Oxidative Polymerization of 2,6-Dimethylphenol to Form Poly(2,6-dimethyl-1,4-phenyleneoxide) in Water

Angewandte Chemie - International Edition

Volumn 43, Issue 6, 2004, Pages 730-733

  Saito, Kei ^a   Tago, Takahiro ^a   Masuyama, Toru ^a   Nishide, Hiroyuki ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

Green chemistry; Oxidation; Polymerization; Radicals; Water chemistry

Indexed keywords

COPPER COMPOUNDS; FILTRATION; OXIDATION; POLYMERIZATION; POLYMERS; SOLUTIONS; WATER;

OXIDATIVE POLYMERIZATION;

PHENOLS;

2,6 XYLENOL; BENZENE DERIVATIVE; OXIDIZING AGENT; PHENOL DERIVATIVE; POLY(2,6 DIMETHYL 1,4 PHENYLENE OXIDE); POLYMER; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; FILTRATION; OXIDATION; POLYMERIZATION; POWDER;

EID: 1042291283     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352764     Document Type: Article

References (34)

1. a) C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997;
2. b) P. Tundo, P. Anastas, D. S. Black, J. Breen, T. Collins, S. Memoli, J. Miyamoto, M. Polyakoff, W. Tumas, Pure Appl. Chem. 2000, 72, 1207-1228;
3. c) J. M. Desimone, Science 2002, 297, 799-803.
4. a) A. S. Hay, H. S. Blanchard, G. F. Endres, J. W. Eustance, J. Am. Chem. Soc. 1959, 81, 6335-6336;
5. b) A. S. Hay, J. Polym. Sci. 1962, 58, 581-591;
6. c) A. S. Hay, Macromolecules 1969, 2, 107-108;
7. d) A. S. Hay, J. Polym. Sci. Part A 1998, 36, 505-517.
8. a) E. Tsuchida, M. Kaneko, H. Nishide, Makromol. Chem. 1972, 151, 221-234;
9. b) E. Tsuchida, H. Nishide, Makromol. Chem. 1975, 176, 1349-1358;
10. c) E. Tsuchida, H. Nishide, Adv. Polym. Sci. 1977, 24, 1-87;
11. d) K. Oyaizu, Y. Kumaki, K. Saito, E. Tuschida, Macromolecules 2000, 33, 5766-5769.
12. D. Aycock, V. Abolins, D. M. White, Encyclopedia of Polymer Science and Engineering, Vol. 13, 2nd ed., Wiley, New York, 1986, pp. 1-30.
13. a) W. Koch, W. Risse, W. Heitz, Makromol. Chem. Suppl. 1985, 12, 105-123;
14. b) E. Tuschida, F. Suzuki, E. Shouji, K. Yamamoto, Macromolecules 1994, 27, 1057-1060;
15. c) P. J. Baesjou, W. L. Driessen, G. Challa, J. Reedijk, J. Am. Chem. Soc. 1997, 119, 12590-12594;
16. d) H. A. M. van Aert, M. H. P. van Gendersen, G. J. M. L. van Steenpaal, L. Nelissen, E. W. Meijer, Macromolecules 1997, 30, 6056-6066;
17. e) H. Higashimura, K. Fujisawa, Y. Moro-oka, M. Kubota, A. Shiga, A. Terahara, H. Uyama, S. Kobayashi, J. Am. Chem. Soc. 1998, 120, 8529-8530.
18. a) G. D. Staffin, C. C. Price, J. Am. Chem. Soc. 1960, 82, 3632-3634;
19. b) C. C. Price, N. S. Chu, J. Polym. Sci. 1962, 61, 135-141.
20. a) H. Komoto, K. Ohmura, Makromol. Chem. 1973, 166, 57-68;
21. b) V. Percec, T. D. Shaffer, J. Polym. Sci. Polym. Lett. Ed. 1986, 24, 439-446;
22. c) K. Mühlbach, V. Percec, J. Polym. Sci. Polym. Chem. Ed. 1987, 25, 2605-2627;
23. d) R. Ikeda, J. Sugihara, H. Uyama, S. Kobayashi, Macromolecules 1996, 29, 8702-8705;
24. e) H. Yonami, H. Uyama, S. Kobayashi, J. Macromol. Sci., Pure Appl. Chem. 1999, 36, 719-730;
25. f) Y. M. Chung, W. S. Ahn, P. K. Lim, J. Mol. Catal. A 1999, 148, 117-126.
26. C. G. Haynes, A. H. Turner, W. A. Waters, J. Chem. Soc. 1956, 2823-2831.
27. -1.
28. g were for the polymer described in Table 1, entry 6.
29. F. E. Karasz, H. E. Bair, J. M. O'Reilly, J. Polym. Sci. Part A-2 1968, 6, 1141-1148.
30. The formation of DPQ in water was hardly affected by temperature, in contrast to the case in organic solvents. G. F. Endres, A. S. Hay, J. W. Eustance, J. Org. Chem. 1963, 28, 1300-1305.
31. max = 421 nm. The formation of DPQ was suppressed dramatically. By comparison, conventional polymerization methods (e.g., catalyzed by a copper-amine complex in toluene at room temperature) give DPQ in 3-5% yield. a) F. J. Viersen, G. Challa, Recl. Trav. Chim. Pays-Bas 1990, 109, 97-102;
32. b) F. J. Viersen, J. Renkema, G. Challa, J. Reedijk, J. Polym. Sci. Part A 1992, 30, 901-911.
33. Normalized plots of magnetization versus the ratio of the magnetic field and effective temperature for the powder product obeyed a theoretical curve corresponding to the S = 1/2 Brillouin function (S = spin quantum number). This showed no contribution of the contaminants such as the potassium ferricyanide oxidant to the measurement of the radical concentration.
34. The half-life of the phenoxyl radical was determined to be approximately 4 min by ESR spectroscopic analysis of the powder sample.