Influence of Polyethylene Glycol Unit on Palladium- and Nickel-Catalyzed Ethylene Polymerization and Copolymerization.

The transition-metal-catalyzed copolymerization of olefins with polar functionalized co-monomers represents a major challenge in the field of olefin polymerization. It is extremely difficult to simultaneously achieve improvements in catalytic activity, polar monomer incorporation, and copolymer molecular weight through ligand modifications. Herein we introduce a polyethylene glycol unit to some phosphine-sulfonate palladium and nickel catalysts, and its influence on ethylene polymerization and copolymerization is investigated. In ethylene polymerization, this strategy leads to enhanced activity, catalyst stability, and increased polyethylene molecular weight. In ethylene copolymerization with polar monomers, improvements in all copolymerization parameters are realized. This effect is most significant for polar monomers with hydrogen-bond-donating abilities.

[1]  Changle Chen,et al.  Accessing Multiple Catalytically Active States in Redox-Controlled Olefin Polymerization , 2017 .

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

[3]  Yun-peng Zhu,et al.  Direct Synthesis of Thermoplastic Polyolefin Elastomers from Nickel-Catalyzed Ethylene Polymerization , 2017 .

[4]  Z. Hou,et al.  Heteroatom-assisted olefin polymerization by rare-earth metal catalysts , 2017, Science Advances.

[5]  T. Liang,et al.  Side-Arm Control in Phosphine-Sulfonate Palladium- and Nickel-Catalyzed Ethylene Polymerization and Copolymerization , 2017 .

[6]  Changle Chen,et al.  Redox control in palladium catalyzed norbornene and alkyne polymerization , 2017 .

[7]  S. Mecking,et al.  Synergetic Effect of Monomer Functional Group Coordination in Catalytic Insertion Polymerization. , 2017, Journal of the American Chemical Society.

[8]  Changle Chen,et al.  Unsymmetrical α-diimine palladium catalysts and their properties in olefin (co)polymerization , 2017 .

[9]  Changle Chen,et al.  Modulating polyolefin properties through the incorporation of nitrogen-containing polar monomers , 2017 .

[10]  Lihua Guo,et al.  Direct Synthesis of Branched Carboxylic Acid Functionalized Poly(1-octene) by α-Diimine Palladium Catalysts , 2017, Polymers.

[11]  Yun-peng Zhu,et al.  Dinuclear α‐Diimine NiII and PdII Complexes that Catalyze Ethylene Polymerization and Copolymerization , 2017 .

[12]  Dongtao Liu,et al.  Stereoselective Copolymerization of Unprotected Polar and Nonpolar Styrenes by an Yttrium Precursor: Control of Polar-Group Distribution and Mechanism. , 2017, Angewandte Chemie.

[13]  R. F. Jordan,et al.  Olefin Insertion into a Pd-F Bond: Catalyst Reactivation Following β-F Elimination in Ethylene/Vinyl Fluoride Copolymerization. , 2017, Angewandte Chemie.

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

[15]  O. Daugulis,et al.  Mechanistic Studies of Pd(II)-Catalyzed Copolymerization of Ethylene and Vinylalkoxysilanes: Evidence for a β-Silyl Elimination Chain Transfer Mechanism. , 2016, Journal of the American Chemical Society.

[16]  Yuguo Ma,et al.  Ethylene (Co)polymerization by Binuclear Nickel Phenoxyiminato Catalysts with Cofacial Orientation , 2016 .

[17]  W. Zhang,et al.  Systematic Investigations of Ligand Steric Effects on α-Diimine Palladium Catalyzed Olefin Polymerization and Copolymerization , 2016 .

[18]  S. Mecking,et al.  Direct Synthesis of Telechelic Polyethylene by Selective Insertion Polymerization. , 2016, Angewandte Chemie.

[19]  Changle Chen,et al.  Direct Synthesis of Functionalized High-Molecular-Weight Polyethylene by Copolymerization of Ethylene with Polar Monomers. , 2016, Angewandte Chemie.

[20]  Minoru Kobayashi,et al.  Crystalline Isotactic Polar Polypropylene from the Palladium-Catalyzed Copolymerization of Propylene and Polar Monomers. , 2016, Angewandte Chemie.

[21]  Jer‐Shing Huang,et al.  Facet-Dependent and Light-Assisted Efficient Hydrogen Evolution from Ammonia Borane Using Gold-Palladium Core-Shell Nanocatalysts. , 2016, Angewandte Chemie.

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

[23]  B. Long,et al.  Redox-Active Ligands: An Advanced Tool To Modulate Polyethylene Microstructure. , 2016, Journal of the American Chemical Society.

[24]  Lihua Guo,et al.  Palladium and Nickel Catalyzed Chain Walking Olefin Polymerization and Copolymerization , 2016 .

[25]  Changle Chen,et al.  Ethylene Polymerization by Xanthene‐Bridged Dinuclear α‐Diimine NiII Complexes , 2016 .

[26]  R. Hatti-Kaul,et al.  Bio-based 3-hydroxypropionic- and acrylic acid production from biodiesel glycerol via integrated microbial and chemical catalysis , 2015, Microbial Cell Factories.

[27]  Changle Chen,et al.  Redox-Controlled Olefin (Co)Polymerization Catalyzed by Ferrocene-Bridged Phosphine-Sulfonate Palladium Complexes. , 2015, Angewandte Chemie.

[28]  L. Do,et al.  Fine-Tuning Nickel Phenoxyimine Olefin Polymerization Catalysts: Performance Boosting by Alkali Cations. , 2015, Journal of the American Chemical Society.

[29]  Changle Chen,et al.  Ethylene Polymerization and Copolymerization with Polar Monomers by Cationic Phosphine Phosphonic Amide Palladium Complexes , 2015 .

[30]  Hassan S. Bazzi,et al.  Activation of Single-Component Nickel(II) Polyethylene Catalysts via Phase Transfer of Fluorous Phosphine Ligands. , 2015, Journal of the American Chemical Society.

[31]  K. Nozaki,et al.  Copolymerization of Propylene and Polar Monomers Using Pd/IzQO Catalysts. , 2015, Journal of the American Chemical Society.

[32]  Changle Chen,et al.  Highly Robust Palladium(II) α-Diimine Catalysts for Slow-Chain-Walking Polymerization of Ethylene and Copolymerization with Methyl Acrylate. , 2015, Angewandte Chemie.

[33]  M. C. Chan,et al.  Chelating σ-Aryl Post-Metallocenes: Probing Intramolecular [C-H···F-C] Interactions and Unusual Reaction Pathways. , 2015, Accounts of chemical research.

[34]  Shihui Li,et al.  Highly isoselective coordination polymerization of ortho-methoxystyrene with β-diketiminato rare-earth-metal precursors. , 2015, Angewandte Chemie.

[35]  S. Mecking,et al.  Suppression of chain transfer in catalytic acrylate polymerization via rapid and selective secondary insertion. , 2015, Journal of the American Chemical Society.

[36]  K. Osakada,et al.  Dipalladium catalyst for olefin polymerization: introduction of acrylate units into the main chain of branched polyethylene. , 2014, Angewandte Chemie.

[37]  R. F. Jordan,et al.  Copolymerization of Ethylene and Methyl Acrylate by Cationic Palladium Catalysts That Contain Phosphine-Diethyl Phosphonate Ancillary Ligands , 2014 .

[38]  T. Marks,et al.  Ni(II) Phenoxyiminato Olefin Polymerization Catalysis: Striking Coordinative Modulation of Hyperbranched Polymer Microstructure and Stability by a Proximate Sulfonyl Group , 2014 .

[39]  Michael C. W. Chan,et al.  Attractive interactions in olefin polymerization mediated by post-metallocene catalysts with fluorine-containing ancillary ligands , 2014 .

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

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

[42]  T. Agapie,et al.  Bimetallic coordination insertion polymerization of unprotected polar monomers: copolymerization of amino olefins and ethylene by dinickel bisphenoxyiminato catalysts. , 2013, Journal of the American Chemical Society.

[43]  T. Marks,et al.  Ligand steric and fluoroalkyl substituent effects on enchainment cooperativity and stability in bimetallic nickel(II) polymerization catalysts. , 2012, Chemistry.

[44]  T. C. Mike Chung,et al.  Functionalization of Polypropylene with High Dielectric Properties: Applications in Electric Energy Storage , 2012 .

[45]  T. Marks,et al.  Suppression of β-Hydride Chain Transfer in Nickel(II)-Catalyzed Ethylene Polymerization via Weak Fluorocarbon Ligand–Product Interactions , 2012 .

[46]  Jean-Christophe Daigle,et al.  Preparation of Functional Polyethylenes by Catalytic Copolymerization , 2011 .

[47]  T. Marks,et al.  Multinuclear olefin polymerization catalysts. , 2011, Chemical reviews.

[48]  S. Mecking,et al.  Direct synthesis of ethylene-acrylic acid copolymers by insertion polymerization. , 2010, Journal of the American Chemical Society.

[49]  H. Möller,et al.  Noncovalent Interactions in o-Fluorinated Post-titanocene Living Ethylene Polymerization Catalyst , 2010 .

[50]  Changle Chen,et al.  Cationic polymerization and insertion chemistry in the reactions of vinyl ethers with (alpha-diimine)PdMe(+) species. , 2010, Journal of the American Chemical Society.

[51]  Cong Wang,et al.  [O-NSR]TiCl3-catalyzed copolymerization of ethylene with functionalized olefins. , 2009, Angewandte Chemie.

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

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

[54]  C. Stevens,et al.  Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. , 2009, ChemSusChem.

[55]  P. Hustad,et al.  Frontiers in Olefin Polymerization: Reinventing the World’s Most Common Synthetic Polymers , 2009, Science.

[56]  Philipp Roesle,et al.  Insertion polymerization of acrylate. , 2009, Journal of the American Chemical Society.

[57]  S. Mecking,et al.  Highly Active Binuclear Neutral Nickel(II) Catalysts Affording High Molecular Weight Polyethylene , 2008 .

[58]  M. Sauer,et al.  Microbial production of organic acids: expanding the markets. , 2008, Trends in biotechnology.

[59]  J. Vela,et al.  Ethylene Polymerization by Palladium Alkyl Complexes Containing Bis(aryl)phosphino-toluenesulfonate Ligands , 2007 .

[60]  R. Benavente,et al.  Ethylene/10‐Undecenoic Acid Copolymers Prepared with Different Metallocene Catalysts , 2007 .

[61]  P. Hustad,et al.  Catalytic Production of Olefin Block Copolymers via Chain Shuttling Polymerization , 2006, Science.

[62]  Jin-Yong Dong,et al.  Design and synthesis of structurally well-defined functional polypropylenes via transition metal-mediated olefin polymerization chemistry , 2006 .

[63]  B. Rieger,et al.  New Phenylnickel‐(2‐phosphinobenzenesulfonate) Triphenylphosphine Complexes as Highly Active Ethylene Polymerization Catalysts , 2005 .

[64]  V. Kravtsov,et al.  Hydrogen bonding assemblies in host -guest complexes with 18-crown-6 , 2003 .

[65]  S. Batsanov,et al.  Van der Waals Radii of Elements , 2001 .

[66]  S. Weng,et al.  The correlation between crystalline behavior of polyethylene segments and hydrogen bonds among carboxyl groups in ethylene–Acrylic Acid copolymers , 2000 .

[67]  McLain,et al.  Chain walking: A new strategy to control polymer topology , 1999, Science.

[68]  Maurice Brookhart,et al.  New Pd(II)- and Ni(II)-Based Catalysts for Polymerization of Ethylene and .alpha.-Olefins , 1995 .

[69]  L. Parenteau,et al.  Structure of the stoichiometric complex 18-crown-6•H2O•succinic acid , 1989 .

[70]  R. Savoie,et al.  Synthesis, crystal and molecular structure, and vibrational spectra of the complex (COOH)2•2H2O•18-crown-6 , 1986 .

[71]  R. Chěnevert,et al.  Synthesis and vibrational spectra of complexes of small carboxylic acids with 18-crown-6 , 1985 .