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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

Postal Subscription Code 80-969

2018 Impact Factor: 2.809

Front Chem Sci Eng    2011, Vol. 5 Issue (1) : 19-25    https://doi.org/10.1007/s11705-010-0546-1
RESEARCH ARTICLE
Polymerization of methyl methacrylate catalyzed by mono-/bis-salicylaldiminato nickel(II) complexes and methylaluminoxane
Jihong LU1, Danfeng ZHANG1(), Qian CHEN2, Buwei YU2
1. School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China; 2. Daqing Petrochemical Research Center of CNPC, Daqing 163714, China
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Abstract

Two types of salicylaldiminato-based nickel complexes, mono-ligated Ni(II) complexes ([O-C6H4-o- C(H)=N-Ar]Ni(PPh3)(Ph) (5), [O-(3,5-Br2)C6H2-o-C(H)=N-Ar]Ni(PPh3)(Ph) (6), [O-(3-t-Bu)C6H3-o-C(H)=N-Ar]Ni(PPh3)(Ph) (7)) and bis-ligated Ni(II) complexes ([O-(3,5-Br2)C6H2-o-C(H)=N-Ar]2Ni (8), [O-(3,5-Br2)C6H2-o-C(H)=N-2-C6H4(PhO)]2Ni (9), Ar=2,6-C6H3(i-Pr)2) were synthesized and characterized by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), mass spectrography (MS) and elemental analysis (EA). In the presence of methylaluminoxane (MAO) as cocatalyst, all the nickel complexes exhibited high activities for the polymerization of methyl methacrylate (MMA) and syndiotactic-rich poly(methyl methacrylate) (PMMA) was obtained. The complexes with less bulky substituents on salicylaldiminato framework possessed higher activities, while with the same salicylaldiminato, the mono-ligated nickel complexes showed higher catalytic activity than bis-ligated ones.

Keywords late transition metal catalyst      methyl methacrylate      polymerization      salicylaldiminato nickel complexes      methylaluminoxane      syndiotactic structure     
Corresponding Author(s): ZHANG Danfeng,Email:zdf93102@ecust.edu.cn   
Issue Date: 05 March 2011
 Cite this article:   
Jihong LU,Danfeng ZHANG,Qian CHEN, et al. Polymerization of methyl methacrylate catalyzed by mono-/bis-salicylaldiminato nickel(II) complexes and methylaluminoxane[J]. Front Chem Sci Eng, 2011, 5(1): 19-25.
 URL:  
https://academic.hep.com.cn/fcse/EN/10.1007/s11705-010-0546-1
https://academic.hep.com.cn/fcse/EN/Y2011/V5/I1/19
Fig.1  Synthesis of ligands - and complexes -
entryAl/Niyield /gactivityb)Mη × 10-4
1500.071.927.5
21000.8922.3125.6
31501.0225.4109.9
42001.0827.199.5
53001.1629.079.7
Tab.1  The influence of MAO/complex ratio
entryCM /( mol·L-1)yield /gactivityb)Mη × 10-4
61.250.4912.282.4
72.000.9223.0103.9
83.001.3032.4120
95.681.7744.1119
Tab.2  The influence of the monomer concentration by complex
entryTp /°Cyield /gactivityb)Mη × 10-4
1000.071.724.6
11201.0826.9117.5
12401.3132.7113.3
13601.1127.892.6
14801.0426.064.7
Tab.3  The influence of polymerization temperature by complex
entrytime /hyield /gactivityb)Mη × 10-4
150.250.1224.838.6
160.51.1411476.5
1711.3065.291.3
1821.5137.8101.3
1941.5819.8105.6
20101.648.21103.7
Tab.4  The influence of polymerization time by complex
entrysolventyield /gactivityb)Mη × 10-4
21n-hexane0.094.7115.2
22toluene1.3165.463.2
23THF
24dichloromethane2.00100105.8
Tab.5  The influence of solvents by complex
entrycomplexyield /gActivityb)Mη × 10-4tacticity
mm /%mr /%rr /%
2552.3011553.55.6817.4176.91
2660.8140.455.36.1218.9974.89
2770.7738.628.56.5220.2473.23
2880.4120.427.88.825.1466.06
2992.1810991.84.6716.6478.69
Tab.6  The influence of the complex structures
1 Boffa L S, Novak B M. Copolymerization of polar monomers with olefins using transition-metal complexes. Chemical Reviews , 2000, 100(4): 1479–1494
doi: 10.1021/cr990251u pmid:11749273
2 Ittel S D, Johnson L K, Brookhart M. Late-metal catalysts for ethylene homo- and copolymerization. Chemical Reviews , 2000, 100(4): 1169–1204
doi: 10.1021/cr9804644 pmid:11749263
3 Mecking S. Olefin polymerization by late transition metal complexes—a root of Ziegler catalysts gains new ground. Angewandte Chemie (International ed. in English) , 2001, 40(3): 534–540
doi: 10.1002/1521-3773(20010202)40:3<534::AID-ANIE534>3.0.CO;2-C pmid:11180362
4 Gibson V C, Spitzmesser S K. Advances in non-metallocene olefin polymerization catalysis. Chemical Reviews , 2003, 103(1): 283–315
doi: 10.1021/cr980461r pmid:12517186
5 Rieger B, Baugh L S, Kacker S, Striegler S. Late Transition Metal Polymerization Catalysis. Weinheim: Wiley-VCH, 2003
6 Nelkenbaum E, Kapon M, Eisen M S. Synthesis and molecular structures of neutral nickel complexes catalytic activity of (benzamidinato)(acetylacetonato)nickel for the addition polymerization of norbornene, the oligomerization of ethylene, and the dimerization of propylene. Organometallics , 2005, 24(11): 2645–2659
doi: 10.1021/om0490379
7 Johnson L K, Killian C M, Brookhart M. New Pd(I1)- and Ni(I1)-based catalysts for polymerization of ethylene and a-olefins. Journal of the American Chemical Society , 1995, 117(23): 6414–6415
doi: 10.1021/ja00128a054
8 Mecking S, Johnson L K, Wang L, Brookhart M. Mechanistic studies of the palladium-catalyzed copolymerization of ethylene and r-olefins with methyl acrylate. Journal of the American Chemical Society , 1998, 120(5): 888–899
doi: 10.1021/ja964144i
9 Liu W, Malinoski J M, Brookhart M. Ethylene polymerization and ethylene/methyl 10-undecenoate copolymerization using nickel(II) and palladium(II) complexes derived from a bulky P,O chelating ligand. Organometallics , 2002, 21(14): 2836–2838
doi: 10.1021/om0201516
10 Sun J, Shan Y, Xu Y, Cui Y, Schumann H, Hummert M. Novel cyclohexyl-substituted salicylaldiminato-nickel(II) complex as a catalyst for ethylene homopolymerization and copolymerization. Journal of Polymer Science. Part A, Polymer Chemistry , 2004, 42(23): 6071–6080
doi: 10.1002/pola.20458
11 Li X F, Li Y G, Li Y S, Chen Y X, Hu N H. Copolymerization of ethylene with methyl methacrylate with neutral nickel(II) complexes bearing β-Ketoiminato chelate ligands. Organometallics , 2005, 24(10): 2502–2510
doi: 10.1021/om049080w
12 Wang C, Friedrich S, Younkin T R, Li R T, Grubbs R H, Bansleben D A, Day M W. Neutral nickel(II)-based catalysts for ethylene polymerization. Organometallics , 1998, 17(15): 3149–3151
doi: 10.1021/om980176y
13 Younkin T R, Connor E F, Henderson J I, Friedrich S K, Grubbs R H, Bansleben D A. Neutral, single-component nickel (II) polyolefin catalysts that tolerate heteroatoms. Science , 2000, 287(5452): 460–462
doi: 10.1126/science.287.5452.460 pmid:10642541
14 Cui Y, Sun J, Wang L, Shan Y. Bulk polymerization of methyl methacrylate with dinuclear neutral nickel(II)catalyst. J Zhejiang University , 2006, 33: 80–84 (Science Edt)
15 Carlini C, Martinelli M, Raspolli G A M, Sbrana G. Copolymerization of ethylene with methyl methacrylate by Ziegler-Natta-type catalysts based on nickel salicylaldiminate/methylalumoxane systems. Macromolecular Chemistry and Physics , 2002, 203(10-11): 1606–1613
doi: 10.1002/1521-3935(200207)203:10/11<1606::AID-MACP1606>3.0.CO;2-P
16 Carlini C, Martinelli M, Passaglia E, Raspolli G A M, Sbrana G. Homopolymerization of methyl methacrylate by novel Ziegler-Natta-type catalysts based on bis(chelate)-nickel(II) complexes and methylaluminoxane. Macromolecular Rapid Communications , 2001, 22(9): 664–668
doi: 10.1002/1521-3927(20010601)22:9<664::AID-MARC664>3.0.CO;2-K
17 Carlini C, Martinelli M, Raspolli G A M, Sbrana G. Highly active methyl methacrylate polymerization catalysts obtained from bis(3,5-dinitro-salicylaldiminate)nickel(II) complexes and methylaluminoxane. Journal of Polymer Science. Part A, Polymer Chemistry , 2003, 41(13): 2117–2124
doi: 10.1002/pola.10758
18 Carlini C, Macinai A, Masi F, Raspolli G A M, Santi R, Sbrana G, Sommazzi A. Ethylene polymerization by bis(salicylaldiminate)nickel(II)/aluminoxane catalysts. Journal of Polymer Science. Part A, Polymer Chemistry , 2004, 42(10): 2534–2542
doi: 10.1002/pola.20102
19 Casiraghi G, Casnati G, Puglia G, Sartori G, Terenghi G. Selective reactions between phenols and formaldehyde: a novel route to salicylaldehydes. J Chem Soc Perkin Trans , 1980, 1: 1862–1865
doi: 10.1039/p19800001862
20 Hidai M, Kashiwagi T, Ikeuchi T, Uchida Y. Oxidative additions to nickel(0): preparation and properties of a new series of arylnickel(II) complexes. Journal of Organometallic Chemistry , 1971, 30(2): 279–282
doi: 10.1016/S0022-328X(00)90208-0
21 Holm R H. Studies on nickel(II) complexes II. On the solution magnetism of bis-(N-methylsalicylaldimine)-nickel(II) and related complexes. Journal of the American Chemical Society , 1961, 83(23): 4683–4690
doi: 10.1021/ja01484a001
22 Hu T, Tang L M, Li X F, Li Y S, Hu N H. Synthesis and ethylene polymerization activity of a novel, highly active single-component binuclear neutral nickel(II) catalyst. Organometallics , 2005, 24(11): 2628–2632
doi: 10.1021/om049223e
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