journal article·2009-01

In situ Generated Dimethyl Dioxirane (DMD)/Copper(II) (2,2'-diamino-4, 4'-bithiazole) Complex as a New Oxidant for Polybutadiene and Hydroxyl Terminated Polybutadiene (HTPB) Epoxidation

Mir Mohammad Alavi Nikje, Majid Soleimani, Zahra Mozaffari

Journal of Elastomers & Plastics· Volume 41· Issue 1
Publisher page

Abstract

Epoxidation of polybutadiene and HTPB are performed by using in situ generated dimethyl dioxirane (DMD) as oxidant and copper(II) (2,2 ' diamino-4,4 ' -bithiazole) (DABTZ) complex as the catalyst at 25°C. For comparison of double bond reactivities, epoxidation reactions are performed on three different types of polybutadiene and HTPBs containing various cis, trans, vinyl microstructures. The tendency of different C=C geometries towards epoxidation are evaluated in detail at various reaction times as well as catalyst concentration and the products are characterized by using 1 H NMR, 13 C NMR, and FT-IR spectroscopies. Spectra analysis did not show the formation of over-oxidation products even at long reaction times. Another important observation is the preservation of hydroxyl end groups in HTPB chain.
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Research context

OpenAlex topics: Carbon dioxide utilization in catalysis · Inorganic and Organometallic Chemistry · Organic Chemistry Cycloaddition Reactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran,

Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran

References (67)

Show source-provided references
1. 10.1016/j.molcata.2005.01.04610.1016/j.molcata.2005.01.046 ↗
2. 10.1021/ja00163a05210.1021/ja00163a052 ↗
3. 10.1016/S1381-1169(96)00432-310.1016/S1381-1169(96)00432-3 ↗
4. 10.1021/ja00201a02610.1021/ja00201a026 ↗
5. 10.1021/ja00315a07110.1021/ja00315a071 ↗
6. 10.1021/ja00276a05110.1021/ja00276a051 ↗
7. 10.1021/ja00168a06310.1021/ja00168a063 ↗
8. 10.1021/ja00019a01610.1021/ja00019a016 ↗
9. Sakthivel, A. · Commun. · 2006 · 7 · 302
10. 10.1021/ja00356a01510.1021/ja00356a015 ↗
11. 10.1016/j.molcata.2004.02.02610.1016/j.molcata.2004.02.026 ↗
12. Agarwal, D.D., Bhatnagar, R.P., Jain, R. and Shrivastava, S. (1990). Oxidation of Alkenes Using the RuCl3/PhIO System , Perkin Trans II, 989-992.
13. Zolezzi, S. · Diphenylethylenediamine and Nitro, Bromo and Methoxy Salicylaldehyde, Polyhedron · 1999 · 18 · 897
14. 10.1016/S0277-5387(01)00960-310.1016/S0277-5387(01)00960-3 ↗
15. 10.1016/j.jcat.2006.04.02810.1016/j.jcat.2006.04.028 ↗
16. 10.1016/S1381-1169(96)00263-410.1016/S1381-1169(96)00263-4 ↗
17. 10.1002/jpp.37910.1002/jpp.379 ↗
18. Che, C.M. · Chem. Rev. · 2003 · 242 · 97
19. Tanasa, T. · Chem. · 1993 · 32 · 3995
20. 10.1006/jcat.1997.182010.1006/jcat.1997.1820 ↗
21. 10.1016/S1381-1169(01)00487-310.1016/S1381-1169(01)00487-3 ↗
22. 10.1016/S0926-860X(99)00423-810.1016/S0926-860X(99)00423-8 ↗
23. 10.1016/S1381-1169(97)00074-510.1016/S1381-1169(97)00074-5 ↗
24. Cativiela, C. , Figueras, F.J., Fraile , M., Garcia, J.I. and Mayoral, J.A. (1995). Hydrotalcite-Promoted Epoxidation of Electron-Deficient Alkenes with Hydrogen Peroxide, Tetrahedron Lett., 36: 4125-4128.10.1016/0040-4039(95)00675-3 ↗
25. 10.1016/S0957-4166(98)00137-210.1016/S0957-4166(98)00137-2 ↗
26. 10.1016/1381-1169(95)00224-310.1016/1381-1169(95)00224-3 ↗
27. 10.1016/S0040-4039(00)91844-610.1016/S0040-4039(00)91844-6 ↗
28. Katsuki, T. · Chem. Rev. · 1995 · 140 · 189
29. 10.1039/a806483k10.1039/a806483k ↗
30. Kim, G.J. · Lett. · 1999 · 63 · 83
31. 10.1021/ja00065a06710.1021/ja00065a067 ↗
32. Klement, P. · Electrochemical and Structural Study, Polyhedron · 1999 · 18 · 3617
33. 10.1016/S1381-1169(00)00432-510.1016/S1381-1169(00)00432-5 ↗
34. Belokon, Y.N. · Asymmetric Synthesis of α-Methyl α-Amino Acids, Tetrahedron · 2004 · 60 · 3191
35. 10.1016/S1381-1169(02)00514-910.1016/S1381-1169(02)00514-9 ↗
36. 10.1021/ja994125j10.1021/ja994125j ↗
37. Santra, A.K. · Lett. · 2000 · 67 · 87
38. 10.1016/S1381-5148(98)00065-010.1016/S1381-5148(98)00065-0 ↗
39. 10.1016/S1385-8947(02)00127-410.1016/S1385-8947(02)00127-4 ↗
40. 10.1021/jo01081a01910.1021/jo01081a019 ↗
41. 10.1016/S0144-8617(01)00344-710.1016/S0144-8617(01)00344-7 ↗
42. 10.1016/S0040-4039(00)00978-310.1016/S0040-4039(00)00978-3 ↗
43. 10.1021/jo01311a04010.1021/jo01311a040 ↗
44. 10.1021/jo00321a03210.1021/jo00321a032 ↗
45. 10.1021/jo00134a03310.1021/jo00134a033 ↗
46. 10.1021/ja00320a05510.1021/ja00320a055 ↗
47. 10.1016/0143-7496(94)90021-310.1016/0143-7496(94)90021-3 ↗
48. 10.1016/S0141-3910(98)00179-710.1016/S0141-3910(98)00179-7 ↗
49. 10.1002/macp.1994.02195121910.1002/macp.1994.021951219 ↗
50. 10.1016/j.molcata.2006.02.04110.1016/j.molcata.2006.02.041 ↗
51. 10.1016/S0920-5861(99)00332-610.1016/S0920-5861(99)00332-6 ↗
52. 10.1016/S0376-7388(02)00180-110.1016/S0376-7388(02)00180-1 ↗
53. 10.1016/S0376-7388(00)00550-010.1016/S0376-7388(00)00550-0 ↗
54. Roy, S. and Gupta, B.R. (1993). ``Epoxidized Rubbers'', In: De, S.K. (ed.), Elastomer Technology Handbook , pp. 635-657, CRC Press, Boca Raton.10.1201/9780138758851-17 ↗
55. 10.1016/0032-3861(80)90217-710.1016/0032-3861(80)90217-7 ↗
56. 10.1002/pol.1990.14028090310.1002/pol.1990.140280903 ↗
57. 10.1016/j.reactfunctpolym.2005.05.00110.1016/j.reactfunctpolym.2005.05.001 ↗
58. Alavi Nikje, M.M. and Mozaffari, Z. (2007). Chemoselective Epoxidation of Hydroxyl-Terminated Polybutadiene (HTPB) Using In-Situ Generated Dimethyl Dioxirane (DMD), Des Monomers Polym., 10: 67-77.10.1163/156855507779763630 ↗
59. 10.1163/15685550778037822110.1163/156855507780378221 ↗
60. 10.1163/15685550677735100910.1163/156855506777351009 ↗
61. 10.1163/15685550677795214710.1163/156855506777952147 ↗
62. Alavi Nikje, M.M. · Sci., Pure Appl. Chem. · 2006 · 43 · 1205
63. 10.1080/1042650049046365510.1080/10426500490463655 ↗
64. 10.1080/1042650021022410.1080/10426500210224 ↗
65. Bigdeli, M.A. , Alavi Nikje, M.M. and Heravi, M.M. (2002). Oxidation of Bisimines to Bisoxaziridines Using Buffered Oxone, Phosphorus Sulfur., 177: 2309-2314.10.1080/10426500214125 ↗
66. 10.1002/zaac.20030003910.1002/zaac.200300039 ↗
67. 10.1002/pol.1978.17016112310.1002/pol.1978.170161123 ↗