Post-Metallocenes in the Industrial Production of Polyolefins
M. Sc. Moritz C. Baier
Department of Chemistry, Chair of Chemical Materials Science, University of Konstanz, Universitätsstrasse 10, 78457 Konstanz (Germany) http://www.chemie.uni-konstanz.de/agmeck/
Search for more papers by this authorDr. Martin A. Zuideveld
Medium and High Throughput Polyolefin Research, SABIC, Science and Technology Center, Geleen, Urmonderbaan 22, P.O. 18, 6160 MD Geleen (Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Stefan Mecking
Department of Chemistry, Chair of Chemical Materials Science, University of Konstanz, Universitätsstrasse 10, 78457 Konstanz (Germany) http://www.chemie.uni-konstanz.de/agmeck/
Department of Chemistry, Chair of Chemical Materials Science, University of Konstanz, Universitätsstrasse 10, 78457 Konstanz (Germany) http://www.chemie.uni-konstanz.de/agmeck/Search for more papers by this authorM. Sc. Moritz C. Baier
Department of Chemistry, Chair of Chemical Materials Science, University of Konstanz, Universitätsstrasse 10, 78457 Konstanz (Germany) http://www.chemie.uni-konstanz.de/agmeck/
Search for more papers by this authorDr. Martin A. Zuideveld
Medium and High Throughput Polyolefin Research, SABIC, Science and Technology Center, Geleen, Urmonderbaan 22, P.O. 18, 6160 MD Geleen (Netherlands)
Search for more papers by this authorCorresponding Author
Prof. Dr. Stefan Mecking
Department of Chemistry, Chair of Chemical Materials Science, University of Konstanz, Universitätsstrasse 10, 78457 Konstanz (Germany) http://www.chemie.uni-konstanz.de/agmeck/
Department of Chemistry, Chair of Chemical Materials Science, University of Konstanz, Universitätsstrasse 10, 78457 Konstanz (Germany) http://www.chemie.uni-konstanz.de/agmeck/Search for more papers by this authorGraphical Abstract
“Post-metallocene” polymerization catalysis research ranges from fundamental mechanistic studies by catalyst design to material properties of polyolefins. A common goal of these studies is the creation of practically useful new materials or processes. A comprehensive overview of post-metallocene polymerization catalysts that have been put into practice is provided. The decisive properties for this success of a given catalyst structure are delineated.
Abstract
Research on “post-metallocene” polymerization catalysis ranges methodologically from fundamental mechanistic studies of polymerization reactions over catalyst design to material properties of the polyolefins prepared. A common goal of these studies is the creation of practically useful new polyolefin materials or polymerization processes. This Review gives a comprehensive overview of post-metallocene polymerization catalysts that have been put into practice. The decisive properties for this success of a given catalyst structure are delineated.
References
- 1W. Kaminsky, K. Külper, H. H. Brintzinger, F. R. W. P. Wild, Angew. Chem. 1985, 97, 507–508; Angew. Chem. Int. Ed. Engl. 1985, 24, 507–508.
- 2H. H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. M. Waymouth, Angew. Chem. 1995, 107, 1255–1283;
10.1002/ange.19951071104 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 1143–1170.
- 3G. J. P. Britovsek, V. C. Gibson, D. F. Wass, Angew. Chem. 1999, 111, 448–468;
10.1002/(SICI)1521-3757(19990215)111:4<448::AID-ANGE448>3.0.CO;2-2 Google ScholarAngew. Chem. Int. Ed. 1999, 38, 428–447.10.1002/(SICI)1521-3773(19990215)38:4<428::AID-ANIE428>3.0.CO;2-3 CAS PubMed Web of Science® Google Scholar
- 4V. C. Gibson, S. K. Spitzmesser, Chem. Rev. 2003, 103, 283–316.
- 5S. D. Ittel, L. K. Johnson, M. Brookhart, Chem. Rev. 2000, 100, 1169–1204.
- 6K. P. Bryliakov, Russ. Chem. Rev. 2007, 76, 253–277.
- 7Polyolefins Planning Service: Executive Report, Global Commercial Analysis 2009; ChemSystems, April 2010.
- 8A. H. Tullo, Chem. Eng. News 2010, 88(42), 10–16.
- 9E. Y.-X. Chen, T. J. Marks, Chem. Rev. 2000, 100, 1391–1434.
- 10F. Rix, (Exxon), WO 0130785, 2001.
- 11R. K. Rosen, D. D. Vanderlende, (Dow), WO 9735893, 1997.
- 12J. F. Walzer, Jr., (Exxon), US 5643847, 1997.
- 13E. M. Carnahan, M. J. Carney, D. R. Neithamer, P. N. Nickias, K.-Y. Shih, L. Spencer, (Dow Chemical Co., W. R. Grace), WO 9719959, 1997.
- 14L. Luo, X. Wu, S. P. Diefenbach, (Albemarle), WO 2008076632, 2008.
- 15Y. Sun, M. V. Metz, C. L. Stern, T. J. Marks, Organometallics 2000, 19, 1625–1627.
- 16N. Millot, S. Soignier, C. C. Santini, A. Baudouin, J.-M. Basset, J. Am. Chem. Soc. 2006, 128, 9361–9370.
- 17N. Popoff, R. M. Gauvin, A. De Mallmann, M. Taoufik, Organometallics 2012, 31, 4763–4768.
- 18J. Klosin, G. R. Roof, E. Y.-X. Chen, K. A. Abboud, Organometallics 2000, 19, 4684–4686.
- 19J. Klosin, (Dow Chemical Co.), WO 2000011006, 2000.
- 20K. P. Bryliakov, E. P. Talsi, M. Bochmann, Organometallics 2004, 23, 149–152.
- 21D. E. Babushkin, H.-H. Brintzinger, J. Am. Chem. Soc. 2002, 124, 12869–12873.
- 22P. D. Bolton, E. Clot, A. R. Cowley, P. Mountford, J. Am. Chem. Soc. 2006, 128, 15005–15018.
- 23S. A. Sangokoya, S. P. Diefenbach, C. Daly, L. S. Simeral, (Albemarle), WO 2007005400, 2007.
- 24L. Luo, S. A. Sangokoya, X. Wu, S. P. Diefenbach, B. Kneale, (Albemarle), WO 2009029857, 2009.
- 25L. Luo, X. Wu, S. P. Diefenbach, (Albemarle), WO 2012122332, 2012.
- 26V. Busico, R. Cipullo, F. Cutillo, N. Friederichs, S. Ronca, B. Wang, J. Am. Chem. Soc. 2003, 125, 12402–12403.
- 27V. C. Williams, C. Dai, Z. Li, S. Collins, W. E. Piers, W. Clegg, M. R. J. Elsegood, T. B. Marder, Angew. Chem. 1999, 111, 3922–3926;
10.1002/(SICI)1521-3757(19991216)111:24<3922::AID-ANGE3922>3.0.CO;2-G Web of Science® Google ScholarAngew. Chem. Int. Ed. 1999, 38, 3695–3698.10.1002/(SICI)1521-3773(19991216)38:24<3695::AID-ANIE3695>3.0.CO;2-E CAS PubMed Web of Science® Google Scholar
- 28R. Sugimoto, T. Iwatani, K. Takeuchi, (Mitsui), JP 06136053, 1992.
- 29R. A. Stapleton, B. R. Galan, S. Collins, R. S. Simons, J. C. Garrison, W. J. Youngs, J. Am. Chem. Soc. 2003, 125, 9246–9247.
- 30J. S. J. McCahill, G. C. Welch, D. W. Stephan, Dalton Trans. 2009, 8555–8561.
- 31A. L. McKnight, R. M. Waymouth, Chem. Rev. 1998, 98, 2587–2598.
- 32H. Braunschweig, F. M. Breitling, Coord. Chem. Rev. 2006, 250, 2691–2720.
- 33P. J. Shapiro, E. Bunel, W. P. Schaefer, J. E. Bercaw, Organometallics 1990, 9, 867–869.
- 34J. Okuda, Chem. Ber. 1990, 123, 1649–1651.
- 35J. C. Stevens, F. J. Timmers, D. R. Wilson, G. F. Schmidt, P. N. Nickias, R. K. Rosen, G. W. Knight, S.-Y. Lai, (Dow Chemical Co., USA), EP 0 416 815 A2, 1991.
- 36
- 36aJ. A. M. Canich, (Exxon Chemical, Inc., USA), US 5 026 798, 1991;
- 36bJ. A. M. Canich, (Exxon Chemical, Inc., USA), EP 0 420 436 A1, 1991;
- 36cJ. A. M. Canich, G. F. Licciardi, (Exxon Chemical, Inc., USA), US 5 057 475, 1991.
- 37J. C. Stevens, Stud. Surf. Sci. Catal. 1994, 89, 277–284.
- 38
- 38aG. A. Luinstra, J. H. Teuben, J. Chem. Soc. Chem. Commun. 1990, 1470–1471;
- 38bF. Amor, J. Okuda, J. Organomet. Chem. 1996, 520, 245–248.
- 39D. D. Devore, (Dow Chemical Co., USA), EP 0 514 828 A1, 1992.
- 40J. Cano, K. Kunz, J. Organomet. Chem. 2007, 692, 4411–4423.
- 41
- 41aJ. C. Stevens, Stud. Surf. Sci. Catal. 1996, 101, 11–20;
- 41bR. E. LaPointe, J. C. Stevens, P. N. Nickias, M. H. McAdon, (Dow Chemical, USA), EP 0 520 732 B1, 1992.
- 42
- 42aJ. Klosin, W. J. Kruper, Jr., P. N. Nickias, G. R. Roof, P. De Waele, K. A. Abboud, Organometallics 2001, 20, 2663–2665;
- 42bJ. Klosin, W. J. Kruper, Jr., P. N. Nickias, J. T. Patton, D. R. Wilson, (Dow Chemical, USA), EP 0 923 589 B1, 1997.
- 43L. J. Irwin, J. H. Reibenspies, S. A. Miller, J. Am. Chem. Soc. 2004, 126, 16716–16717.
- 44L. J. Irwin, S. A. Miller, J. Am. Chem. Soc. 2005, 127, 9972–9973.
- 45
- 45aBP/Dow. Technology co-operation for licensing metallocenes in gas phase process. Press release of Aug. 5, 1996;
- 45bBP Frontiers Magazine, September 2001, 17–20;
- 45cINEOS Eltex PF product brochure;
- 45dINEOS Eltex TUB 220-RT product brochure.
- 46DuPont Dow Elastomers. DuPont plans EPDM output. Press release of Aug. 24, 1998.
- 47
- 47aS. L. Martin, L. C. Cady, D. P. Denton, D. L. Ramage, ACS Rubber Division Technical Papers 2002, 262–278;
- 47bM. S. Edmondson, Rubber World, November 2008.
- 48Dow. Dow closings to include EPDM plant. Press release of Dec. 10, 2008.
- 49P. S. Chum, K. W. Swogger, Prog. Polym. Sci. 2008, 33, 797–819.
- 50P. S. Chum, W. J. Kruper, M. J. Guest, Adv. Mater. 2000, 12, 1759–1767.
- 51K. Soga, T. Uozumi, S. Nakamura, T. Toneri, T. Teranishi, T. Sano, T. Arai, T. Shiono, Macromol. Chem. Phys. 1996, 197, 4237–4251.
- 52W.-J. Wang, D. Yan, S. Zhu, A. E. Hamielec, Macromolecules 1998, 31, 8677–8683.
- 53T. K. Woo, P. M. Margl, T. Ziegler, P. E. Blöchl, Organometallics 1997, 16, 3454–3468.
- 54J. Wang, H. Li, N. Guo, L. Li, C. L. Stern, T. J. Marks, Organometallics 2004, 23, 5112–5114.
- 55M. Delferro, T. J. Marks, Chem. Rev. 2011, 111, 2450–2485.
- 56H. Li, T. J. Marks, Proc. Natl. Acad. Sci. USA 2006, 103, 15295–15302.
- 57L. Li, M. V. Metz, H. Li, M.-C. Chen, T. J. Marks, L. Liable-Sands, A. L. Rheingold, J. Am. Chem. Soc. 2002, 124, 12725–12741.
- 58F. G. Sernetz, R. Mülhaupt, R. M. Waymouth, Macromol. Chem. Phys. 1996, 197, 1071–1083.
- 59D. J. Arriola, M. Bokota, R. E. Campbell, Jr., J. Klosin, R. E. LaPointe, O. D. Redwine, R. B. Shankar, F. J. Timmers, K. A. Abboud, J. Am. Chem. Soc. 2007, 129, 7065–7076.
- 60
- 60aN. Guo, L. Li, T. J. Marks, J. Am. Chem. Soc. 2004, 126, 6542–6543;
- 60bN. Guo, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 2008, 130, 2246–2261.
- 61Dow. ESI production ends: Dow rethinks uses. Press release of July 12, 2002.
- 62G.-J. M. Gruter in Metallocene Technology: a one-day seminar; Rapra Technology Limited, 1997, Paper 3.
- 63
- 63aJ. A. M. van Beek, G. H. J. van Doremaele, G. J. M. Gruter, H. J. Arts, G. H. M. R. Eggels, (DSM), WO 96/13529, 1996;
- 63bG. J. M. Gruter, M. Kranenburg, M. Herklots, (DSM), EP 0 919 571 A1, 1997.
- 64R. E. v. H. Spence, X. Gao, L. Koch, S. J. Brown, D. G. Harrison, (Nova Chemicals), US 6 124 487, 1998.
- 65H. Katayama, M. Nabika, A. Imai, A. Miyashita, T. Watanabe, H. Johohji, Y. Oda, H. Hanaoka, (Sumitomo Chemical Company), EP 0 842 939 B1, 1996.
- 66M. Nabika, H. Katayama, T. Watanabe, H. Kawamura-Kuribayashi, K. Yanagi, A. Imai, Organometallics 2009, 28, 3785–3792.
- 67T. Senda, H. Hanaoka, T. Hino, Y. Oda, H. Tsurugi, K. Mashima, Macromolecules 2009, 42, 8006–8009.
- 68T. Senda, H. Hanaoka, Y. Okado, Y. Oda, H. Tsurugi, K. Mashima, Organometallics 2009, 28, 6915–6926.
- 69T. Senda, H. Hanaoka, S. Nakahara, Y. Oda, H. Tsurugi, K. Mashima, Macromolecules 2010, 43, 2299–2306.
- 70T. V. Lubben, P. T. Wolczanski, G. D. Van Duyne, Organometallics 1984, 3, 977–983.
- 71
- 71aS. Anfang, K. Harms, F. Weller, O. Borgmeier, H. Lueken, H. Schilder, K. Dehnicke, Z. Anorg. Allg. Chem. 1998, 624, 159–166;
- 71bT. Rübenstahl, F. Weller, S. Wocadlo, W. Massa, K. Dehnicke, Z. Anorg. Allg. Chem. 1995, 621, 953–958.
- 72D. W. Stephan, Organometallics 2005, 24, 2548–2560.
- 73D. W. Stephan, J. C. Stewart, F. Guérin, R. E. v. H. Spence, W. Xu, D. G. Harrison, Organometallics 1999, 18, 1116–1118.
- 74
- 74aK. Dehnicke, F. Weller, Coord. Chem. Rev. 1997, 158, 103–169;
- 74bK. Dehnicke, M. Krieger, W. Massa, Coord. Chem. Rev. 1999, 182, 19–65.
- 75H. Staudinger, J. Meyer, Helv. Chim. Acta 1919, 2, 635–646.
- 76D. W. Stephan, J. C. Stewart, F. Guérin, S. Courtenay, J. Kickham, E. Hollink, C. Beddie, A. Hoskin, T. Graham, P. Wei, R. E. v. H. Spence, W. Xu, L. Koch, X. Gao, D. G. Harrison, Organometallics 2003, 22, 1937–1947.
- 77D. W. Stephan, Macromol. Symp. 2001, 173, 105–116.
- 78
- 78aJ. E. Kickham, F. Guérin, J. C. Stewart, D. W. Stephan, Angew. Chem. 2000, 112, 3406–3409;
10.1002/1521-3757(20000915)112:18<3406::AID-ANGE3406>3.0.CO;2-U Google ScholarAngew. Chem. Int. Ed. 2000, 39, 3263–3266;10.1002/1521-3773(20000915)39:18<3263::AID-ANIE3263>3.0.CO;2-H CAS PubMed Web of Science® Google Scholar
- 78bJ. E. Kickham, F. Guérin, J. C. Stewart, E. Urbanska, D. W. Stephan, Organometallics 2001, 20, 1175–1182.
- 79D. W. Stephan, F. Guérin, R. E. v. H. Spence, L. Koch, X. Gao, S. J. Brown, J. W. Swabey, Q. Wang, W. Xu, P. Zoricak, D. G. Harrison, Organometallics 1999, 18, 2046–2048.
- 80F. Guérin, J. C. Stewart, C. Beddie, D. W. Stephan, Organometallics 2000, 19, 2994–3000.
- 81J. E. Kickham, F. Guérin, D. W. Stephan, J. Am. Chem. Soc. 2002, 124, 11486–11494.
- 82C. Baar, S. Brown, P. Zoricak, Commercial Development of Single-Site Catalyst Technologies for Polyethylene Production, 2005, Presentation by Nova Chemicals Corporation.
- 83
- 83aN. Yue, E. Hollink, F. Guérin, D. W. Stephan, Organometallics 2001, 20, 4424–4433;
- 83bE. Hollink, P. Wei, D. W. Stephan, Organometallics 2004, 23, 1562–1569.
- 84N. L. S. Yue, D. W. Stephan, Organometallics 2001, 20, 2303–2308.
- 85E. Hollink, J. C. Stewart, P. Wei, D. W. Stephan, Dalton Trans. 2003, 3968–3974.
- 86E. Hollink, P. Wei, D. W. Stephan, Can. J. Chem. 2004, 82, 1304–1313.
- 87C. Beddie, E. Hollink, P. Wei, J. Gauld, D. W. Stephan, Organometallics 2004, 23, 5240–5251.
- 88J. McMeeking, X. Gao, R. E. v. H. Spence, S. J. Brown, D. Jeremic, (Nova Chemicals), WO 99/14250, 1999.
- 89M. J. Ferreira, A. M. Martins, Coord. Chem. Rev. 2006, 250, 118–132.
- 90A. R. Dias, M. T. Duarte, A. C. Fernandes, S. Fernandes, M. M. Marques, A. M. Martins, J. F. da Silva, S. S. Rodrigues, J. Organomet. Chem. 2004, 689, 203–213.
- 91K. Nomura, K. Fujita, M. Fujiki, J. Mol. Catal. A 2004, 220, 133–144.
- 92K. Nomura, J. Liu, Dalton Trans. 2011, 40, 7666–7682.
- 93H. Zhang, K. Nomura, J. Am. Chem. Soc. 2005, 127, 9364–9365.
- 94
- 94aDSM Elastomers. DSM continues to invest in innovative growth in performance materials cluster. Press release of March 27, 2007;
- 94bA. Leblanc, M. A. Zuideveld, V. Quiroga, E. Ijpei, E. Arts, G. van Doremaele, 3rd Blue Sky Conference on Catalytic Olefin Polymerization, 2010, P43;
- 94cV. Quiroga, A. Leblanc, M. A. Zuideveld, E. Ijpeij, E. Arts, G. van Doremaele, 3rd Blue Sky Conference on Catalytic Olefin Polymerization, 2010, P62;
- 94dM. A. Zuideveld, B. Coussens, E. Ijpeij, E. Arts, A. Leblanc, V. Quiroga, G. van Doremaele, 3rd Blue Sky Conference on Catalytic Olefin Polymerization, 2010, P92.
- 95E. G. Ijpeij, B. Coussens, M. A. Zuideveld, G. H. J. van Doremaele, P. Mountford, M. Lutz, A. L. Spek, Chem. Commun. 2010, 46, 3339–3341.
- 96
- 96aE. G. Ijpeij, P. J. H. Windmuller, H. J. Arts, F. van der Burgt, G. H. J. van Doremaele, M. A. Zuideveld, (DSM), WO 2005/090418 A1, 2005;
- 96bP. J. H. Windmuller, G. H. J. van Doremaele, (DSM), WO 2005/005496 A2, 2005;
- 96cE. G. Ijpeij, M. A. Zuideveld, H. J. Arts, F. van der Burgt, G. H. J. van Doremaele, (DSM), WO 2007/031295 A1, 2007.
- 97
- 97aW. P. Kretschmer, C. Dijkhuis, A. Meetsma, B. Hessen, J. H. Teuben, Chem. Commun. 2002, 608–609;
- 97bW. P. Kretschmer, (Stichting Dutch Polymer Institute), EP 1 373 332 B1, 2002.
- 98G. H. J. van Doremaele, M. A. Zuideveld, A. Leblanc, V. F. Quiroga Norambuena, (DSM), EP 2 319 874 A1, 2009.
- 99M. Dees, M. van Duin, C. Twigg, H. Dikland, Rubber World 2009, 240, 13–24.
- 100
- 100aLanxess. LANXESS to acquire DSM Elastomers. Press release of Dec. 14, 2010;
- 100bLanxess. LANXESS completes acquisition of DSM Elastomers. Press release of May 3, 2011.
- 101Lanxess. LANXESS successfully completes conversion to ACE technology at Geleen EPDM site. Press release of July 1, 2013.
- 102Lanxess. LANXESS to build world’s largest EPDM plant in China. Press release of Sept. 5, 2012.
- 103J. D. Scollard, D. H. McConville, N. C. Payne, J. J. Vittal, Macromolecules 1996, 29, 5241–5243.
- 104J. D. Scollard, D. H. McConville, J. Am. Chem. Soc. 1996, 118, 10008–10009.
- 105L.-C. Liang, R. R. Schrock, W. M. Davis, D. H. McConville, J. Am. Chem. Soc. 1999, 121, 5797–5798.
- 106
- 106aR. R. Schrock, A. L. Casado, J. T. Goodman, L.-C. Liang, P. J. Bonitatebus, Jr., W. M. Davis, Organometallics 2000, 19, 5325–5341;
- 106bR. R. Schrock, P. J. Bonitatebus, Jr., Y. Schrodi, Organometallics 2001, 20, 1056–1058;
- 106cY. Schrodi, R. R. Schrock, P. J. Bonitatebus, Jr., Organometallics 2001, 20, 3560–3573.
- 107D. H. McConville, R. R. Schrock, (Univation Technologies, Massachusetts Institute of Technology), WO 00/69922, 2000.
- 108H.-T. Liu, C. R. Mure, (Univation Technologies), WO 2010/008964 A1, 2010.
- 109
- 109aD. H. McConville, D. R. Loveday, M. W. Holtcamp, J. F. Szul, K. A. Erickson, S. Mawson, T. H. Kwack, F. J. Karol, D. J. Schreck, M. G. Goode, P. T. Daniell, M. G. McKee, C. C. Williams, (Univation Technologies), WO 01/30861 A1, 2001;
- 109bT. H. Kwalk, (Univation Technologies), US 2006/0036041 A1, 2006.
- 110I. Burdett, Hydrocarbon Eng. 2008, 13(6), 67–76.
- 111S.-C. Kao, F. C. Rix, D. Li, C. J. Harlan, P. A. Khokhani, (Univation Technologies), WO 2010/132811 A1, 2010.
- 112
- 112aR. E. Murray, (Union Carbide), US 6 096 676, 2000;
- 112bR. E. Murray, (Univation Technologies), WO 03/051935 A1, 2003;
- 112cR. E. Murray, A. M. Harrison, (Univation Technologies), US 7 199 255 B2, 2007.
- 113P. De Waele, B. A. Jazdzewski, J. Klosin, R. E. Murray, C. N. Theriault, P. C. Vosejpka, J. L. Petersen, Organometallics 2007, 26, 3896–3899.
- 114H. Tsurugi, R. Ohnishi, H. Kaneko, T. K. Panda, K. Mashima, Organometallics 2009, 28, 680–687.
- 115R. D. J. Froese, B. A. Jazdzewski, J. Klosin, R. L. Kuhlman, C. N. Theriault, D. M. Welsh, K. A. Abboud, Organometallics 2011, 30, 251–262.
- 116
- 116aR. Figueroa, R. D. Froese, Y. He, J. Klosin, C. N. Theriault, K. A. Abboud, Organometallics 2011, 30, 1695–1709;
- 116bP. P. Fontaine, R. Figueroa, S. D. McCann, D. Mort, J. Klosin, Organometallics 2013, 32, 2963–2972.
- 117T. R. Boussie, G. M. Diamond, C. Goh, K. A. Hall, A. M. LaPointe, M. K. Leclerc, V. Murphy, J. A. W. Shoemaker, H. Turner, R. K. Rosen, J. C. Stevens, F. Alfano, V. Busico, R. Cipullo, G. Talarico, Angew. Chem. 2006, 118, 3356–3361;
10.1002/ange.200600240 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 3278–3283.
- 118T. R. Boussie, G. M. Diamond, C. Goh, K. A. Hall, A. M. LaPointe, M. Leclerc, C. Lund, V. Murphy, J. A. W. Shoemaker, U. Tracht, H. Turner, J. Zhang, T. Uno, R. K. Rosen, J. C. Stevens, J. Am. Chem. Soc. 2003, 125, 4306–4317.
- 119G. J. Domski, E. B. Lobkovsky, G. W. Coates, Macromolecules 2007, 40, 3510–3513.
- 120R. D. J. Froese, P. D. Hustad, R. L. Kuhlman, T. T. Wenzel, J. Am. Chem. Soc. 2007, 129, 7831–7840.
- 121C. Zuccaccia, V. Busico, R. Cipullo, G. Talarico, R. D. J. Froese, P. C. Vosejpka, P. D. Hustad, A. Macchioni, Organometallics 2009, 28, 5445–5458.
- 122C. Zuccaccia, A. Macchioni, V. Busico, R. Cipullo, G. Talarico, F. Alfano, H. W. Boone, K. A. Frazier, P. D. Hustad, J. C. Stevens, P. C. Vosejpka, K. A. Abboud, J. Am. Chem. Soc. 2008, 130, 10354–10368.
- 123V. Busico, R. Cipullo, R. Pellecchia, L. Rongo, G. Talarico, A. Macchioni, C. Zuccaccia, R. D. J. Froese, P. D. Hustad, Macromolecules 2009, 42, 4369–4373.
- 124http://www.dow.com/elastomers/products/versify.htm,accessed July 18, 2014.
- 125P. G. Cozzi, E. Gallo, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1995, 14, 4994–4996.
- 126H. Makio, H. Terao, A. Iwashita, T. Fujita, Chem. Rev. 2011, 111, 2363–2449.
- 127T. Fujita, Y. Thoi, M. Mitani, S. Matsui, J. Saito, M. Nitabaru, K. Sugi, H. Makio, T. Tsutsui, (Mitsui Chemicals), EP 0 874 005 B1, 1997.
- 128S. Matsui, T. Fujita, Catal. Today 2001, 66, 63–73.
- 129H. Makio, N. Kashiwa, T. Fujita, Adv. Synth. Catal. 2002, 344, 477–493.
- 130S. Matsui, M. Mitani, J. Saito, Y. Tohi, H. Makio, N. Matsukawa, Y. Takagi, K. Tsuru, M. Nitabaru, T. Nakano, H. Tanaka, N. Kashiwa, T. Fujita, J. Am. Chem. Soc. 2001, 123, 6847–6856.
- 131
- 131aJ. Saito, M. Mitani, J.-i. Mohri, Y. Yoshida, S. Matsui, S.-i. Ishii, S.-i. Kojoh, N. Kashiwa, T. Fujita, Angew. Chem. 2001, 113, 3002–3004;
Angew. Chem. Int. Ed. 2001, 40, 2918–2920;
10.1002/1521-3773(20010803)40:15<2918::AID-ANIE2918>3.0.CO;2-S CAS PubMed Web of Science® Google Scholar
- 131bM. Mitani, J.-i. Mohri, Y. Yoshida, J. Saito, S. Ishii, K. Tsuru, S. Matsui, R. Furuyama, T. Nakano, H. Tanaka, S.-i. Kojoh, T. Matsugi, N. Kashiwa, T. Fujita, J. Am. Chem. Soc. 2002, 124, 3327–3336.
- 132
- 132aJ. Tian, G. W. Coates, Angew. Chem. 2000, 112, 3772–3775;
Angew. Chem. Int. Ed. 2000, 39, 3626–3629;
10.1002/1521-3773(20001016)39:20<3626::AID-ANIE3626>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 132bJ. Tian, P. D. Hustad, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 5134–5135.
- 133
- 133aE. Talsi, K. P. Bryliakov, Top. Catal. 2013, 56, 914–922;
- 133bA. Iwashita, M. C. W. Chan, H. Makio, T. Fujita, Catal. Sci. Technol. 2014, 4, 599–610.
- 134G. Talarico, V. Busico, L. Cavallo, Organometallics 2004, 23, 5989–5993.
- 135S.-M. Yu, S. Mecking, J. Am. Chem. Soc. 2008, 130, 13204–13205.
- 136
- 136aK. P. Bryliakov, E. P. Talsi, H. M. Möller, M. C. Baier, S. Mecking, Organometallics 2010, 29, 4428–4430;
- 136bH. M. Möller, M. C. Baier, S. Mecking, E. P. Talsi, K. P. Bryliakov, Chem. Eur. J. 2012, 18, 848–856.
- 137A. Sakuma, M.-S. Weiser, T. Fujita, Polym. J. 2007, 39, 193–207.
- 138G. Milano, L. Cavallo, G. Guerra, J. Am. Chem. Soc. 2002, 124, 13368–13369.
- 139P. Corradini, G. Guerra, L. Cavallo, Acc. Chem. Res. 2004, 37, 231–241.
- 140A. V. Prasad, H. Makio, J. Saito, M. Onda, T. Fujita, Chem. Lett. 2004, 33, 250–251.
- 141H. Makio, T. Fujita, Bull. Chem. Soc. Jpn. 2005, 78, 52–66.
- 142J. B. Edson, Z. Wang, E. J. Kramer, G. W. Coates, J. Am. Chem. Soc. 2008, 130, 4968–4977.
- 143E. Y. Tshuva, I. Goldberg, M. Kol, J. Am. Chem. Soc. 2000, 122, 10706–10707.
- 144A. Cohen, J. Kopilov, M. Lamberti, V. Venditto, M. Kol, Macromolecules 2010, 43, 1689–1691.
- 145K. Press, A. Cohen, I. Goldberg, V. Venditto, M. Mazzeo, M. Kol, Angew. Chem. 2011, 123, 3591–3594; Angew. Chem. Int. Ed. 2011, 50, 3529–3532.
- 146J. Saito, M. Mitani, S. Matsui, N. Kashiwa, T. Fujita, Macromol. Rapid Commun. 2000, 21, 1333–1336.
- 147J. Saito, Y. Suzuki, H. Makio, H. Tanaka, M. Onda, T. Fujita, Macromolecules 2006, 39, 4023–4031.
- 148W.-Q. Hu, X.-L. Sun, C. Wang, Y. Gao, Y. Tang, L.-P. Shi, W. Xia, J. Sun, H.-L. Dai, X.-Q. Li, X.-L. Yao, X.-R. Wang, Organometallics 2004, 23, 1684–1688.
- 149X.-H. Yang, C.-R. Liu, C. Wang, X.-L. Sun, Y.-H. Guo, X.-K. Wang, Z. Wang, Z. Xie, Y. Tang, Angew. Chem. 2009, 121, 8243–8246; Angew. Chem. Int. Ed. 2009, 48, 8099–8102.
- 150G. G. Hlatky, Chem. Rev. 2000, 100, 1347–1376.
- 151Y. Nakayama, J. Saito, H. Bando, T. Fujita, Chem. Eur. J. 2006, 12, 7546–7556.
- 152H. Makio, T. Ochiai, J.-i. Mohri, K. Takeda, T. Shimazaki, Y. Usui, S. Matsuura, T. Fujita, J. Am. Chem. Soc. 2013, 135, 8177–8180.
- 153H. Makio, T. Fujita, Acc. Chem. Res. 2009, 42, 1532–1544.
- 154Mitsui will use the PI catalyst production HDPE. News article on ourchemical.com. Oct. 18, 2011. Accessed July 24, 2013.
- 155S. Rastogi, D. R. Lippits, G. W. M. Peters, R. Graf, Y. Yao, H. W. Spiess, Nat. Mater. 2005, 4, 635–641.
- 156S. E. Rastogi, K. Garkhail, R. Duchateau, G. J. M. Gruter, D. R. Lippits, (Stichting Dutch Polymer Institute), US 7 671 159 B2, 2010.
- 157S. Rastogi, Y. Yao, S. Ronca, J. Bos, J. van der Eem, Macromolecules 2011, 44, 5558–5568.
- 158Y. Suzuki, S. Kinoshita, A. Shibahara, S. Ishii, K. Kawamura, Y. Inoue, T. Fujita, Organometallics 2010, 29, 2394–2396.
- 159A. Sattler, J. A. Labinger, J. E. Bercaw, Organometallics 2013, 32, 6899–6902.
- 160I. E. Soshnikov, N. V. Semikolenova, J. Ma, K.-Q. Zhao, V. A. Zakharov, K. P. Bryliakov, C. Redshaw, E. P. Talsi, Organometallics 2014, 33, 1431–1439.
- 161
- 161aThe Catalyst Review 2011, 24(4), 6;
- 161bMitsui Chemicals. Mitsui Chemicals to Develop a Highly Active Catalyst for 1-Hexene Production. Press release of June 23, 2008;
- 161cMitsui Chemicals. Mitsui Chemicals to Strengthen Added-Value Ethylene Derivative Products of Ichihara Works. Press release of Jan. 30, 2009.
- 162
- 162aD. J. Arriola, E. M. Carnahan, P. D. Hustad, R. L. Kuhlman, T. T. Wenzel, Science 2006, 312, 714–719;
- 162bP. D. Hustad, R. L. Kuhlman, D. J. Arriola, E. M. Carnahan, T. T. Wenzel, Macromolecules 2007, 40, 7061–7064;
- 162cP. D. Hustad, R. L. Kuhlman, E. M. Carnahan, T. T. Wenzel, D. J. Arriola, Macromolecules 2008, 41, 4081–4089;
- 162dT. T. Wenzel, D. J. Arriola, E. M. Carnahan, P. D. Hustad, R. L. Kuhlman, Topics in Organometallic Chemistry, Vol. 26 (Ed.: ), Springer, Berlin/Heidelberg, 2009, pp. 65–104.
- 163D. J. Arriola, E. M. Carnahan, Y. W. Cheung, D. D. Devore, D. D. Graf, P. D. Hustad, R. L. Kuhlman, C. Li Pi Shan, B. C. Poon, G. R. Roof, J. C. Stevens, P. J. Stirn, T. T. Wenzel, (Dow Global Technologies), WO 2005/090427 A2, 2005.
- 164Mitsui Chemicals. Joint Research Agreement with the Dow Chemical Company. Press release of June 21, 2006.
- 165Dow. Dow Introduces Breakthrough Technology for Effectively Combining PE and PP. Press release of Oct. 17, 2013.
- 166
- 166aT. T. Wenzel, T. P. Clark, D. R. Wilson, S. B. Klamo, D. J. Arriola, C. N. Theriault, R. D. Froese, (Dow Global Technologies), WO 2012/061706 A1, 2012;
- 166bT. P. Clark, N. E. Kamber, S. B. Klamo, P. D. Hustad, D. R. Wilson (Dow Chemical, USA), US 2011/0028657 A1, 2011.
- 167R. L. Kuhlman, J. Klosin, Macromolecules 2010, 43, 7903–7904.
- 168
- 168aR. Kempe, Chem. Eur. J. 2007, 13, 2764–2773;
- 168bL. R. Sita, Angew. Chem. 2009, 121, 2500–2508;
10.1002/ange.200802661 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 2464–2472;
- 168cJ. Mazzolini, E. Espinosa, F. D′Agosto, C. Boisson, Polym. Chem. 2010, 1, 793–800.
- 169J. Wei, W. Zhang, R. Wickham, L. R. Sita, Polym. Prepr. 2011, 52(1), 225–226.
- 170J. Wei, W. Zhang, R. Wickham, L. R. Sita, Angew. Chem. 2010, 122, 9326–9330; Angew. Chem. Int. Ed. 2010, 49, 9140–9144.
- 171J. Wei, W. Zhang, L. R. Sita, Angew. Chem. 2010, 122, 1812–1816; Angew. Chem. Int. Ed. 2010, 49, 1768–1772.
- 172L. K. Johnson, C. M. Killian, M. Brookhart, J. Am. Chem. Soc. 1995, 117, 6414–6415.
- 173V. M. Möhring, G. Fink, Angew. Chem. 1985, 97, 982–984;
10.1002/ange.19850971123 Google ScholarAngew. Chem. Int. Ed. Engl. 1985, 24, 1001–1003.
- 174Z. Guan, P. M. Cotts, E. F. McCord, S. J. McLain, Science 1999, 283, 2059–2062.
- 175
- 175aL. K. Johnson, S. Mecking, M. Brookhart, J. Am. Chem. Soc. 1996, 118, 267–268;
- 175bS. Mecking, L. K. Johnson, L. Wang, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 888–899.
- 176D. P. Gates, S. A. Svejda, E. Oñate, C. M. Killian, L. K. Johnson, P. S. White, M. Brookhart, Macromolecules 2000, 33, 2320–2334.
- 177
- 177aL. Johnson, A. Bennett, K. Dobbs, E. Hauptman, A. Ionkin, S. Ittel, E. McCord, S. McLain, C. Radzewich, Z. Yin, L. Wang, Y. Wang, M. Brookhart, Polym. Mater. Sci. Eng. 2002, 86, 319;
- 177bL. Wang, E. Hauptman, L. K. Johnson, W. J. Marshall, E. F. McCord, Y. Wang, S. D. Ittel, C. E. Radzewich, K. Kunitsky, A. S. Ionkin, Polym. Mater. Sci. Eng. 2002, 86, 322;
- 177cL. Johnson, L. Wang, S. McLain, A. Bennett, K. Dobbs, E. Hauptman, A. Ionkin, S. Ittel, K. Kunitsky, W. Marshall, E. McCord, C. Radzewich, A. Rinehart, K. J. Sweetman, Y. Wang, Z. Yin, M. Brookhart, ACS Symp. Ser. 2003, 857, 131–142.
- 178
- 178aL. S. Moody, P. B. MacKenzie, C. M. Killian, G. G. Lavoie, J. A. Ponasik, Jr., A. G. M. Barrett, T. W. Smith, J. C. Pearson, (Eastman Chemical), WO 00/50470, 2000;
- 178bL. S. Moody, P. B. MacKenzie, C. M. Killian, G. G. Lavoie, J. A. Ponasik, Jr., T. W. Smith, J. C. Pearson, A. G. M. Barrett, (Eastman Chemical), US 6 946 532, 2005.
- 179M. Schmid, R. Eberhardt, M. Klinga, M. Leskelä, B. Rieger, Organometallics 2001, 20, 2321–2330.
- 180M. A. Zuideveld, P. Wehrmann, C. Röhr, S. Mecking, Angew. Chem. 2004, 116, 887–891;
10.1002/ange.200352062 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 869–873.
- 181D. Meinhard, M. Wegner, G. Kipiani, A. Hearley, P. Reuter, S. Fischer, O. Marti, B. Rieger, J. Am. Chem. Soc. 2007, 129, 9182–9191.
- 182D. H. Camacho, E. V. Salo, J. W. Ziller, Z. Guan, Angew. Chem. 2004, 116, 1857–1861;
10.1002/ange.200353226 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 1821–1825.
- 183S. Mecking, Macromol. Rapid Commun. 1999, 20, 139–143.
10.1002/(SICI)1521-3927(19990301)20:3<139::AID-MARC139>3.0.CO;2-R CAS Web of Science® Google Scholar
- 184L. C. Simon, H. Patel, J. B. P. Soares, R. F. de Souza, Macromol. Chem. Phys. 2001, 202, 3237–3247.
- 185J. R. Severn, J. C. Chadwick, V. V. A. Castelli, Macromolecules 2004, 37, 6258–6259.
- 186R. Huang, C. E. Koning, J. C. Chadwick, Macromolecules 2007, 40, 3021–3029.
- 187H. S. Schrekker, V. Kotov, P. Preishuber-Pflugl, P. White, M. Brookhart, Macromolecules 2006, 39, 6341–6354.
- 188A. Dorcier, N. Merle, M. Taoufik, F. Bayard, C. Lucas, A. de Mallmann, J. M. Basset, Organometallics 2009, 28, 2173–2178.
- 189M. M. Wegner, A. K. Ott, B. Rieger, Macromolecules 2010, 43, 3624–3633.
- 190M. Brookhart, B. L. Small, 9th IUPAC Symposium on Organometallic Chemistry, Göttingen, Germany, July 20–25, 1997, Poster 447.
- 191B. L. Small, M. Brookhart, A. M. A. Bennett, J. Am. Chem. Soc. 1998, 120, 4049–4050.
- 192G. J. P. Britovsek, V. C. Gibson, B. S. Kimberley, P. J. Maddox, S. J. McTavish, G. A. Solan, A. J. P. White, D. J. Williams, Chem. Commun. 1998, 849–850.
- 193A. M. A. Bennett, (DuPont), WO 98/27124, 1998.
- 194G. J. P. Britovsek, M. Bruce, V. C. Gibson, B. S. Kimberley, P. J. Maddox, S. Mastroianni, S. J. McTavish, C. Redshaw, G. A. Solan, S. Strömberg, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 8728–8740.
- 195S. K. Moore, Chem. Week 2000, Feb. 16, 21.
- 196B. L. Small, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 7143–7144.
- 197
- 197aS. Mecking, (Targor GmbH), US 6 262 196 B1, 2001;
- 197bS. Mecking, (Basell Polyolefine GmbH), EP 963 385 B1, 2004;
- 197cS. Mecking, (Basell Polypropylen GmbH), US 6 384 144 B1, 2002.
- 198aS. Mihan, F. Fantinel, (Basell Polyolefine GmbH), US 7 723 448 B2, 2010;
- 198bS. Mihan, R. Karer, H. Schmitz, D. Lilge, (Basell Polyolefine GmbH), US 8 003 740 B2, 2011.
- 199A. Kurek, S. Mark, M. Enders, M. O. Kristen, R. Mülhaupt, Macromol. Rapid Commun. 2010, 31, 1359–1363.
- 200
- 200aG. Natta, P. Pino, P. Corradini, F. Danusso, E. Mantica, G. Mazzanti, G. Moraglio, J. Am. Chem. Soc. 1955, 77, 1708–1710;
- 200bG. Natta, F. Danusso, D. Sianesi, Makromol. Chem. 1958, 28, 253–261.
- 201N. Ishihara, T. Seimiya, M. Kuramoto, M. Uoi, Macromolecules 1986, 19, 2464–2465.
- 202 Syndiotactic Polystyrene (Ed.: ), Wiley, Hoboken, 2010.
- 203N. Ishihara, M. Kuramoto, M. Uoi, Macromolecules 1988, 21, 3356–3360.
- 204C. Pellecchia, P. Longo, A. Grassi, P. Ammendola, A. Zambelli, Makromol. Chem. Rapid Commun. 1987, 8, 277–279.
- 205N. Tomotsu, N. Ishihara, T. H. Newman, M. T. Malanga, J. Mol. Catal. A 1998, 128, 167–190.
- 206W. Kaminsky, S. Lenk, V. Scholz, H. W. Roesky, A. Herzog, Macromolecules 1997, 30, 7647–7650.
- 207J. Schellenberg, N. Tomotsu, Prog. Polym. Sci. 2002, 27, 1925–1982.
- 208J. Schellenberg, Prog. Polym. Sci. 2009, 34, 688–718.
- 209A.-S. Rodrigues, E. Kirillov, J.-F. Carpentier, Coord. Chem. Rev. 2008, 252, 2115–2136.
- 210T. H. Newman, M. T. Malanga, J. Macromol. Sci. Pure Appl. Chem. 1997, 34, 1921–1927.
- 211J. C. W. Chien, Z. Salajka, S. Dong, Macromolecules 1992, 25, 3199–3203.
- 212A. Zambelli, C. Pellecchia, A. Proto, Macromol. Symp. 1995, 89, 373–382.
- 213A. Grassi, S. Saccheo, A. Zambelli, F. Laschi, Macromolecules 1998, 31, 5588–5591.
- 214J. Schellenberg, H.-J. Leder, Adv. Polym. Technol. 2006, 25, 141–151.
- 215M. Malanga, Adv. Mater. 2000, 12, 1869–1872.
- 216N. Ishihara, Macromol. Symp. 1995, 89, 553–562.
- 217B. L. Goodall in Late Transition Metal Polymerization Catalysis (Eds.: ), Wiley-VCH, Weinheim, 2003, pp. 101–154.
10.1002/3527601805.ch4 Google Scholar
- 218H. Kajiura, H. Oda, S. Minami, (Mitsui), EP 0 156 464 B1, 1985.
- 219H. Cherdron, M.-J. Brekner, F. Osan, Angew. Makromol. Chem. 1994, 223, 121–133.
- 220
- 220aC. Mehler, W. Risse, Makromol. Chem. Rapid Commun. 1991, 12, 255–259;
- 220bN. Seehof, C. Mehler, S. Breunig, W. Risse, J. Mol. Catal. 1992, 76, 219–228;
- 220cA. Sen, T.-W. Lai, Organometallics 1982, 1, 415–417;
- 220dA. Sen, T.-W. Lai, R. R. Thomas, J. Organomet. Chem. 1988, 358, 567–588.
- 221
- 221aF. Blank, C. Janiak, Coord. Chem. Rev. 2009, 253, 827–861;
- 221bC. Janiak, P. G. Lassahn, Macromol. Rapid Commun. 2001, 22, 479–493;
- 221cC. Janiak, P. G. Lassahn, J. Mol. Catal. A 2001, 166, 193–209.
- 222G. Wilke, Angew. Chem. 1988, 100, 189–211; Angew. Chem. Int. Ed. Engl. 1988, 27, 185–206.
- 223R. Taube, U. Schmidt, J.-P. Gehrke, P. Böhme, J. Langlotz, S. Wache, Makromol. Chem. Macromol. Symp. 1993, 66, 245–260.
- 224M. D. Walter, R. A. Moorhouse, P. S. White, M. Brookhart, J. Polym. Sci. Part A 2009, 47, 2560–2573.
- 225A. Bell, L. F. Rhodes, B. L. Goodall, J. C. Fondran, (B. F. Goodrich), US 6 350 832 B1, 2002.
- 226R. G. Gastinger, B. B. Anderson, K. J. Klabunde, J. Am. Chem. Soc. 1980, 102, 4959–4966.
- 227D. A. Barnes, G. M. Benedikt, B. L. Goodall, S. S. Huang, H. A. Kalamarides, S. Lenhard, L. H. McIntosh, III, K. T. Selvy, R. A. Shick, L. F. Rhodes, Macromolecules 2003, 36, 2623–2632.
- 228A. D. Hennis, J. D. Polley, G. S. Long, A. Sen, D. Yandulov, J. Lipian, G. M. Benedikt, L. F. Rhodes, J. Huffman, Organometallics 2001, 20, 2802–2812.
- 229J. Lipian, R. A. Mimna, J. C. Fondran, D. Yandulov, R. A. Shick, B. L. Goodall, L. F. Rhodes, J. C. Huffman, Macromolecules 2002, 35, 8969–8977.
- 230M. Yamashita, I. Takamiya, K. Jin, K. Nozaki, Organometallics 2006, 25, 4588–4595.