, K., Robbins, W.K., J. High Resolut. Chromatogr., 1994, 17, 271–276.CrossRefGoogle Scholar
  65. 65.
    McKay J.F., Weber, J.H., Latham, D.R., Anal.Chem., 1976, 48, 891–898.CrossRefGoogle Scholar
  66. 66.
    Nondek, L., Chvalovsky, V., J. Chromatogr. 1984, 372, 303–312.Google Scholar
  67. 67.
    Schmitter, J.M., Colin, H., Excoffler, J. L., Arpino, P., Guichon, G., Anal. Chem., 1982, 54, 769–772.CrossRefGoogle Scholar
  68. 68.
    . Ali, M.F., Ali, M.A., Fuel Sci. Technol. Int. 1988, 6, 259–290.CrossRefGoogle Scholar
  69. 69.
    Qian, K., Rodgers, R.P.; Hendrickson, C.L., Emmett, M.R.; Marshall, A.G. Energy Fuels 2001, 75, 492–498.CrossRefGoogle Scholar
  70. 70.
    Rodgers, R.P., Hendrickson, C.L., Emmett, M.R., Marshall, A.G., Greaney, M., Qian, K., Can. J. Chem. in pressGoogle Scholar
  71. 71.
    Whitehurst, D.; Isoda, T.; Mochida, I. Adv. Catal. 1998, 42, 345–471.CrossRefGoogle Scholar
  72. 72.
    Nishioka, M. Energy Fuels 1988, 2, 214–219.CrossRefGoogle Scholar
  73. 73.
    Milenkovic, A.; Schultz, E.; Meille, V.; Loffreda, D.; Forissier, M.; Vrinat, M.; Sautet, P.; Lemaire, M. Energy Fuels, 1999, 13, 881–887.CrossRefGoogle Scholar
  74. 74.
    Wright, B.W.; Peaden, P.A.; Lee, M.L.; Stark, T. J. Chromatogr. 1982, 248, 17–34.CrossRefGoogle Scholar
  75. 75.
    Grang, B.Y. Anal. Lett. 1985, 18, 193–202CrossRefGoogle Scholar
  76. 76.
    Nishioka, M.; Campbell, R.M.; Lee, M.L.; Castle, R.N. Fuel 1986, 65, 270 –273.CrossRefGoogle Scholar
  77. 77.
    Nishioka, M; Whiting, D.G.; Campbell, D.G.; Lee, M.L., Anal. Chem, 1986, 58, 2251–2255.CrossRefGoogle Scholar
  78. 78.
    Nishioka, M.; Tomich, R.S. Fuel 1993, 72, 1007–1010.CrossRefGoogle Scholar
  79. 79.
    Nishioka, M.; Lee, M.L.; Castle, R.N. Fuel 1986, 65, 390–395.CrossRefGoogle Scholar
  80. 80.
    Andersson, J.T. Anal. Chem. 1987, 59, 2207–2209.CrossRefGoogle Scholar
  81. 81.
    Rudzinski, W.E., Sassman, Watkins, L.M., Prepr.- Am. Chem. Soc., Div. Petr. Chem. 2000, 45(4), 564–566.Google Scholar
  82. 82.
    Ma, X., Sakanishi, K., Isoda, T. Mochida, I., Fuel, 1997, 76, 329–339.CrossRefGoogle Scholar
  83. 83.
    Rudzinski, W.E.; Sassman, S. Proceedings of the 47th ASMS Conference on Mass Spectrometry and Allied Topics, Dallas, TX, June 13th, 1999.Google Scholar
  84. 84.
    Rudzinski, W.E.; Rodriguez, R.; Sassman, S.; Sheedy, M.; Smith, T; Watkins, L.M., Prepr.-Am. Chem. Soc., Div. Fuel. Chem. 1999, 44(1), 28–31.Google Scholar
  85. 85.
    Rudzinski, W.E., Aminabhavi, T.M., Spencer, L., Sassman, S., and Watkins, L., Energy Fuels 2000, 14, 839–844.CrossRefGoogle Scholar
  86. 86.
    Andersson, J.T.; Schmid, B. J. Chromatogr. 1995, 693, 325–338.CrossRefGoogle Scholar
  87. 87.
    Rebbert, R.E., Chesler, S.N., Guenther, F.R., Parris, R.M., J. Chromatogr. 1984, 284, 211–217.CrossRefGoogle Scholar
  88. 88.
    Palmentier, J.-P.F., Britten, A.J., Charbonneau, G., M., Karasek, F.W., J. Chromatogr. 1989, 469, 241–251.CrossRefGoogle Scholar
  89. 89.
    Mossner, S.G., Lopez de Alda, M.J., Sander, L.C., Lee, M.L., Wise, S.A., J. Chromatogr. 1999, 841, 207–228.CrossRefGoogle Scholar
  90. 90.
    Hunt, D.F. Shabanowitz, J., Anal. Chem. 1982, 54, 574–578CrossRefGoogle Scholar
  91. 91.
    Christensen, R.G., White, E., J. Chromatogr. 1985, 323, 33–36.CrossRefGoogle Scholar
  92. 92.
    Bayer, E., Gfrorer, P., Rental, C, Angew. Chem. Int. Ed. 1998, 38, 992–995.CrossRefGoogle Scholar
  93. 93.
    Roussis, S.G., Prouix, R., Anal. Chem. 2002, 74, 1408.CrossRefGoogle Scholar
  94. 94.
    Rudzinski, W.E.; Zhang, Y.. Proceedings of the 50th ASMS Conference on Mass Spectrometry and Allied Topics, Orlando, FL, June 6th, 2002.Google Scholar

Copyright information

© Springer Science+Business Media New York 2003

Authors and Affiliations

  • Walter E. Rudzinski
    • 1
  1. 1.Department of Chemistry and Institute for Environmental and Industrial ScienceSouthwest Texas State UniversitySan Marcos

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