Synthesis of low density poly(ethylene) using nickel iminophosphonamide complexes

Macromolecules

Volumn 40, Issue 9, 2007, Pages 2993-3004

  Stapleton, Russell A ^a   Chai, Jianfang ^a   Nuanthanom, Anuttra ^b   Flisak, Zygmunt ^c,d   Nele, Marcio ^e   Ziegler, Tom ^c   Rinaldi, Peter L ^b   Soares, Joao B P ^f   Collins, Scott ^b  

^a The University of Akron   (United States)

^b UNIVERSITY OF AKRON   (United States)

^c UNIVERSITY OF CALGARY   (Canada)

^d UNIVERSITY OF OPOLE   (Poland)

^e FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^f UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEXES; NICKEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERIZATION; POLYMERIZATION; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

BRANCHING DISTRIBUTION; METHYL BRANCHES; NICKEL IMINOPHOSPHONAMIDE COMPLEXES; PHOSPHORANE;

POLYETHYLENES;

EID: 34248550471     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma062332f     Document Type: Article

References (132)

1. (a) Stadler, F. J.; Piel, C.; Klimke, K.; Kaschta, J.; Parkinson, M.; Wilhelm, M.; Kaminsky, W.; Muenstedt, H. Macromolecules 2006, 39, 1474-1482.
2. (b) Arikan, B.; Kaminsky, W. Des. Monomers Polym. 2005, 8, 589-600.
3. (c) Li, H.; Stern, C. L.; Marks, T. J. Macromolecules 2005, 38, 9015-9027.
4. (d) Bianchini, C.; Frediani, M.; Giambastiani, G.; Kaminsky, W.; Meli, A.; Passaglia, E. Macromol. Rapid Commun. 2005, 26, 1218-1223.
5. (e) Wang, J.; Li, H.; Guo, N.; Li, L.; Stern, C. L.; Marks, T. J. Organometatlics 2004, 23, 5112-5114.
6. (f) Sworen, J. C.; Smith, J. A.; Berg, J. M.; Wagener, K. B. J. Am. Chem. Soc. 2004, 126, 11238-11246.
7. (g) Capacchione, C.; Proto, A.; Okuda, J. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 2815-2822.
8. (h) Sperber, O.; Kaminsky, W. Macromolecules 2003, 36, 9014-9019.
9. (i) Heinicke, J.; Koehler, M.; Peulecke, N.; He, M.; Kindermann, M. K.; Keim, W.; Fink, G. Chem.-Eur. J. 2003, 9, 6093-6107.
10. (j) Kasi, R. M.; Coughlin, E. B. Macromolecules 2003, 36, 6300-6304.
11. (k) Kunrath, F. A.; Mota, F. F.; Casagrande, O. L., Jr.; Mauler, R. S.; de Souza, R. F. Macromol. Chem. Phys. 2002, 203, 2407-2411.
12. (l) Komon, Z. J. A.; Diamond, G. M.; Leclerc, M. K.; Murphy, V.; Okazaki, M.; Bazan, G. C. J. Am. Chem. Soc. 2002, 124, 15280-15285.
13. (m) Li, L.; Metz, M. V.; Li, H.; Chen, M.-C.; Marks, T. J.; Liable-Sands, L.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12725-12741.
14. (n) Schroeder, D. L.; Keim, W.; Zuideveld, M. A.; Mecking, S. Macromolecules 2002, 35, 6071-6073.
15. (o) Galland, G. B.; Quijada, R.; Rojas, R.; Bazan, G.; Komon, Z. J. A. Macromolecules 2002, 35, 339-345.
16. (p) Guan, Z. Chem. - Eur. J. 2002, 8, 3086-3092.
17. (q) Coates, G. W.; Hustad, P. D.; Reinartz, S. Angew. Chem., Int. Ed. 2002, 41, 2236-2257.
18. (r) Beigzadeh, D.; Soares, J. B. P.; Duever, T. A. Macromol. Symp. 2001, 173, 179-194.
19. (s) Komon, Z. J. A.; Bazan, G. C. Macromol. Rapid Commun. 2001, 22, 467-478.
20. (t) Gottfried, A. C.; Brookhart, M. Macromolecules 2001, 34, 1140-1142.
21. (u) Walter, P.; Trinkle, S.; Suhm, J.; Mader, D.; Friedrich, C.; Mulhaupt, R. Macromol Chem. Phys. 2000, 201, 604-612.
22. (v) Hadjichristidis, N.; Xenidou, M.; Iatrou, H.; Pitsikalis, M.; Poulos, Y.; Avgeropoulos, A.; Sioula, S.; Paraskeva, S.; Velis, G.; Lohse, D. J.; Schulz, D. N.; Fetters, L. J.; Wright, P. J.; Mendelson, R. A.; Garcia-Franco, C. A.; Sun, T.; Ruff, C. J. Macromolecules 2000, 33, 2424-2436.
23. (w) Held, A.; Mecking, S. Chem. - Eur. J. 2000, 6, 4623-4629.
24. (x) Simon, L. C.; Mauler, R. S.; De Souza, R. F. J. Plym. Sci., Part A: Polym. Chem. 1999, 37, 4656-4663.
25. (y) Mecking, S. Macromol. Rapid Commun. 1999, 20, 139-143.
26. (a) Malmberg, A.; Kokko, E.; Lehmus, P.; Loefgren, B.; Seppaelae, J. V. Macromolecules 1998, 31, 8448-8454.
27. (b) Harrison, D.; Coulter, I. M.; Wang, S.; Nistala, S.; Kuntz, B. A.; Pigeon, M.; Tian, J.; Collins, S. J. Mol. Catal. A: Chem. 1998, 128, 65-77.
28. (b) Lai, S.-Y.; Wilson, J. R.; Knight, G. W.; Stevens, J. C.; Chum, P.-W. S. PCT Int. Appl. WO 9607680, 1996.
29. (c) Stevens, J. C. Stud. Surf. Sci. Catal. 1994, 89, 277-84.
30. (d) Lai, S.-Y.; Wilson, J. R.; Knight, G. W.; Stevens, J. C. U.S. Patent 5,278,272, 1994.
31. (e) Lai, S.-Y.; Wilson, J. R.; Knight, G. W.; Stevens, J. C. PCT Int. Appl. WO 9308221, 1993.
32. (f) Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S.-Y. Eur. Pat. Appl. EP 416815, 1991.
33. (a) Simon, L. C.; Soares, J. B. P. Ind. Eng. Chem. Res. 2005, 44, 2461-2468.
34. (b) Soares, J. B. P. Macromol Mater. Eng. 2004, 289, 70-87.
35. (c) Arjunan, P.; Dekmezian, A. H.; Markel, E. J.; Weng, W.; Garcia-Franco, C.; Jiang, P.; Soares, J. B. P.; Bonchev, D. PMSE Prepr. 2004, 91, 47-48.
36. (d) Nele, M.; Soares, J. B. P. Macromol. Theory Simul. 2002, 11, 939-943.
37. (e) Simon, L. C.; Soares, J. B. P. Macromol. Theory Simul. 2002, 11, 222-232.
38. (f) Soares, J. B. P. Macromol. Theory Simul. 2002, 11, 184-198.
39. (g) Soares, J. B. P. Chem. Eng. Sci. 2001, 56, 4131-4153.
40. (h) Soares, J. B. P.; Penlidis, A. Metallocene-Based Polyolefins 2000, 2, 237-267.
41. (i) Beigzadeh, D.; Soares, J. B. P.; Duever, T. A.; Hamielec, A. E. Polym. React. Eng. 1999, 7, 195-205.
42. (j) Beigzadeh, D.; Soares, J. B. P.; Hamielec, A. E. J. Appl. Polym. Sci. 1999, 71, 1753-1770.
43. (k) Beigzadeh, D.; Soares, J. B. P.; Hamielec, A. E. Polym. React. Eng. 1997, 5, 141-180.
44. (a) Liu, W.; Brookhart, M. Organometallics 2004, 23, 6099-6107.
45. (b) Leatherman, M. D.; Svejda, S. A.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 3068-3081.
46. (b) Gottfried, A. C.; Brookhart, M. Macromolecules 2003, 36, 3085-3100.
47. (c) Shultz, L. H.; Tempel, D. J.; Brookhart, M. J. Am. Chem. Soc. 2001, 123, 11539-11555.
48. (d) Shultz, L. H.; Brookhart, M. Organometallics 2001, 20, 3975-3982.
49. (e) Gottfried, A. C.; Brookhart, M. Macromolecules 2001, 34, 1140-1143.
50. (e) Tempel, D. J.; Johnson, L. K.: Huff, R. L.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 2000, 122, 6686-6700.
51. (f) Gates, D. P.; Svejda, S. A.; Onate, E.; Killian, C. M.; Johnson, L. K.; White, P. S.; Brookhart, M. Macromolecules 2000, 33, 2320-2334.
52. (g) Svejda, S. A.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 10634-10635.
53. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1995, 119, 7617-7618.
54. (i) Killian, C. M.; Tempel, D. J.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 11664-11665.
55. (j) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414-6415.
56. (a) Plentz-Meneghetti, S.; Kress, J.: Peruch, F.; Lapp, A.; Duval, M.; Muller, R.; Lutz, P. J. Polymer 2005, 46, 8913-8925.
57. (b) Patil, R.; Colby, R. H.; Read, D. J.; Chen, G.; Guan, Z. Macromolecules 2005, 38, 10571-10579.
58. (c) Ye, Z.; Al-Obaidi, F.; Zhu, S. Macromol. Chem. Phys. 2004, 205, 897-906.
59. (d) Guan, Z. J. Polym. Sci., Part A: Polym, Chem. 2003, 41, 3680-3692.
60. (e) Guan, Z.; Cotts, P. M. Polym. Mater. Sci. Eng. 2001, 84, 382-383.
61. (f) Cotts, P. M.; Guan, Z.; McCord, E.; McLain, S. Macromolecules 2000, 33, 6945-6952.
62. (g) Guan, Z.; Cotts, P. M.; McCord, E. F.; McLain, S. J. Science 1999, 283, 2059-2062.
63. Odian, G. Principles of Polymerization, 3rd ed.; John Wiley and Sons, Inc.: New York, 1991; pp 304-306. However see ref 1c.
64. For a recent example, using an unhindered Ni diimine catalyst, see: Zou, H.; Zhu, F. M.; Wu, Q.; Ai, J. Y.; Lin, S. A. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1325-1330.
65. Keim, W.; Appel, R.; Storeck, A.; Kruger, C.; Goddard, R. Angew. Chem., Int. Ed. Engl. 1981, 20, 116-117.
66. (a) Möhring, V. M.; Fink, G. Angew. Chem. 1985, 97, 982-984.
67. (b) Fink, G.; Möhring, V. M. Patent Application EP 01/94456 A2, 1986.
68. (c) Schubbe, R.; Angermund, K.; Fink, G.; Goddard, R. Macromol. Chem. Phys. 1995, 196, 467-478.
69. (a) Yano, A.; Hasegawa, S.; Yamada, S. Kobunshi Ronbunshu 2002, 59, 377-381;
70. cf. Chem. Abstr. 2002, 137, 201636.
71. (b) Yano, A.; Yamada, S.; Yamada, K. U.S. Patent 5,324,799, 1994; Cont.-in-part of U.S. Ser. No. 662, 167, abandoned.
72. (c) Yano, A.; Yamada, S.; Yamada, K. Eur. Pat. Appl. 0446013, 1991.
73. (d) Yano, A.; Naito, Y.; Yamada, K.; Ohtsuru, M. Eur. Pat. Appl. 0381495, 1990.
74. (a) Stapleton, R. A.; Chai, J.; Taylor, N. J.; Collins, S. Organometallics 2006, 25, 2514-2524.
75. (b) Stapleton, R. A.; Nuamthanom, A.; Rinaldi, P. L.; Taylor, N. J.; Collins, S. Polym. Prepr. 2004, 45, 93-94.
76. (a) Soares, J. B. P.; Simon, L. C.; De Souza, R. F. Polym. Reaction Eng. 2001, 9, 199-223.
77. (b) Simon, L. C.; Williams, C. P.; Soares, J. B. P.; de Souza, R. F. Chem. Eng. Sci. 2001, 56, 4181-4190.
78. (c) Simon, L. C.; Soares, J. B. P.; De Souza, R. F. AIChE J. 2000, 46, 1234-1240.
79. (a) Michalak, A.; Ziegler, T. Organometallics 2003, 22, 2069-2079.
80. (b) Michalak, A.; Ziegler, T. Macromolecules 2003, 36, 928-933.
81. (c) Michalak, A.; Ziegler, T. J. Am. Chem. Soc. 2002, 124, 7519-7528.
82. (d) Michalak, A.; Ziegler, T. J. Am. Chem. Soc. 2001, 123, 12266-12278.
83. (e) Michalak, A.; Ziegler, T. Organometallics 2000, 19, 1850-1858.
84. (f) Woo, T. K.; Bloechl, P. E.; Ziegler, T. J. Phys. Chem. A 2000, 104, 121-129.
85. (g) Michalak, A.; Ziegler, T. Organometallics 1999, 18, 3998-4004.
86. (h) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1995, 119, 6177-6186.
87. (i) Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1995, 119, 1094-1100.
88. (a) Jolly, P. W. in Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E., Eds.; Pergamon: Oxford, U.K., 1982; Vol. 6, pp 145-182.
89. (b) Henc, B.; Jolly, P. W.; Salz, R.; Stobbe, S.; Wilke, G.; Benn, R.; Mynott, R.; Seevogel, K.; Goddard, R.; Krueger, C. J. Organomet. Chem. 1980, 191, 449-475.
90. (c) Jolly, P. W.; Wilke, G. The Organic Chemistry of Nickel; Academic: New York, 1974; Vol. 1.
91. (d) Wilke, G.; Bogdanovic, B.; Hardt, P.; Heimbach, P.; Keim, W.; Kroner, M.; Oberkirch, W.; Tanaka, K.; Walter, D. Angew. Chem., Int. Ed. Engl. 1966, 5, 151-164.
92. (e) Walter, D.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1966, 5, 897-898.
93. (f) Wilke, G.; Bogdanovic, B. Angew. Chem. 1961, 73, 756.
94. Boennemann, H.; Bogdanovic, B.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1965, 6, 804.
95. (a) Piel, C.; Stadler, F. J.; Kaschta, J.; Rulhoff, S.; Muenstedt, H.; Kaminsky, W. Macromol. Chem. Phys. 2006, 207, 26-38.
96. (b) Wang, W.-J.; Kharchenko, S.; Migler, K.; Zhu, S. Polymer 2004, 45, 6495-6505.
97. (b) Yu, Y.; DesLauriers, P. J.; Rohlfing, D. C. Polymer 2005, 46, 5165-5182.
98. (c) Cotts, P. M. Polym. Prepr. 2002, 43, 297-298.
99. (d) Cotts, P. M.; Guan, Z.; McCord, E.; McLain, S. Macromolecules 2000, 33, 6945-6952.
100. 1-2 Therefore it can be concluded that the higher MW PE sample prepared using the Keim catalyst must have higher levels of
101. LCB than the "linear" PE standard used.
102. (a) Guangxue Xu, G.; Cheng, G. Macromolecules 2001, 34, 2040-2047.
103. (b) McLain, S. J.; McCord, E. F.; Johnson, L. K.; Ittel, S. D.; Nelwson, L. T. J.; Arthur, S. D.; Halfhill, M. J.; Teasley, M. F. Polym. Prepr. 1997, 38, 772-773.
104. Collins, S.; Ziegler, T. Manuscript in preparation.
105. Flisak, Z.; Ziegler, T. Macromolecules 2005, 38, 9865-72.
106. Press, W. H.; Teukolsky, S. A.; Vetterling, W. T.; Flannery, B. P. Numerical recipes in Fortran 77. The Art of Scientific Computing, 2nd ed.; Press Syndicate of the University of Cambridge: Cambridge, U.K., New York, and Melbourne, Australia, 1992.
107. 4] (as opposed to P) is used as the variable, the simulations predict extensive (but unproductive) chain-walking compared to insertion. The use of eq 6 to calculate reaction probabilities under such conditions is not valid; Curtin Hammett conditions would apply to the various Ni-R present. In this case, it is the relative stability of the π complexes and the insertion barriers that will dictate the branching distribution.
108. Chen, Z.; Gospodinov, I.; Escobedo, F. A. Macromol. Theory Simul. 2002, 11, 1022-1344.
109. (a) Reinking, M. K.; Orf, G.; Mcfaddin, D. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2889-2898.
110. (b) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025-32.
111. -1) but with a very unfavorable pre-equilibrium in forming the relevant agostic alkyl from the most stable β-agostic structure.
112. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
113. Hidai, M.; Kashiwagi, T.; Ikeuchi, T.; Uchida, Y. J. Organomet. Chem. 1971, 30, 279-282.
114. Krysan, D. J.; Mackenzie, P. B. J. Org. Chem. 1990, 55, 4229-4230.
115. Birkofer, L.; Wegner, P.; Merritt, R. F.; Emmons, W. D. Org. Synth. 1970, 50, 107-110.
116. (a) Niecke, E.; Oberdorfer, R.; Bajorat, V. Synth. Met. Organomet. Inorg. Chem. 1996, 3, 36-37.
117. (b) Niecke, E.; Oberdorfer, R.; Bajorat, V. Synth. Met. Organomet. Inorg. Chem. 1996, 3, 84-85.
118. (a) Romanenko, V. D.; Shul'gin, V. F.; Skopenko, V. V.; Markovskii, L. N. Zh. Obshch. Khim. 1985, 55, 538-43.
119. (b) Romanenko, V. D.; Shul'gin, V. F.; Brusilovets, A. I.; Skopenko, V. V.; Markovskii, L. N. Zh. Obshch. Khim. 1983, 53, 1428-9.
120. (a) Becke, A. Phys. Rev. A 1988, 38, 3098.
121. (b) Perdew, J. P. Phys. Rev. B 1986, 34, 7406.
122. (c) Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
123. (a) Te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Fonseca Guerra, C.; Van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T J. Comput. Chem. 2001, 22, 931, and references therein.
124. (b) Te, Velde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84.
125. (c) Boerrigter, P. M.; te Velde, G.; Baerends, E. J. Int. J. Quantum Chem. 1988, 33, 87.
126. (d) Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322.
127. (e) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
128. Fonesca Geurra, C.; Visser, O.; Snijders, J. G.; te Velde, G.; Baerends, E. J. In Methods and Techniques in Computational Chemistry METACC-95; dementi, E., Corongiu, G., Eds.; STEP: Cagliari, Italy, 1995.
129. Snijders, J. G.; Baerends, E. J.; Vernoijs, P. At. Nucl. Data Tables 1982, 26, 483.
130. Woo, T. K.; Cavallo, L.; Ziegler, T. Theor. Chem. Acc. 1998, 100, 307.
131. Clark, M.; Cramer, R. D., III; van Opdenbosch, N. J. Comput. Chem. 1989, 10, 982.
132. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.