Ethylene Polymerization and Copolymerization with Polar Monomers Using Nickel Complexes Bearing Anilinobenzoic Acid Methyl Ester Ligand

Neutral nickel complexes containing an anilinobenzoic acid methyl ester ligand are prepared and applied for the ethylene polymerization and copolymerization with polar monomers. The complex C2 containing isopropyl substituent on the aniline ligand conducts ethylene polymerization with high activity and good thermal stability. Most importantly, the catalyst promotes the copolymerization of ethylene and polar monomers with high activity (up to 277 kg·mol−1·h−1), affording ester-functionalized semicrystalline polyethylene with reasonable polar monomer content (up to 3.20 mol %).

[1]  Changle Chen,et al.  A Versatile Ligand Platform for Palladium- and Nickel-Catalyzed Ethylene Copolymerization with Polar Monomers. , 2018, Angewandte Chemie.

[2]  Zhengguo Cai,et al.  (Anilino)anthraquinone Nickel‐Catalyzed Random Copolymerization of Norbornene and Ethylene , 2018 .

[3]  K. Nozaki,et al.  Nickel-Catalyzed Propylene/Polar Monomer Copolymerization. , 2018, ACS macro letters.

[4]  T. Shiono,et al.  Highly Robust Nickel Catalysts Containing Anilinonaphthoquinone Ligand for Copolymerization of Ethylene and Polar Monomers , 2017 .

[5]  Changle Chen,et al.  Influence of Polyethylene Glycol Unit on Palladium- and Nickel-Catalyzed Ethylene Polymerization and Copolymerization. , 2017, Angewandte Chemie.

[6]  Yi Luo,et al.  A Second-Coordination-Sphere Strategy to Modulate Nickel- and Palladium-Catalyzed Olefin Polymerization and Copolymerization. , 2017, Angewandte Chemie.

[7]  Y. Oishi,et al.  Nickel Catalyzed Copolymerization of Ethylene and Alkyl Acrylates. , 2017, Journal of the American Chemical Society.

[8]  Changle Chen,et al.  Rational Design of High-Performance Phosphine Sulfonate Nickel Catalysts for Ethylene Polymerization and Copolymerization with Polar Monomers , 2017 .

[9]  G. Coates,et al.  Semi-Crystalline Polar Polyethylene: Ester-Functionalized Linear Polyolefins Enabled by a Functional-Group-Tolerant, Cationic Nickel Catalyst. , 2016, Angewandte Chemie.

[10]  K. Nozaki,et al.  Copolymerization of Ethylene and Polar Monomers by Using Ni/IzQO Catalysts. , 2016, Angewandte Chemie.

[11]  Rolf Mülhaupt,et al.  From Multisite Polymerization Catalysis to Sustainable Materials and All-Polyolefin Composites. , 2016, Chemical reviews.

[12]  T. Shiono,et al.  Highly soluble polynorbornene prepared by an anilinonaphthoquinone-ligated nickel complex via coordination-insertion polymerization , 2015 .

[13]  Yue-sheng Li,et al.  Neutral Nickel Catalysts for Olefin Homo- and Copolymerization: Relationships between Catalyst Structures and Catalytic Properties. , 2015, Chemical reviews.

[14]  O. Daugulis,et al.  Synthesis of Branched Ultrahigh-Molecular-Weight Polyethylene Using Highly Active Neutral, Single-Component Ni(II) Catalysts , 2015 .

[15]  T. Shiono,et al.  Heterogenization of an Anilinonaphthoquinone‐Chelated Nickel Complex for Ethylene Polymerization Using Silica‐Supported Modified Methylaluminoxane , 2014 .

[16]  K. Nozaki,et al.  Transition-Metal-Catalyzed Functional Polyolefin Synthesis: Effecting Control through Chelating Ancillary Ligand Design and Mechanistic Insights , 2014 .

[17]  Peng Xiang,et al.  Designing polyethylenes of complex chain architectures via Pd-diimine-catalyzed "living" ethylene polymerization. , 2013, Chemical communications.

[18]  Nicole M. G. Franssen,et al.  Synthesis of functional 'polyolefins': state of the art and remaining challenges. , 2013, Chemical Society reviews.

[19]  Ayusman Sen,et al.  Ortho-phosphinobenzenesulfonate: a superb ligand for palladium-catalyzed coordination-insertion copolymerization of polar vinyl monomers. , 2013, Accounts of chemical research.

[20]  Yue-sheng Li,et al.  Ligand Steric and Electronic Effects on β-Ketiminato Neutral Nickel(II) Olefin Polymerization Catalysts , 2012 .

[21]  Zhibin Ye,et al.  Hyperbranched polyethylenes by chain walking polymerization: synthesis, properties, functionalization, and applications , 2012 .

[22]  Yue-sheng Li,et al.  Observations and Mechanistic Insights on Unusual Stability of Neutral Nickel Complexes with a Sterically Crowded Metal Center , 2011 .

[23]  Z. Guan,et al.  Designing late-transition metal catalysts for olefin insertion polymerization and copolymerization. , 2010, Chemical communications.

[24]  Dongpo Song,et al.  Accessible, Highly Active Single-Component β-Ketiminato Neutral Nickel(II) Catalysts for Ethylene Polymerization , 2010 .

[25]  K. Nozaki,et al.  Coordination-insertion copolymerization of fundamental polar monomers. , 2009, Chemical reviews.

[26]  Yue-sheng Li,et al.  Highly Active Neutral Nickel(II) Catalysts for Ethylene Polymerization Bearing Modified β-Ketoiminato Ligands , 2009 .

[27]  E. Chen.  Coordination polymerization of polar vinyl monomers by single-site metal catalysts. , 2009, Chemical reviews.

[28]  C. Ha,et al.  Neutral Ni(II) complexes based on keto-enamine salicylideneanilines active for selective dimerization of ethylene , 2009 .

[29]  H. Terao,et al.  Ethylene/polar monomer copolymerization behavior of bis(phenoxy-imine)Ti complexes: formation of polar monomer copolymers. , 2008, Journal of the American Chemical Society.

[30]  T. Shiono,et al.  Synthesis of anilinonaphthoquinone-based nickel complexes and their application for olefin polymerization , 2007 .

[31]  S. Mecking,et al.  Synthesis of Aqueous Polyethylene Dispersions with Electron-Deficient Neutral Nickel(II) Catalysts with Enolatoimine Ligands , 2007 .

[32]  T. Ikeda,et al.  Synthesis of uniquely branched polyethylene by anilinonaphthoquinone ligated nickel complex activated with tris(pentafluorophenyl)borane , 2006 .

[33]  P. White,et al.  Synthesis, Characterization, and Ethylene Polymerization Activities of Neutral Nickel(II) Complexes Derived from Anilino-Substituted Enone Ligands Bearing Trifluoromethyl and Trifluoroacetyl Substituents , 2006 .

[34]  I. Beletskaya,et al.  Palladium‐Catalyzed Amination of 1,8‐ and 1,5‐Dichloroanthracenes and 1,8‐ and 1,5‐Dichloroanthraquinones. , 2005 .

[35]  Qinmin Pan,et al.  Solubility of ethylene in toluene and toluene/styrene–butadiene rubber solutions , 2005 .

[36]  Yue-sheng Li,et al.  Copolymerization of Ethylene with Methyl Methacrylate with Neutral Nickel(II) Complexes Bearing β-Ketoiminato Chelate Ligands , 2005 .

[37]  G. Bazan,et al.  Remote activation of nickel catalysts for ethylene oligomerization. , 2005, Angewandte Chemie.

[38]  I. Beletskaya,et al.  Palladium‐Catalysed Amination of 1,8‐ and 1,5‐Dichloroanthracenes and 1,8‐ and 1,5‐Dichloroanthraquinones , 2005 .

[39]  R. Grubbs,et al.  Insights into the Deactivation of Neutral Nickel Ethylene Polymerization Catalysts in the Presence of Functionalized Olefins , 2004 .

[40]  L. Weng,et al.  Synthesis, Molecular Structures, and Norbornene Addition Polymerization Activity of the Neutral Nickel Catalysts Supported by β-Diketiminato [N, N], Ketiminato [N, O], and Schiff-Base [N, O] Ligands⊥ , 2004 .

[41]  M. Brookhart,et al.  A mechanistic investigation of the polymerization of ethylene catalyzed by neutral Ni(II) complexes derived from bulky anilinotropone ligands. , 2004, Journal of the American Chemical Society.

[42]  R. Grubbs,et al.  Synthesis of neutral nickel catalysts for ethylene polymerization--the influence of ligand size on catalyst stability. , 2003, Chemical communications.

[43]  M. Brookhart,et al.  Synthesis and Ethylene Polymerization Activity of a Series of 2-Anilinotropone-Based Neutral Nickel(II) Catalysts , 2003 .

[44]  E. Herdtweck,et al.  Structural Characterization and a New One‐Pot Synthesis of trans‐Chloro(phenyl)bis(triphenylphosphane)nickel(II) , 2003 .

[45]  M. Brookhart,et al.  A highly active anilinoperinaphthenone-based neutral nickel(II) catalyst for ethylene polymerization , 2003 .

[46]  M. Brookhart,et al.  A Highly Active Anilinotropone-Based Neutral Nickel(II) Catalyst for Ethylene Polymerization , 2001 .

[47]  M. Brookhart,et al.  Late-metal catalysts for ethylene homo- and copolymerization. , 2000, Chemical reviews.

[48]  Friedrich,et al.  Neutral, single-component nickel (II) polyolefin catalysts that tolerate heteroatoms , 2000, Science.

[49]  R. Grubbs,et al.  Neutral Nickel(II)-Based Catalysts for Ethylene Polymerization , 1998 .

[50]  S. D. Ittel,et al.  Nickel catalysis for ethylene homo- and co-polymerization , 1987 .

[51]  K. Starzewski,et al.  Highly Active Ylide-Nickel Catalysts for the Polymerization of Ethylene† , 1985 .

[52]  W. Keim,et al.  Novel Coordination of (Benzoylmethylene)triphenylphosphorane in a Nickel Oligomerization Catalyst , 1978 .