Selective epoxidation of hydroxyl terminated polybutadiene using in situ generated dimethyl dioxirane in the presence of MoO3

M. M. Alavi Nikje; Z. Mozaffari

Published : 2022-08-26

Vol. 52 No. 11-12 (2007)

Selective epoxidation of hydroxyl terminated polybutadiene using in situ generated dimethyl dioxirane in the presence of MoO3

M. M. Alavi Nikje Z. Mozaffari

Abstract

Hydroxyl terminated polybutadiene (HTPB) was epoxidized using in situ generated dimethyl dioxirane (DMD) as an oxidant and MoO3 as a catalyst at 25°C. Different reaction factors such as reaction time and catalyst concentration were examined. The ability of different C=C geometries toward epoxidation was evaluated in detail at various reaction times and the products were characterized by 1H NMR, 13C NMR and FT-IR techniques and no side reaction were detected. It was found that hydroxyl group of the polymer chain was preserved in the oxidation reaction without using any conditional control and relative reactivity depended on chain microstructure in the following way: 1,4-cis > 1,4-trans > 1,2-vinyl. This method is easy, environmentally friendly, convenient and the reaction conditions are straightforward.

Keywords

polibutadien z końcowymi grupami wodorotlenowymi ; epoksydowanie ; dimetylodioksiran ; mikrostruktura hydroxyl terminated polybutadiene ; epoxidation ; dimethyl dioxirane ; microstructure

Details

References

Statistics

Authors

Download files

PDF

Zasady cytowania

Alavi Nikje, M. M., & Mozaffari, Z. (2022). Selective epoxidation of hydroxyl terminated polybutadiene using in situ generated dimethyl dioxirane in the presence of MoO3. Polimery, 52(11-12), 820–826. Retrieved from https://polimery.ichp.vot.pl/index.php/p/article/view/1476

References

Baker C. S. L., Barnard D.: "Advances in Elastomer and Rubber Elasticity", Plenum, New York 1987, p. 175.

2. Gallucci R. R , Going R. C.: J. Appl. Polym. Sci. 1982, 27, 425.

3. Wang X. H., Zhang H. X., Wang Z. G., Jiang B. Z.: Polymer 1997, 38, 1569.

4. Latha P. B., Adhinarayanan K., Ramaswamy R.: Inter J. Adhesion Adhesives 1994, 14, 57.

5. Stenberg B., Ahlblad G., Reitberger T., Terselius B.: Polym. Degrad. Stab. 1999, 65, 179.

6. Akcelrud L., Aguiar M., Menezes S. C. D.: Macromol. Chem. Phys. 1994, 195, 3937 and references cited there in.

7. a) Martinez-Mández S., Henriques Y., Domingues O., D'Ornelas L., Krrentzien H.: Mol. Catal. A Chem. 2006, 252, 226; b) Gerbase A. E., Gregorio J. R., Martinelli M., von Holleben M. L. A., Jacobi M. A. M., Freitas L., Calcagno C. I. W., Mendes A. N. F., Pires M. L.: Catal. Today 2000, 57, 241.

8. Roy S., Gupta B. R., De S. K.: "Elastomer Technology Handbook", CRC Press, Boca Raton, 1993, Chapter 17.

9. Yang J. M., Lin H. T., Lai W. Ch.: J. Memb. Sci. 2002, 208, 105.

10. Yang J. M., Lai W. Ch., Lin H. T.: J. Memb. Sci. 2001, 183, 37.

11. Żuchowska D.: Polymer 1980, 21, 514.

12. a) Veronique N., Jean-Marie A., Dirk E. D. V., Ronny N., Waldemar A., Rui Z., Johan E. E., Peter T. W., Paul L. A.: J. Mol. Catal. A Chemical 2006, in press; b) Jian X., Hay A. S.: J. Polym. Sci. C, Polym. Lett. 1990, 28, 285.

13. a) Da Palma Carreiro E., Burke A. J. B.: J. Mol. Catal. A Chemical 2006, 249, 123; b) Gholamhossein G., Tangestaninejad S., Mohammad H. H., Mirkhani V., Mogbadam M.: Appl. Catal. A General 2006, 299, 131; c) Gahagan M., Iraqi A., Cupertino D. C., Mackie R. K., Cole-Hamilton D. J.: J. Chem. Soc. Chem. Commun. 1989, 1688.

14. Jian X., Hay A.: J. Polym. Sci. Part A, Polym. Chem. 1991, 29, 1183.

15. a) Liu S. Y., Nocera D. G.: Tetrahedron Lett. 2006, 47, 1923; b) Bahramian B., Mirkhani V., Moghadam M., Tangestaninejad S.: Catal. Commun. 2006, 7, 289; c) Bahramian B., Mirkhani V., Moghadam M., Tangestaninejad S.: Appl. Catal. A General 2006, 301, 169; d) Bahramian B., Mirkhani V., Moghadam M., Tangestaninejad S.: J. Mol. Catal. A Chemical 2006, 244, 139; e) Tornaritis M. J., Coutsolelos A. G.: Polymer 1992, 33, 1771.

16. Sheldon R. A.: "Aspects of Homogeneous Catalysis", Dordrecht 1981, Vol 4., p. 3.

17. Sheldon R. A.: Recl. Trav. Chim. Pays-Bas 1973, 92, 253.

18. Sharpless K. B., Verhoeven T. R.: Aldrichim Acta 1979, 12, 63.

19. Sheldon R. A.: "The Chemistry of Peroxides", Wiley, New York 1983, p. 161.

20. Gregòrio J. R., Gerbase A. E., Mendes A. N. F., Mortico P. D., Rigs A.: React. Funct. Polym. 2005, 64, 83.

21. a) Alavi Nikje M. M., Rafiee A., Haghshenas M.: Design Mon. Polym. 2006, 9, 293; b) Rajabi F. H., Alavi Nikje M. M., Vasheghani Frahani B., Sabouri N.: Design. Mon. Polym. 2006, 9, 383; c) Alavi Nikje M. M., Motahari S., Haghshenas M., Khenar Sanami R.: J. Macromol. Sci. A Pure Appl. Chem. 2006, 43, 1205; d) Alavi Nikje M. M., Bigdeli M. A.: Phosphorus, Sulfur Silicon 2004, 179, 1445; e) Alavi Nikje M. M., Bigdeli M. A., Heravi M. M.: Phosphorus, Sulfur Silicon 2002, 177, 15; f) Bigdeli M. A., Alavi Nikje M. M., Heravi M. M.: Phosphorus, Sulfur Silicon 2002, 177, 2309.

22. Kennedy R. J., Stock A. M.: J. Org. Chem. 1960, 25, 1901.

23. Besemer A. C., van Bekkum H., Bragd P. L.: Carbohydr. Polym. 2002, 49, 397.

24. Brown Ripin D. H., Cai W., Brenek S. J.: Tetrahedron Lett. 2000, 41, 5817.

25. Curci R., Fiorentino M., Troisi L., Edwards J. O., Pater R. H.: J. Org. Chem. 1980, 45, 4758.

26. Gallopo A. R., Edwards J. O.: J. Org. Chem. 1981, 46, 1684.

27. Cicala G., Curci R., Fiorentino M., Laricchiuta O.: J. Org. Chem. 1982, 47, 2670.

28. Jeyaraman R., Murray R. W.: J. Am. Chem. Soc. 1984, 106, 2462.

29. Gemmer R. V., Golub M. A.: J. Polym. Sci. 1978, 16, 2985.

Google Scholar

Altmetric indicators

Citing articles via

Statistics

Total abstract views : 0

PDF Downloads : 0