Advertisement

Springer Nature is making Coronavirus research free. View research | View latest news | Sign up for updates

Synthesis and characterization of 2,3-dialkyl-1,4-butanediols and copolyesters containing these moieties

  • 30 Accesses

Summary

Reaction of the 2,3-dimethylene-1,3-butadiene dianion (made using Lochmann's base) with a series of primary alkyl halides yielded 2,3-dialkyl-1,3-butadienes, which were converted to the corresponding 2,3-dialkyl-1,4-butanediols via hydroboration/oxidation. Along with ethylene glycol and dimethyl terephthalate these disubstituted butanediols were incorporated into copolyesters using melt condensation polymerization. The resultant copolymers were characterized by 1H NMR, inherent viscosity, and DSC. From this data the effects of varying the length and amount of alkyl side groups on the copolyester syntheses and properties were studied.

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

References

  1. 1.

    L. Lochmann, J. Popisil, and D. Lim., Tetrahedron Lett, 2, 257 (1966).

  2. 2.

    J. J. Bahl, R. B. Bates, and B. Gordon III, J. Org. Chem., 44, 2290 (1979).

  3. 3.

    B. Gordon III, M. J. Blumenthal, A. E. Mera, and R. J. Kumpf, J. Org. Chem., 50, 1540 (1985).

  4. 4.

    B. Gordon III and M. Blumenthal, Polym. Bulletin, 14, 69 (1985).

  5. 5.

    G. Zweifel and H. C. Brown In “Organic Reactions, Volume 13”, A. C. Cope, Ed., John Wiley and Sons, Inc., New York, 1963.

  6. 6.

    G. Zweifel, K. Nagase, and H. C. Brown, J. Am. Chem. Soc., 84, 183 (1962).

  7. 7.

    G. M. L. Cragg, “Organoboranes in Organic Synthesis”, Marcel Dekker, Inc., New York, 1973.

  8. 8.

    J. Majnusz, J. M. Catala, and R. W. Lenz, Eur. Polym. J., 19, 1043 (1983).

  9. 9.

    H.-R. Dicke and R. W. Lenz, J. Polym. Sci. Polym. Chem. Ed., 21, 2581 (1983).

  10. 10.

    Q.-F. Zhou and R. W. Lenz, J. Polym. Sci. Polym. Chem. Ed., 21, 3313 (1983).

  11. 11.

    D. R. Fagerburg, J. Appl. Polym. Sci., 30, 889 (1985).

  12. 12.

    Z. Florjanczyk, B. Deopura, R. S. Stein, and O. Vogl, J. Polym. Sci. Polym. Chem. Ed., 20, 1051 (1982).

  13. 13.

    A. Yamada, S. Grossman, and O. Vogl, J. Polym. Sci. Polym. Chem. Ed., 18, 1739 (1980).

  14. 14.

    H. K. Hall, Jr. and A. B. Padias, U.S. Patent 4,439,597, 1984.

  15. 15.

    G. R. Chipman, M. G. Henk, J. A. De Boer, and E. W. Blaha, U.S. Patent 4,014,858, 1977.

  16. 16.

    M. Hayashi, H. Ikeuchi, and M. Tanaka, U.S. Patent 3,936,421, 1976.

  17. 17.

    R. M. Beesley, C. K. Ingold, and J. F. Thorpe, J. Chem. Soc., London Trans., 107, 1080 (1915).

  18. 18.

    C. K. Ingold, J. Chem. Soc., London Trans., 119, 305 (1921).

  19. 19.

    E. L. Eliel, “Elements of Stereochemistry”, John Wiley and Sons, Inc., New York, 1969.

  20. 20.

    S. S. Rogers and L. Mandelkern, J. Phys. Chem., 61, 985 (1957).

  21. 21.

    T. G. Fox, Bull. Am. Phys. Soc., Ser. 2, 1, 123 (1956).

Download references

Author information

Correspondence to Bernard Gordon III.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Gordon, B., Mera, A.E. Synthesis and characterization of 2,3-dialkyl-1,4-butanediols and copolyesters containing these moieties. Polymer Bulletin 22, 379–386 (1989). https://doi.org/10.1007/BF00263076

Download citation

Keywords

  • Polymer
  • Ethylene
  • Viscosity
  • Ethylene Glycol
  • Dimethyl