Skip to main content
SpringerLink
Log in

Synthesis of polyynes (and ene-ynes) segments by dechlorination reactions of chlorinated polyethylene wax and chlorinated docosane

  • Published:
Journal of Materials Science Aims and scope Submit manuscript

Abstract

High density polyethylene oligomers and docosane (C22H46) were subjected to a photochlorination reaction to a chlorine content above 70% as checked by thermogravimetry. The resulting chlorinated materials were dehydrohalogenated by potassium hydroxide in different conditions with simple reaction routes. It is shown by FT-IR, C13-NMR and electronic spectroscopy that soluble low molecular weight polymers were formed having polyyne-ene and polyene-yne segments. These new soluble polymeric materials are of potential interest both in the field of optics and electronics as well as in the understanding the cosmochemical problem of the molecules in interstellar space.

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. R. B. Heimann, S. E. Evsyukov and L. Kavan, “Carbyne and Carbynoid Structures” (Kluwer Academic Publishers. Dordrecht, 1999).

    Google Scholar 

  2. Yu, P. Kudriavtsev, R. B. Heimann and S. E. Evsyukov, J. Mater. Sci. 31 (1997) 5557.

    Google Scholar 

  3. L. Kavan, Chem. Rev. 97 (1997) 3061.

    Google Scholar 

  4. M. Kijima, Recent Res. Dev. Pure Appl. Chem. 1 (1997) 27.

    Google Scholar 

  5. R. J. Lagow, J. J. Kampa, H. C. Wei, S. L. Battle, J. W. Genge, D. A. Laude, C. J. Harper, R. Bau, R. C. Stevens, J. F. Haw and E. Munson, Science 267 (1995) 362.

    Google Scholar 

  6. J. Bagott, “Perfect Symmetry: The Accidental Discovery of Buckminsterfullerne” (Oxford University Press, Oxford, 1996).

    Google Scholar 

  7. S. Iijima, Nature 354 (1991) 56.

    Google Scholar 

  8. F. Cataldo, Polymer International 48 (1999) 143.

    Google Scholar 

  9. J. P. Hare and H. W. Kroto, Acc. Chem. Res. 25 (1992) 106.

    Google Scholar 

  10. T. Grosser and A. Hirsch, Angew, Chem. Int. Ed. Engl. 32 (1993) 1340.

    Google Scholar 

  11. T. P. Snow, V. Le Page, Y. Keheyan and V. M. Bierbaum, Nature 391 (1998) 259.

    Google Scholar 

  12. A. G. G. M. Tielens and T. P. Snow (ed.), “The Diffuse Interstellar Bands” (Kluwer Academic Publishers, Dordrecht, 1995).

    Google Scholar 

  13. F. Cataldo, Eur. J. Solid State Inorg. Chem. 34 (1997) 53.

    Google Scholar 

  14. Idem., Polym. International 44 (1997) 191.

    Google Scholar 

  15. Idem., Fullerene Sci. Technol. 5 (1997) 1615.

    Google Scholar 

  16. Idem., Eur. J. Solid State Inorg. Chem. 35 (1998) 281.

    Google Scholar 

  17. Idem., ibid. 35 (1998) 293.

    Google Scholar 

  18. Idem., Polym. International 48 (1999) 15.

    Google Scholar 

  19. Idem., ibid. 48 (1999) 143.

    Google Scholar 

  20. Idem., Angew, Makromol, Chem. 264 (1999) 65.

    Google Scholar 

  21. Idem., Eur. Polym. J., in press.

  22. S. E. Evsyukov, Yu.P. Kudryavtsev and Yu. V. Korshak, Russian Chem. Rev. 60 (1991) 373.

    Google Scholar 

  23. J. Kastner, H. Kuzmany, L. Kavan, F. P. Dousek and J. Kurti, Macromolecules 28 (1995) 344.

    Google Scholar 

  24. F. Cataldo, Eur. Polym. J. 29 (1993) 1635.

    Google Scholar 

  25. K. Akagi, T. Kadokura and H. Shirakawa, Polymer 33 (1992) 4058.

    Google Scholar 

  26. J. A. Brydson, “Rubber Chemistry” (Applied Science Publishers, London. 1978) p. 342.

    Google Scholar 

  27. W. G. Oakes and R. B. Richards. Trans. Faraday Soc. 42A (1946) 197.

    Google Scholar 

  28. B. S. Furniss, A. J. Hannaford. V. Rogers. P. W. G. Smith and A. R. Tatchell, “Vogel'sTextbook of Practical Organic Chemistry” (Longman Group Ltd. Harlow, 1986) Section II-2.

    Google Scholar 

  29. L. F. Fieser and M. Fieser, “Advanced Organic Chemistry” (Reinhold Publishing Corp., New York, 1961) p. 119.

    Google Scholar 

  30. J. March, “Advanced Organic Chemistry,” 3rd ed. (John Wiley & Sons, New York, 1985) p. 620.

    Google Scholar 

  31. R. M. Silverstein, G. C. Bassler and T. C. Morrill, “Spectrometric Identification of Organic Compounds,” 40th ed. (J. Wiley & Sons, New York, 1981).

    Google Scholar 

  32. C. Altona and H. J. Hageman, Rec. Trav. Chim. Pays-Bas 88 (1969) 33.

    Google Scholar 

  33. C. Altona, H. J. Hageman and E. Havinga, ibid. 88 (1969) 43.

    Google Scholar 

  34. S. E. Evsyukov, S. Paasch, B. Thomas and R. B. Heimann, Ber. Bunsenges. Phys. Chem. 101 (1997) 837.

    Google Scholar 

  35. F. Cataldo, Carbon 37 (1999) 161.

    Google Scholar 

  36. F. Cataldo and D. Capitani, Mater. Chem. Phys. 59 (1999) 225.

    Google Scholar 

  37. R. M. Silverstein, G. C. Bassler and T. C. Morrill, “Spectrometric Identification of Organic Compounds,” 4th ed. (J. Wiley & Sons, New York, 1981) p. 263.

    Google Scholar 

  38. M. Hesse, H. Meier and B. Zeeh, “Spectroscopic Methods in Organic Chemistry” (G. Thieme Verlag, Stuttgart, 1997) p. 186.

    Google Scholar 

  39. E. Pretsch, J. Seibl, T. Clerc and W. Simon, “Tables of Spectral Data for Structure Determination of Organic Compounds,” 2nd ed. (Springer-Verlag, Berlin, 1989) p. C110.

    Google Scholar 

  40. N. J. Long, Angew, Chem. Int. Ed. Engl. 34 (1995) 21.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Progega snc, Via Casilina 1626/A, 00133, Rome, Italy

    F. Cataldo

Authors
  1. F. Cataldo
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cataldo, F. Synthesis of polyynes (and ene-ynes) segments by dechlorination reactions of chlorinated polyethylene wax and chlorinated docosane. Journal of Materials Science 35, 2413–2419 (2000). https://doi.org/10.1023/A:1004745013535

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1004745013535

Keywords

Search

Navigation