Citation: Su Biyun, Jia Peiyu, Wang Yanzhao, Li Yaning, Huang He, Li Qianding. Copolymerization of Ethylene/Polar Monomer Catalyzed by Phosphinoarenesulfonate (PO) Metal Catalysts and the Catalytic Mechanism[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2344-2352. doi: 10.6023/cjoc201603048 shu

Copolymerization of Ethylene/Polar Monomer Catalyzed by Phosphinoarenesulfonate (PO) Metal Catalysts and the Catalytic Mechanism

  • Corresponding author: Su Biyun, subiyun@xsyu.edu.cn.
  • Received Date: 30 March 2016
    Revised Date: 11 May 2016

    Fund Project: ProjectProject of Shaanxi Education Department No.12JK0620and the Science and Technology Research Program of Shaanxi Province No.2013 KJXX-33

Figures(2)

  • The metal catalysts based on phosphinoarenesulfonate (PO) ligand display interesting olefin polymerization prop-erties, which not only polymerize ethylene to linear polyethylene, but also copolymerize ethylene with polar vinyl monomers or CO to functional linear copolymers. The structural features of PO ligand and the novel polymerization reactions initiated by (PO)Pd(Ⅱ) complexes are assumed. Then the application of (PO)Ni(Ⅱ) catalysts in the copolymerization of ethylene with polar monomers, as well as the rare catalytic properties of Pd(Ⅱ), Ru(Ⅳ) catalysts based on phosphine-bis(arenesulfonate) (OPO) ligands are reviewed. At last, the influence of PO ligand structural features such as symmetry, flexibility, steric effect in axial direction, as well as the pure electronic effect on the insertion and polymerization reactivity of PO metal catalyst are explored, at the same time, the catalytic reaction mechanism is also studied.
  • 加载中
    1. [1]

       

    2. [2]

      Nakamura, A.; Ito, S, Nozaki, K. Chem. Rev. 2009, 109, 5215.

    3. [3]

      Berkefeld, A.; Mecking, S. Angew. Chem., Int. Ed. 2008, 47, 2538. 

    4. [4]

      Ito, S.; Nozaki, K. Chem. Rec. 2010, 10, 315.

    5. [5]

      Chung, T. C. Functionalization of Polyolefins, Academic Press, USA, 2002, p. 69.

    6. [6]

      Osakada, K. Organometallic Reactions and Polymerization, Lecture Notes in Chemistry, Springer-Verlag, Berlin Heidelberg, 2014.

    7. [7]

      Desurmont, G.; Tokimitsu, T.; Yasuda, H. Macromolecules 2000, 33(21), 7679.

    8. [8]

      Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414. 

    9. [9]

      Contrella, N. D.; Sampson, J. R.; Jordan, R. F. Organometallics 2014, 33, 3546. 

    10. [10]

      Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169.

    11. [11]

      Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888. 

    12. [12]

      Hou, Z. M.; Luo, Y. J.; Li, X. F. J. Organomet. Chem. 2006, 691(14), 3114. 

    13. [13]

      Yamamoto, A.; Nishiura, M.; Oyamada, J.; Koshino, H.; Hou, Z. M. Macromolecules 2016, 49(7), 2458. 

    14. [14]

      Kang, X. H.; Zhou, G. L.; Wang, X. B.; Qu, J. P.; Hou, Z. M.; Luo, Y. Organometallics 2016, 35(6), 913. 

    15. [15]

      Soller, B. S.; Sun, Q.; Salzinger, S.; Jandl, C.; Pöthig, A.; Rieger, B. Macromolecules 2016, 49(5), 1582.

    16. [16]

      Wang, Z. C.; Liu, D. T.; Cui, D. M. Macromolecules 2016, 49(3), 781. 

    17. [17]

      Kuhn, P.; Semeril, D.; Matt, D.; Chetcuti, M. J.; Lutz, P. Dalton. Trans. 2007, 515.

    18. [18]

      Murray, R. E.; Charleston, W. V. US 4689437, 1987[Chem. Abstr. 1988, 108, 6646].

    19. [19]

      Murray, R. E.; Wenzel, T. T. Am. Chem. Soc. Div. Pet. Chem. 1989, 34, 599.

    20. [20]

      Drent, E.; Van, D. R.; Van, G. R.; Van, O. B.; Pugh, R. I. Chem. Commun. 2002, 744.

    21. [21]

      Drent, E.; Van, D. R.; Van, G. R.; Van, O. B.; Pugh, R. I. Chem. Commun. 2002, 964.

    22. [22]

      Hearley, A. K.; Nowack, R. J.; Rieger, B. Organometallics 2005, 24, 2755. 

    23. [23]

      Kochi, T.; Yoshimura, K.; Nozaki, K. Dalton. Trans. 2006, 25.

    24. [24]

      Kryuchkov, V. A.; Daigle, J. C.; Skupov, K. M.; Winnik, F. M.; Claverie,J. P. J. Am. Chem. Soc. 2010, 132, 15573. 

    25. [25]

      Friedberger, T.; Wucher, P.; Mecking, S. J. Am. Chem. Soc. 2012, 134, 1010. 

    26. [26]

      Runzi, T.; Frohlich, D.; Mecking, S. J. Am. Chem. Soc. 2014, 132, 17690.

    27. [27]

      Daigle, J. C.; Piche, L. C.; Claverie, J. P. Macromolecules 2011, 44, 1760. 

    28. [28]

      Shen, Z. L.; Jordan, R. F. Macromolecules 2010, 43, 8706. 

    29. [29]

      Luo, S. J.; Vela, J.; Lief, G. R.; Jordan, R. F. J. Am. Chem. Soc. 2007, 129, 8946. 

    30. [30]

      Skupov, K. M.; Piche, L.; Claverie, J. P. Macromolecules 2008, 41, 2309. 

    31. [31]

      Bouilhac, C.; Runzi, T.; Mecking, S. Macromolecules 2010, 43, 3589.

    32. [32]

      Nakamura, A.; Anselment, T. M. J.; Claverie. J. P.; Goodall, B.; Jordan, R. F.; Mecking, S.; Rieger, B.; Sen, A.; Leeuwen, P. W. N. M.; Nozaki, K. Acc. Chem. Res. 2013, 46(7), 1438. 

    33. [33]

      Guironnet, D.; Roesle, P.; Rünzi, T.; Göttker-Schnetmann, I.; Mecking, S. J. Am. Chem. Soc. 2009, 131, 422. 

    34. [34]

      Berkefeld, A.; Guironnet, D.; Neuwald, B.; Roesle, P.; Rünzi, T.; Wucher, P.; Göttker-Schnetmann, I.; Dürr, C.; Mecking, S. Polym. Prepr. 2010, 51(2), 367.

    35. [35]

      Matthew, P. C.; Richard, F. J. Angew. Chem., Int. Ed. 2011, 50, 3744. 

    36. [36]

      Albietz, P. J.; Cleary, B. P.; Paw, W.; Eisenberg, R. Inorg. Chem. 2002, 41, 2095.

    37. [37]

      Casares, J. A.; Espinet, P. Inorg. Chem. 1997, 36, 5428.

    38. [38]

      Carrow, B. P.; Nozaki, K. J. Am. Chem. Soc. 2012, 134, 8820.

    39. [39]

      Wilkes, C. E.; Daniels, C. A.; Summers, J. W. PVC Handbook, Carl Hanser Verlag, Munich, 2005.

    40. [40]

      Boone, H. W.; Athey, P. S.; Mullins, M. J.; Philipp, D.; Muller, R.; Goddard, W. A. J. Am. Chem. Soc. 2002, 124, 8790. 

    41. [41]

      Philipp, D. M.; Muller, R. P.; Goddard, W. A.; Storer, J.; McAdon, M.; Mullins, M. J. Am. Chem. Soc. 2002, 124, 10198. 

    42. [42]

      Foley, S. R.; Stockland, R. A.; Shen, H. J.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350. 

    43. [43]

      Nozaki, K.; Carrow, B. P. J. Am. Chem. Soc. 2012, 134, 8802. 

    44. [44]

      Leicht, H.; Göttker-Schnetmann, I.; Mecking, S. Angew. Chem., Int. Ed. 2013, 52, 3963. 

    45. [45]

      Zhang, D.; Guironnet, D.; Göttker-Schnetmann, I.; Mecking, S. Organometallics 2009, 28, 4072.

    46. [46]

      Perrotin, P.; McCahill, J. S. J.; Wu, G.; Scott, L. S. Chem. Commun. 2011, 47, 6948. 

    47. [47]

      Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685. 

    48. [48]

      Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338. 

    49. [49]

      Zhou, X. Y.; Bontemps, S.; Jordan, R. F. Organometallics 2008, 27(19), 4822.

    50. [50]

      Nowack, J. R.; Hearley, K. A.; Rieger, B. Z. Anorg. Allg. Chem. 2005, 631, 2775. 

    51. [51]

      Guironnet, D.; Runzi, T.; Göttker-Schnetmann, I.; Mecking, S. Med. Chem. Commun. 2008, 4965.

    52. [52]

      Contrella, N. D.; Sampson, J. R.; Jordan, R. F. Organometallics 2014, 33, 3546. 

    53. [53]

      Shen, Z,; Jordan, R. F. J. Am. Chem. Soc. 2010, 132, 52. 

    54. [54]

      Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888. 

    55. [55]

      Kuwabara, J.; Tekeuchi, D.; Osakada, K. Chem. Commun. 2006, 3815.

    56. [56]

      Rodriguez, B. A.; Delferro, M.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 5902. 

    57. [57]

      Shen, Z. L.; Jordan, R. F. Macromolecules 2010, 43, 8706. 

    58. [58]

      Carrow, B. P.; Nozaki, K. Macromolecules 2014, 47(8), 2541. 

    59. [59]

      Friedberger, T.; Ziller, J. W.; Guan, Z. B. Organometallics 2014, 33, 1913. 

    60. [60]

      Neuwald, B.; Falivene, L.; Caporaso, L.; Cavallo, L.; Mecking, S. Chem. Eur. J. 2013, 19, 17773. 

    61. [61]

      Neuwald, B.; Caporaso, L.; Cavallo, L.; Mecking, S. J. Am. Chem. Soc. 2013, 135, 1026 

    62. [62]

      Anselment, T. M. J.; Wichmann, C.; Anderson, C. E.; Herdtweck, E.; Rieger, B. Organometallics 2011, 30, 6602.

    63. [63]

      Wucher, P.; Goldbach, V.; Mecking, S. Organometallics 2013, 32, 4516.

    64. [64]

      Rünzi, T.; Tritschler, U.; Roesle, P.; Göttker-Schnetmann, I.; Möller, H. M.; Caporaso, L.; Poater, A.; Cavallo, L.; Mecking, S. Organometallics 2012, 31, 8388.

    65. [65]

      Guo, L. H.; Dai, S. Y.; Sui, X. L.; Chen, C. L. ACS Catal. 2016, 6(1), 428. 

    66. [66]

      Ito, S.; Wang, W. H.; Nozaki, K. Polym. J. 2015, 47, 474.

    67. [67]

      Jian, Z. B.; Falivene, L.; Wucher, P.; Roesle, P.; Caporaso, L.; Cavallo, L.; Inigo G., S.; Mecking, S. J. Chem. Eur. 2015, 21, 2062. 

    68. [68]

      Labed, A.; Jiang, F.; Labed, I.; Lator, A.; Peters, M.; Achard, M.; Kabouche, A.; Kabouche, Z.; Sharma, G. V. M.; Bruneau, C. ChemCatChem 2015, 7, 1090. 

    69. [69]

      Li, M. L.; Song; H. B.; Wang, B. Q. Organometallics 2015, 34(10), 1969. 

    70. [70]

      Nakano, R.; Nozaki, K. J. Am. Chem. Soc. 2015, 137(34), 10934. 

    71. [71]

      Schuster, N.; Rünzi, T.; Mecking, S. Macromolecules 2016, 49(4), 1172.

  • 加载中
    1. [1]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    2. [2]

      Wenliang Wang Weina Wang Tian Sheng Nan Wei Sufan Wang Tao Zhou . 过渡金属/氧化物催化CO2加H2还原生成甲醇的甲酸盐与甲酰基路径的前线轨道对称性分析. University Chemistry, 2026, 41(9): 405-411. doi: 10.12461/PKU.DXHX202508059

    3. [3]

      Liu LinZemin SunHuatian ChenLian ZhaoMingyue SunYitao YangZhensheng LiaoXinyu WuXinxin LiCheng Tang . Recent Advances in Electrocatalytic Two-Electron Water Oxidation for Green H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(4): 2305019-0. doi: 10.3866/PKU.WHXB202305019

    4. [4]

      Yingying Wang Yang Yu . 基于统计能量分析的酶催化机理探究:以丝氨酸水解酶为例. University Chemistry, 2026, 41(9): 373-381. doi: 10.12461/PKU.DXHX202508066

    5. [5]

      Dan Li Hui Xin Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046

    6. [6]

      Shunyi TangHeng GuoBo YuJuan LiuLinqiu LiHaoran WuWeijun TianFengying ZhangYing Zhou . Hydrogen shuttle relay on Pd-Ru dual sites for high-efficiency nitrate electroreduction to ammonia. Acta Physico-Chimica Sinica, 2026, 42(10): 100299-0. doi: 10.1016/j.actphy.2026.100299

    7. [7]

      Linjie ZHUXufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207

    8. [8]

      Xuhu GUOChuntao ZHANGJinshu LIYuanyuan TANQaiowen CHANGJuan YU . Structure and catalytic performance of [Pd(1, 5-cyclooctadiene)X2] (X=Cl, Br) modulated by organophosphine ligands. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1247-1260. doi: 10.11862/CJIC.20250299

    9. [9]

      Jiaxuan YANGChenfa DENGJingyang LIUChenzexi XUHongxin CHENYahui ZHUYing LIShuhua WANGRongping ZHOUChao CHEN . Advances in selective hydrogenation of α, β-unsaturated aldehydes/ketones catalyzed by metal-organic frameworks and their derivatives: A review. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1973-2010. doi: 10.11862/CJIC.20250175

    10. [10]

      Xuejie WangGuoqing CuiCongkai WangYang YangGuiyuan JiangChunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044

    11. [11]

      Lele FengXueying BaiJifeng PangHongchen CaoXiaoyan LiuWenhao LuoXiaofeng YangPengfei WuMingyuan Zheng . Single-atom Pd boosted Cu catalysts for ethanol dehydrogenation. Acta Physico-Chimica Sinica, 2025, 41(9): 100100-0. doi: 10.1016/j.actphy.2025.100100

    12. [12]

      Huiwei DingBo PengZhihao WangQiaofeng Han . Advances in Metal or Nonmetal Modification of Bismuth-Based Photocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2305048-0. doi: 10.3866/PKU.WHXB202305048

    13. [13]

      Yushan CaiFang-Xing Xiao . Revisiting MXenes-based Photocatalysis Landscape: Progress, Challenges, and Future Perspectives. Acta Physico-Chimica Sinica, 2024, 40(8): 2306048-0. doi: 10.3866/PKU.WHXB202306048

    14. [14]

      Yuanyin CuiJinfeng ZhangHailiang ChuLixian SunKai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-0. doi: 10.3866/PKU.WHXB202405016

    15. [15]

      Enqi CHENXinyi MAXiang HANYutong YEKexin QINShenghui LIChangli ZHANGMin YUChangyun CHEN . Research progress on MOF-based electrocatalysts for the urea oxidation reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(9): 1871-1892. doi: 10.11862/CJIC.20260168

    16. [16]

      Mian WeiChang ChengBowen HeBei ChengKezhen QiChuanbiao Bie . Inorganic-organic CdS/YBTPy S-scheme photocatalyst for efficient hydrogen production and its mechanism. Acta Physico-Chimica Sinica, 2025, 41(12): 100158-0. doi: 10.1016/j.actphy.2025.100158

    17. [17]

      Linjie ZHUXufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416

    18. [18]

      Xue LiuLipeng WangLuling LiKai WangWenju LiuBiao HuDaofan CaoFenghao JiangJunguo LiKe Liu . Research on Cu-Based and Pt-Based Catalysts for Hydrogen Production through Methanol Steam Reforming. Acta Physico-Chimica Sinica, 2025, 41(5): 100049-0. doi: 10.1016/j.actphy.2025.100049

    19. [19]

      Qing LiGuangxun ZhangYuxia XuYangyang SunHuan Pang . P-Regulated Hierarchical Structure Ni2P Assemblies toward Efficient Electrochemical Urea Oxidation. Acta Physico-Chimica Sinica, 2024, 40(9): 2308045-0. doi: 10.3866/PKU.WHXB202308045

    20. [20]

      Wen YANGDidi WANGZiyi HUANGYaping ZHOUYanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO2 methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276

Metrics
  • PDF Downloads(0)
  • Abstract views(3319)
  • HTML views(317)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return