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Methods for Studying Petroleum Porphyrins (Review)

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Abstract

The presented review considers the currently relevant methods for studying petroleum porphyrins. For this purpose, the experimental approaches used during the investigation of the structure, concentration, and properties of metal complexes of petroleum porphyrins and their free bases are systematized, and the capabilities and limitations of the used methods (mass spectrometric, spectroscopic (electron paramagnetic resonance, UV–visible electronic absorption spectroscopy, and X-ray techniques) as well as high-performance and gel penetration liquid chromatography) are discussed. Published approaches to the concentration, fractionation, and purification of petroleum porphyrins based on the extraction and chromatographic methods of recovery of chemical compounds from complex multicomponent mixtures are also analyzed.

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REFERENCES

  1. S. R. Upreti, A. Lohi, R. A. Kapadia, and R. El-Haj, Energy Fuels 21, 1562 (2007).

    Article  CAS  Google Scholar 

  2. R. F. Meyer, E. D. Attanasi, and P. A. Freeman, in Heavy Oil and Natural Bitumen Resources in Geological Basins of the World (US Geological Survey, Reston, 2007), p. 42.

    Book  Google Scholar 

  3. E. D. Attanasi and R. F. Meyer, 2004 Survey of Energy Resources, Ed. by J. Trinnaman and A. Clarke (Elsevier, Amsterdam), 20th Ed., p. 93

    Google Scholar 

  4. V. P. Yakutseni, Yu. E. Petrova, and A. A. Sukhanov, Pet. Geol., Theor. Appl. Stud. 1, 20 (2009).

    Google Scholar 

  5. J. G. Reynolds, Liq. Fuels Technol 3, 73 (1985).

    Article  CAS  Google Scholar 

  6. D. Strong and R. H. Filby, ACS Symp. Ser. 344, 154 (1987).

    Article  CAS  Google Scholar 

  7. P. R. Sundararaman, Appl. Geochem. 8, 245 (1993).

    Article  Google Scholar 

  8. A. Treibs and J. Lieb, Ann. Chem. 509, 103 (1934).

    Article  CAS  Google Scholar 

  9. E. A. Glebovskaya and M. V. Vol’keshtein, Zh. Obshch. Khim., No. 18, 1440 (1948).

  10. D. G. Erdman, in Organic Geochemistry (Nedra, Moscow, 1967), p. 105 [in Russian].

    Google Scholar 

  11. M. D. Lewan and J. B. Maynard, Geochim. Cosmochim. Acta 46, 2547 (1982).

    Article  CAS  Google Scholar 

  12. S. Faramawy, S. M. El-Sabagh, Y. M. Moustafa, and A. Y. El-Naggar, Pet. Sci. Technol. 28, 603 (2010).

    Article  CAS  Google Scholar 

  13. R. Bodnnett, P. J. Burke, and F. Czechowski, ACS Symposium Series, vol. 344: Metal Complexes in Fossil Fuels, Ed. by R. H. Filby and J. F. Branthaver (American Chemical Society, Washington, D.C., 1987), p. 173.

  14. Y. D. Zeng and P. C. Uden, J. High Resolut. Chromatogr. 17, 223 (1994).

    Article  CAS  Google Scholar 

  15. C. K. Junium, K. H. Freeman, and M. A. Arthur, Org. Geochem. 80, 60 (2015).

    Article  CAS  Google Scholar 

  16. Y. Kashiyama, N. O. Ogawa, S. Nomoto, et al., Earth, Life, Isot. 12, 313 (2010).

    Google Scholar 

  17. V. R. Antipenko, O. V. Serebrennikova, and V. I. Titov, Neftekhimiya, No. 3, 323 (1979).

  18. A. M. Shul’ga, T. K. Mozzhelina, and O. V. Serebrennikova, Neftekhimiya, No. 2, 273 (1980).

  19. K. M. Smith, Porphyrins and Metalloporphyrins, Ed. by K. M. Smith, (Elsevier, Amsterdam, 1975), p. 1.

    Google Scholar 

  20. A. A. El Bassoussi, S. M. El-Sabagh, F. M. Harb, and M. M. El Nady, Energy Sources, Part A: Recover. Util. Environ. Eff. 39, 110 (2017).

    CAS  Google Scholar 

  21. G. P. Dechaine and M. R. Gray, Energy Fuels 24, 2795 (2010).

    Article  CAS  Google Scholar 

  22. T. M. Halasinski, J. L. Weisman, R. Ruiterkamp, et al., Phys. Chem. A 107, 3660 (2003).

    Article  CAS  Google Scholar 

  23. D. H. Freeman and T. C. O’Haver, Energy Fuels 4, 688 (1990).

    Article  CAS  Google Scholar 

  24. D. H. Freeman, D. C. Saint Martin, and C. J. Boreham, Energy Fuels 7, 194 (1993).

    Article  CAS  Google Scholar 

  25. R. A. Galimov, L. B. Krivonozhkina, and G. V. Romanov, RU Patent No. 2054670; Byull. Izobret., No. 5 (1996).

  26. X. Zhao, C. Xu, and Q. Shi, Struct. Bond. 119, 193 (2015).

    Google Scholar 

  27. E. W. Baker and S. E. Palmer, The Porphyrins, Ed. by D. Dolphin (Academic, New York, 1978), Vol. 1, p. 485.

    Google Scholar 

  28. A. Doukhali, A. Saoiabi, A. Zrineh, et al., Fuel 81, 467 (2002).

    Article  Google Scholar 

  29. B. M. Rytting, I. D. Singh, M. R. Harper, et al., Energy Fuels 32, 5711 (2018).

    Article  CAS  Google Scholar 

  30. R. D. Grigsby and J. B. Green, Energy Fuels 11, 602 (1997).

    Article  CAS  Google Scholar 

  31. M. Nali, M. Fabbi, and A. Scilingo, Pet. Sci. Technol. 15, 307 (1997).

    Article  CAS  Google Scholar 

  32. S. M. El-Sabagh, Fuel Process. Technol. 57, 65 (1998).

    Article  CAS  Google Scholar 

  33. A. J. G. Barwise and E. V. Whitehead, Phys. Chem. Earth 12, 181 (1980).

    Article  CAS  Google Scholar 

  34. M. F. Ali, H. Perzanowski, A. Bukhari, and A. Al-haji, Energy Fuels 1, 179 (1993).

    Article  Google Scholar 

  35. M. Espinosa Pena, A. Manjarréz, and A. Campero, Fuel Process. Technol. 46, 171 (1996).

    Article  CAS  Google Scholar 

  36. E. W. Baker, J. Am. Chem. Soc. 88, 2311 (1966).

    Article  CAS  Google Scholar 

  37. E. W. Baker, T. F. Yen, J. P. Dickie, et al., J. Am. Chem. Soc. 89, 3631 (1967).

    Article  CAS  Google Scholar 

  38. D. Thomas and M. Blumer, Geochim. Cosmochim. Acta 28, 1147 (1964).

    Article  CAS  Google Scholar 

  39. T. F. Yen, The Role of Trace Metals in Petroleum, Ed. by T. F. Yen (Ann Arbor Science: Ann Arbor, MI, 1975), p. 1.

  40. L. Qi, R. Liang, and X. Wang, Acta Pet. Sinica 2, 108 (1981).

    Google Scholar 

  41. W. Prowse, M. Chicarelli, B. Keely, et al., Geochim. Cosmochim. Acta 51, 2875 (1987).

    Article  CAS  Google Scholar 

  42. Z. Liao, D. Huang, and J. Shi, Sci. Sinica, Ser. B 33, 631 (1990).

    CAS  Google Scholar 

  43. P. J. Marriot, J. Chromatogr. 236, 395 (1982).

  44. P. J. Marriott, J. P. Gill, R. P. Evershed, et al., J. Chromatogr. 301, 107 (1984).

    Article  CAS  PubMed  Google Scholar 

  45. C. S. Hein, J. P. Gill, R. P. Evershed, and G. Eglinton, Anal. Chem. 20, 1872 (1985).

    Article  Google Scholar 

  46. R. Alexander, G. Eglinton, J. P. Gill, and J. K. Volkman, J. High Resol. Chromatogr. 3, 521 (1980).

    CAS  Google Scholar 

  47. J. Quirke, G. Eglinton, S. Palmer, and E. Baker, Chem. Geol. 35, 69 (1982).

    Article  CAS  Google Scholar 

  48. J. M. E. Quirke, ACS Symposium Series, vol. 344: Metal Complexes in Fossil Fuels, Ed. by R. H. Filby and J. F. Branthaver (American Chemical Society, Washington, D.C., 1987), p. 308.

  49. J. D. Laycock, J. A. Ferguson, R. A. Yost, et al., J. Mass Spectrom. 32, 978 (1997).

    Article  CAS  Google Scholar 

  50. B. G. J. Shaw, J. M. E. Quirke, G. Eglinton, and O. G. Unit, J. Chem. Soc., Perkin Trans. 1, 1655 (1978).

    Article  Google Scholar 

  51. G. Eglinton, Philos. Trans. R. Soc. London A 293, 1400 (1979).

    Article  Google Scholar 

  52. G. J. Shaw, G. Eglinton, and J. M. E. Quirke, Anal. Chem. 6, 2014 (1981).

    Article  Google Scholar 

  53. A. Rosell-Melé, J. F. Carter, and J. R. Maxwell, J. Am. Soc. Mass Spectrom. 7, 965 (1996).

    Article  PubMed  Google Scholar 

  54. G. J. van Berkel, M. A. Quinones, and J. M. E. Quirke, Energy Fuels 7, 411 (1993).

    Article  CAS  Google Scholar 

  55. R. P. Rodgers, C. L. Hendrickson, M. R. Emmett, et al., Can. J. Chem. 79, 546 (2001).

    Article  CAS  Google Scholar 

  56. X. Zhao, Y. Liu, C. Xu, et al., Energy Fuels 27, 2874 (2013).

    Article  CAS  Google Scholar 

  57. X. Zhao, Q. Shi, M. R. Gray, and C. Xu, Sci. Rep. 4, 5373 (2014).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  58. H. Liu, J. Mu, Z. Wang, et al., Energy Fuels 29, 4803 (2015).

    Article  CAS  Google Scholar 

  59. T. Liu, J. Lu, X. Zhao, et al., Energy Fuels 29, 2089 (2015).

    Article  CAS  Google Scholar 

  60. J. C. Putman, S. M. Rowland, Y. E. Corilo, and A. M. McKenna, Anal. Chem. 86, 10708 (2014).

    Article  CAS  PubMed  Google Scholar 

  61. F. Zheng, C. S. Hsu, Y. Zhang, et al., Energy Fuels 32, 10382 (2018).

    Article  CAS  Google Scholar 

  62. K. Qian, A. S. Mennito, K. E. Edwards, and D. T. Ferrughelli, Rapid Commun. Mass Spectrom. 22, 2153 (2008).

    Article  CAS  PubMed  Google Scholar 

  63. A. M. McKenna, J. M. Purcell, R. P. Rodgers, and A. G. Marshall, Energy Fuels 23, 2122 (2009).

    Article  CAS  Google Scholar 

  64. K. Qian, K. E. Edwards, A. S. Mennito, et al., Anal. Chem. 82, 413 (2010).

    Article  CAS  PubMed  Google Scholar 

  65. A. M. McKenna, J. T. Williams, J. C. Putman, et al., Energy Fuels 28, 2454 (2014).

    Article  CAS  Google Scholar 

  66. M. Woltering, S. Tulipani, C. J. Boreham, et al., Chem. Geol. 441, 81 (2016).

    Article  CAS  Google Scholar 

  67. K. Akbarzadeh, A. Hammami, A. Kharrat, et al., Oilfield Rev., 22 (2007).

  68. A. R. Hortal, P. Hurtado, B. Martinez-Haya, and O. C. Mullins, Energy Fuels 21, 2863 (2007).

    Article  CAS  Google Scholar 

  69. J. M. Purcell, R. P. Rodgers, C. L. Hendrickson, and A. G. Marshall, J. Am. Soc. Mass Spectrom. 18, 1265 (2007).

    Article  CAS  PubMed  Google Scholar 

  70. L. A. Stanford, R. P. Rodgers, A. G. Marshall, et al., Energy Fuels 21, 963 (2007).

    Article  CAS  Google Scholar 

  71. S. Acevedo, T. J. M. Cordero, H. Carrier, et al., Energy Fuels 23, 842 (2009).

    Article  CAS  Google Scholar 

  72. Y. Y. Borisova, E. G. Tazeeva, N. A. Mironov, et al., Energy Fuels 31, 13382 (2017).

    Article  CAS  Google Scholar 

  73. K. Qian, K. E. Edwards, M. Siskin, et al., Energy Fuels 21, 1042 (2007).

    Article  CAS  Google Scholar 

  74. D. Giraldo-Dávila, M. L. Chacón-Patiño, J. S. Ramirez-Pradilla, et al., Fuel 226, 103 (2018).

    Article  CAS  Google Scholar 

  75. H. Xu, D. Yu, and G. Que, Fuel 84, 647 (2005).

    Article  CAS  Google Scholar 

  76. Y. Cho, M. Witt, J. M. Jin, et al., Energy Fuels 28, 6699 (2014).

    Article  CAS  Google Scholar 

  77. M. R. Yakubov, D. V. Milordov, S. G. Yakubova, et al., Pet. Sci. Technol. 34, 177 (2016).

    Article  CAS  Google Scholar 

  78. N. A. Mironov, G. R. Abilova, K. O. Sinyashin, et al., Energy Fuels 32, 161 (2018).

    Article  CAS  Google Scholar 

  79. M. R. Yakubov, G. R. Abilova, K. O. Sinyashin, et al., Phthalocyanines and Some Current Applications, Ed. by Y. Yilmaz (InTech, Rijeka, 2017), Ch. 7.

    Google Scholar 

  80. N. A. Mironov, G. R. Abilova, Y. Y. Borisova, et al., Energy Fuels 32, 12435 (2018).

    Article  CAS  Google Scholar 

  81. N. A. Mironov, K. O. Sinyashin, G. R. Abilova, et al., Russ. Chem. Bull. 66, 1450 (2017).

    Article  CAS  Google Scholar 

  82. X. Lou, M. Fransen, P. J. M. Stals, et al., J. Am. Soc. Mass Spectrom. 24, 1405 (2013).

    Article  CAS  PubMed  Google Scholar 

  83. L. J. Castellanos-García, B. C. Agudelo, H. F. Rosales, et al., J. Am. Soc. Mass Spectrom. 28, 2548 (2017).

    Article  CAS  PubMed  Google Scholar 

  84. J. Wert and J. R. Bolton, Electron Spin Resonance: Elementary Theory and Practical Applications (McGraw-Hill, New York, 1972).

    Google Scholar 

  85. L. J. Boucher, E. C. Tynan, and T. F. Yen, In Electron Spin Resonance of Metal Complexes (Plenum Pres, New York, 1969).

    Google Scholar 

  86. V. M. Malhotra and R. M. William, Fuel 62, 1255 (1983).

    Article  CAS  Google Scholar 

  87. V. Ramachandran, J. van Tol, A. M. McKenna, et al., Anal. Chem. 87, 2306 (2015).

    Article  CAS  PubMed  Google Scholar 

  88. P. I. Premović, T. Allard, N. D. Nikolić, et al., Fuel 79, 813 (2000).

    Article  Google Scholar 

  89. M. I. Tagirzyanov, M. R. Yakubov, and G. V. Romanov, in Proceedings of Canadian International Petroleum Conference (Petroleum Society of Canada, 2004).

  90. T. Biktagirov, M. Gafurov, G. Mamin, et al., Energy Fuels 31, 1243 (2017).

    Article  CAS  Google Scholar 

  91. G. V. Mamin, M. R. Gafurov, R. V. Yusupov, Iet al., Energy Fuels 30, 6942 (2016).

    Article  CAS  Google Scholar 

  92. S. N. Trukhan, S. G. Kazarian, and O. N. Martyanov, Energy Fuels 31, 387 (2016).

    Article  CAS  Google Scholar 

  93. V. M. Malhotra and H. A. Buckmaster, Fuel 64, 335 (1985).

    Article  CAS  Google Scholar 

  94. F. E. Dickson, C. J. Kunesh, E. L. McGinnis, and L. Petrakis, Anal. Chem. 44, 978 (1972).

    Article  CAS  Google Scholar 

  95. R. A. Bozis and B. J. McCormick, Inorg. Chem. 9, 1541 (1970).

    Article  CAS  Google Scholar 

  96. V. M. Malhotra and H. A. Buckmaster, Fuel 64, 335 (1985).

    Article  CAS  Google Scholar 

  97. L. G. Gilinskaya, L. S. Borisova, and E. A. Kostyreva, J. Struct. Chem. 56, 436 (2015).

    Article  CAS  Google Scholar 

  98. S. Asaoka, S. Nakata, Y. Shiroto, and C. Takeuchi, Ind. Eng. Chem. Proc. Des. Dev. 22, 242 (1983).

    Article  CAS  Google Scholar 

  99. J. G. Reynolds, E. J. Gallegos, R. H. Fish, and J. J. Komlenic, Energy Fuels 1, 36 (1987).

    Article  CAS  Google Scholar 

  100. J. G. Reynolds, W. R. Biggs, and J. C. Fetzer, Liq. Fuels Technol. 3, 423 (1985).

    Article  CAS  Google Scholar 

  101. O. N. Mart’yanov, Yu. V. Larichev, E. V. Morozov, and S. N. Trukhan, Usp. Khim. 86, 999 (2017).

    Article  Google Scholar 

  102. C. M. Guzy, J. B. Raynor, and M. C. R. Symons, J. Chem. Soc. A, 2721 (1969).

  103. L. G. Gilinskaya, Zh. Strukt. Khim. 49, 259 (2008).

    Google Scholar 

  104. T. Yen, Energy Sources 3, 339 (1978).

    Article  CAS  Google Scholar 

  105. J. Goulon, A. Retournard, P. Friant, et al., J. Chem. Soc., Dalton Trans. 6, 1095 (1984).

    Article  Google Scholar 

  106. M. Loos, I. Ascone, P. Friant, et al., Catal. Today 7, 497 (1990).

    Article  CAS  Google Scholar 

  107. J. L. Poncet, R. Guilard, P. Friant, et al., New J. Chem. 8, 583 (1984).

    CAS  Google Scholar 

  108. J. Miller, R. Fisher, P. Thiyagarajan, et al., Energy Fuels 12, 1290 (1998).

    Article  CAS  Google Scholar 

  109. J. T. Miller, R. B. Fisher, A. M. J. van der Eerden, and D. C. Koningsberger, Energy Fuels 13, 719 (1999).

    Article  CAS  Google Scholar 

  110. H. Xu, G.-H. Que, J.-Q. Wang, et al., Acta Chim. Sinica 61, 450 (2003).

    CAS  Google Scholar 

  111. P. Sundararaman, Anal. Chem. 57, 2204 (1985).

    Article  CAS  Google Scholar 

  112. F. G. Wandekoken, C. B. Duyck, T. C. O. Fonseca, and T. D. Saint’pierre, Spectrochim. Acta, Part A 119, 1 (2016).

    Article  CAS  Google Scholar 

  113. N. Márquez, F. Ysambertt, and C. de la Cruz, Anal. Chim. Acta 395, 343 (1999).

    Article  Google Scholar 

  114. M. Espinosa, U. S. Pacheco, F. Leyte, and R. Ocampo, J. Porphyrins Phthalocyanines 18, 542 (2014).

  115. Y. Kashiyama, H. Kitazato, and N. Ohkouchi, J. Chromatogr. A 1138, 73 (2007).

    Article  CAS  PubMed  Google Scholar 

  116. P. Chen, Z. Xing, M. Liu, et al., J. Chromatogr. A 839, 239 (1999).

    Article  CAS  Google Scholar 

  117. J. Castillo and V. Vargas, Pet. Sci. Technol. 34, 873 (2016).

    Article  CAS  Google Scholar 

  118. A. L. Johnson and D. H. Freeman, Energy Fuels 4, 695 (1990).

    Article  CAS  Google Scholar 

  119. C. X. Yin, J. M. Stryker, and M. R. Gray, Energy Fuels 23, 2600 (2009).

    Article  CAS  Google Scholar 

  120. V. Vargas, J. Castillo, R. Ocampo, et al., Fuel Process. Technol. 162, 37 (2017).

    Article  CAS  Google Scholar 

  121. V. K. Bhatia Chakarhorty, Indian J. Technol., 92 (1981).

  122. M. R. Yakubov, P. I. Gryaznov, S. G. Yakubova et al., Pet. Sci. Technol 34, 1805 (2016).

    Article  CAS  Google Scholar 

  123. M. R. Yakubov, P. I. Gryaznov, S. G. Yakubova, et al., Pet. Sci. Technol. 35, 2152 (2017).

    Article  CAS  Google Scholar 

  124. K. Saitoh, H. Tan, and Y. Zheng, Anal. Sci. 17, 1511 (2001).

    Article  Google Scholar 

  125. R. Ocampo, A. Riva, J. M. Trendel, et al., Energy Fuels 7, 191 (1993).

    Article  CAS  Google Scholar 

  126. J. Verne-Mismer, R. Ocampo, C. Bauder, et al., Energy Fuels 4, 639 (1990).

    Article  CAS  Google Scholar 

  127. G. Caumette, C.-P. Lienemann, I. Merdrignac, et al., J. Anal. At. Spectrom. 25, 1123 (2010).

    Article  CAS  Google Scholar 

  128. C. B. Duyck, T. D. Saint’Pierre, N. Miekeley, et al., Spectrochim. Acta, Part B 66, 362 (2011).

    Article  CAS  Google Scholar 

  129. A. J. Barwise, R. P. Evershed, G. A. Wolff, et al., J. Chromatogr. A 368, 1 (1986).

    Article  CAS  Google Scholar 

  130. J. H. Chen and R. P. Philp, Chem. Geol. 91, 139 (1991).

    Article  CAS  Google Scholar 

  131. P. Sundararaman, W. R. Biggs, J. G. Reynolds, and J. C. Fetzer, Geochim. Cosmochim. Acta 52, 2337 (1988).

    Article  CAS  Google Scholar 

  132. S. Acevedo, L. A. Garcia, and P. Rodriguez, Energy Fuels 26, 1814 (2012).

    Article  CAS  Google Scholar 

  133. G. Gascon, V. Vargas, L. Feo, et al., Energy Fuels 31, 7783 (2017).

    Article  CAS  Google Scholar 

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  1. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 420088, Kazan, Tatarstan, Russia

    N. A. Mironov, D. V. Milordov, G. R. Abilova, S. G. Yakubova & M. R. Yakubov

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  1. N. A. Mironov
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Mironov, N.A., Milordov, D.V., Abilova, G.R. et al. Methods for Studying Petroleum Porphyrins (Review). Pet. Chem. 59, 1077–1091 (2019). https://doi.org/10.1134/S0965544119100074

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