New chromium complexes for ethylene oligomerization: Extended use of tridentate ligands in metal-catalyzed olefin polymerization

Macromolecules

Volumn 37, Issue 12, 2004, Pages 4375-4386

  Small, Brooke L ^a   Carney, Michael J ^b   Holman, Danah M ^b   O'Rourke, Colleen E ^b   Halfen, Jason A ^b  

^a CHEVRON PHILLIPS CHEMICAL COMPANY LP   (United States)

^b UNIVERSITY OF WISCONSIN EAU CLAIRE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMONOMERS; LIGANDS; OLIGOMERIZATION;

ACTIVATION ENERGY; CATALYSIS; CHEMICAL BONDS; CHROMIUM COMPOUNDS; KETONES; OXIDATION; POLYETHYLENES; POLYMERIZATION; POLYPROPYLENES; SUSPENSIONS (FLUIDS);

OLEFINS;

EID: 3042565835     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma035554b     Document Type: Article

References (65)

1. (a) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. Engl. 1999, 38, 428 and references therein.
2. (b) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-316.
3. Supported chromium oxide catalysts: (a) Hogan, J. P. J. Polym. Sci., Polym. Chem. Ed. 1970, 8, 2637-2652. (b) McDaniel, M. P. Adv. Catal. 1985, 33, 47-96. Supported chromocene catalysts: (c) Karol, F. J.; Karapinka, G. L.; Wu, C.; Dow, A. W.; Johnson, R. N.; Carrick, W. L. J. Polym. Sci., Polym. Chem. Ed. 1972, 10, 2621-2637, (d) Karol, F. J.; Brown, G. L.; Davison, J. M. J. Polym. Sci., Polym. Chem. Ed. 1973, 11, 413-424.
4. Supported chromium oxide catalysts: (a) Hogan, J. P. J. Polym. Sci., Polym. Chem. Ed. 1970, 8, 2637-2652. (b) McDaniel, M. P. Adv. Catal. 1985, 33, 47-96. Supported chromocene catalysts: (c) Karol, F. J.; Karapinka, G. L.; Wu, C.; Dow, A. W.; Johnson, R. N.; Carrick, W. L. J. Polym. Sci., Polym. Chem. Ed. 1972, 10, 2621-2637, (d) Karol, F. J.; Brown, G. L.; Davison, J. M. J. Polym. Sci., Polym. Chem. Ed. 1973, 11, 413-424.
5. Supported chromium oxide catalysts: (a) Hogan, J. P. J. Polym. Sci., Polym. Chem. Ed. 1970, 8, 2637-2652. (b) McDaniel, M. P. Adv. Catal. 1985, 33, 47-96. Supported chromocene catalysts: (c) Karol, F. J.; Karapinka, G. L.; Wu, C.; Dow, A. W.; Johnson, R. N.; Carrick, W. L. J. Polym. Sci., Polym. Chem. Ed. 1972, 10, 2621-2637, (d) Karol, F. J.; Brown, G. L.; Davison, J. M. J. Polym. Sci., Polym. Chem. Ed. 1973, 11, 413-424.
6. Supported chromium oxide catalysts: (a) Hogan, J. P. J. Polym. Sci., Polym. Chem. Ed. 1970, 8, 2637-2652. (b) McDaniel, M. P. Adv. Catal. 1985, 33, 47-96. Supported chromocene catalysts: (c) Karol, F. J.; Karapinka, G. L.; Wu, C.; Dow, A. W.; Johnson, R. N.; Carrick, W. L. J. Polym. Sci., Polym. Chem. Ed. 1972, 10, 2621-2637, (d) Karol, F. J.; Brown, G. L.; Davison, J. M. J. Polym. Sci., Polym. Chem. Ed. 1973, 11, 413-424.
7. In addition to the examples of chromium polymerization catalysts shown in Figure 1 in this report, the growing number of chromium systems that are selective for producing 1-hexene must also be noted. Although such a discussion is beyond the scope of this work, a few noteworthy references are hereby included: (a) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Morgan, D.; Dixon, J. T.; Bollmann, A.; Maumela, H.; Hess, F.; Englert, U. J. Am. Chem. Soc. 2003, 125, 5272. (b) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Hu, C.; Englert, U.; Dixon, J. T.; Grove, C. Chem. Commun. 2003, 334. (c) Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858. (d) Reagan, W. K.; Pettijohn, T. M.; Freeman, J. W. (Phillips Petroleum) U.S. Patent 5523507, 1996. (e) Wu, F.J. (Amoco) U.S. Patent 5811618, 1998. (f) Briggs, J. R. (Union Carbide) U.S. Patent 4668838, 1987.
8. In addition to the examples of chromium polymerization catalysts shown in Figure 1 in this report, the growing number of chromium systems that are selective for producing 1-hexene must also be noted. Although such a discussion is beyond the scope of this work, a few noteworthy references are hereby included: (a) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Morgan, D.; Dixon, J. T.; Bollmann, A.; Maumela, H.; Hess, F.; Englert, U. J. Am. Chem. Soc. 2003, 125, 5272. (b) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Hu, C.; Englert, U.; Dixon, J. T.; Grove, C. Chem. Commun. 2003, 334. (c) Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858. (d) Reagan, W. K.; Pettijohn, T. M.; Freeman, J. W. (Phillips Petroleum) U.S. Patent 5523507, 1996. (e) Wu, F.J. (Amoco) U.S. Patent 5811618, 1998. (f) Briggs, J. R. (Union Carbide) U.S. Patent 4668838, 1987.
9. In addition to the examples of chromium polymerization catalysts shown in Figure 1 in this report, the growing number of chromium systems that are selective for producing 1-hexene must also be noted. Although such a discussion is beyond the scope of this work, a few noteworthy references are hereby included: (a) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Morgan, D.; Dixon, J. T.; Bollmann, A.; Maumela, H.; Hess, F.; Englert, U. J. Am. Chem. Soc. 2003, 125, 5272. (b) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Hu, C.; Englert, U.; Dixon, J. T.; Grove, C. Chem. Commun. 2003, 334. (c) Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858. (d) Reagan, W. K.; Pettijohn, T. M.; Freeman, J. W. (Phillips Petroleum) U.S. Patent 5523507, 1996. (e) Wu, F.J. (Amoco) U.S. Patent 5811618, 1998. (f) Briggs, J. R. (Union Carbide) U.S. Patent 4668838, 1987.
10. In addition to the examples of chromium polymerization catalysts shown in Figure 1 in this report, the growing number of chromium systems that are selective for producing 1-hexene must also be noted. Although such a discussion is beyond the scope of this work, a few noteworthy references are hereby included: (a) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Morgan, D.; Dixon, J. T.; Bollmann, A.; Maumela, H.; Hess, F.; Englert, U. J. Am. Chem. Soc. 2003, 125, 5272. (b) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Hu, C.; Englert, U.; Dixon, J. T.; Grove, C. Chem. Commun. 2003, 334. (c) Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858. (d) Reagan, W. K.; Pettijohn, T. M.; Freeman, J. W. (Phillips Petroleum) U.S. Patent 5523507, 1996. (e) Wu, F.J. (Amoco) U.S. Patent 5811618, 1998. (f) Briggs, J. R. (Union Carbide) U.S. Patent 4668838, 1987.
11. In addition to the examples of chromium polymerization catalysts shown in Figure 1 in this report, the growing number of chromium systems that are selective for producing 1-hexene must also be noted. Although such a discussion is beyond the scope of this work, a few noteworthy references are hereby included: (a) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Morgan, D.; Dixon, J. T.; Bollmann, A.; Maumela, H.; Hess, F.; Englert, U. J. Am. Chem. Soc. 2003, 125, 5272. (b) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Hu, C.; Englert, U.; Dixon, J. T.; Grove, C. Chem. Commun. 2003, 334. (c) Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858. (d) Reagan, W. K.; Pettijohn, T. M.; Freeman, J. W. (Phillips Petroleum) U.S. Patent 5523507, 1996. (e) Wu, F.J. (Amoco) U.S. Patent 5811618, 1998. (f) Briggs, J. R. (Union Carbide) U.S. Patent 4668838, 1987.
12. In addition to the examples of chromium polymerization catalysts shown in Figure 1 in this report, the growing number of chromium systems that are selective for producing 1-hexene must also be noted. Although such a discussion is beyond the scope of this work, a few noteworthy references are hereby included: (a) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Morgan, D.; Dixon, J. T.; Bollmann, A.; Maumela, H.; Hess, F.; Englert, U. J. Am. Chem. Soc. 2003, 125, 5272. (b) McGuinness, D. S.; Wasserscheid, P.; Keim, W.; Hu, C.; Englert, U.; Dixon, J. T.; Grove, C. Chem. Commun. 2003, 334. (c) Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858. (d) Reagan, W. K.; Pettijohn, T. M.; Freeman, J. W. (Phillips Petroleum) U.S. Patent 5523507, 1996. (e) Wu, F.J. (Amoco) U.S. Patent 5811618, 1998. (f) Briggs, J. R. (Union Carbide) U.S. Patent 4668838, 1987.
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43. Syntheses for the Type 2 unsymmetrical ligands, as well as their iron and cobalt transition-metal complexes, can be found in the following references: (a) Bennett, A. M. A. (DuPont) U.S. Patent 5955555, 1999. (b) Small, B. L.; Brookhart, M. Macromolecules 1909, 32, 2120. (c) Gibson, V. C.; Kimberley, B. S.; Solan, G. A. (BP) WO0020427, 2000. (d) Sommazzi, A.; Milani, B.; Proto, A.; Corso, G.; Mestroni, G.; Masi, F. (Enichem) WO0110875, 2001. (e) de Boer, E. J. M.; Deuling, H. H.; van der Heijden, H.; Meijboom, N.; van Oort, A. B. (Shell) W00158874, 2001.
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45. Syntheses for the Type 2 unsymmetrical ligands, as well as their iron and cobalt transition-metal complexes, can be found in the following references: (a) Bennett, A. M. A. (DuPont) U.S. Patent 5955555, 1999. (b) Small, B. L.; Brookhart, M. Macromolecules 1909, 32, 2120. (c) Gibson, V. C.; Kimberley, B. S.; Solan, G. A. (BP) WO0020427, 2000. (d) Sommazzi, A.; Milani, B.; Proto, A.; Corso, G.; Mestroni, G.; Masi, F. (Enichem) WO0110875, 2001. (e) de Boer, E. J. M.; Deuling, H. H.; van der Heijden, H.; Meijboom, N.; van Oort, A. B. (Shell) W00158874, 2001.
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47. Modified methylalumoxane refers to MMAO-3A (Al 7% by wt), an isobutyl-modified MAO supplied by Akzo Nobel.
48. The activity of the 2-tert-butyl complex 5 in entry 5 of Table 3 agrees reasonably well with the activity reported in ref 11a.
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60. Batch studies of the Cr(II) and Cr(III) systems showed similar activities, product distributions, and product compositions when the same ligand was used with either metal source. To further evaluate the similarity of the Cr(II) and Cr(III) systems, a side-by-side comparison was performed using a Multiclave 10x reactor from Autoclave Engineers. This reactor possesses 10 individual 30 mL cells, with each cell having stirring and temperature control capabilities. A 2.0 mg amount of five different Cr(II) and Cr(III) complexes was activated with MMAO (1000:1 Al:Cr) in heptane (15 mL) and exposed to 13.6 bar of ethylene, fed "on demand" for 30 min. In each case, as in the larger batch studies, the products were the same, depending entirely on the ligand rather than the oxidation state of the precatalyst. The only difference observed was that the Cr(III) complexes appeared to activate slightly faster, which was noted by watching the comparative temperature profiles for the Cr(II) and Cr(III) catalysts, respectively.
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