Kataliza procesów hydrosililowania z udziałem cieczy jonowych

Bartlewicz, Olga; Szymańska, Anna; Jankowska-Wajda, Magdalena; Dąbek, Izabela; Maciejewski, Hieronim

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Tytuł artykułu

Kataliza procesów hydrosililowania z udziałem cieczy jonowych

Autorzy

Bartlewicz Olga , Szymańska Anna , Jankowska-Wajda Magdalena , Dąbek Izabela , Maciejewski Hieronim

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Warianty tytułu

Catalysis of hydrosilylation processes with the participation of ionic liquids

Języki publikacji

Abstrakty

Hydrosilylation is a fundamental and elegant method for the laboratory and industrial synthesis of organosilicon compounds. The hydrosilylation reaction is usually performed in a single-phase homogeneous system. A major problem, particularly in homogeneous catalysis, is the separation of catalyst from the reaction mixture. The presence of metals in the reaction products, even in trace quantities, is unacceptable for many applications, therefore efforts have been made at applying heterogeneous catalysts or immobilised metal complexes in order to obtain high catalytic activity and easy product isolation at the same time. One of the methods for producing such catalysts is the employment of ionic liquids as agents for the immobilization of metal complexes. Biphasic catalysis in a liquid-liquid system is an ideal approach through which to combine the advantages of both homogeneous and heterogeneous catalysis. The ionic liquids (ILs) generally form the phase in which the catalyst is dissolved and immobilized. In our research we have obtained a number of catalytic systems of such a type which were based on rhodium and platinum complexes dissolved in phosphonium, imidazolium, pyridinium and ammonium liquids. Currently, there has a common trend to obtain heterogenized systems that combine advantages of homogeneous and heterogeneous catalysis, which makes the hydrosilylation process more cost- effective. Such integration of homo- and heterogeneous catalysts is realized in several variants, as supported IL phase catalysts (SILPC) and solid catalysts with ILs layer (SCILL). Although all the above systems show high catalytic activities, their structure is unknown. This is why we have made attempts to modify selected ionic liquids (corresponding to our most effective systems) and we have applied them as ligands in the synthesis of platinum and rhodium complexes. Another group of catalysts comprises anionic complexes of rhodium and platinum which were obtained by reactions between halide complexes of metals and a respective ionic liquid. Most of the obtained complexes are solids insoluble in hydrosilylation reagents and are characterized by a high catalytic activity. A considerable development of heterogeneous catalysts of this type and their application in many hydrosilylation processes can be expected in the future. This mini-review briefly describes the recent progress in the design and development of catalysts based on the presence of ionic liquids and their applications for hydrosilylation processes.

Słowa kluczowe

hydrosililowanie kompleksy Rh kompleksy Pt ciecze jonowe SILPC kataliza heterogeniczna

hydrosilylation Rh complexes Pt complexes ionic liquids SILPC heterogeneous catalysis

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2021

Tom

[Z] 75, 1-2

Strony

5--29

Opis fizyczny

Bibliogr. 66 poz., schem., tab.

Twórcy

autor

Bartlewicz Olga

Wydział Chemii, Zakład Chemii i Technologii Związków Krzemu, Uniwersytet im. A. Mickiewicza w Poznaniu, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań

https://orcid.org/0000-0003-2848-744X

autor

Szymańska Anna

Poznański Park Naukowo-Technologiczny Fundacji Uniwersytetu im. A. Mickiewicza w Poznaniu, ul. Rubież 46, 61-612 Poznań

https://orcid.org/0000-0003-0062-764X

autor

Jankowska-Wajda Magdalena

Wydział Chemii, Zakład Chemii i Technologii Związków Krzemu, Uniwersytet im. A. Mickiewicza w Poznaniu, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań

https://orcid.org/0000-0003-1278-3789

autor

Dąbek Izabela

Poznański Park Naukowo-Technologiczny Fundacji Uniwersytetu im. A. Mickiewicza w Poznaniu, ul. Rubież 46, 61-612 Poznań

https://orcid.org/0000-0003-4602-6364

autor

Maciejewski Hieronim

Wydział Chemii, Zakład Chemii i Technologii Związków Krzemu, Uniwersytet im. A. Mickiewicza w Poznaniu, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań
Poznański Park Naukowo-Technologiczny Fundacji Uniwersytetu im. A. Mickiewicza w Poznaniu, ul. Rubież 46, 61-612 Poznań

https://orcid.org/0000-0003-2771-3089

Bibliografia

[1] B. Marciniec, H. Maciejewski, C. Pietraszuk, P. Pawluć, Hydrosilylation. A Comprehensive Review on Recent Advances, (B. Marciniec ed.), Springer, 2009.
[2] D. Trogel, J. Strohrer, Coord. Chem. Rev., 2011, 255, 1440.
[3] Y. Nakajima, S. Shimada, RSC Adv., 2015, 5, 20603.
[4] B. Marciniec, H. Maciejewski, С. Pietraszuk, P. Pawluć, Applied Homogeneus Catalysis with Organometallic Compounds (B. Cornils, W.A. Hermann, M. Beller, R. Paciello, eds.), Wiley, 2017, 2, 569.
[5] R. J. Hoffmann, M. Vlathovic, F. Wiesbrock, Polymers, 2017, 9, 534.
[6] B. Marciniec, H. Maciejewski, P. Pawluć, Organosilicon Compounds. (V. Y. Lee, ed.), Academic Press, London, 2017, 169.
[7] R.Y. Lukin, A.M. Kuchkaev, A.V. Sukhov, G.E. Bekmukhamedov, D.G. Yakhvarov, Polymers, 2020, 12, 2174.
[8] B. Marciniec (ed.), Comprehensive Handbook on Hydrosilylation, Pergamon Press, Oxford 1992.
[9] P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.
[10] D.J. Adams, P.J. Dyson, S.J. Tavener, Chemistry in Alternative Reaction Media; Wiley: Chichester, United Kingdom, 2004.
[11] S.K. Singh, A.W. Savoy, J. Mol. Liq., 2020, 297, 112038.
[12] J.P. Hallet, T. Welton, Chem. Rev., 2011, 111, 3508.
[13] D. Ozokwelu, S. Zhang, O.C. Okafor, W. Cheng, N. Litombe, Novel Catalytic and Separation Processes based on Ionic Liquids. Elsevier: Amsterdam, The Netherlands 2017.
[14] P.J. Dyson, T.J. Geldbach, Metal Catalysed Reactions in Ionic Liquids. Springer: Dordrecht, The Netherlands, 2005
[15] J. Dupont, L. Kollar, Ionic Liquids (ILs) in Organometallic Catalysis. Springer: Dordrecht, The Netherlands, 2015.
[16] C. Hardacre, V. Parvulescu, Catalysis in Ionic Liquids. From Catalysts Synthesis to Applications. RS: Cambridge, United Kingdom, 2014.
[17] R.L.A. Vekariya, J. Mol. Liq., 2017, 227, 44.
[18] S. Aubin, F. le Floch, D. Carric, J.P. Guegan, M. Vaultier, W.D. Rogers, K.R. Seddon (eds.), Ionic Liquids: Industrial Applications for Green Chemistry, ACS, Washington, 2002.
[19] J. van den Broeke, F. Winter, B.-J. Deelman, G. van Koten, Org. Lett., 2002, 22, 3851.
[20] B. Weyershausen, K. Hell, U. Hesse, Green Chem., 2005, 7, 283.
[21] T.J. Geldbach, D. Zhao, N.C. Castillo, G. Laurenczy, B. Weyershausen, P.J. Dyson, J. Am. Chem. Soc., 2006, 128, 9773.
[22] H. Maciejewski, A. Wawrzyńczak, M. Dutkiewicz, R. Fiedorow, J. Mol. Cat. A: Chem., 2006, 257, 141.
[23] B. Marciniec, H. Maciejewski, K. Szubert, M. Kurdykowska, Monatshefte fur Chem., 2006, 137, 605.
[24] H. Maciejewski, K. Szubert, B. Marciniec, J. Pernak, Green Chem., 2009, 11, 1045.
[25] R. Kukawka, R. Januszewski, I. Kownacki, M. Smiglak, H. Maciejewski, Catal. Com., 2018, 108, 59.
[26] H. Maciejewski, K. Szubert, B. Marciniec, Catal. Com, 2012, 24, 1.
[27] J. Pernak, A. Świerczyńska, M. Kot, F. Walkiewicz, H. Maciejewski, Tetrahedron Letters, 2011, 52, 4342.
[28] M. Jankowska-Wajda, I. Dąbek, R. Fiedorow, H. Maciejewski, RSC Adv., 2018, 8, 26922.
[29] H. Maciejewski, K. Szubert, R. Fiedorow, R. Giszter, M. Niemczak, J. Pernak, W. Klimas, App. Cat. A: General, 2013, 451, 168.
[30] C. Wu, J. Peng, J. Li, Y. Bai, Y. Hu, G. Lai, Cat. Com., 2008, 10, 248.
[31] Y. Xu, Y. Bai, J. Peng, J. Li, W. Xiao, G. Lai, J. Organometal. Chem., 2014, 765, 59.
[32] Y. Bai, F. Zhang, J. Li, Y. Xu, J. Peng, W. Xiao, J. Organometal. Chem., 2015, 794, 65.
[33] Y. Qiao, W. Ma, N. Theyssen, C. Chen, Z. Hou, Chem. Rev., 2017, 117, 6881.
[34] J.J. Peng, J. Li, Y. Bai, H. Qiu, K. Jiang, J. Jiang, G. Lai, Cat. Com., 2008, 9, 2236.
[35] J.J. Peng, J.Y. Li, Y. Bai, W.H. Gao, H.Y. Qiu, H. Wu, Y. Deng, G. Lai, J. Mol. Cat. A: Chem., 2007, 278, 97.
[36] M. Hejazifar, O. Lanaridi, K. Bica-Schroder, J. Mol. Liq., 2020, 303, 112264.
[37] O. Bartlewicz, I. Dąbek, A. Szymańska, H. Maciejewski, Catalysts, 2020, 10, 1227.
[38] R. Fehrmann, A.M. Riisager, A. Haumann, Supported Ionic Liquids. Fundamentals and Applications, Wiley-VCH, Weinheim, Germany 2014.
[39] Y. Gu, G. Li, Adv. Synth. Cat., 2009, 351, 817.
[40] P. Kaur, H. Chopra, Curr. Org. Chem., 2019, 23, 2881.
[41] C. Feher, M. Papp, B. Urban, R. Skoda-Foldes, Catalytic Applications of Supported Ionic Liquid Phases, in Advances in Asymmetric Autocatalysis and Related Topics, Academic Press, chap. 17, 2017.
[42] T. Itoh, Y-M. Koo, Application of Ionic Liquids in Biotechnology, Springer, Switzerland, 2019.
[43] U. Kernchen, B. Etzold, W. Korth, A. Jess, Chem. Eng. Technol., 2007, 79, 807.
[44] S. Werner, N. Szesni, M. Kaiser, M. Haumann, P. Wasserscheid, Chem Eng. Technol., 2012, 11, 1962.
[45] N. O’Reilly, N. Giri, S.L. James, Chem. Eur. J., 2007, 13, 3020.
[46] S. Zhang, K. Dokko; M. Watanabe, Chem. Sci., 2015, 6, 3684.
[47] E. Kuhmann, M. Haumann, A. Jess, A. Seeberger, P. Wasserscheid, ChemSusChem. 2009, 2, 969.
[48] H.P. Steinruck, P. Wasserscheid, Catal. Lett., 2015, 145, 380.
[49] R. Kukawka, A. Pawłowska-Zygarowicz, J. Działkowska, M. Pietrowski, H. Maciejewski, K. Bica, M. Śmiglak, ACS Sus. Chem. Eng., 2019, 7, 4699.
[50] R. Kukawka, A. Pawłowska-Zygarowicz, R. Januszewski, J. Działkowska, M. Pietrowski, M. Zieliński, H. Maciejewski, M. Śmiglak, Catalysts, 2020,10, 1414
[51] J. Li, J. Peng, Y. Bai, G. Zhang, G. Lai, X. Li, J. Org. Chem., 2010, 695, 431.
[52] J. Li, J. Peng, D. Wang, Y. Bai, J. Jiang, G. Lai, J. Org. Chem., 2011, 696, 263.
[53] M. Jankowska-Wajda, O. Bartlewicz, A. Szpecht, A. Zając, M. Śmiglak, H. Maciejewski, RSC Adv., 2019, 9, 29396.
[54] O. Bartlewicz, M. Jankowska-Wajda, H. Maciejewski, Catalysts, 2020, 10, 608.
[55] J.S. Wilkes, Green Chem., 2002, 4, 73.
[56] M. Jankowska-Wajda, O. Bartlewicz, A. Walczak, A.R. Stefankiewicz, J. Cat., 2019, 374, 266.
[57] M. Jankowska-Wajda, O. Bartlewicz, P. Pietras, H. Maciejewski, Catalysts, 2020, 10, 919.
[58] O. Bartlewicz, M. Jankowska-Wajda, H. Maciejewski, RSC Adv., 2019, 9, 711.
[59] N. Hofmann, A. Bauer, T. Frey, M. Auer, V. Stanjek, P.S. Schulz, N. Taccardi, P. Wasserscheid, Adv. Synth. Catal., 2008, 350, 2599.
[60] P. Watts, C. Wiles, Stereoselective Synthesis of Drugs and Natural Products, Willey-VCH, Weinheim, 2013, vol. 1.
[61] K. Takasu, Microreactors in Organic Chemistry and Catalysis, (T. Wirth, ed.) Willey-VCH, Weiheim, 2013, str. 151-196.
[62] M. Miyazaki, M.P. Briones-Nagata, T. Honda, H. Yamaguchi, Microreactors in Organic Chemistry and Catalysis, (T. Wirth, ed.) Willey-VCH, Weiheim, 2013, str. 181-193.
[63] W. Zieliński, R. Kukawka, H. Maciejewski, M. Śmiglak, Molecules, 2016, 21, 1115.
[64] W. Zieliński, R. Kukawka, H. Maciejewski, M. Śmiglak, Molecules, 2017, 22, 1203.
[65] R. Kukawka, A. Pawłowska-Zygarowicz, M. Dutkiewicz, H. Maciejewski, M. Śmiglak, RSC Adv. 2016, 6, 61860.
[66] M. Jankowska-Wajda, R. Kukawka, M. Śmiglak, H. Maciejewski, New J. Chem., 2018, 42, 5229.

Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).

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Bibliografia

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