Late Transition Metal Complex Catalysts for Olefin Polymerization Kotohiro Nomura* This review summarizes the recent developments in the field of olef

Similar documents
Degradation Mechanism of Ethylene-propylene-diene Terpolymer by Ozone in Aqueous Solution Satoshi MIWA 1 *, 2, Takako KIKUCHI 1, 2, Yoshito OHTAKE 1 a

Surface Morphology for Poly-L-lactide Fibers Subjected to Hydrolysis Suong-Hyu Hyon Institute for Frontier Medical Sciences, Kyoto University 53, Shog

Rate of Oxidation of Liquid Iron by Pure Oxygen Shiro BAN-YA and Jae-Dong SHIM Synopsis: The rate of oxidation of liquid iron by oxygen gas has been s

Fig. 4. Configuration of fatigue test specimen. Table I. Mechanical property of test materials. Table II. Full scale fatigue test conditions and test

光学

Fig, 1 Effect of isopropyl alcohol on polymerization rate of acrylamide. Fig. Effect of tent-butyl alcohol and n- dodecyl mercaptane on polymerization

放水の物理的火災抑制効果に着目した地域住民の消火活動モデル

プラズマ核融合学会誌11月【81‐11】/小特集5

1) K. J. Laidler, "Reaction Kinetics", Vol. II, Pergamon Press, New York (1963) Chap. 1 ; P. G. Ashmore, "Catalysis and Inhibition of Chemical Reactio

…h…L…–…†…fi…g1

名称未設定

X線分析の進歩36 別刷

スライド 1

30) Theoretical investigation of the mechanism of syndiospecific propylene polymerization using ansa-dimethylsilylene(fluorenyl)(amido)titanium comple

** Department of Materials Science and Engineering, University of California, Los Angeles, CA 90025, USA) Preparation of Magnetopulmbite Type Ferrite

渡辺(2309)_渡辺(2309)

2007 Vol.56 No.6 総説 丸山浩樹

水素移動型不斉還元触媒|関東化学株式会社

06_学術_技師の現状および将来需要_武藤様1c.indd


teionkogaku43_527

The Plasma Boundary of Magnetic Fusion Devices

untitled

mm mm , ,000 Fig. 1 Locality map of the investigation area NE SW Fi

FUJII, M. and KOSAKA, M. 2. J J [7] Fig. 1 J Fig. 2: Motivation and Skill improvement Model of J Orchestra Fig. 1: Motivating factors for a

04-“²†XŒØ‘�“_-6.01

e.g., Mahoney, Vandell, Simpkins, & Zarrett, Bohnert, Fredricks, & Randall2010 breadth intensitydurationengagement e.g., Mahone

Reaction Mechanism and Liquefaction Process of Coal Yosuke MAEKAWA

Hideki MATSUOKA: An Introduction to Small-angle Scattering Fundamental aspects of small-angle scattering technique are duly explained from the very ba

IR0036_62-3.indb

) ,

X X 1. 1 X 2 X 195 3, 4 Ungár modified Williamson-Hall/Warren-Averbach 5-7 modified modified Rietveld Convolutional Multiple Whole Profile CMWP 8 CMWP

J. Soc. Cosmet. Chem. Jpn. 7-chome, Edogawa-ku, Tokyo 132, Japan 2.1 J. Soc. Cosmet. Chem. Japan. Vol. 31, No

1

寄稿論文 規則性無機ナノ空間が創り出す新しい触媒能 | 東京化成工業

Non-Deliverable Forwards NDF BIS BIS

Fig. 2 Signal plane divided into cell of DWT Fig. 1 Schematic diagram for the monitoring system

1

202

Table 1. St-VAc blockcopolymers Table 2. Stability of dispersion of blockcopolymers in unsaturated polyester

* Meso- -scale Features of the Tokai Heavy Rainfall in September 2000 Shin-ichi SUZUKI Disaster Prevention Research Group, National R

Scheme 1 Scheme 2 Chart 1 Scheme ( 44 )

SAXS Table 1 DSC POM SAXSSAXS PF BL-10C BL-15A Fig. 2 LC12 DSC SAXS 138 C T iso T iso SAXS q=1.4 nm -1 q=(4π/λ)sin(θ/2), λ:, θ: Fig. 3 LC12 T iso Figu

肺癌第49巻第1号

Fig. ph Si-O-Na H O Si- Na OH Si-O-Si OH Si-O Si-OH Si-O-Si Si-O Si-O Si-OH Si-OH Si-O-Si H O 6

δδ 1 2 δ δ δ δ μ H 2.1 C 2.5 N 3.0 O 3.5 Cl 3.0 S μ

(43) Vol.33, No.6(1977) T-239 MUTUAL DIFFUSION AND CHANGE OF THE FINE STRUCTURE OF WET SPUN ANTI-PILLING ACRYLIC FIBER DURING COAGULATION, DRAWING AND

Juntendo Medical Journal

The Phase Behavior of Monooleoylglycerol-Water Systems Mivoshi Oil & Fat Co.. Ltd. Faculty of Science and Technology, Science University of Tokyo Inst

Appropriate Disaster Preparedness Education in Classrooms According to Students Grade, from Kindergarten through High School Contrivance of an Educati

Tf dvi

Mikio Yamamoto: Dynamical Measurement of the E-effect in Iron-Cobalt Alloys. The AE-effect (change in Young's modulus of elasticity with magnetization

1 Web [2] Web [3] [4] [5], [6] [7] [8] S.W. [9] 3. MeetingShelf Web MeetingShelf MeetingShelf (1) (2) (3) (4) (5) Web MeetingShelf

The Eevaluation One Bottle Type Silane Coupling Agents Masahiro Aida, Hideo Kanaya, Taira Kobayashi, Keiji Utsugizaki, Yoshizumi Murata, Tohru Hayakaw

第117号(A4、E)4C/3 湯浅ほか

Journal of the Combustion Society of Japan Vol.58 No.185 (2016) ORIGINAL PAPER 火災旋風近傍の流れに関する研究 Flow Around a Fire Whirl *

Japanese Journal of Applied Psychology


.L.....C1109.qxd

udc-4.dvi

01_梅村佳代_紀要_2007最終

i

1) Y. Kobuke, K. Hanji, K. Horiguchi, M. Asada, Y. Nakayama, J. Furukawa, J. Am. Chem. Soc., 98, 7414(1976). 2) S. Yoshida, S. Hayano, J. Memb. Sci.,

) BPA ECN EPICLON N-600 Fig.2 Fig Fig.4 DCPD EPICLON HP-7200 ECN Fig.5 DCPD ECN DCPD 6-28) Table 1 BPA Fig.4 Chemical str

Application of Solid Electrolyte Sensors to Hot Corrosion Studies Nobuo Otsuka* *Iron & Steel Research Laboratories, Sumitomo Metal Industries, Ltd. C

Vol.53 No (Mar. 2012) 1, 1,a) 1, 2 1 1, , Musical Interaction System Based on Stage Metaphor Seiko Myojin 1, 1,a

Input image Initialize variables Loop for period of oscillation Update height map Make shade image Change property of image Output image Change time L


9) H. SCHMCLZRIED: Z. Elektrochem. 66 (l%1) p ) W. D. KINGERY et al.: J. Am. Chem. Soc., 42 (1959), p ) F. HUND: Z. Phys. Chem., 199 (195

Fig. 1 Trends of TB incidence rates for all forms and smear-positive pulmonary TB in Kawasaki City and Japan. Incidence=newly notified cases of all fo

EQUIVALENT TRANSFORMATION TECHNIQUE FOR ISLANDING DETECTION METHODS OF SYNCHRONOUS GENERATOR -REACTIVE POWER PERTURBATION METHODS USING AVR OR SVC- Ju

Fig.1 A location map for the continental ultradeep scientific drilling operations.

.L.....C1208.qxd


Phonetic Perception and Phonemic Percepition

<31315F985F95B62D899C8CA98E8182D982A92E696E6464>

Financial Reporting Standard 17 FRS17 FAS87 87 Financial Accounting Standard 87 FAS87 International Accounting Standard Board IASB 19 Internat

<Measurements of Isobaric Boiling Point Curves at High and Low Pressures> Received on July 12, 1968 ** Kazuo Kojima (Dept. Eng. Chem., Nihon Univ., To

Web Stamps 96 KJ Stamps Web Vol 8, No 1, 2004

yasi10.dvi

-Vol.88.3/前.indd

a L = Ψ éiγ c pa qaa mc ù êë ( - )- úû Ψ 1 Ψ 4 γ a a 0, 1,, 3 {γ a, γ b } η ab æi O ö æo ö β, σ = ço I α = è - ø çèσ O ø γ 0 x iβ γ i x iβα i

資源と素材

Instability of Aerostatic Journal Bearings with Porous Floating Bush at High Speeds Masaaki MIYATAKE *4, Shigeka YOSHIMOTO, Tomoaki CHIBA and Akira CH

Table 1 Table 2

Vol. 29, No. 2, (2008) FDR Introduction of FDR and Comparisons of Multiple Testing Procedures that Control It Shin-ichi Matsuda Department of

Microsoft Excelを用いた分子軌道の描画の実習

& Vol.5 No (Oct. 2015) TV 1,2,a) , Augmented TV TV AR Augmented Reality 3DCG TV Estimation of TV Screen Position and Ro

’ÓŠ¹/‰´„û

Precisely Designed Catalysts News Letter Vol. 5 May, 2016

スライド 1

PDF用-表紙.pdf

P036-P041

技術創造の社会的条件

Computer Simulation in Thermoplastic Injection Molding Takaaki Matsuoka Toyota Central Research and Development Laboratories, Inc. 41-1, Yokomichi, Na

1) T. L. Cottrel, A. J. Matheson, Trans. Farad. Soc., 58, 2336(1962). 2) E. N. Chesnokov, V. N. Panfilov, Teor. Eksp. Khimiya, 17, 699(1981). 3) M. Ko

fl™‹ä1.eps

LAGUNA LAGUNA 8 p Saline wedge at River Gonokawa, Shimane Pref., Japan Saline water intrusion at estuary r

Table 2 DENSO Port Injection Fuel Injectors Fig.1 Port Fuel Injection System and Module 1996 CO ポート噴射システム 1 ( 1) HC 2 UC [2] (

Kyoto University * Filipino Students in Japan and International Relations in the 1930s: An Aspect of Soft Power Policies in Imperial Japan

Transcription:

Late Transition Metal Complex Catalysts for Olefin Polymerization Kotohiro Nomura* This review summarizes the recent developments in the field of olefin polymerization, especially focuses on the topic by nickel, palladium, iron, cobalt, and ruthenium complex catalysts including the brief summary of this research background. A lot of studies have been explored concerning olefin polymerization by nickel and palladium complex catalysts especially after the discovery of results introduce new possibilities for making new type of olefin-based copolymers by these catalysts. In particular, recent discovery concerning ethylene polymerization by iron and cobalt complexes containing 2,6-bis (imino) pyridine ligand attracted particular attention due to the exceptionally high catalytic activity, and the contents concerning this topic have also been summarized briefly. We also wish to introduce our recent results concerning olefin polymerization by ruthenium and iron complexes-cocatalyst Key words: systems. olefin polymerization, ethylene, propylene, methyl acrylate, nickel, palladium, iron, ruthenium, cobalt, homogeneous catalysts Fig. 1 Typical nickel catalyst for olefin polymerization (W. Keim et al., 1978-)5). * Nara Institute of Science and Technology (NAIST), Graduate School of Materials Science Vol.58 No.4 2000 (23) 293

Scheme 1 Insertion mode of a-olefins. Table 1 Ethylene polymerization by nickel catalyst containing P-0 chelate ligand8a). 294 ( 24 )

Fig. 3 Explanatory figure for side chain branching. Fig. 2 Genaral formula of nickel and palladium complexes containing Vol.58 No.4 2000 ( 25 ) 295

Table 2 Ethylene polymerization by nickel-diimine complexes, (Ar2DABR2)NiBr2, -MAO catalyst11d). -Effect of ligand, reaction temperature, and ethylene pressure- Table 3 Ethylene polymerization by [(2, 6-113r2Ph) DABAn]NiBr2-MAO catalystlle). -Effect of ethylene pressure- Scheme 2 Proposed reaction scheme for ethylene polymerization catalyzed by nickel-diimine complexes-cocatalyst systemlla). 296 ( 26 )

Table 4 Polymerization of propylene and 1-hexeneli'd). Scheme 3 1, co-enchainment in a-olefin polymerization. Vol.58 No.4 2000 ( 27 )

Table 5 Copolymerization of ethylene and propylene with functionalized vinyl monomers by palladium catalystsild). 298 ( 28 )

21 22 23 Scheme 4 Reaction of complex B with acrylatellm). Scheme 5 Insertion of ethylene into complex C. Scheme 6 Proposed reaction scheme for copolymerization of ethylene with methyl acrylatellb'f). Vol.58 No.4 2000 ( 29 ) 299

28 29 30 Fig. 4 Nickel complexes reported by Cavell et al23). [Basic Concept for Designing the Catalyst Precursor] 1) Help shield the axial faces and retard chain termination 2) Reduce chain migratory processes (influences branching) by increasing in-plane bulk 3) Enhance catalyst activity by increasing dissociation rate of ancillary PPh3 4) Prevent disproportionation and ligand rearrangement Fig. 6 Nickel and cobalt complexes reported by Laine et al26). 31 32 Fig. 5 Nickel catalyst reported by Grubbs et aim). Table 6 Polymerization of ethylene by substituted nickel salicylaldimines and phosphine complex catalyst24b). Reaction conditions: catalyst 75 Rmol, Ni(COD)2 (cocatalyst) 150 innol, toluene 90 ml, ethylene 85-100 psig (ca. 5.8-6.8 atm), ice bath was used to control the reaction temperature. Fig. 7 Nickel catalyst reported by Kanemasa et al28). Table 7 Effect of temperature on ethylene polymerization by nickel catalyst24b). Reaction conditions: catalyst (32) 60 gmol, toluene 1000 ml, ethylene 400 psig (ca. 27.2 atm). Fig. 8 Nickel catalyst containing bis(oxazoline)ligands for olefin polymerization29). 300 ( 30 )

Table 8 Cobalt catalyzed living polymerization of ethylene35b). Fig. 9 Nickel and palladium complexes containing bis- (pyrazolyl)methane ligand30,31). Scheme 7 Proposed reaction scheme for cobalt catalyzed living polymerization of ethylene35b). Fig. 10 Iron and cobalt complexes for ethylene polymerization32'33). Vol.58 No.4 2000 ( 31 ) 301

Table 9 Ethylene polymerization catalyzed by iron and cobalt complexes-cocatalyst systems32b). Table 10 Effect of ligand in ethylene polymerization catalyzed by cobalt complexes. Table 11 Effect of ethylene pressure34b). 302 ( 32 )

Scheme 8 Ethylene oligomerization catalyzed by iron complexes33c). Fig. 11 Iron complexes for propylene polymerization336. Table 12 Propylene polymerization catalyzed by iron complexescocatalyst systems336. Scheme 9 Proposed reaction scheme for propylene polymerization catalyzed by iron complexes33c). Vol.58 No.4 2000 ( 33 ) 303

1) Review: (a) K. H. Brintzinger, D. Fischer, R. Mulhaupt, B. Rieger, R. M. Waymouth, Angew. Chem., Int. Ed. Engl., 34, 1143 (1995); (b) W. Kaminsky, Macromol. Chem. Phys., 197, 3903 (1996); (c) W. Kaminsky, M. Alndt, Advanced in Polymer Science, 127, 143 (1997); (d) J. Suhm, J. Heinemann, C. Worner, P. Muller, F. Stricker, J. Kressler, J. Okuda, R. Mulhaupt, Macromol. Symp., 129, 1 (1998); (e) A. L. Mc- Knight, R. M. Waymouth, Chem. Rev., 98, 2587 (1998); (f) G. J. P. Britovsek, V. C. Gibson, D. F. Wass, Angew. Chem., Int. Ed. Engl., 38, 429 (1999) 3) (a) P. W. Jolly, G. Wilke, "Organic Chemistry of Nickel", Academic Press, New York (1974); (b) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988); (c) W. Keim, ibid., 29, 235 (1990) 4) (a) M. Peuckert, W. Keim, Organometallics, 2, 594 (1983);(b) M. Peuckert, W. Keim, S. Storp, R. S. Weber, J. Mol. Catal., 20, 115 (1983); (c) W. Keim, Chem. Ing. Tech., 56, 850 (1984); (d) W. Keim, Ann. N. Y. Acad. Sc., 425, 775 (1983) 5) (a) W. Keim, F. H. Kowaldt, R. Goddard, C. Kruger, Angew. Chem., Int. Ed. Engl., 17, 466 (1978); (b) W. Keim, R. Appel, A. Storeck, C. Kruger, R. Goddard, ibid., 20, 116 (1981); (c) W. Keim, R. Appel, S. Gruppe, F. Knoch, ibid., 26, 1012 (1987) 6) V. M. Mohring, G. Fink, Angew. Chem., Int. Ed. Engl., 24, 1001 (1985) 7) K. A. O. Strarzewski, J. Witte, Angew. Chem., 97, 610 (1985); idem, ibid., 99, 76 (1987) 8) (a) U. Klabunde, S. D. Ittel., J. Mol. Catal., 41, 123 (1987); (b) U. Klabunde, R. Mulhaupt, T. Herskovitz, A. H. Janowicz, J. Calabrese, S. D. Ittel., J. Polym. Sci., A, Polym. Chem., 25, 1989 (1987); (c) U. Klabunde, T. H. Tulip, D. C. Roe, S. D. Ittel., J. Organomet. Chem., 334, 141 (1987) 9) K. Kurtev, A. Tomov, J. Mol. Catal., 88, 141 (1994); idem, ibid., 103, 95 (1995) 10) K. Nomura,`Recent developments in oligomerization of olefins by homogeneous nickel and palladium catalysts', in "R ecent Research Developments in Pure & Appl. Chem.", S. G. Pandalai, ed., Transworld Research Network, 2, Part II, 473-513 (1998) 11) (a) L. K. Johnson, C. M. Killian, M. Brookhart, J. Am. Chem. Soc., 117, 6414 (1995); (b) L. K. Johnson, S. Mecking, M. Brookhart, ibid., 118, 267 (1996); (c) C. M. Killian, D. J. Tempel, L. K. Johnson, M. Brookhart, ibid., 118, 11664 (1996); (d) M. Brookhart et al., WO 96/2310; (e) M. Brookhart, C. M. Killian, L. K. Johnson, D. J. Tempel, S. D. Ittel, S. McLain, E.

F. McCord, S. D. Arthur, Abstract of MetCon '97, "Polymers in Transition", June 4-5, Houston, Texas (1997); (f) S. Mecking, L. K. Johnson, L. Wang, M. Brookhart, J. Am. Chem. Soc., 1 20, 888 (1998) 14) (a) C. M. Killian, L. K. Johnson, M. Brookhart, Organometallics, 16, 2005 (1997); (b) S. A. Svejda, M. Brookhart, ibid., 18, 65 (1999) 15) (a) T. Schleis, J. Heinemann, T. P. Spaniol, R. Mulhaupt, J. Okuda, Inorg. Chem. Commun., 1, 431 (1998); (b) T. Schleis, T. P. Spaniol, J. Okuda, J. Heinemann, R. Mulhaupt, J. Organomet. Chem., 569, 159 (1998) 16) J. Feldman, S. J. McLain, A. Parthasarathy, W. J. Marshall, J. C. Calabrese, S. D. Arthur, Organometallics, 16, 1514 (1997) 17) R. F. de Souza, R. S. Mauler, L. C. Simon, F. F. Nunes, D. V. S. Vescia, A. Cavagnolli, Macromol. Rapid. Commun., 18, 795 (1997) 18) J. C. Randall, J. Polym. Sci., Polym. Phys Ed., 11, 275 (1973); Rev. Macromol. Chem. Phys., C 29 (2&3), 201 (1989). The assignment of the signals was carried out with the help of the increment rules of the following literature: L. P. Lindemann, J. Q. Adams, Anal. Chem., 43, 1245 (1981) 19) (a)c. Pellecchia, A. Zambelli, Macromol. Rapid Commun., 17, 333 (1996); (b) C. Pellecchia, A. Zambelli, L. Oliva, D. Pappalardo, Macromolecules, 29, 6990 (1996) 20) S. J. McLain, J. Feldman, E. F. McCord, K. H. Gardner, M. F. Teasley, E. B. Coughlin, K. J. Sweetman, L. K. Johnson, M. Brookhart, Macromolecules, 31, 6705 (1998) Int. Ed. Engl., 35, 2475 (1996) 23) S. Y. Desjardins, K. J. Cavell, J. L. Hoare, B. W. Skelton, A. N. Sobolev, A. H. White, W. Keim, J. Organomet. Chem., 544, 163 (1997) 24) (a) C. Wang, S. Friedlich, R. T. Li, R. H. Grubbs, D. A. Bransleben, M. W. Day, Organometallics, 17, 3149 (1998); (b) D. A. Bransleben, R. H. Grubbs, C. Wang, S. Friedlich, T. R. Youkin, R. T. Li, Abstract of MetCon '98,"Polymer in Transition", June 10-11, Houston, TX (1998) 25) R. H. Grubbs, E. F. Connor, T. R. Younkin, J. I. Henderson, Abstracts of 218th ACS National Meeting, No. 204 and 205, New Orleans, August 22-26 (1999) 26) T. V. Laine, K. Lappalainen, J. Liimatta, E. Aitola, B. Lofgren, M. Lcskcla, Macromol. Rapid. Commun., 20, 487 (1999) 27) J. W. Park, T. S. Seo, S. I. Woo, Y. K. Do, J. T. Park, Abstract in 6th Japan-Korea Polyolefin Workshop, November 1-2, Tokyo (1999) 30) S. Ikeda, K. Kamei, T. Mimani, F. Ozawa, Preprint of 46th Symposium on Organometallic Chemistry, Japan, September 16-17, PA 218, Osaka (1999) 31) S. Tsuji, D. C. Swenson, R. F. Jordan, Organometallics, 18, 4758 (1999) 32) (a) G. J. P. Britovsek, V. C. Gibson, B. S. Kimberley, P. J. Maddox, S. J. McTavish, G. A. Solan, A. J. P. White, D. J. Williams, Chem. Commun., 1998, 849; (b) G. J. P. Britovsek, M. Bruce, V. C. Gibson, B. S. Kimberely, P. J. Maddox, S. Mastroianni, S. J. McTavish, C. Redshaw, G. A. Solan, S. Stromberg, A. J. D. White, D.J. Williams, J. Am. Chem. Soc., 121, 8728 (1999); (c) G. J. P. Britovsek, B. A. Dorer, V. C. Gibson, B. S. Kimberely, G. A. Solan, WO 99/12981 (1999) 33) (a) B. L. Small, M. Brookhart, A. M. A. Bennett, J. Am. Chem. Soc., 120, 4049 (1998); (b) B. L. Small, M. Brookhart, ibid., 120, 7143 (1998); (c) idem, Macromolecules, 32, 2120 (1999); (d) A. M. A. Bennett, WO 98/27174 (1998) 34) (a) G. Marsh, Materials Today, 1(2), 6 (1998); (b) A. M. A. 35) (a) G. F. Schmidt, M. Brookhart, J. Am. Chem. Soc., 107, 1443 (1985); (b) M. Brookhart, J. M. DeSimone, B. E. Grant, M. J. Tanner, Macromolecules, 28, 5378 (1995) 36) (a) K. Nomura, W. Sidokmai, Y. Imanishi, Macromolecules, 32, 4732 (1999); (b) idem., Preprint of 46th Symposium on Organometallic Chemistry, Japan, September 16-17, PB 204, Osaka (1999) PROFILE