Skip to main content
SpringerLink
Log in

Mechanism of low-molecular alkenes interaction with sulfur-containing spatially hindered phenols under conditions of thermal modification of polymer materials

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Transformations in the course of high-temperature modification of polyolefins under action of sulfur-containing modifiers have been studied using hexene-1 and hexane as model compounds. Composition of products of thermolysis of bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl] disulfide and bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl] sulfide at 200–270°C has been elucidated by means of thermogravimetry and gas chromatography-mass spectrometry. Mechanism of olefins modification with sulfides and disulfides involving the formation of biradical intermediates is discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Babayan, V.G., Tarkhanova, G.P., and Baranova, A.S., Vysokomolekulyarnye i prishivayushchiesya stabilizatory dlya elastomerov (Macromolecular and Sew Stabilizers for Elastomers), Moscow: NIITEneftehim, 1981.

    Google Scholar 

  2. Rosenberger, S., Evans, S., Glig, B., ER Patent 0035472, 1981, C. A., 1982, vol. 96, 19816z.

    Google Scholar 

  3. Gurvich, Ya.A., Kumok, S.T., Lopatin, V.V., and Starikova, O.F., Fenol’nye antioksidanty. Sostoyanie i perspektivy (Phenolic Antioxidants. Condition and Perspectives), Moscow: NIITEneftekhim, 1990, no. 5.

    Google Scholar 

  4. Nikulicheva, O.N., Krysin, A.P., and Fadeeva, V.P., Russ. J. Appl. Chem., 2008, vol. 81, no. 9, p. 1592. DOI: 10.1134/S10704272080922X.

    Article  CAS  Google Scholar 

  5. Roginskii, V.A., Fenoksil’nye radikaly. Reaktsionnaya sposobnost’ i effektivnost’ (Phenoxyl Radicals. Reactivity and Efficiency), Moscow: Nauka, 1988.

    Google Scholar 

  6. Lugova, L.I., Makarova, G.P., Tsvetkova, A.I., Sotnikova, L.K., Dudinova, L.N., and Lazareva, N.P., Sb. nauch. tr. ONPO Plastpolimer. Organicheskie soedineniya — novye stabilizatory. Sintez, svoistva. Pererabotka poliolefinov (Coll. Sci. Works of ONPO Plastpolymer. Organic Compounds — New Stabilizers. Synthesis, Properties. Waste of Polyolefins), Leningrad, 1984, p. 152.

    Google Scholar 

  7. Perevozkina, M.G., Storozhok, N.M., Krysin, A.P., and Borisenko, V.E., Russ. Chem. Bull. Int. Ed., 2006, vol. 55, no. 8, p. 1380. DOI: 10.1007/S1117200604292.

    Article  CAS  Google Scholar 

  8. The Chemistry of Alkenes, Patai, S., Ed., New York: Interscience, 1964. Translated under the title Khimiya alkenov, Leningrad: Khimiya, 1969, p. 481.

    Google Scholar 

  9. Energiya razryva khimicheskikh svyazei. Potentsialy ionizatsii i srodstvo k elektronu (Bond Dissociation Energy. Ionization Potentials and Electron Affinities), Kondrat’ev, V.N., Ed., Moscow: Nauka, 1974.

    Google Scholar 

  10. Krysin, A.P., Nogina, N.I., Kuzubova, L.I., and Prosenko, A.E., RF Patent 1367361, 1996, Byull. Izobret., 1997, no. 14.

    Google Scholar 

  11. Krysin, A.P., Egorova, T.G., Komarova, N.I., Vasil’ev, V.G., and Pokrovskii, V.G., Russ. J. Appl. Chem., 2009, vol. 82, no. 11, p. 1965. DOI: 10.1134/S1070427209110123.

    Article  CAS  Google Scholar 

  12. Krysin, A.P. and Yakovlev, O.I., Russ. J. Appl. Chem., 2013, vol. 86, no. 7, p. 997. DOI: 10.1134/ S1070427213070094.

    Article  CAS  Google Scholar 

  13. Murashov, B.A., Krysin, A.P., and Mozhaeva, L.N., Author’s Certificate 1657517, 1989, Byull. Izobret., 1991, no. 23.

    Google Scholar 

  14. Krysin, A.P. and Khlebnikova, T.B., Russ. J. Org. Chem., 2011, vol. 81, no. 6, p. 1159. DOI: 10.1134/S1070363211060144.

    Article  CAS  Google Scholar 

  15. Volod’kin, A.A., Ershov, V.V., Gorodetskaya, N.I., Tupikina, N.A., and Kudinova, L.I., Dokl. Akad. Nauk SSSR, 1976, vol. 227, no. 4, p. 896.

    Google Scholar 

  16. Titova, T.F. and Krysin, A.P., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., 1987, vol. 19, no. 6, p. 140.

    Google Scholar 

  17. Bartelink, H.J.M., Beulen, J., Bielders, G., Cremers, L., Duynstee, E.F.J., and Koniinenberg, E., Chem. Ind., 1978, no. 15, p. 586.

    Google Scholar 

  18. Prosenko, A.E., Pinko, P.I., Khalikova, N.U., Krysin, A.P., and Koptyug, V.A., RF Patent 1642708, 1995, Byull. Izobret., 1995, no. 26.

    Google Scholar 

  19. Prosenko, A.E., Markov, A.F., Pinko, P.I., Krysin, A.P., and Koptyug, V.A., Author’s Certificate 1658601, Byull. Izobret., 1995, no. 26.

    Google Scholar 

  20. Khimiya serosoderzhashchikh soedinenii, soderzhashchikhsya v nefti i nefteproduktakh (Chemistry of Sulfur-Containing Compounds Contained in the Petroleum and Petroleum Products), Moscow: Vysshaya Shkola, 1968, vol. 8, p. 163.

  21. Prostranstvenno-zatrudnennye fenoly (Sterically Hindered Phenols), Moscow: Khimiya, 1972, p. 207.

  22. Caserio, M.C., Fisher, C.L., and Cim, J.K., J. Org. Chem., 1985, vol. 50, no., 20, p. 4390. DOI: 10.1021/jo00222a041.

    Article  CAS  Google Scholar 

  23. Beckwith Athestan, L.J. and Duggan Sandhya, A.M., J. Chem. Soc., Perkin Trans. 2, 1994, vol. 7, p. 1509. DOI: 10.1039/p29940001509.

    Article  Google Scholar 

  24. Germany Patent 2734239, 1979, C. A., 1979, vol. 90, 168239.

  25. Neiman, M.B., Mamedova, Yu.G., Blenke, P., and Buchachenko, A.L., Dokl. Akad. Nauk SSSR, 1962, vol. 144, no. 2, p. 392.

    CAS  Google Scholar 

  26. Krysin, A.P., Mashkina, A.V., and Knyazev, V.V., RF Patent 2184727, 2002, Byull. Izobret., 2002, no. 19.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    A. P. Krysin, L. M. Pokrovskii, A. A. Nefedov, I. K. Shundrina & B. A. Selivanov

  2. Novosibirsk State University, Novosibirsk, Russia

    A. A. Nefedov

Authors
  1. A. P. Krysin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. M. Pokrovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Nefedov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. K. Shundrina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. B. A. Selivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. P. Krysin.

Additional information

Original Russian Text © A.P. Krysin, L.M. Pokrovskii, A.A. Nefedov, I.K. Shundrina, B.A. Selivanov, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 3, pp. 498–505.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Krysin, A.P., Pokrovskii, L.M., Nefedov, A.A. et al. Mechanism of low-molecular alkenes interaction with sulfur-containing spatially hindered phenols under conditions of thermal modification of polymer materials. Russ J Gen Chem 85, 659–666 (2015). https://doi.org/10.1134/S1070363215030226

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215030226

Keywords

Search

Navigation