REVIEW

Advances in Mechanistic Research of Ethylene Selective Oligomeri-zation Catalyzed by Homogeneous Chromium-Based Catalysts

  • Song Chuang ,
  • Mao Guoliang ,
  • Liu Zhenhua ,
  • Ning Yingnan ,
  • Jiang Tao
Expand
  • a Provincial Key Laboratory of Oil & Gas Chemical Technology, College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318;
    b College of Material Science and Chemical Engineering, Tianjin University of Science & Technology, Tianjin 300222

Received date: 2016-02-29

  Revised date: 2016-04-21

  Online published: 2016-05-03

Supported by

Project supported by the National Natural Science Foundation of China (Nos.51534004, U1362110), and the Program for New Century Excellent Talents in University (No.NCET-07-0142).

Abstract

Linear α-olefin is an important feed stock for chemical industry. Production of specific α-olefin through selective ethylene oligomerization catalyzed by homogeneous chromium-based catalysts is an important research on orientation under rapid development in recent years. The research of catalytic mechanism plays an important role in guiding the exploration of novel high-efficient catalysts. The application of methods such as labelled atom, organometallic precursor, EPR-XAS, density functional theory (DFT) calculation etc. in the research of reaction path and the metal oxidation state is introduced, with the latest achievement in the mechanistic research summarized. Research works carried out by various researchers are compared and discussed from methodology. New perspective on binuclear Cr metal ring mechanistic research is proposed and an outlook on the further research orientation is presented.

Cite this article

Song Chuang , Mao Guoliang , Liu Zhenhua , Ning Yingnan , Jiang Tao . Advances in Mechanistic Research of Ethylene Selective Oligomeri-zation Catalyzed by Homogeneous Chromium-Based Catalysts[J]. Chinese Journal of Organic Chemistry, 2016 , 36(9) : 2105 -2120 . DOI: 10.6023/cjoc201602034

References

[1] Skupinska,J.Chem.Rev.1991,91,613.
[2] Forestière A.;Olivier-Bourbigou H.;Saussine L.Oil Gas Sci.Technol.2009,64,649.
[3] Qian,B.Z.Petrochem.Ind.Technol.2011,18,58(in Chinese). (钱伯章,石化技术,2011,18,58.)
[4] Jin,W.Petroleum.Knowl.2014,4,24(in Chinese). (金文,石油知识,2014,4,24.)
[5] Carter,A.;Cohen,S.A.;Cooley,N.A.;Murphy,A.;Scutt,J.;Wass,D.F.Chem.Commun.2002,8,858.
[6] Commereuc,D.;Chauvin,Y.;Gaillard,J.;Leonard,J.;Andrews,J.Hydrocarbon Process.1984,63,118.
[7] Al-Jarallah,A.M.;Anabtawi,J.A.;Siddiqui,M.A.B.;Aitani,A.M.;Al-Sa'doun,A.W.Catal.Today 1992,14,1.
[8] Pillai,S.M.;Ravindranathan,M.;Sivaram,S.Chem.Rev.1986,86,353.
[9] Al-Sherehy,F.A.Stud.Surf.Sci.Catal.1996,100,515.
[10] Van Leeuwen,P.W.;Clément,N.D.;Tschan,M.J.L.Coord.Chem.Rev.2011,255,1499.
[11] Xu,J.Y.Pet.Process.Petrochem.2014,45,67(in Chinese). (许建耘,石油炼制与化工,2014,45,67.)
[12] McGuinness,D.S.Chem.Rev.2010,111,2321.
[13] Agapie,T.Coord.Chem.Rev.2011,255,861.
[14] Bryliakov,K.P.;Talsi,E.P.Coord.Chem.Rev.2012,256,2994.
[15] Dixon,J.T.;Green,M.J.;Hess,F.M.;Morgan,D.H.J.Organomet.Chem.2004,689,3641.
[16] Belov,G.P.Pet.Chem.2012,52,139.
[17] Suttil,J.A.;McGuinness,D.S.Organometallics 2012,31,7004.
[18] Ziegler,K.;Martin,H.US 2943125,1960[Chem.Abstr.1983,54,134637].
[19] Belov,G.P.;Dzhabiev,T.S.;Kolesnikov,I.M.J.Mol.Catal.1982,14,105.
[20] Robinson Jr,R.;McGuinness,D.S.;Yates,B.F.ACS Catal.2013,3,3006.
[21] Al-Sa'doun,A.W.Appl.Catal.,A 1993,105,1.
[22] McDermott,J.X.;White,J.F.;Whitesides,G.M.J.Am.Chem.Soc.1973,95,4451.
[23] Manyik,R.M.;Walker,W.E.;Wilson,T.P.J.Catal.1977,47,197.
[24] Pettijohn,T.M.;Reagen,W.K.;Martin,S.J.US 5331070,1994[Chem.Abstr.1994,122,56808].
[25] Reagen,W.K.;Pettijohn,T.M.;Freeman,J.W.;Benham,E.A.US 5786431,1998[Chem.Abstr.1998,115,93172].
[26] Freeman,J.W.;Buster,J.L.;Knudsen,R.D.US 5919996,1999[Chem.Abstr.1999,130,95984].
[27] Briggs,J.R.J.Chem.Soc.,Chem.Commun.1989,11,674.
[28] Emrich,R.;Heinemann,O.;Jolly,P.W.,Krüger,C.;Verhovnik,G.P.Organometallics 1997,16,1511.
[29] Liu,R.;Xiao,S.M.;Zhong,X.H.;Cao,Y.C.;Liang,S.B.;Liu,Z.Y.;Ye,X.F.;Shen,A.;Zhu,H.P.Chin.J.Org.Chem.2015,35,1861(in Chinese). (刘睿,肖树萌,钟向宏,曹育才,梁胜彪,刘振宇,叶晓峰,沈安,朱红平,有机化学,2015,35,1861.)
[30] Agapie,T.;Schofer,S.J.;Labinger,J.A.;Bercaw,J.E.J.Am.Chem.Soc.2004,126,1304.
[31] Agapie,T.;Labinger,J.A.;Bercaw,J.E.J.Am.Chem.Soc.2007,129,14281.
[32] Klemps,C.;Payet,E.;Magna,L.;Saussine,L.;Le Goff,X.F.;Le Floch,P.Chem.Eur.J.2009,15,8259.
[33] Yang,Y.;Liu,Z.;Zhong,L.;Qiu,P.Y.;Dong,Q.;Cheng,R.H.;Vanderbilt,J.;Liu,B.P.Organometallics 2011,30,5297.
[34] Yu,Z.X.;Houk,K.N.Angew.Chem.,Int.Ed.2003,42,808.
[35] Qi,Y.;Dong,Q.;Zhong,L.;Liu,Z.;Qiu,P.;Cheng,R.H.;He,X.L.;Vanderbilt,J.;Liu,B.P.Organometallics 2010,29,1588.
[36] Budzelaar,P.H.Can.J.Chem.2009,87,832.
[37] Albahily,K.;Koç,E.;Al-Baldawi,D.;Savard,D.;Gambarotta,S.;Burchell,T.J.;Duchateau,R.Angew.Chem.,Int.Ed.2008,47,5816.
[38] 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.
[39] 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.
[40] Blok,A.N.;Budzelaar,P.H.;Gal,A.W.Organometallics 2003,22,2564.
[41] Britovsek,G.J.;McGuinness,D.S.;Wierenga,T.S.;Young,C.T.ACS Catal.2015,5,4152.
[42] Young,J.F.;Yap,G.Theopold,K H.In INOR 554-Reactivity of Chromium (Ⅱ) Bimetallocycles and Their Role in Ethylene Trimerization,Abstracts of Papers of the 234th ACS National Meeting,American Chemical Society,America,2007,p.234.
[43] Peitz,S.;Aluri,B.R.;Peulecke,N.;Müller,B.H.;Wöhl,A.;Müller,W.;Al-Hazmi,M.H.;Mosa,F.M.;Rosenthal,U.Chem.Eur.J.2010,16,7670.
[44] Breslow,D.S.;Newburg,N.R.J.Am.Chem.Soc.1957,79,5072.
[45] Long,W.P.;Breslow,D.S.J.Am.Chem.Soc.1960,82,1953.
[46] Lee,P.Y.;Liang,L.C.Inorg.Chem.2009,48,5480.
[47] Long,W.P.J.Am.Chem.Soc.1959,81,5312.
[48] Chien,J.C.J.Am.Chem.Soc.1959,81,86.
[49] Zefirova,A.K.;Shilov,A.E.Dokl.Akad.Nauk SSSR 1961,136,599.
[50] Dyachkovskii,F.S.;Shilova,A.K.;Shilov,A.E.J.Polym.Sci.,Part C:Polym.Symp.1967,16,2333.
[51] Jabri,A.;Crewdson,P.;Gambarotta,S.;Korobkov,I.;Duchateau,R.Organometallics 2006,25,715.
[52] 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.
[53] McGuinness,D.S.;Brown,D.B.;Tooze,R.P.;Hess,F.M.;Dixon,J.T.;Slawin,A.M.Organometallics 2006,25,3605.
[54] Temple,C.;Jabri,A.;Crewdson,P.;Gambarotta,S.;Korobkov,I.;Duchateau,R.Angew.Chem.2006,118,7208.
[55] Zhang,J.;Li,A.;Hor,T.A.Organometallics 2009,28,2935.
[56] Yoshida,T.;Yamamoto,T.;Okada,H.;Murakita,H.US 0035029,2002[Chem.Abstr.2002,136,249387].
[57] McGuinness,D.S.;Overett,M.;Tooze,R.P.;Blann,K.;Dixon,J.T.;Slawin,A.M.Organometallics 2007,26,1108.
[58] Deckers,P.J.;van der Linden,A.J.;Meetsma,A.;Hessen,B.Eur.J.Inorg.Chem.2000,5,929.
[59] Jabri,A.;Mason,C.B.;Sim,Y.;Gambarotta,S.;Burchell,T.J.;Duchateau,R.Angew.Chem.,Int.Ed.2008,47,9717.
[60] Vidyaratne,I.;Nikiforov,G.B.;Gorelsky,S.I.;Gambarotta,S.;Duchateau,R.;Korobkov,I.Angew.Chem.,Int.Ed.2009,48,6552.
[61] Reagan,W.K.EP 0417477,1991[Chem.Abstr.1991,115,93172].
[62] Evans,D.F.J.Chem.Soc.1959,2003.
[63] Rucklidge,A.J.;McGuinness,D.S.;Tooze,R.P.;Slawin,A.M.;Pelletier,J.D.;Hanton,M.J.;Webb,P.B.Organometallics 2007,26,2782.
[64] Brückner,A.;Jabor,J.K.;McConnell,A.E.;Webb,P.B.Organometallics 2008,27,3849.
[65] Skobelev,I.Y.;Panchenko,V.N.;Lyakin,O.Y.;Bryliakov,K.P.;Zakharov,V.A.;Talsi,E.P.Organometallics 2010,29,2943.
[66] Freeman,J.W.;Buster,J.L.;Knudsen,R.D.US 5856257,1999[Chem.Abstr.1999,130,95984].
[67] Rabeah,J.;Bauer,M.;Baumann,W.;McConnell,A.E.;Gabrielli,W.F.;Webb,P.B.;Selent,D.;Bruckner,A.ACS Catal.2012,3,95.
[68] Weckhuysen,B.M.;Schoonheydt,R.A.;Jehng,J.M.;Wachs,I.E.;Cho,S.J.;Ryoo,R.;Kijlstra,S.;Poels,E.J.Chem.Soc.,Faraday Trans.1995,91,3245.
[69] Monillas,W.H.;Yap,G.;Theopold,K.H.Angew.Chem.,Int.Ed.2007,46,6692.
[70] Poli,R.;Harvey,J.N.Chem.Soc.Rev.2003,32,1.
[71] Köhn,R.D.Angew.Chem.,Int.Ed.2008,47,245.
[72] Bhaduri,S.;Mukhopadhyay,S.;Kulkarni,S.A.J.Organomet.Chem.2009,694,1297.
[73] Janse van Rensburg,W.;van den Berg,J.A.;Steynberg,P.J.Organometallics 2007,26,1000.
[74] McGuinness,D.S.;Chan,B.;Britovsek,G.J.;Yates,B.F.Aust.J.Chem.2014,67,1481.
[75] Tang,S.Y.;Liu,Z,;Zhan,X.W.;Cheng,R.H.;He,X.L.;Liu,B.P.J.Chem.Eng.2014,65,131(in Chinese). (唐思扬,刘振,占兴稳,程瑞华,何雪莲,刘柏平,化工学报,2014,65,131.)
[76] Mason,M.R.;Smith,J.M.;Bott,S.G.;Barron,A.R.J.Am.Chem.Soc.1993,115,4971.
[77] Harlan,C.J.;Mason,M.R.;Barron,A.R.Organometallics 1994,13,2957.
[78] Babushkin,D.E.;Semikolenova,N.V.;Panchenko,V.N.;Sobolev,A.P.;Zakharov,V.A.;Talsi,E.P.Macromol.Chem.Phys.1997,198,3845.
[79] Zakharov,I.I.;Zakharov,V.A.Macromol.Theory Simul.2001,10,108.
[80] Pasha,F.A.;Basset,J.M.;Toulhoat,H.;de Bruin,T.Organometallics 2015,34,426.
[81] Grubbs,R.H.;Coates,G.W.Acc.Chem.Res.1996,29,85.
[82] Harvey,J.N.;Poli,R.;Smith,K.M.Coord.Chem.Rev.2003,238,347.
[83] Salomon,O.;Reiher,M.;Hess,B.A.J.Chem.Phys.2002,117,4729.
[84] Reiher,M.;Salomon,O.;Hess,B.A.Theor.Chim.Acta 2001,107,48.
[85] Tomov,A.K.;Chirinos,J.J.;Jones,D.J.;Long,R.J.;Gibson,V.C.J.Am.Chem.Soc.2005,127,10166.
[86] Tomov,A.K.;Chirinos,J.J.;Long,R.J.;Gibson,V.C.;Elsegood,M.R.J.Am.Chem.Soc.2006,128,7704.
[87] Blann,K.;Bollmann,A.;de Bod,H.;Dixon,J.T.;Killian,E.;Nongodlwana,P.;Maumela,M.C.;Maumela,H.;McConnell,A.E.;Morgan,D.H.;Overett,M.J.;Prétoriusa,M.;Kuhlmannb,S.;Wasserscheidb,P.J.Catal.2007,249,244.
[88] Overett,M.J.;Blann,K.;Bollmann,A.;de Villiers,R.;Dixon,J.T.;Killian,E.;Maumela,M.C.;Maumela,H.McGuineess,D.S.;Morgan,D.H.;Rucklidge,A.;Slawin,A.M.Z.J.Mol.Catal.A:Chem.2008,283,114.
[89] Jiang,T.;Liu,X.Y.;Ning,Y.N.;Chen,H.X.;Luo,M.J.;Wang,L.B.;Huang,Z.J.Catal.Commun.2007,8,1145.
[90] McGuinness,D.S.;Rucklidge,A.J.;Tooze,R.P.;Slawin,A.M.Organometallics 2007,26,2561.
[91] Chen,H.X.;Liu,X.Y.;Hu,W.B.;Ning,Y.N.;Jiang,T.J.Mol.Catal.A:Chem.2007,270,273.
[92] Kuhlmann,S.;Blann,K.;Bollmann,A.;Dixon,J.T.;Killian,E.;Maumela,M.C.;Maumela,H.;Morgan,D.H.;Prétoriusb,M.;Taccardia,N.;Wasserscheid,P.J.Catal.2007,245,279.
[93] 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.
[94] Killian,E.;Blann,K.;Bollmann,A.;Dixon,J.T.;Kuhlmann,S.;Maumela,M.C.;Maumela,H.;Morgan,D.H.;Nongodlwanaa,P.;Overetta,M.J.;Pretoriusa,M.;Höfenerb,K.;Wasserscheidb,P.J.Mol.Catal.A:Chem.2007,270,214.
[95] Jiang,T.;Zhang,S.;Jiang,X.L.;Yang,C.F.;Niu,B.;Ning,Y.N.J.Mol.Catal.A:Chem.2008,279,90.
[96] Kuhlmann,S.;Dixon,J.T.;Haumann,M.;Morgan,D.H.;Ofili,J.;Spuhl,O.;Taccardi,N.;Wasserscheid,P.Adv.Synth.Catal.2006,348,1200.
[97] 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.2005,5,622.
[98] Mao,G.L.;Ning,Y.N.;Hu,W.B.;Li,S.M.;Song,X.F.;Niu,B.;Jiang,T.Chin.Sci.Bull.2008,53,3511.
[99] Aluri,B.R.;Peulecke,N.;Müller,B.H.;Peitz,S.;Spannenberg,A.;Hapke,M.;Rosenthal,U.Organometallics 2010,29,226. (Cheng,F.)

Outlines

/