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

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Analytical Advances for Hydrocarbon Research

Part of the book series: Modern Analytical Chemistry ((MOAC))

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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.

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References

  1. Tomczyk, N.A., Winans, R.E., Shinn, J.H., and Robinson, R.C., Energy Fuels, 2001, 151498–1504.

    Article  CAS  Google Scholar 

  2. Qian, K., Robbins, W.K., Hughey, C.A., Cooper, H.J.; Rodgers, R.P.; Marshall, A.G., Energy Fuels, 2001, 15. 1505–1511.

    Article  CAS  Google Scholar 

  3. Lai, J.W.S., Pinto, L.J., Kiehlmann, E., BendellYoung, L.I., Moore, M.M., Environ. Toxicol. Chem. 1996, 15, 1482–1491.

    Article  CAS  Google Scholar 

  4. Guisnet, M., Magnoux, P., Appl. Catal. 1989, 54, 1–27.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  6. Harding, R.H., Zhao, X., Qian, K., Rajagopalan, K., Cheng, W.-C. Ind. Eng. Chem. Res. 1996, 35, 2561–2569.

    Article  CAS  Google Scholar 

  7. Speight, J.G. Fuel Science and Technology Handbook, Marcel Dekker, New York, 1990.

    Google Scholar 

  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. 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. 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. Corbett, L.W., Anal. Chem. 1969, 41, 576–579.

    Article  CAS  Google Scholar 

  12. Campbell, R.M.; Lee, M.L. Anal.Chem. 1986, 58, 2247–2251.

    Article  CAS  Google Scholar 

  13. Later, D.W.; Lee, M.L.; Bartle, K.D.; Kong, R.C.; Vassilaros, D.L. Anal. Chem. 1981, 53, 1612–1620.

    Article  CAS  Google Scholar 

  14. Fan, T.P., Energy & Fuels, 1991, 5, 371–375.

    Article  CAS  Google Scholar 

  15. Nali, M.; Fabbi, M.; Scilingo, A. Petroleum Science and Technology 1997, 75, 307–322.

    Article  Google Scholar 

  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. Altgelt, K.H., Boduszynski, M.M., Composition and Analysis of Heavy Petroleum Fractions Marcel Dekker: New York, 1994; pp. 203–255.

    Google Scholar 

  18. Leontaritis, K.J., Proc. Int. Symp. Oilfield Chem. 1997, 421–440.

    Google Scholar 

  19. Mansfield, C.T.; Barman, B.N.; Thomas, J.V.; Mehrotra, A.K.; McCann, J.M., Anal. Chem. 1999, 71, 81R–107R.

    Article  CAS  Google Scholar 

  20. Barman, B.N., Cebolla, V.L., Membrado, L., Crit. Rev. Anal. Chem., 2000, 30, 75–120.

    Article  CAS  Google Scholar 

  21. Ali, M.F.; Bukhari, A.; Hassan, M. Fuel Sci. Technol. 1989, 7, 1179–1208.

    Article  CAS  Google Scholar 

  22. Akhlaq, M.S. J. Chromatogr. 1993, 644, 253–258.

    Article  CAS  Google Scholar 

  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. McKerrell, E.H., Fuel, 1993, 72, 1403–1409.

    Article  CAS  Google Scholar 

  25. Matsunaga, A., Anal. Chem., 1983, 55, 1375–1379.

    Article  CAS  Google Scholar 

  26. Hayes, P.C., Jr., Anderson, S.D., Anal. Chem. 1985, 57, 2094–2098.

    Article  CAS  Google Scholar 

  27. Hayes, P.C., Jr., Anderson, S.D., Anal. Chem. 1986, 58, 2384–2388.

    Article  CAS  Google Scholar 

  28. Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. 1987, 387, 333–344.

    Article  CAS  Google Scholar 

  29. Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. Sci, 1988, 26, 210–217.

    CAS  Google Scholar 

  30. Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. Sci., 1988, 26, 250–257.

    CAS  Google Scholar 

  31. Hayes, P.C., Jr., Anderson, S.D., J. Chromatogr. 1988, 437, 365–377.

    Article  CAS  Google Scholar 

  32. Robbins, W.K., J. Chromatogr. Sci., 1998, 36, 457–466.

    CAS  Google Scholar 

  33. Heine, CE., Geddes, M.M., Org. Mass Spectrom. 1994, 29, 277–282.

    Article  CAS  Google Scholar 

  34. Pfeifer, S., Beckey, H.D., Schulten, H.R., Fresenius Z. Anal. Chem. 1977, 284,193–195.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  36. Rahimi, P.M., Fouda, S.A., Kelly, J.F., Malhotra, R., McMillen, D.F., Fuel, 1989, 68, 422–429.

    Article  CAS  Google Scholar 

  37. Boduszynski, M.M., Energy & Fuels, 1987, 2, 697.

    Google Scholar 

  38. Hsu, C.S., Qian, K., Energy & Fuels, 1993, 7, 268–272.

    Article  CAS  Google Scholar 

  39. Cole, R.B., Electrospray Ionization Mass Spectrometry, John Wiley & Sons, New York, 1997.

    Google Scholar 

  40. Zhan, D., Fenn, J.B., Int. J. Mass Spec. 2000, 194, 197–208.

    Article  CAS  Google Scholar 

  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. Tomczyk, N.A., Winans, R.E. Shinn, J.H., Robinson, R.C. Prepr. -Am. Chem. Soc. Div. Pet. Chem. 1998, 43, 123–125

    CAS  Google Scholar 

  43. McCarthy, R., Duthie, A., J. Lipid Res. 1962, 3, 117–119.

    CAS  Google Scholar 

  44. Green, J.B., Hoff, R.J., Woodward, P.W., Stevens, L.L., Fuel 1984, 63, 1290–1301.

    Article  CAS  Google Scholar 

  45. Green, B.J., J. Chromatogr. 1986, 358, 65–75.

    Google Scholar 

  46. Robbins, W.K. Prepr.-Am. Chem. Soc., Div. Pet. Chem. 1998 43 137–140.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  48. Schmeltz, I. Phytochemistry 1967, 6, 33–38.

    Article  CAS  Google Scholar 

  49. Willsch, H.; Clegg, H.; Horsfield, B.; Radke, M.; Wilkes, H. Anal. Chem. 1997, 69, 4203–4209.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  52. Jones, D.M. Watson, J.S., Meredith, W., Chen, M., Bennett, B. Anal. Chem., 2001, 73, 703–707.

    Article  CAS  Google Scholar 

  53. Green, J.B., Yu, S. K-T; Vrana, R.P., J. High Res. Chromatogr. 1994, 17, 427–438.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  55. Hsu, C.S.; Dechert, G.J.; Robbins, W.K.; Fukuda E.K., Energy Fuels 2000,14, 217–223.

    Article  CAS  Google Scholar 

  56. Seifert, W., Teeter, R., Howells, W., Cantow, M., Anal. Chem., 1969, 47,1639–1646.

    Google Scholar 

  57. Seifert, W., Fortzchr. Chem. Org. Naturst., 1975, 32, 1–49

    Article  CAS  Google Scholar 

  58. Headley, J.V., Peru, K.M., McMartin, D.W., Winkler, M., J. AOAC, 2002, 85, 182–187.

    CAS  Google Scholar 

  59. Rudzinski, W.E., Oehlers, L., Zhang, Y., Najera, B., Energy & Fuels, 2002 (submitted for publication).

    Google Scholar 

  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. Snyder, L.R., Buell, B.E., Anal. Chem. 1968, 40, 1295–1302.

    Article  CAS  Google Scholar 

  62. Snyder, L.R., Buell, B.E., Howard, H.E., Anal. Chem. 1968, 40, 1303–1317.

    Article  CAS  Google Scholar 

  63. Yoshida, T., Chantai, P.D., Sawatzky, H., Energy & Fuels, 1991, 5, 299–303.

    Article  CAS  Google Scholar 

  64. Hsu, C.S., Qian, K., Robbins, W.K., J. High Resolut. Chromatogr., 1994, 17, 271–276.

    Article  CAS  Google Scholar 

  65. McKay J.F., Weber, J.H., Latham, D.R., Anal.Chem., 1976, 48, 891–898.

    Article  CAS  Google Scholar 

  66. Nondek, L., Chvalovsky, V., J. Chromatogr. 1984, 372, 303–312.

    Google Scholar 

  67. Schmitter, J.M., Colin, H., Excoffler, J. L., Arpino, P., Guichon, G., Anal. Chem., 1982, 54, 769–772.

    Article  CAS  Google Scholar 

  68. . Ali, M.F., Ali, M.A., Fuel Sci. Technol. Int. 1988, 6, 259–290.

    Article  CAS  Google Scholar 

  69. Qian, K., Rodgers, R.P.; Hendrickson, C.L., Emmett, M.R.; Marshall, A.G. Energy Fuels 2001, 75, 492–498.

    Article  Google Scholar 

  70. Rodgers, R.P., Hendrickson, C.L., Emmett, M.R., Marshall, A.G., Greaney, M., Qian, K., Can. J. Chem. in press

    Google Scholar 

  71. Whitehurst, D.; Isoda, T.; Mochida, I. Adv. Catal. 1998, 42, 345–471.

    Article  CAS  Google Scholar 

  72. Nishioka, M. Energy Fuels 1988, 2, 214–219.

    Article  CAS  Google Scholar 

  73. Milenkovic, A.; Schultz, E.; Meille, V.; Loffreda, D.; Forissier, M.; Vrinat, M.; Sautet, P.; Lemaire, M. Energy Fuels, 1999, 13, 881–887.

    Article  CAS  Google Scholar 

  74. Wright, B.W.; Peaden, P.A.; Lee, M.L.; Stark, T. J. Chromatogr. 1982, 248, 17–34.

    Article  CAS  Google Scholar 

  75. Grang, B.Y. Anal. Lett. 1985, 18, 193–202

    Article  Google Scholar 

  76. Nishioka, M.; Campbell, R.M.; Lee, M.L.; Castle, R.N. Fuel 1986, 65, 270 –273.

    Article  CAS  Google Scholar 

  77. Nishioka, M; Whiting, D.G.; Campbell, D.G.; Lee, M.L., Anal. Chem, 1986, 58, 2251–2255.

    Article  CAS  Google Scholar 

  78. Nishioka, M.; Tomich, R.S. Fuel 1993, 72, 1007–1010.

    Article  CAS  Google Scholar 

  79. Nishioka, M.; Lee, M.L.; Castle, R.N. Fuel 1986, 65, 390–395.

    Article  CAS  Google Scholar 

  80. Andersson, J.T. Anal. Chem. 1987, 59, 2207–2209.

    Article  CAS  Google Scholar 

  81. Rudzinski, W.E., Sassman, Watkins, L.M., Prepr.- Am. Chem. Soc., Div. Petr. Chem. 2000, 45(4), 564–566.

    CAS  Google Scholar 

  82. Ma, X., Sakanishi, K., Isoda, T. Mochida, I., Fuel, 1997, 76, 329–339.

    Article  CAS  Google Scholar 

  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. 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.

    CAS  Google Scholar 

  85. Rudzinski, W.E., Aminabhavi, T.M., Spencer, L., Sassman, S., and Watkins, L., Energy Fuels 2000, 14, 839–844.

    Article  CAS  Google Scholar 

  86. Andersson, J.T.; Schmid, B. J. Chromatogr. 1995, 693, 325–338.

    Article  CAS  Google Scholar 

  87. Rebbert, R.E., Chesler, S.N., Guenther, F.R., Parris, R.M., J. Chromatogr. 1984, 284, 211–217.

    Article  CAS  Google Scholar 

  88. Palmentier, J.-P.F., Britten, A.J., Charbonneau, G., M., Karasek, F.W., J. Chromatogr. 1989, 469, 241–251.

    Article  CAS  Google Scholar 

  89. Mossner, S.G., Lopez de Alda, M.J., Sander, L.C., Lee, M.L., Wise, S.A., J. Chromatogr. 1999, 841, 207–228.

    Article  CAS  Google Scholar 

  90. Hunt, D.F. Shabanowitz, J., Anal. Chem. 1982, 54, 574–578

    Article  CAS  Google Scholar 

  91. Christensen, R.G., White, E., J. Chromatogr. 1985, 323, 33–36.

    Article  CAS  Google Scholar 

  92. Bayer, E., Gfrorer, P., Rental, C, Angew. Chem. Int. Ed. 1998, 38, 992–995.

    Article  Google Scholar 

  93. Roussis, S.G., Prouix, R., Anal. Chem. 2002, 74, 1408.

    Article  CAS  Google Scholar 

  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 

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  1. Department of Chemistry and Institute for Environmental and Industrial Science, Southwest Texas State University, San Marcos, Texas, 78666

    Walter E. Rudzinski

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  1. ExxonMobil Research and Engineering Co., Baton Rouge, LA, 07821

    Chang Samuel Hsu

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Rudzinski, W.E. (2003). Chromatographic Separation and Atmospheric Pressure Ionization/Mass Spectrometric Analysis of Nitrogen, Sulfur and Oxygen Containing Compounds in Crude Oils. In: Hsu, C.S. (eds) Analytical Advances for Hydrocarbon Research. Modern Analytical Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4419-9212-3_13

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