Vanadium catalysts for ethylene-norbornene copolymerization

Bihun-Kisiel, Anna; Ochędzan-Siodłak, Wioletta

doi:10.14314/polimery.2020.11.2

Artykuł - szczegóły

Tytuł artykułu

Vanadium catalysts for ethylene-norbornene copolymerization

Autorzy

Bihun-Kisiel Anna , Ochędzan-Siodłak Wioletta

Treść / Zawartość

Pełne teksty:

Pobierz

Identyfikatory

DOI

10.14314/polimery.2020.11.2

Warianty tytułu

Katalizatory wanadowe w kopolimeryzacji etylenu z norbornenem

Języki publikacji

Abstrakty

Cyclic olefin copolymers (COCs) are a promising group of materials with specific, projectable properties. In this group, copolymers of ethylene and norbornene are of particular interest. A variety of transition metal complexes are used for their synthesis, mostly elements from group 4. This review presents the application of vanadium catalysts with various types of ligands in the synthesis of ethylene-norbornene copolymers. The influence of ligands and reaction conditions on the activity of catalyst and selected properties of copolymers are described in this paper.

Kopolimery cyklicznych olefin (COCs) stanowią obiecującą grupę materiałów o specyficznych, możliwych do zaprojektowania właściwościach. Szczególnym zainteresowaniem w tej grupie związków cieszą się kopolimery etylenu z norbornenem. Do ich syntezy stosuje się różnorodne kompleksy metali przejściowych, przede wszystkim pierwiastków z grupy 4. Artykuł stanowi przegląd literatury dotyczącej wykorzystania katalizatorów wanadowych z różnego rodzaju ligandami w syntezie kopolimerów etylenu z norbornenem. Opisano wpływ ligandów i warunków prowadzenia reakcji na aktywność oraz wybrane właściwości otrzymanych kopolimerów.

Słowa kluczowe

vanadium catalyst copolymerization ethylene norbornene cyclic olefin copolymers

katalizator wanadowy kopolimeryzacja etylen norbornen kopolimery cyklicznych olefin

Wydawca

Sieć Badawcza Łukasiewicz – Instytut Chemii Przemysłowej

Czasopismo

Polimery

Rocznik

2020

Tom

T. 65, nr 11-12

Strony

757--770

Opis fizyczny

Bibliogr. 98 poz., rys.

Twórcy

autor

Bihun-Kisiel Anna

abihun@uni.opole.pl

Opole University, Faculty of Chemistry, Chair of Chemical Technology and Polymer Chemistry, Oleska 48, 45-052 Opole, Poland

autor

Ochędzan-Siodłak Wioletta

Opole University, Faculty of Chemistry, Chair of Chemical Technology and Polymer Chemistry, Oleska 48, 45-052 Opole, Poland

Bibliografia

[1] Welz B., Sperling M.: “Atomabsorptionsspektrometrie”, John Wiley & Sons, Weinheim 2012, p. 1857.
[2] Vilter H.: Metal Ions in Biological Systems 1995, 31, 325.
[3] Christman D.L., Keim G.I.: Macromolecules 1968, 1,358. https://doi.org/10.1021/ma60004a017
[4] Lorber C.: Coordination Chemistry Reviews 2016, 308, 76. 768 POLIMERY 2020, 65, nr 11–12 https://doi.org/10.1016/j.ccr.2015.02.021
[5] Crans D.C., Smee J.J.: “Comprehensive Coordination Chemistry II”, (Eds. McCleverty J.A., Meyer T.J., Wedd A.G.) Elsevier, Amsterdam 2004, p. 175.
[6] Nomura K., Zhang W.: Chemical Science 2010, 1, 161. https://doi.org/10.1039/C0SC00163E
[7] Pellissier H.: Coordination Chemistry Reviews 2015, 284, 93. https://doi.org/10.1016/j.ccr.2014.09.014
[8] Nomura K., Zhang S.: Chemical Reviews 2011, 111, 2342. https://doi.org/10.1021/cr100207h
[9] Wu J.Q., Li Y.S.: Coordination Chemistry Reviews 2011, 255, 2303. https://doi.org/10.1016/j.ccr.2011.01.048
[10] Gambarotta S.: Coordination Chemistry Reviews 2003, 237, 229. https://doi.org/10.1016/S0010-8545(02)00298-9
[11] Hagen H., Boersma J., van Koten G.: Chemical Society Reviews 2002, 31, 357. https://doi.org/10.1039/b205238e
[12] Natta G., Zambelli A., Lanzi G. et al.: Die Makromolekulare Chemie 1965, 81, 161. https://doi.org/10.1002/macp.1965.020810118
[13] Zambelli A., Pasquon I., Signorini R. et al.: Die Makromolekulare Chemie 1968, 112, 160. https://doi.org/10.1002/macp.1968.021120115
[14] Natta G., Mazzanti G., Valvassori A. et al.: Journal of Polymer Science 1961, 51, 411. https://doi.org/10.1002/pol.1961.1205115603
[15] Soshnikov I.E., Semikolenova N.V., Bryliakov K.P. et al.: Journal of Organometallic Chemistry 2018, 867, 4. http://dx.doi.org/10.1016/j.jorganchem.2017.08.020
[16] EP 0 156 464 B1 (1985).
[17] Noordermeer J.W.M.: “Kirk-Othmer Encyclopedia of Chemical Technology” Vol. 10, 5th Ed., J. Wiley & Sons, New York 2005, p. 704.
[18] Redshaw C.: Dalton Transactions 2010, 39, 5595. https://doi.org/10.1039/B924088H
[19] Clowes L., Walton M., Redshaw C. et al.: Catalysis Science and Technology 2013, 3, 152. https://doi.org/10.1039/c2cy20571h
[20] Ma J., Zhao K.Q., Walton M. et al.: Dalton Transactions 2014, 43, 16698. https://doi.org/10.1039/C4DT01448K
[21] Ma J., Zhao K.Q., Walton M.J. et al: Dalton Transactions 2014, 43, 8300. https://doi.org/10.1039/c4dt00021h
[22] Redshaw C., Walton M., Michiue K. et al.: Dalton Transactions 2015, 44, 12292. https://doi.org/10.1039/C5DT00376H
[23] Redshaw C., Walton M.J., Elsegood M.R.G. et al.: RSC Advances 2015, 5, 89783. https://doi.org/10.1039/C5RA20177B
[24] Redshaw C., Walton M.J., Lee D.S. et al.: Chemistry: A European Journal 2015, 21, 5199. https://doi.org/10.1002/chem.201406084
[25] Cheng X.P., Fenf L.F., Gu X.P. et al.: Reaction Engineering, Kinetics and Catalysis 2019, 66, 316784. https://doi.org/10.1002/aic.16784
[26] Zanhin G., Bertini F., Vendier L. et al.: Polymer Chemistry 2019, 10, 6200. https://doi.org/10.1039/C9PY01415B
[27] Henrici-Olivé G., Olivé S.: Angewandte Chemie 1971, 10, 776. https://doi.org/10.1002/anie.197107761
[28] Feghali K., Harding D.J., Reardon D. et al.: Organometallics 2002, 21, 968. https://doi.org/10.1021/om011040u
[29] Zhao W., Nomura K.: Catalysts 2016, 6, 175. https://doi.org/10.3390/catal6110175
[30] Leone G., Pierro I., Zanchin G. et al.: Journal of Molecular Catalysis A: Chemical 2016, 424, 220. https://doi.org/10.1016/j.molcata.2016.09.002
[31] Tritto I., Boggioni L., Ferro D.R.: Coordination Chemistry Reviews 2006, 250, 212. https://doi.org/10.1016/j.ccr.2005.06.019
[32] Li X., Hou Z.: Coordination Chemistry Reviews 2008, 252, 1842. https://doi.org/10.1016/j.ccr.2007.11.027
[33] https://topas.com/ sites/default/ﬁles/ﬁles/TOPAS_Brochure_E_2014_06(1).pdf (access data 27.02.2020).
[34] Pei L., Tang Y., Gao H.: Polymers 2016, 8, 69. https://doi.org/10.3390/polym8030069
[35] Leone G., Mauri M., Losio S. et al.: Polymer Chemistry 2014, 5, 3412. https://doi.org/10.1039/C3PY01674A
[36] Nomura K., Wang W., Fujiki M. et al.: Chemical Communications 2006, 2659. https://doi.org/10.1039/b605005k
[37] Makio H., Terao H., Iwashita A. et al.: Chemical Reviews 2011, 111, 2363. https://doi.org/10.1021/cr100294r
[38] Chen M., Zou W., Cai Z. et al.: Polymer Chemistry 2015, 6, 2669. https://doi.org/10.1039/C5PY00010F
[39] Ravasio A., Boggioni L., Tritto I.: Macromolecules 2011, 44, 4180. https://doi.org/10.1021/ma2006427
[40] Li Y., Gao M., Gao H. et al.: European Polymer Journal 2011, 47, 1964. https://doi.org/10.1016/j.eurpolymj.2011.07.012
[41] Zhao M., Chen C.: ACS Catalysis 2017, 7, 7490. https://doi.org/10.1021/acscatal.7b02564
[42] Chen M., Chen C.: ACS Catalysis 2017, 7, 1308. https://doi.org/10.1021/acscatal.6b03394
[43] Na Y., Zhang D., Chen C.: Polymer Chemistry 2017, 8, 2405. https://doi.org/10.1039/C7PY00127D
[44] Song G., Pang W., Li W. et al.: Polymer Chemistry 2017, 8, 7400. https://doi.org/10.1039/C7PY01661A
[45] Li X., Baldamus J., Hou Z.: Angewandte Chemie International Edition 2005, 44, 962. https://doi.org/10.1002/anie.200461971
[46] Ravasio A., Zampa C., Boggioni L. et al.: Macromolecules 2008, 41, 9565 https://doi.org/10.1021/ma802448n
[47] Burt J., Levason W., Reid G.: Coordination Chemistry Reviews 2009, 260, 65. https://doi.org/10.1016/j.ccr.2013.09.020
[48] Cheng C., Hartwig J.F.: Science 2014, 343, 853. https://doi.org/10.1126/science.1248042
[49] Scheuermann M.L., Johnson E.J., Chirik P.J.: Organic Letters 2015, 17, 2716. https://doi.org/10.1021/acs.orglett.5b01135
[50] Murai M., Takeshima H., Morita H. et al.: The Journal of Organic Chemistry 2015, 80, 5407. https://doi.org/10.1021/acs.joc.5b00920
[51] Ricci G., Sommazzi A., Masi F. et al.: Coordination Chemistry Reviews 2010, 254, 661. https://doi.org/10.1016/j.ccr.2009.09.023
[52] Zanchin G., Vendier L., Pierro I. et al.: Organometallics 2018, 37, 3181. https://doi.org/10.1021/acs.organomet.8b00502
[53] Zanchin G., Pierro I., Parisini E.: Journal of Organometallic Chemistry 2018, 861, 142. https://doi.org/10.1016/j.jorganchem.2018.02.042
[54] Zanchin G., Gavezzoli A., Bertini F. et al.: Molecules 2019, 24, 2088. https://doi.org/10.3390/molecules24112088
[55] Yoshida Y., Mohri J.I., Ishii S.I. et al.: Journal of the American Chemical Society 2004, 126, 12023. https://doi.org/10.1021/ja048357g
[56] Lasarov H., Mönkkönen K., Pakkanen T.: Macromolecular Chemistry and Physics 1998, 199, 1939. h t t p s : / / d o i . o r g / 1 0 . 1 0 0 2 / ( S I C I ) 1 5 2 1 -3 9 3 5 ( 1 9 9 8 0 9 0 1 ) 1 9 9 : 9 < 1 9 3 9 : : A I D -MACP1939>3.0.CO;2-F
[57] Zhao W., Yan Q., Tsutsumi K. et al.: Organometallics2016, 35, 1895. https://doi.org/10.1021/acs.organomet.6b00242
[58] van Doremaele G., van Duin M., Valla M. et al.: Journal of Polymer Science Part A: Polymer Chemistry 2017, 55, 2877. https://doi.org/10.1002/pola.28634
[59] Flisak Z., Sun W. H.: ACS Catalysis 2015, 5, 4713. https://doi.org/10.1021/acscatal.5b00820
[60] Coles M.P., Gibson V.C.: Polymer Bulletin 1994, 33, 529. https://doi.org/10.1007/BF00296160
[61] Coles M.P., Dalby C., Gibson V.C. et al.: Journal of Organometallic Chemistry 1999, 591, 78. https://doi.org/10.1016/S0022-328X(99)00452-0
[62] Nomura K., Bahuleyan B.K., Zhang S. et al.: Inorganic Chemistry 2014, 53, 607. https://doi.org/10.1021/ic402747d
[63] Nagai G., Mitsudome T., Tsutsumi K. et al.: Journal of the Japan Petroleum Institute 2017, 60, 256. https://doi.org/10.1627/jpi.60.256
[64] Nomura K., Oshima M., Mitsudome T. et al.: ACS Omega 2017, 2, 8660. https://doi.org/10.1021/acsomega.7b01225
[65] Wang W., Nomura K.: Macromolecules 2005, 38, 5905. https://doi.org/10.1021/ma050629s
[66] Wang W., Nomura K.: Advanced Synthesis & Catalysis 2006, 348, 743. https://doi.org/10.1002/adsc.200505446
[67] Nomura K., Tsutsumi K., Nagai G. et al.: Journal of the Japan Petroleum Institute 2018, 61, 282. https://doi.org/10.1627/jpi.61.282
[68] Diteepeng N., Tang X., Hou X. et al.: Dalton Transactions 2015, 44, 12273. https://doi.org/10.1039/c4dt04026k
[69] Wu J.Q., Mu J.S., Zhang S.W. et al.: Journal of Polymer Science: Part A: Polymer Chemistry 2010, 48, 1122. https://doi.org/10.1002/pola.23868
[70] Wang J.B., Lu L.P., Liu J.Y. et al.: Dalton Transactions 2014, 43, 12926. https://doi.org/10.1039/c4dt01166j
[71] Wang J.B., Lu L.P., Liu J.Y. et al.: Journal of Polymer Science: Part A: Polymer Chemistry 2015, 398, 289. http://dx.doi.org/10.1016/j.molcata.2014.12.016
[72] Tomov A.K., Gibson V.C., Zaher D. et al.: Chemical Communications 2004, 10, 1956. https://doi.org/10.1039/b407065h
[73] Lorber C., Wolff F., Choukroun R. et al.: European Journal of Inorganic Chemistry 2005, 14, 2850. https://doi.org/10.1002/ejic.200500149
[74] Lorber C.: Pure and Applied Chemistry 2009, 81, 1205. https://doi.org/10.1351/PAC-CON-08-08-05
[75] Long Y.Y., Wang Y.X., Li B.X. et al.: Journal of Polymer Science: Part A: Polymer Chemistry 2017, 55, 2787. https://doi.org/10.1002/pola.28681
[76] Hong M., Yang G.F., Long Y.Y. et al.: Journal of Polymer Science: Part A: Polymer Chemistry 2013, 51, 3144. https://doi.org/10.1002/pola.26699
[77] Yang G., Hong M., Li Y. et al.: Macromolecular Chemistry and Physics 2012, 213, 2311. https://doi.org/10.1002/macp.201200350
[78] Li Y.G., Hong M., Zhang G.B. et al.: Chinese Journal of Polymer Science 2013, 31, 574. https://doi.org/10.1007/s10118-013-1249-0
[79] Tao P., Tang X.Y., Li B.X. et al.: Dalton Transactions 2012, 41, 7390. https://doi.org/10.1039/c2dt30326d
[80] Tang L.M., Wu J.Q., Duan Y.Q. et al.: Journal of Polymer Science: Part A: Polymer Chemistry 2008, 46, 2038. https://doi.org/10.1002/pola.22538
[81] Wang K.T., Wang Y.X., Wang B. et al.: Chinese Journal of Polymer Science 2017, 35, 1110. https://doi.org/10.1007/s10118-017-1956-z
[82] Ochędzan-Siodłak W., Bihun A.: Polymer Bulletin 2017, 74, 2799. https://doi.org/10.1007/s00289-016-1866-1
[83] Lu L.P., Wang K.T., Liu Y., Wu J.J.: Acta Polymerica Sinica 2020, 51, 174. h t t p s://d o i . o r g / 10 .117 7 7/ j . issn1000-3304.2019.19128
[84] Wang K., Cui L., Li Y., Li Y.: Journal of Polymer Science & Applications 2017, 1 (1).
[85] Tshuva E.Y., Goldberg I., Kol M.: Journal of the American Chemical Society 2000, 122, 10706. https://doi.org/10.1021/ja001219g
[86] Tshuva E.Y., Goldberg I., Kol M. et al.: Chemical Communications 2000, 5, 379. https://doi.org/10.1039/b000396o
[87] Hu W.Q., Sun X.L., Wang C. et al.: Organometallics 2004, 23, 1684. https://doi.org/10.1021/om0303808
[88] Wang C., Ma Z., Sun X.L. et al.: Organometallics 2006, 25, 3259. https://doi.org/10.1021/om060062j
[89] Gao M., Wang C., Sun X. et al.: Macromolecular Rapid Communications 2007, 28, 1511. https://doi.org/10.1002/marc.200700305
[90] Yang X.H., Sun X.L., Han F.B.: Organometallics 2008, 27, 4618. https://doi.org/10.1021/om800302f
[91] Gao M.L., Sun X.L., Gu Y.F. et al.: Journal of Polymer Science: Part A: Polymer Chemistry 2008, 46, 2807. https://doi.org/10.1002/pola.22614
[92] Yang X.H., Liu C.R., Wang C. et al.: Angewandte Chemie International Edition 2009, 48, 8099. https://doi.org/10.1002/anie.200903334
[93] Wu J.Q., Pan L., Liu S.R. et al.: Journal of Polymer Science: Part A: Polymer Chemistry 2009, 47, 3573. https://doi.org/10.1002/pola.23441
[94] Wu J.Q, Pan L., Li Y.G. et al.: Organometallics 2009, 28, 1817. https://doi.org/10.1021/om801028g
[95] Hafeez M., Lippert S., Bauer T. et al.: Journal of the Iranian Chemical Society 2015, 12, 957. https://doi.org/10.1007/s13738-014-0558-8
[96] Imanishi Y., Nomura K.: Journal of Polymer Science: Part A: Polymer Chemistry 2000, 38, 4613. h t t p : / / d x . d o i . o r g / 1 0 . 1 0 0 2 / 1 0 9 9 -0518(200012)38:1+<4613::AID-POLA10>3.0.CO;2-N
[97] Ochędzan-Siodłak W., Bihun-Kisiel A., Siodłak D. et al.: European Polymer Journal 2018, 106, 148. https://doi.org/10.1016/j.eurpolymj.2018.07.019
[98] Ochędzan-Siodłak W., Siodłak D., Piontek A. et al.: Catalysts 2019, 9, 1041. https://doi.org/10.3390/catal9121041

Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2020).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-9d8df0a8-bf4c-431f-88a6-8cfec60eef9f