One-pot screening of titanium catalysts for ethylene polymerization

Organometallics

Volumn 27, Issue 18, 2008, Pages 4618-4624

  Yang, Xiao Hong ^c   Sun, Xiu Li ^c   Han, Fu Bin ^c   Liu, Bo ^c   Tang, Yong ^a   Wang, Zheng ^c   Gao, Ming Li ^c   Xie, Zuowei ^b   Bu, Shi Zhen ^c  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ABS RESINS; CATALYSTS; CHEMICAL REACTIONS; ETHYLENE; MONOMERS; NITROGEN COMPOUNDS; OLEFINS; POLYMERIZATION; POLYMERS; TITANIUM;

ENAMINE; ETHYLENE POLYMERIZATION; OLEFIN POLYMERIZATIONS; ONE-POT; ONE-STEP METHODS; SALICYL ALDEHYDE; TITANIUM CATALYSTS;

CATALYSIS;

EID: 53849128869     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800302f     Document Type: Article

References (55)

1. Boor, J. Ziegler-Natta Catalysts and Polymerizations; Academic Press: New York, 1979; pp 587-598.
2. For recent reviews on the catalysts of olefin polymerization, see:(a) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428.
3. (b) Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169.
4. (c) Mecking, S. Angew. Chem., Int. Ed. 2001, 40, 534.
5. (d) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283.
6. (e) Yoshida, Y.; Matsui, S.; Fujita, T. J. Organomet. Chem. 2005, 690, 4382.
7. (f) Furuyama, R.; Saito, J.; Ishii, S.; Makio, H.; Mitani, M.; Tanaka, H.; Fujita, T. J. Organomet. Chem. 2005, 690, 4398.
8. (g) Bianchini, C.; Giambastiani, G.; Rios, I. G.; Mantovani, G.; Meli, A.; Segaria, A. M. Coord. Chem. Rev. 2006, 250, 1391.
9. (h) Gibson, V. C.; Redshaw, C.; Solan, G. A. Chem. Rev. 2007, 107, 1745.
10. For sulfur-containing catalysts, see:(a) Miyatake, T.; Mizunuma, K.; Seki, Y.; Kakugo, M. Makromol. Chem, Rapid Commun. 1989, 10, 349.
11. (b) Miyatake, T.; Mizunuma, K.; Kakugo, M. Makromol. Symp. 1993, 66, 203.
12. (c) van der Linden, A.; Schaverien, C. J.; Meijboom, N.; Ganter, C.; Orpen, A. G. J. Am. Chem Soc. 1995, 117, 3008.
13. (d) Graf, D. D.; Schrock, R. R.; Davis, W. M.; Stumpf, R. Organometallics 1999, 18, 843.
14. (e) Gibson, V. C.; Nicholas, C. P.; Long, J.; Martin, J.; Solan, G. A.; Stichbury, J. C. J. Organomet. Chem 1999, 590, 115.
15. (f) Janas, Z.; Jerzykiewicz, L. B.; Richards, R. L.; Sobota, P. Chem. Commun. 1999, 1015.
16. (g) Takaoki, K.; Miyatake, T. Macromol. Symp. 2000, 157, 251.
17. (h) Janas, Z.; Jerzykiewicz, L. B.; Prybylak, K.; Sobta, P.; Szczegot, K. Eur. J. Inorg. Chem. 2004, 1639.
18. For [O-NX] complexes as catalysts for olefin polymerization, see: (a) Tshuva, E. Y.; Goldberg, I.; Kol, M. J. Am Chem. Soc. 2000, 122, 10706.
19. (b) Tshuva, E. Y.; Goldberg, I.; Kol, M.; Weitman, H.; Goldschmidt, Z. Chem. Commun. 2000, 379.
20. (c) Tshuva, E. Y.; Goldberg, I.; Kol, M.; Goldschmidt, Z. Organometallics 2001, 20, 3017.
21. (d) Tshuva, E. Y.; Goldberg, I.; Kol, M.; Goldschmidt, Z. Chem Commun. 2001, 2120.
22. (e) Tshuva, E. Y.; Groysman, S.; Goldberg, I.; Kol, M. Organometallics 2002, 21, 662.
23. (f) Groysman, S.; Goldberg, I.; Kol, M.; Genizi, E.; Goldschmidt, Z. Inorg. Chim. Acta 2003, 345, 137.
24. (g) Segal, S.; Goldberg, I.; Kol, M. Organometallics 2005, 24, 200.
25. (h) Yeori, A.; Goldberg, I.; Shuster, M.; Kol, M. J. Am Chem. Soc. 2006, 128, 13062.
26. (i) Gendler, S.; Groysman, S.; Goldschmidt, Z.; Shuster, M.; Kol, M. J. Polym. Sci. Part A: Polym Chem 2006, 44, 1136.
27. For β-enaminoketonato metal complexes as olefin polymerization catalysts, see: (a) Guan, Z.; Marshall, W. J. Organometallics 2002, 21, 3580.
28. (b) Li, X.; Dai, K.; Ye, W.-P.; Pan, L.; Li, Y. Organometallics 2004, 23, 1223.
29. (c) Tang, L.; Hu, T.; Bo, Y.; Li, Y.; Hu, N. J. Organomet. Chem. 2005, 690, 3125.
30. (d) Tang, L.; Duan, Y.; Pan, L.; Li, Y. J. Polym Sci. Part A: Polym Chem. 2005, 43, 1681.
31. (e) Zhang, L.; Brookhart, M.; White, P. S. Organometallics 2006, 25, 1868.
32. For leading references on the development of screening strategies for the discovery of olefin polymerization catalyst, see:(a) Tian, J.; Coates, G. W. Angew. Chem., Int. Ed. 2000, 39, 3626.
33. (b) Jones, D. J.; Gibson, V. C.; Green, S. M.; Maddox, P. J. Chem. Commun. 2002, 1038.
34. (c) Murphy, V.; Volpe, A. F.; Weinberg, W. H. Curr. Opin. Chem. Biol. 2003, 7, 427.
35. (d) Boussie, T. R.; Diamond, G. M.; Goh, C.; Hall, K. A.; LaPointe, A. M.; Leclerc, M.; Lund, C.; Murphy, V.; Shoemaker, J. A. W.; Tracht, U.; Turner, H.; Zhang, J.; Uno, T.; Rosen, R. K.; Stevens, J. C. J. Am. Chem. Soc. 2003, 125, 4306.
36. (e) Mason, A. F.; Coates, G. W. J. Am. Chem. Soc. 2004, 126, 10798.
37. (f) Adams, N.; Arts, H. J.; Bolton, P. D.; Cowell, D.; Dubberley, S. R.; Friederichs, N.; Grant, C. M.; Kranenburg, M.; Sealey, A. J.; Wang, B.; Wilson, P. J.; Cowley, A. R.; Mountford, P.; Schroder, M. Chem. Commun. 2004, 434.
38. (g) Jones, D. J.; Gibson, V. C.; Green, S. M.; Maddox, P. J.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 2005, 127, 11037.
39. For details, please see the Supporting Information.
40. (a) Huang, B. T., Chen, W. Metallocene Catalysts and Their Olefin Polymers; Chemical Engineering Press: Beijing, 2000.
41. (b) Ready, T. E.; Gurge, R.; Chien, J. C. W.; Rausch, M. D. Organometallics 1998, 17, 5236.
42. (c) Hlatky, G. G. Chem. Rev. 2000, 100, 1347.
43. For leading references on phenoxyimine-derived catalysts, see: (a) Matsui, S.; Tohi, Y.; Mitani, M.; Saito, J.; Makio, H.; Tanaka, H.; Nitabaru, M.; Nakano, T.; Fujita, T. Chem. Lett. 1999, 1065.
44. (b) Matsui, S.; Mitani, M.; Saito, J.; Tohi, Y.; Makio, H.; Tanaka, H.; Fujita, T. Chem. Lett. 1999, 1263.
45. (c) Yoshida, Y.; Matsui, S.; Takagi, Y.; Mitani, M.; Nitabaru, M.; Nakano, T.; Tanaka, H.; Fujita, T. Chem. Lett. 2000, 1270.
46. (d) Younkin, T. R.; Connor, E. F.; Henderson, J. I.; Friedrich, S. K.; Grubbs, R. H.; Bansleben, D. A. Science 2000, 287, 460.
47. (e) Gibson, V. C.; Mastroianni, S.; Newton, C.; Redshaw, C.; Solan, G. A.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Dalton Trans., 2000, 1969.
48. (f) Bott, R. K. J. H.; David, L.; Schormann, M.; Bochmann, M.; Lancaster, S. J. J. Organomet. Chem 2003, 665, 135.
49. (g) Zhang, H.; Katao, S.; Nomura, K.; Huang, J. Organometallics 2007, 26, 5967.
50. 3 as olefin catalysts, see:(a) Hu, W.; Sun, X.; Wang, C.; Gao, Y.; Tang, Y.; Shi, L.; Xia, W.; Sun, J.; Dai, H.; Li, X.; Yao, X.; Wang, X. Organometallics 2004, 23, 1684.
51. (b) Wang, C.; Sun, X.; Guo, Y.; Gao, Y.; Liu, B.; Ma, Z.; Xia, W.; Shi, L.; Tang, Y. Macromol. Rapid Commun. 2005, 26, 1609.
52. (c) Wang, C.; Ma, Z.; Sun, X.; Gao, Y.; Guo, Y.; Tang, Y.; Shi, L. Organometallics 2006, 25, 3259.
53. (d) Gao, M.; Wang, C.; Sun, X.; Qian, Cc; Ma, Z.; Bu, S.; Tang, Y.; Xie, Z. Macromol. Rapid Commun. 2007, 28, 1511.
54. In the polymerization conditions, MMAO can promote the formation of complex since MAO as well as alkylaluminium in MMAO is known as a base that is able to abstract the active hydrogen of alcohol; see: Marques, M. M.; Correia, S. G.; Ascenso, J. R.; Ribeiro, A. F. G.; GOMES, P. T.; Dias, A. R.; Foster, P.; Rausch, M. D.; Chien, J. C. W J. Polym Sci. Part A: Polym. Chem 1999, 37, 2457.
55. For details, please see the Supporting Information. CCDC 667769 (11) contains the supplementary crystallography data. This data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk /data request/cif.