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Oxidation of Petroleum Asphaltenes Coupled with Iodination

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Chemistry and Technology of Fuels and Oils Aims and scope

Oxidation of petroleum asphaltenes by potassium iodide (KI) is described. Oxidation under mild conditions is shown to be accompanied by iodination of the asphaltene aromatic core. The inducing reaction is the oxidation of sulfide sulfur atoms in the asphaltenes with reduction of iodate anion to molecular iodine; the coupled reaction, electrophilic substitution. X-ray photoelectron spectroscopy detected an increase in the mass fraction of oxygen as compared with the initial sample and formation of C–I bonds. IR spectroscopy found that oxidation of the asphaltenes is accompanied by the formation of carboxyl and sulfoxide groups. Raman spectroscopy revealed a decrease in the size of the oxidized asphaltene molecules as compared to the native asphaltenes. X-ray powder diffraction analysis showed a decrease in the interplanar spacing of the asphaltene oxidation product that was due to ordering and a denser arrangement of the aliphatic fragments.

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Acknowledgments

We thank staff members of the Distributed Collective Spectral and Analytical Center for Research on the Structure, Composition and Properties of Compounds and Materials, Federal Research Center, Kazan Scientific Center, Russian Academy of Sciences, for assistance with the research. The work was performed in the framework of a State Task for FRC, KSC, RAS.

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Authors and Affiliations

  1. Federal Research Center, Kazan Scientific Center, Russian Academy of Sciences, Kazan’, Russia

    K. V. Shabalin, L. E. Foss, L. I. Musin, O. A. Nagornova & D. N. Borisov

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center, Kazan Scientific Center, Russian Academy of Science, Kazan’, Russia

    A. T. Gubaidullin & A. F. Saifina

  3. Kazan (Volga Region) Federal University, Kazan’, Russia

    A. A. Khannanov & I. R. Vakhitov

Authors
  1. K. V. Shabalin
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  2. L. E. Foss
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  3. L. I. Musin
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  4. O. A. Nagornova
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  5. A. T. Gubaidullin
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  6. A. F. Saifina
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  7. A. A. Khannanov
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  8. I. R. Vakhitov
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  9. D. N. Borisov
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Corresponding author

Correspondence to K. V. Shabalin.

Additional information

Translated from Khimiya i Tekhnologiya Topliv i Masel, No. 4, pp. 33 – 40, July – August, 2020.

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Shabalin, K.V., Foss, L.E., Musin, L.I. et al. Oxidation of Petroleum Asphaltenes Coupled with Iodination. Chem Technol Fuels Oils 56, 558–569 (2020). https://doi.org/10.1007/s10553-020-01168-w

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  • DOI: https://doi.org/10.1007/s10553-020-01168-w

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