氮配位单茂金属烯烃聚合催化剂
|
摘要
本文综述了近些年来以含氮基团为阴离子配体的单茂金属化合物作为烯烃精确聚合的催化剂的研究。氮配位单茂金属催化剂在烯烃聚合中显示出独特的特性,特别是对于乙烯的共聚合,不仅能得到Ziegler-Natta催化剂和传统茂金属催化剂不能合成的新的共聚物,还有优于其他单茂金属催化剂的共聚活性。环戊二烯基和含氮阴离子配体的改性是所得催化剂聚合效果的关键。本文涉及了乙烯均聚以及乙烯与α-烯烃(己烯-1、辛烯-1等)、苯乙烯和环烯烃(降冰片烯、四环十二碳烯等)的共聚合。
The recent study of the half-metallocene compounds ligated with nitrogen-containing groups as catalysts for precise olefin polymerization has been reviewed in this article. Studies have found that these nitrogen-coordinated catalysts exhibit unique properties in the polymerization of olefin monomers, especially for the copolymerization of ethylene. These catalysts can not only obtain new copolymers, which cannot be synthesized by Ziegler-Natta catalysts and traditional metallocene catalysts, but also show the copolymerization activities superior to other half-metallocene catalysts. Modification of both cyclopentadienyl fragments and anionic ancillary donor ligands is the key for the improvement of polymerization behaviors. This article relates to the homopolymerization of ethylene and the copolymerization of ethylene with α-olefins(hexene-1, octene-1, etc.), styrene and cyclic olefins(norbornene, tetracyclododecene, etc).
The recent study of the half-metallocene compounds ligated with nitrogen-containing groups as catalysts for precise olefin polymerization has been reviewed in this article. Studies have found that these nitrogen-coordinated catalysts exhibit unique properties in the polymerization of olefin monomers, especially for the copolymerization of ethylene. These catalysts can not only obtain new copolymers, which cannot be synthesized by Ziegler-Natta catalysts and traditional metallocene catalysts, but also show the copolymerization activities superior to other half-metallocene catalysts. Modification of both cyclopentadienyl fragments and anionic ancillary donor ligands is the key for the improvement of polymerization behaviors. This article relates to the homopolymerization of ethylene and the copolymerization of ethylene with α-olefins(hexene-1, octene-1, etc.), styrene and cyclic olefins(norbornene, tetracyclododecene, etc).
引文
[1] Gladysz J A.Chem.Rev.,2000,100(4):1167.
[2] Gibson V C,Spitzmesser S K.Chem.Rev.,2003,103(1):283.
[3] Rodriguez-Delgado A,Chen E Y X.Macromolecules,2005,38(7):2587.
[4] Kaminsky W.Adv.Catal.,2001,46(02):89.
[5] Klosin J,Fontaine P P,Figueroa R.Acc.Chem.Res.,2015,48(7):2004.
[6] Collins R A,Russell A F,Mountford P.Appl.Petrochem.Res.,2015,5(3):153.
[7] Alt H G,Koppl A.Chem.Rev.,2000,100(4):1205.
[8] Nomura K,Liu J Y,Padmanabhan S,Kitiyanan B.J.Mol.Catal.A:Chem.,2007,267:1.
[9] Makio H,Terao H,Iwashita A,Fujita T,.Chem.Rev.,2011,111:2363.
[10] Ittel S D,Johnson L K,Brookhart M.Chem.Rev.,2000,100(4):1169.
[11] McKnight A L,Waymouth R M.Chem.Rev.,2010,30(4):2587.
[12] Nomura K,Naga N,Miki M,Yanagi K,Imai A.Organometallics,1998,17(11):2152.
[13] Stephan D W,Guérin F,Spence R E V H,Koch L,Gao X,Brown S J,Swabey J W,Wang Q,Xu W,Zoricak P,Harrison D G.Organometallics,2000,18(11):2046.
[14] Kretschmer W P,Dijkhuis C,Meetsma A,Hessen B,Teuben J H.Chem.Commun.,2002,114(6):608.
[15] Zhang S,Piers W E,Gao X,Parvez M.J.Am.Chem.Soc.,2000,122(23):5499.
[16] Jayaratne K C,Sita L R.J.Am.Chem.Soc.,2000,122(5):958.
[17] Wang W,Zheng G,Wang H T.e-Polymers,2014,14:277.
[18] 王伟(Wang W),郑刚(Zheng G).化学进展(Progress in Chemistry),2009,21(4):677.
[19] Rusli W,Tay B Y,Stubbs L P,Meurs M V,Tan J,Jacob C,Chia S C,Woo Y L,Wang C.J.Organomet.Chem.,2011,696(11):2414.
[20] Dureen M A,Brown C C,Morton J G,Stephan D W.Dalton Trans.,2011,40(12):2861.
[21] Rajesh A,Sivaram S.Polymer.Eng.Sci.,2011,51(10):2103.
[22] 米普科(Mi P K),孔晓娟(Kong X J),许胜(Xu S),朱玉玲(Zhu Y L),任迎春(Ren Y C).分子催化(Journal of Molecular Catalysis(China)),2012,26(6):493.
[23] Nomura K,Fujii K.Macromolecules,2003,36(8):2633.
[24] Liu,K,Wu Qn,Gao W,Mu Y,Ye L.Eur.J.Inorg.Chem.,2011(12):1901.
[25] Saeed I,Katao S,Nomura K.Organometallics,2009,28(1):111.
[26] Narayana G V,Xu G,Wang D,Frey W,Buchmeiser M R.ChemPlusChem,2014,79(1):151.
[27] Narayana G V,Xu G,Wang D,Speiser M,Frey W,Buchmeiser M R.Macromol.Chem.Phys.,2014,215(20):2007.
[28] Xu G,Narayana G V,Speiser M,Wang D,Zhou Y L,Buchmeiser M R.Macromol.Chem.Phys.,2014,215(9):893.
[29] Park J H,Do S H,Cyriac A,Yun H,Lee B Y.Dalton Trans.,2010,39(41):9994.
[30] Kim S H,Park J H,Song B G,Yoon S W,Go M J,Lee J S,Lee B Y.Catalysts,2013,3:104.
[31] Dias A R,Duarte M T,Fernandes A C,Fernandes S,Marques M M,Martins A M,Silva J F,Rodrigues S S.J.Organomet.Chem.,2004,689(1):203.
[32] Nomura K,Fujita K,Fujiki M.J.Mol.Catal.A,2004,220(2):133.
[33] Nomura K,Yamada J,Wang W,Liu J.J.Organomet.Chem.,2007,692(21):4675.
[34] Itagaki K,Nomura K.Macromolecules,2009,42(14):5097.
[35] Nomura K,Kakinuki K,Fujiki M,Itagaki K.Macromolecules,2008,41(23):8974.
[36] Zhao W,Nomura K.Macromolecules,2016,49(1):59.
[37] Zhang H,Nomura K.J.Am.Chem.Soc.,2005,127(26):9364.
[38] Park E S,Ji H P,Yun H,Lee B Y.J.Organomet.Chem.,2011,696(11):2451.
[39] Nomura K,Fukuda H,Katao S,Fujiki M,Kim H J,Kim DH,Zhang S.Dalton Trans.,2011,40(31):7842.
[40] Nomura K,Fukuda H,Apisuk W,Trambitas A J,Kitiyanan B,Tamm M.J.Mol.Catal.A.,2012,363-364(12):501.
[41] Nomura K,Fukuda H,Matsuda H,Katao S,Patamma S.J.Organomet.Chem.,2015,798:375.
[42] Nomura K,Patamma S,Matsuda H,Katao S,Tsutsumia K,Fukudab H.RSC Adv.,2015,5(79):64503.
[43] Apisuk W,Trambitas A G,Kitiyanan B,Tamm M,Nomura K.J.Polym.Sci.A,2013,51(12):2575.
[44] Apisuk W,Ito H,Nomura K.J.Polym.Sci.A,2016,54(17):2662.
[45] Stelzig S H,Tamm M,Waymouth R M.J.Polym.Sci.A,2008,46(18):6064.
[46] Ijpeij E G,Coussens B,Zuideveld M A,Doremaele GH,Mountford P,Lutz M,Spek AL.Chem.Commun.,2010,46(19):3339.
[47] Collins R A,Russell A F,Scott R T W,Bernardoet R,Doremaele G H J,Berthoud A,Mountford P.Organometallics,2017,36:2167.
[48] Varga V,Ve■e■a M,Gyepes R,Pinkas J,Horá■ek M,Merna J,Lama■ M.Chemcatchem,2017,9(16):3270.
[49] Stephan D W,Stewart J C,Guérin F,Spence R E H,Xu W,Harrison D G.Organometallics,1999,18(7):1116.
[50] Spence R E H,Stephan D W,Brown S J,Wurz R P,Jeremic D.US 6355744,2000.
[51] Carraz C A,Stephan D W.Organometallics,2000,19(19):3791.
[52] Yue N L S,Stephan D W.Organometallics,2001,20(11):2303.
[53] Stephan D W,Stewart J C,Guérin F,Courtenay S,Kickham J,Hollink E,Beddie C,Hoskin A,Graham T,Wei PR,Spence R E H,Xu W,Koch L,Gao X L,Harrison D G.Organometallics,2003,22(9):1937.
[54] Hollink E,Wei P,Stephan D W.Organometallics,2004,23(7):1562.
[55] Alhomaidan O,Bai G,Stephan D W.Organometallics,2008,27(27):6343.
[56] Ramos A,Stephan D W.Dalton Trans.,2010,39(5):1328.
[57] Yadav K,McCahill J S,Bai G,Stephan D W.Dalton Trans,2009,9(9):1636.
[58] Hollink E,Wei P,Stephan D W.Can.J.Chem.,2004,82(8):1304.
[59] Beddie C,Wei P,Stephan D W.Can.J.Chem.,2006,84(5):755.
[60] Huang J L,Lian B,Qian Y L,Zhou W Z,Chen W,Zheng G.Macromolecules,2002,35(13):4871.
[61] Yan Q,Yang W H,Chen L Q,Wang L,Redshaw C,Sun W H.J.Organomet.Chem.,2014,753(1):34.
[62] Huang W,Sun W H,Redshaw C.Dalton Trans.,2011,40(25):6802.
[63] Huang W,Li B X,Wang Y H,Zhang W J,Wang L,Li Y S,Sun W H,Redshaw C.Catal.Sci.Technol.,2011,1:1208.
[64] Huang W,Zhang W J,Sun W H,Wang L,Redshaw C.Catal.Sci.Technol.,2012,2(10):2090.
[65] Zuo W W,Zhang M,Sun W H.J.Polym.Sci.A,2009,47(2):357.
[66] Liu S R,Li B X,Liu J Y,Li Y S.Polymer,2010,51(9):1921.
[67] Shi X C,Jin G X.Dalton Trans.,2011,40(44):11914.
[68] Qiao Y L,Hu P,Jin G X.Chinese J.Polym.Sci.,2013,31(5):760.
[69] Larocque T G,Dastgir S,Lavoie G G.Organometallics,2013,32(15):4314.
[70] Bott R K J,Hughes D L,Bochmann M,Schormann M,Lancaster S.J.Organomet.Chem.,2003,665(1/2):135.
[71] Chen Q H,Huang J L,Yu J.Inorg.Chem.Commun.,2005,8(5):444.
[72] Coles S R,Clarkson G J,Gott A L,Munslow L J,Spitzmesser S K,Scott P.Organometallics,2006,25(26):6019.
[73] Zhang J,Lin Y J,Jin G X.Organometallics,2007,26(16):4042.
[74] Zhang H,Katao S,Nomura K,Huang J L.Organometallics,2007,26(24):5967.
[75] Zuo W W,Zhang S,Sun W H.J.Polym.Sci.A,2008,46(10):3396.
[76] Zhang W J,Huang W,Liang T L,Sun W H.Chinese J.Polym.Sci.,2013,31(4):601.
[77] Zhang Q,Tao X,Gao W,Song T T,Mu Y.J.Organomet.Chem.,2016,804:18.
[78] Qi C H,Zhang S B,Sun J H.J.Organomet.Chem.,2005,690(12):2941.
[79] Dove A P,Xie X,Waymouth R M.Chem.Commun.,2005,(16):2152.
[80] Dove A P,Kiesewetter E T,Ottenwaelder X,Waymouth R M.Organometallics,2009,28(2):405.
[81] Liu S,Sun W H,Zeng Y,Wang D,Zhang W J,Li Y.Organometallics,2010,29(11):2459.
[82] Harkness M B,Alvarado E,Badaj A C,Skrela B C,Fan L,Lavoie G G.Organometallics,2013,32(11):3309.
[83] Nomura K,Fukuda H,Katao S,Fujiki M,Kim H J,Kim D H,Saeed I.Macromolecules,2011,44(7):1986.
[2] Gibson V C,Spitzmesser S K.Chem.Rev.,2003,103(1):283.
[3] Rodriguez-Delgado A,Chen E Y X.Macromolecules,2005,38(7):2587.
[4] Kaminsky W.Adv.Catal.,2001,46(02):89.
[5] Klosin J,Fontaine P P,Figueroa R.Acc.Chem.Res.,2015,48(7):2004.
[6] Collins R A,Russell A F,Mountford P.Appl.Petrochem.Res.,2015,5(3):153.
[7] Alt H G,Koppl A.Chem.Rev.,2000,100(4):1205.
[8] Nomura K,Liu J Y,Padmanabhan S,Kitiyanan B.J.Mol.Catal.A:Chem.,2007,267:1.
[9] Makio H,Terao H,Iwashita A,Fujita T,.Chem.Rev.,2011,111:2363.
[10] Ittel S D,Johnson L K,Brookhart M.Chem.Rev.,2000,100(4):1169.
[11] McKnight A L,Waymouth R M.Chem.Rev.,2010,30(4):2587.
[12] Nomura K,Naga N,Miki M,Yanagi K,Imai A.Organometallics,1998,17(11):2152.
[13] Stephan D W,Guérin F,Spence R E V H,Koch L,Gao X,Brown S J,Swabey J W,Wang Q,Xu W,Zoricak P,Harrison D G.Organometallics,2000,18(11):2046.
[14] Kretschmer W P,Dijkhuis C,Meetsma A,Hessen B,Teuben J H.Chem.Commun.,2002,114(6):608.
[15] Zhang S,Piers W E,Gao X,Parvez M.J.Am.Chem.Soc.,2000,122(23):5499.
[16] Jayaratne K C,Sita L R.J.Am.Chem.Soc.,2000,122(5):958.
[17] Wang W,Zheng G,Wang H T.e-Polymers,2014,14:277.
[18] 王伟(Wang W),郑刚(Zheng G).化学进展(Progress in Chemistry),2009,21(4):677.
[19] Rusli W,Tay B Y,Stubbs L P,Meurs M V,Tan J,Jacob C,Chia S C,Woo Y L,Wang C.J.Organomet.Chem.,2011,696(11):2414.
[20] Dureen M A,Brown C C,Morton J G,Stephan D W.Dalton Trans.,2011,40(12):2861.
[21] Rajesh A,Sivaram S.Polymer.Eng.Sci.,2011,51(10):2103.
[22] 米普科(Mi P K),孔晓娟(Kong X J),许胜(Xu S),朱玉玲(Zhu Y L),任迎春(Ren Y C).分子催化(Journal of Molecular Catalysis(China)),2012,26(6):493.
[23] Nomura K,Fujii K.Macromolecules,2003,36(8):2633.
[24] Liu,K,Wu Qn,Gao W,Mu Y,Ye L.Eur.J.Inorg.Chem.,2011(12):1901.
[25] Saeed I,Katao S,Nomura K.Organometallics,2009,28(1):111.
[26] Narayana G V,Xu G,Wang D,Frey W,Buchmeiser M R.ChemPlusChem,2014,79(1):151.
[27] Narayana G V,Xu G,Wang D,Speiser M,Frey W,Buchmeiser M R.Macromol.Chem.Phys.,2014,215(20):2007.
[28] Xu G,Narayana G V,Speiser M,Wang D,Zhou Y L,Buchmeiser M R.Macromol.Chem.Phys.,2014,215(9):893.
[29] Park J H,Do S H,Cyriac A,Yun H,Lee B Y.Dalton Trans.,2010,39(41):9994.
[30] Kim S H,Park J H,Song B G,Yoon S W,Go M J,Lee J S,Lee B Y.Catalysts,2013,3:104.
[31] Dias A R,Duarte M T,Fernandes A C,Fernandes S,Marques M M,Martins A M,Silva J F,Rodrigues S S.J.Organomet.Chem.,2004,689(1):203.
[32] Nomura K,Fujita K,Fujiki M.J.Mol.Catal.A,2004,220(2):133.
[33] Nomura K,Yamada J,Wang W,Liu J.J.Organomet.Chem.,2007,692(21):4675.
[34] Itagaki K,Nomura K.Macromolecules,2009,42(14):5097.
[35] Nomura K,Kakinuki K,Fujiki M,Itagaki K.Macromolecules,2008,41(23):8974.
[36] Zhao W,Nomura K.Macromolecules,2016,49(1):59.
[37] Zhang H,Nomura K.J.Am.Chem.Soc.,2005,127(26):9364.
[38] Park E S,Ji H P,Yun H,Lee B Y.J.Organomet.Chem.,2011,696(11):2451.
[39] Nomura K,Fukuda H,Katao S,Fujiki M,Kim H J,Kim DH,Zhang S.Dalton Trans.,2011,40(31):7842.
[40] Nomura K,Fukuda H,Apisuk W,Trambitas A J,Kitiyanan B,Tamm M.J.Mol.Catal.A.,2012,363-364(12):501.
[41] Nomura K,Fukuda H,Matsuda H,Katao S,Patamma S.J.Organomet.Chem.,2015,798:375.
[42] Nomura K,Patamma S,Matsuda H,Katao S,Tsutsumia K,Fukudab H.RSC Adv.,2015,5(79):64503.
[43] Apisuk W,Trambitas A G,Kitiyanan B,Tamm M,Nomura K.J.Polym.Sci.A,2013,51(12):2575.
[44] Apisuk W,Ito H,Nomura K.J.Polym.Sci.A,2016,54(17):2662.
[45] Stelzig S H,Tamm M,Waymouth R M.J.Polym.Sci.A,2008,46(18):6064.
[46] Ijpeij E G,Coussens B,Zuideveld M A,Doremaele GH,Mountford P,Lutz M,Spek AL.Chem.Commun.,2010,46(19):3339.
[47] Collins R A,Russell A F,Scott R T W,Bernardoet R,Doremaele G H J,Berthoud A,Mountford P.Organometallics,2017,36:2167.
[48] Varga V,Ve■e■a M,Gyepes R,Pinkas J,Horá■ek M,Merna J,Lama■ M.Chemcatchem,2017,9(16):3270.
[49] Stephan D W,Stewart J C,Guérin F,Spence R E H,Xu W,Harrison D G.Organometallics,1999,18(7):1116.
[50] Spence R E H,Stephan D W,Brown S J,Wurz R P,Jeremic D.US 6355744,2000.
[51] Carraz C A,Stephan D W.Organometallics,2000,19(19):3791.
[52] Yue N L S,Stephan D W.Organometallics,2001,20(11):2303.
[53] Stephan D W,Stewart J C,Guérin F,Courtenay S,Kickham J,Hollink E,Beddie C,Hoskin A,Graham T,Wei PR,Spence R E H,Xu W,Koch L,Gao X L,Harrison D G.Organometallics,2003,22(9):1937.
[54] Hollink E,Wei P,Stephan D W.Organometallics,2004,23(7):1562.
[55] Alhomaidan O,Bai G,Stephan D W.Organometallics,2008,27(27):6343.
[56] Ramos A,Stephan D W.Dalton Trans.,2010,39(5):1328.
[57] Yadav K,McCahill J S,Bai G,Stephan D W.Dalton Trans,2009,9(9):1636.
[58] Hollink E,Wei P,Stephan D W.Can.J.Chem.,2004,82(8):1304.
[59] Beddie C,Wei P,Stephan D W.Can.J.Chem.,2006,84(5):755.
[60] Huang J L,Lian B,Qian Y L,Zhou W Z,Chen W,Zheng G.Macromolecules,2002,35(13):4871.
[61] Yan Q,Yang W H,Chen L Q,Wang L,Redshaw C,Sun W H.J.Organomet.Chem.,2014,753(1):34.
[62] Huang W,Sun W H,Redshaw C.Dalton Trans.,2011,40(25):6802.
[63] Huang W,Li B X,Wang Y H,Zhang W J,Wang L,Li Y S,Sun W H,Redshaw C.Catal.Sci.Technol.,2011,1:1208.
[64] Huang W,Zhang W J,Sun W H,Wang L,Redshaw C.Catal.Sci.Technol.,2012,2(10):2090.
[65] Zuo W W,Zhang M,Sun W H.J.Polym.Sci.A,2009,47(2):357.
[66] Liu S R,Li B X,Liu J Y,Li Y S.Polymer,2010,51(9):1921.
[67] Shi X C,Jin G X.Dalton Trans.,2011,40(44):11914.
[68] Qiao Y L,Hu P,Jin G X.Chinese J.Polym.Sci.,2013,31(5):760.
[69] Larocque T G,Dastgir S,Lavoie G G.Organometallics,2013,32(15):4314.
[70] Bott R K J,Hughes D L,Bochmann M,Schormann M,Lancaster S.J.Organomet.Chem.,2003,665(1/2):135.
[71] Chen Q H,Huang J L,Yu J.Inorg.Chem.Commun.,2005,8(5):444.
[72] Coles S R,Clarkson G J,Gott A L,Munslow L J,Spitzmesser S K,Scott P.Organometallics,2006,25(26):6019.
[73] Zhang J,Lin Y J,Jin G X.Organometallics,2007,26(16):4042.
[74] Zhang H,Katao S,Nomura K,Huang J L.Organometallics,2007,26(24):5967.
[75] Zuo W W,Zhang S,Sun W H.J.Polym.Sci.A,2008,46(10):3396.
[76] Zhang W J,Huang W,Liang T L,Sun W H.Chinese J.Polym.Sci.,2013,31(4):601.
[77] Zhang Q,Tao X,Gao W,Song T T,Mu Y.J.Organomet.Chem.,2016,804:18.
[78] Qi C H,Zhang S B,Sun J H.J.Organomet.Chem.,2005,690(12):2941.
[79] Dove A P,Xie X,Waymouth R M.Chem.Commun.,2005,(16):2152.
[80] Dove A P,Kiesewetter E T,Ottenwaelder X,Waymouth R M.Organometallics,2009,28(2):405.
[81] Liu S,Sun W H,Zeng Y,Wang D,Zhang W J,Li Y.Organometallics,2010,29(11):2459.
[82] Harkness M B,Alvarado E,Badaj A C,Skrela B C,Fan L,Lavoie G G.Organometallics,2013,32(11):3309.
[83] Nomura K,Fukuda H,Katao S,Fujiki M,Kim H J,Kim D H,Saeed I.Macromolecules,2011,44(7):1986.