Selective Ethylene Oligomerization Catalyzed by the Chromium Complex Bearing N-Tetrahydrofurfuryl PNP Ligand

doi:10.6023/cjoc201703010

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2315-2321.DOI: 10.6023/cjoc201703010 Previous Articles Next Articles

Articles

N-四氢糠基PNP配体/铬催化体系及其乙烯选择性齐聚性能

刘睿^a, 钟向宏b^b, 刘振宇^b, 梁胜彪^b, 朱红平^a

a 厦门大学化学化工学院固体表面物理化学国家重点实验室厦门 361005;
b 中国石油化工股份有限公司茂名分公司茂名 525011

收稿日期:2017-03-03 修回日期:2017-05-05 发布日期:2017-05-17
通讯作者: 钟向宏, 朱红平 E-mail:zhongxh.mmsh@sinopec.com;hpzhu@xmu.edu.cn
基金资助:
国家自然科学基金面上（Nos.21473142，21673191）、创新群体基金（No.IRT_14R31）资助项目.

Selective Ethylene Oligomerization Catalyzed by the Chromium Complex Bearing N-Tetrahydrofurfuryl PNP Ligand

Liu Rui^a, Zhong Xianghong^b, Liu Zhenyu^b, Liang Shengbiao^b, Zhu Hongping^a

a State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005;
b Maoming Branch R & D Institute, SINOPEC, Maoming 525011

Received:2017-03-03 Revised:2017-05-05 Published:2017-05-17
Contact: 10.6023/cjoc201703010 E-mail:zhongxh.mmsh@sinopec.com;hpzhu@xmu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21473142, 21673191) and the Innovative Research Team Program (No. IRT_14R31).

1. Selective Ethylene Oligomerization Catalyzed by the Chromium Complex Bearing N-Tetrahydrofurfuryl PNP Ligand.PDF(971KB)

Abstract

The N-tetrahydrofurfuryl diphoshinoamine (PNP) ligand (E) was synthesized by means of two-step salt elimination reactions where separation of the two kinds of the aminyl lithium salts for the respective reactions is necessary for obtaining a high yield of E. The ligand reacted with CrCl₃(THF)₃ and Cr(CO)₆ to give P,P-chelation complexes[{Ph₂PN(CH₂OC₄H₇)-PPh₂}CrCl₂(μ-Cl)]₂ (1) and[Ph₂PN(CH₂OC₄H₇)PPh₂]Cr(CO)₄ (2), respectively. Complexes E, 1 and 2 were characterized by spectroscopy and elemental analysis, of which complex 2 was further confirmed by X-ray crystallography. Upon activation with methylaluminoxane (MAO) or AlEt₃, the catalyst systems including 1, 2, E/CrCl₃(THF)₃, E/Cr(acac)₃ and E/CrCl₂(THF)₂ were investigated. The best catalytic activity was achieved by 15.9 kg (product)/g (Cr)·h in which a selectivity of 63.6% for 1-C₈ was obtained.

Key words: chromium complexes, catalytic property, ethylene tri-/tetramerization, catalytic reaction conditions

Cite this article

Liu Rui, Zhong Xianghong, Liu Zhenyu, Liang Shengbiao, Zhu Hongping. Selective Ethylene Oligomerization Catalyzed by the Chromium Complex Bearing N-Tetrahydrofurfuryl PNP Ligand[J]. Chin. J. Org. Chem., 2017, 37(9): 2315-2321.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) McGuinness, D. S. Chem. Rev., 2011, 111, 2321.
(b) Dixon, J. T.; Green, M. J.; Hess, F. M. Morgan, D. H. J. Organomet. Chem. 2004, 689, 3641.
(c) Agapie, T. Coord. Chem. Rev., 2011, 255, 861.
(d) Qian, B. Z. Petrochem. Ind. Technol. 2011, 18, 58(in Chinese). (钱伯章, 石化技术, 2011, 18, 58.)
[2] (a) Lappin, G. Butene-1 and Other LLDPE Comonmers, Chem SysSystems, Inc, New York, 1986.
(b) Sauser, J. Alpha-olefins Applications Handbook, Marcel Dekker, New York, 1989.
(c) Britovsek, G. J. P.; Bruse, M.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J.; Redshaw, C.; Solan, G. A.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 8728.
(d) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
(e) Brookhart, B. L.; Small, M. J. Am. Chem. Soc. 1998, 120, 7143.
[3] Robert, M. M.; Albans, S. US 3300458, 1967[Chem. Abstr. 1967, 66, 66008].
[4] Manyik, R. M.; Walker, W. E.; Wilson, T. P. J. Catal. 1977, 47, 197.
[5] Freeman, J. W.; Buster, J. L.; Knudsen, R. D. Phillips Petroleum Company, US 5856257, 1999[Chem. Abstr. 1999, 130, 95984].
[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] (a) Shaikh, Y.; Albahily, K.; Sutcliffe, M.; Fomitcheva, V.; Gambarotta, S, Korobkov, I.; Duchateau, R. Angew. Chem. Int. Ed. 2012, 51, 1366.
[9] (a) 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.
(b) Jiang, T.; Zhang, S.; Jiang, X. L.; Yang, C. F.; Niu, B.; Ning, Y. N. J. Mol. Catal. A:Chem. 2008, 279, 90.
(c) Jiang, T.; Tao, Y. Q.; Gao, X. L.; Mao, G. L.; Chen, H. X.; Chen, C. G..; Ning, Y. N. Chin. Sci. Bull. 2012, 57, 1510.
(d) Zhang, J.; Wang, X.; Zhang, X.; Wu, W.; Zhang, G.; Xu, S.; Shi, M. ACS Catal. 2013, 3, 2311.
[10] Liu, R.; Xiao, S.; Zhong, X.; Cao, Y.; Liang, S.; Liu, Z.; Ye, X.; Shen, A.; Zhu, H. Chin. J. Org. Chem. 2015, 35, 1861(in Chinese).
[11] Elowe, P. R.; McCann, C.; Pringle, P. G.; Spitzmesser, S. K.; Bercaw, J. E. Organometallics 2006, 25, 5255.
[12] Maumela, M.; Blann, K.; de Bod, H. T.; Dixon, J.; Gabrielli, W.; Williams, D. B. Synthesis 2007, 3863.
[13] Dulai, A.; de Bod, H. T.; Hanton, M. J.; Smith, D. M.; Downing, S.; Mansell, S. M.; Wass, D. F. Organometallics 2009, 28, 4613.
[14] 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.
[15] Liu, R.; Zhu, K. T.; Zhong, X. H.; Li, J. C.; Liu, Z. Y.; Chen, S. B.; Zhu, H. P. Dalton Trans. 2016, 45, 17020.
[16] (a) 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.
(b) Blann, K.; Bollmann, A.; Debod, H.; Dixon, J.; Killian, E.; Nongodlwana, P.; Maumela, M.; Maumela, H.; McConnell, A.; Morgan, D. J. Catal. 2007, 249, 244.
(c) 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.
[17] Dulai, A.; McMullin, C. L.; Tenza, K.; Wass, D. F. Organometallics 2011, 30, 935.
[18] Herwig, W.; Zeiss, H. J. Org. Chem. 1958, 23, 1404.
[19] Carter, E.; Cavell, K. J.; Gabrielli, W. F.; Hanton, M. J.; Hallett, A. J.; McDyre, L.; Platts, J. A.; Smith, D. M.; Murphy, D. M. Organometallics 2013, 32, 1924.
[20] Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen:Göttingen, Germany, 1997.

N-四氢糠基PNP配体/铬催化体系及其乙烯选择性齐聚性能

Selective Ethylene Oligomerization Catalyzed by the Chromium Complex Bearing N-Tetrahydrofurfuryl PNP Ligand

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	Zehui Li, Haoyu Zou, Lincai Li, Yiling Zhao, Hongping Zhu. Synthesis and Propylene Oxide Carbonylation Hydroesterification Catalytic Property of N,O-Ligand Coordination Cobalt Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3907-3915.
[2]	Cheng Yong, Sun Lilin . Recent Progress in the Complexes Functionalized N, C Bidentate N-Heterocyclic Carbenes [J]. Chin. J. Org. Chem., 2012, (03): 511-519.