Selective ethylene oligomerization: Recent advances in chromium catalysis and mechanistic investigations

Coordination Chemistry Reviews

Volumn 255, Issue 7-8, 2011, Pages 861-880

  Agapie, Theodor ^a  

^a California Institute of Technology   (United States)

Author keywords

1 Hexene; 1 Octene; Alpha olefins; Catalytic olefin oligomerization; Chromium catalysis; Ethylene trimerization; Isotopic labeling; Selective oligomerization; Tetramerization

Indexed keywords

EID: 79952105252     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2010.11.035     Document Type: Review

References (127)

1. Lappin G.R., Nemec L.H., Sauer J.D., Wagner J.D. Higher Olefins. Kirk-Othmer Encyclopedia of Chemical Technology 2005, Wiley & Sons, Inc.
2. Kissin Y.V. Polymers of Higher Olefins. Kirk-Othmer Encyclopedia of Chemical Technology 2005, Wiley & Sons, Inc.
3. Dixon J.T., Green M.J., Hess F.M., Morgan D.H. J. Organomet. Chem. 2004, 689:3641.
4. Wass D.F. Dalton Trans. 2007, 816.
5. Briggs J.R. Chem. Commun. 1989, 674.
6. Carter A., Cohen S.A., Cooley N.A., Murphy A., Scutt J., Wass D.F. Chem. Commun. 2002, 858.
7. Bollmann A., Blann K., Dixon J.T., Hess F.M., Killian E., Maumela H., McGuinness D.S., Morgan D.H., Neveling A., Otto S., Overett M., Slawin A.M.Z., Wasserscheid P., Kuhlmann S. J. Am. Chem. Soc. 2004, 126:14712.
8. McGuinness D.S., Wasserscheid P., Morgan D.H., Dixon J.T. Organometallics 2005, 24:552.
9. Overett M.J., Blann K., Bollmann A., Dixon J.T., Haasbroek D., Killian E., Maumela H., McGuinness D.S., Morgan D.H. J. Am. Chem. Soc. 2005, 127:10723.
10. McGuinness D.S., Wasserscheid P., Keim W., Hu C.H., Englert U., Dixon J.T., Grove C. Chem. Commun. 2003, 334.
11. 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.
12. Agapie T., Schofer S.J., Labinger J.A., Bercaw J.E. J. Am. Chem. Soc. 2004, 126:1304.
13. Agapie T., Day M.W., Henling L.M., Labinger J.A., Bercaw J.E. Organometallics 2006, 25:2733.
14. Agapie T., Labinger J.A., Bercaw J.E. J. Am. Chem. Soc. 2007, 129:14281.
15. Bluhm M.E., Walter O., Doring M. J. Organomet. Chem. 2005, 690:713.
16. Elowe P.R., McCann C., Pringle P.G., Spitzmesser S.K., Bercaw J.E. Organometallics 2006, 25:5255.
17. Schofer S.J., Day M.W., Henling L.M., Labinger J.A., Bercaw J.E. Organometallics 2006, 25:2743.
18. Blann K., Bollmann A., Dixon J.T., Hess F.M., Killian E., Maumela H., Morgan D.H., Neveling A., Otto S., Overett M.J. Chem. Commun. 2005, 620.
19. Weng Z.Q., Teo S.H., Hor T.S.A. Dalton Trans. 2007, 3493.
20. Zhang J., Braunstein P., Hor T.S.A. Organometallics 2008, 27:4277.
21. Zhang J., Li A.F., Hor T.S.A. Dalton Trans. 2009, 9327.
22. Wohl A., Muller W., Peulecke N., Muller B.H., Peitz S., Heller D., Rosenthal U. J. Mol. Catal. A: Chem. 2009, 297:1.
23. Peitz S., Peulecke N., Aluri B.R., Hansen S., Muller B.H., Spannenberg A., Rosenthal U., Al-Hazmi M.H., Mosa F.M., Wohl A., Muller W. Eur. J. Inorg. Chem. 2010, 1167.
24. Jiang T., Ning Y.N., Zhang B.J., Li J.Z., Wang G., Yi J.J., Huang Q. J. Mol. Catal. A: Chem. 2006, 259:161.
25. Klemps C., Payet E., Magna L., Saussine L., Le Goff X.F., Le Floch P. Chem. A Eur. J. 2009, 15:8259.
26. Deckers P.J.W., Hessen B., Teuben J.H. Angew. Chem. Int. Ed. Engl. 2001, 40:2516.
27. Deckers P.J.W., Hessen B., Teuben J.H. Organometallics 2002, 21:5122.
28. Huang J.L., Wu T.Z., Qian Y.L. Chem. Commun. 2003, 2816.
29. Wu T., Qian Y., Huang J. J. Mol. Catal. A: Chem. 2004, 214:227.
30. Hessen B. J. Mol. Catal. A: Chem. 2004, 213:129.
31. Hagen H., Kretschmer W.P., van Buren F.R., Hessen B., van Oeffelen D.A. J. Mol. Catal. A: Chem. 2006, 248:237.
32. Otten E., Batinas A.A., Meetsma A., Hessen B. J. Am. Chem. Soc. 2009, 131:5298.
33. Suzuki Y., Kinoshita S., Shibahara A., Ishii S., Kawamura K., Inoue Y., Fujita T. Organometallics 2010, 29:2394.
34. Andes C., Harkins S.B., Murtuza S., Oyler K., Sen A. J. Am. Chem. Soc. 2001, 123:7423.
35. Arteaga-Muller R., Tsurugi H., Saito T., Yanagawa M., Oda S., Mashima K. J. Am. Chem. Soc. 2009, 131:5370.
36. Forestiere A., Olivier-Bourbigou H., Saussine L. Oil Gas Sci. Technol. Rev. De L Institut Francais Du Petrole 2009, 64:649.
37. Theopold K.H. Eur. J. Inorg. Chem. 1998, 15.
38. Smith K.M. Curr. Org. Chem. 2006, 10:955.
39. R.M. Manyik, W.E. Walker, T. P. Wilson, US Pat. 3300458 (1967).
40. Manyik R.M., Walker W.E., Wilson T.P. J. Catal. 1977, 47:197.
41. W.K. Reagen, B.K. Conroy, 90 (1991), CA Pat. 2020509.
42. W.K. Reagen, T.M. Pettijohn, J.W. Freeman, E.A. Benham (1995), US Pat. 5451645.
43. F.-j. Wu, 95 (1998), US Pat. 519277.
44. Y. Araki, H. Nakamura, Y. Nanba, T. Okano (1999), US Pat. 5856612.
45. Staff C.W.E. Chem. Eng. (N.Y.) 2005, 112:28.
46. Overett M.J., Blann K., Bollmann A., Dixon J.T., Hess F., Killian E., Maumela H., Morgan D.H., Neveling A., Otto S. Chem. Commun. 2005, 622.
47. Overett M.J., Blann K., Bollmann A., de Villiers R., Dixon J.T., Killian E., Maumela M.C., Maumela H., McGuinness D.S., Morgan D.H., Rucklidge A., Slawin A.M.Z. J. Mol. Catal. A: Chem. 2008, 283:114.
48. Dulai A., Bod H., Hanton M.J., Smith D.M., Downing S., Mansell S.M., Wass D.F. Organometallics 2009, 28:4613.
49. Rucklidge A.J., McGuinness D.S., Tooze R.P., Slawin A.M.Z., Pelletier J.D.A., Hanton M.J., Webb P.B. Organometallics 2007, 26:2782.
50. Jiang T., Zhang S., Jiang X., Yang C., Niu B., Ning Y. J. Mol. Catal. A: Chem. 2008, 279:90.
51. McGuinness D.S., Overett M., Tooze R.P., Blann K., Dixon J.T., Slawin A.M.Z. Organometallics 2007, 26:1108.
52. McDyre L.E., Hamilton T., Murphy D.M., Cavell K.J., Gabrielli W.F., Hanton M.J., Smith D.M. Dalton Trans. 2010, 39:7792.
53. Wohl A., Muller W., Peitz S., Peulecke N., Aluri B.R., Muller B.H., Heller D., Rosenthal U., Al-Hazmi M.H., Mosa F.M. Chem. A Eur. J. 2010, 16:7833.
54. Peitz S., Aluri B.R., Peulecke N., Muller B.H., Wohl A., Muller W., Al-Hazmi M.H., Mosa F.M., Rosenthal U. Chem. A Eur. J. 2010, 16:7670.
55. Albahily K., Al-Baldawi D., Gambarotta S., Duchateau R., Koc E., Burchell T.J. Organometallics 2008, 27:5708.
56. Albahily K., Al-Baldawi D., Gambarotta S., Koc E., Duchateau R. Organometallics 2008, 27:5943.
57. Albahily K., Koc E., Al-Baldawi D., Savard D., Gambarotta S., Burchell T.J., Duchateau R. Angew. Chem. Int. Ed. 2008, 47:5816.
58. McGuinness D.S., Brown D.B., Tooze R.P., Hess F.M., Dixon J.T., Slawin A.M.Z. Organometallics 2006, 25:3605.
59. Jabri A., Temple C., Crewdson P., Gambarotta S., Korobkov I., Duchateau R. J. Am. Chem. Soc. 2006, 128:9238.
60. Temple C.N., Gambarotta S., Korobkov I., Duchateau R. Organometallics 2007, 26:4598.
61. Moulin J.O., Evans J., McGuinness D.S., Reid G., Rucklidge A.J., Tooze R.P., Tromp M. Dalton Trans. 2008, 1177.
62. Kohn R.D., Haufe M., Kociok-Kohn G., Grimm S., Wasserscheid P., Keim W. Angew. Chem. Int. Ed. Engl. 2000, 39:4337.
63. Kohn R.D., Haufe M., Mihan S., Lilge D. Chem. Commun. 2000, 1927.
64. Kohn R.D., Smith D., Mahon M.F., Prinz M., Mihan S., Kociok-Kohn G. J. Organomet. Chem. 2003, 683:200.
65. Wasserscheid P., Grimm S., Kohn R.D., Haufe M. Adv. Synth. Catal. 2001, 343:814.
66. Kilpatrick A.F.R., Kulangara S.V., Cushion M.G., Duchateau R., Mountford P. Dalton Trans. 2010, 39:3653.
67. Zhang J., Li A.F., Hor T.S.A. Organometallics 2009, 28:2935.
68. Temple C., Jabri A., Crewdson P., Gambarotta S., Korobkov I., Duchateau R. Angew. Chem. Int. Ed. Engl. 2006, 45:7050.
69. Jabri A., Crewdson P., Gambarotta S., Korobkov I., Duchateau R. Organometallics 2006, 25:715.
70. Vidyaratne I., Nikiforov G.B., Gorelsky S.I., Gambarotta S., Duchateau R., Korobkov I. Angew. Chem. Int. Ed. 2009, 48:6552.
71. Jabri A., Mason C., Sim Y., Gambarotta S., Burchell T., Duchateau R. Angew. Chem. Int. Ed. 2008, 47:9717.
72. McGuinness D.S., Rucklidge A.J., Tooze R.P., Slawin A.M.Z. Organometallics 2007, 26:2561.
73. Bowen L.E., Haddow M.F., Orpen A.G., Wass D.F. Dalton Trans. 2007, 1160.
74. Chen H., Liu X., Hu W., Ning Y., Jiang T. J. Mol. Catal. A: Chem. 2007, 270:273.
75. Bruckner A., Jabor J.K., McConnell A.E.C., Webb P.B. Organometallics 2008, 27:3849.
76. Meijboom N., Schaverien C.J., Orpen A.G. Organometallics 1990, 9:774.
77. Emrich R., Heinemann O., Jolly P.W., Krueger C., Verhovnik G.P.J. Organometallics 1997, 16:1511.
78. Morgan D., Schwikkard S., Dixon J., Nair J., Hunter R. Adv. Synth. Catal. 2003, 345:939.
79. Fang Y.Q., Liu Y.X., Ke Y.C., Guo C.Y., Zhu N., Mi X., Ma Z., Hu Y.L. Appl. Catal. A: Gen. 2002, 235:33.
80. van Rensburg W.J., Grove C., Steynberg J.P., Stark K.B., Huyser J.J., Steynberg P.J. Organometallics 2004, 23:1207.
81. Qi Y., Dong Q., Zhong L., Liu Z., Qiu P.Y., Cheng R.H., He X.L., Vanderbilt J., Liu B.P. Organometallics 2010, 29:1588.
82. Bhaduri S., Mukhopadhyay S., Kulkarni S.A. J. Organomet. Chem. 2009, 694:1297.
83. Janse van Rensburg W., van den Berg J.-A., Steynberg P.J. Organometallics 2007, 26:1000.
84. Monillas W.H., Yap G.P.A., Theopold K.H. Angew. Chem. Int. Ed. 2007, 46:6692.
85. Benard M., Rohmer M.M., Lopez X., Theopold K.H. Angew. Chem. Int. Ed. 2008, 47:5597.
86. Kohn R.D. Angew. Chem. Int. Ed. 2008, 47:245.
87. Blom B., Klatt G.n., Fletcher J.C.Q., Moss J.R. Inorg. Chim. Acta 2007, 360:2890.
88. Tomov A.K., Chirinos J.J., Jones D.J., Long R.J., Gibson V.C. J. Am. Chem. Soc. 2005, 127:10166.
89. Tomov A.K., Chirinos J.J., Long R.J., Gibson V.C., Elsegood M.R.J. J. Am. Chem. Soc. 2006, 128:7704.
90. Tomov A.K., Gibson V.C., Britovsek G.J.P., Long R.J., van Meurs M., Jones D.J., Tellmann K.P., Chirinos J.J. Organometallics 2009, 28:7033.
91. McGuinness D.S., Suttil J.A., Gardiner M.G., Davies N.W. Organometallics 2008, 27:4238.
92. Zhang S., Jie S.Y., Shi Q.S., Sun W.H. J. Mol. Catal. A: Chem. 2007, 276:174.
93. Amolegbe S.A., Asma M., Zhang M., Li G., Sun W.H. Aus. J. Chem. 2008, 61:397.
94. Gao R., Liang T.L., Wang F.S., Sun W.H. J. Organomet. Chem. 2009, 694:3701.
95. Zhang M., Wang K.F., Sun W.H. Dalton Trans. 2009, 6354.
96. Xiao L.W., Zhang M., Sun W.H. Polyhedron 2010, 29:142.
97. Bowen L.E., Wass D.F. Organometallics 2006, 25:555.
98. Bowen L.E., Charernsuk M., Hey T.W., McMullin C.L., Orpen A.G., Wass D.F. Dalton Trans. 2010, 39:560.
99. McGuinness D.S. Organometallics 2009, 28:244.
100. Bowen L.E., Charernsuk M., Wass D.F. Chem. Commun. 2007, 2835.
101. Hey T.W., Wass D.F. Organometallics 2010, 29:3676.
102. Son K.S., Waymouth R.M. Organometallics 2010, 29:3515.
103. Cossee P. J. Catal. 1964, 3:80.
104. Flory P.J. J. Am. Chem. Soc. 1940, 62:1561.
105. Schulz G.V. Zeitschrift Fur Physikalische Chemie-Abteilung B-Chemie Der Elementarprozesse Aufbau Der Materie 1935, 30:379.
106. Schulz G.V. Zeitschrift Fur Physikalische Chemie-Abteilung B-Chemie Der Elementarprozesse Aufbau Der Materie 1939, 43:25.
107. Skupinska J. Chem. Rev. 1991, 91:613.
108. McDermott J.X., White J.F., Whitesides G.M. J. Am. Chem. Soc. 1976, 98:6521.
109. Yu Z.X., Houk K.N. Angew. Chem. Int. Ed. Engl. 2003, 42:808.
110. Blok A.N.J., Budzelaar P.H.M., Gal A.W. Organometallics 2003, 22:2564.
111. de Bruin T.J.M., Magna L., Raybaud P., Toulhoat H. Organometallics 2003, 22:3404.
112. de Bruin T., Raybaud P., Toulhoat H. Organometallics 2008, 27:4864.
113. Tobisch S., Ziegler T. Organometallics 2003, 22:5392.
114. Tobisch S., Ziegler T. J. Am. Chem. Soc. 2004, 126:9059.
115. Tobisch S., Ziegler T. Organometallics 2004, 23:4077.
116. Tobisch S., Ziegler T. Organometallics 2005, 24:256.
117. MacAdams L.A., Buffone G.P., Incarvito C.D., Golen J.A., Rheingold A.L., Theopold K.H. Chem. Commun. 2003, 1164.
118. Jolly P.W. Acc. Chem. Res. 1996, 29:544.
119. Balakrishna M.S., Reddy V.S., Krishnamurthy S.S., Nixon J.F., Stlaurent J. Coord. Chem. Rev. 1994, 129:1.
120. Walsh R., Morgan D.H., Bollmann A., Dixon J.T. Appl. Catal. A: Gen. 2006, 306:184.
121. Kuhlmann S., Paetz C., Hagele C., Blann K., Walsh R., Dixon J.T., Scholz J., Haumann M., Wasserscheid P. J. Catal. 2009, 262:83.
122. Yang Y., Kim H., Lee J., Paik H., Jang H.G. Appl. Catal. A: Gen. 2000, 193:29.
123. Hagen H. Ind. Eng. Chem. Res. 2006, 45:3544.
124. Hanton M.J., Daubney L., Lebl T., Polas S., Smith D.M., Willemse A. Dalton Trans. 2010, 39:7025.
125. Wright W.R.H., Batsanov A.S., Howard J.A.K., Tooze R.P., Hanton M.J., Dyer P.W. Dalton Trans. 2010, 39:7038.
126. Peuckert M., Keim W. Organometallics 1983, 2:594.
127. van Leeuwen P.W.N.M., Clément N.D., Tschan M.J.L. Coord. Chem. Rev. 2010, doi:10.1016/j.ccr.2010.10.009.