Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter September 24, 2020

Ionic liquids: green solvents and reactive compounds? Reaction of tri-n-butylmethylphosphonium dimethylphosphate with elemental sulfur

  • Natalia Tarasova , Efrem Krivoborodov EMAIL logo , Alexey Zanin and Yaroslav Mezhuev

Abstract

The opening of the S8 ring with the formation of linear sulfur oligomers in the presence of tri-n-butylmethylphosphonium dimethylphosphate is shown. The reaction products are separated and characterized with 1H, 13C, 31P, 17O NMR spectroscopy, HD-MS, MALDI spectroscopy and XRD. It is shown that dimethylphosphate-anion is active in the reaction, and the addition of sulfur atoms occurs via the oxygen atom of dimethylphosphate-anion. It is found that a mixture of products is formed, which differ in the number of sulfur atoms in the chain. The assumptions were made about the mechanism of interaction of sulfur with tri-n-butylmethylphosphonium dimethylphosphate.


Corresponding author: Efrem Krivoborodov, D. Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russia, e-mail:

Article note: A collection of invited papers based on presentations at the 8th IUPAC International Conference on Green Chemistry (ICGC-8), Bangkok, Thailand, 9–14 September 2018.


Funding source: Dmitry Mendeleev University of Chemical Technologies of Russia

Award Identifier / Grant number: 2020-040

  1. Research funding: This research was supported by Mendeleev University of Chemical Technology of Russia. Project Number 2020-040.

References

[1] E. A. Chernikova, L. M. Glukhov, V. G. Krasovskiy, L. M. Kustov, M. G. Vorobyeva, A. A. Koroteev. Russ. Chem. Rev.84, 875 (2015).Search in Google Scholar

[2] A. E. Rosamilia, C. R. Strauss, J. L. Scott. Pure Appl. Chem.79, 1869 (2007).Search in Google Scholar

[3] K. J. Fraser, D. R. MacFarlane. Austral. J. Chem.62, 309 (2009).Search in Google Scholar

[4] H. Choudhary, P. Berton, G. Gurau, A. S. Myerson, R. D. Rogers. Chem. Comm.54, 2056 (2018).Search in Google Scholar

[5] J. Li, S. Yang, W. Wu, H. Jiang. Eur. J. Org. Chem.11, 1284 (2018).Search in Google Scholar

[6] M. H. G. Prechtl, J. D. Scholten, J. Dupont. Molecules15, 3441 (2010).Search in Google Scholar

[7] F. Bellina, C. Chiappe. Molecules15, 2211 (2010).Search in Google Scholar

[8] V. Beniwal, A. Kumar. Phys. Chem. Chem. Phys.19, 4297 (2017).Search in Google Scholar

[9] V. Beniwal, A. Manna, A. Kumar. Chem. Phys. Chem.17, 196 (2016).Search in Google Scholar

[10] E. Baciocchi, C. Chiappe, C. Fasciani, O. Lanzalunga, A. Lapi. Org. Lett.12, 5116 (2010).Search in Google Scholar

[11] C. Dai, J. Zhang, C. Huang, Z. Lei. Chem. Rev.117, 6929 (2017).Search in Google Scholar

[12] A. A. M. Lapis, L. F. de Oliveira, B. A. D. Neto, J. Dupont. Chem. Sus. Chem.1, 759 (2008).Search in Google Scholar

[13] H. P. Steinrück, P. Wasserscheid. Cat. Lett.145, 380 (2015).Search in Google Scholar

[14] M. Baidossi, A. V. Joshi, S. Mukhopadhyay, Y. Sasson. Tetr. Lett.46, 1885 (2005).Search in Google Scholar

[15] V. I. Pârvulescu, C. Hardacre. Chem. Rev.107, 2615 (2007).Search in Google Scholar

[16] S. T. Keaveney, R. S. Haines, J. B. Harper. Pure Appl. Chem.89, 745 (2017).Search in Google Scholar

[17] K. S. Schaffarczyk McHale, R. R. Hawker, J. B. Harper. New J. Chem.40, 7437 (2016).Search in Google Scholar

[18] K. S. Schaffarczyk McHale, R. S. Haines, J. B. Harper. Chem. Plus Chem.83, 1162 (2018).Search in Google Scholar

[19] K. S. Schaffarczyk McHale, R. S. Haines, J. B. Harper. Chem. Plus Chem.84, 465 (2019).Search in Google Scholar

[20] C. Chiappe, D. Pieraccini, P. Saullo. J. Org. Chem.68, 6710 (2003).Search in Google Scholar

[21] R. Bini, C. Chiappe, C. S. Pomelli, B. Parisi. J. Org. Chem.74, 8522 (2009).Search in Google Scholar

[22] G. Ranieri, J. P. Hallett, T. Welton. Ind. Eng. Chem. Res.47, 638 (2008).Search in Google Scholar

[23] R. Bini, C. Chiappe, E. Marmugi, D. Pieraccini. Chem. Comm.8, 897 (2006).Search in Google Scholar

[24] F. C. Binks, G. Cavalli, M. Henningsen, B. J. Howlin, I. Hamerton. Polymers11, 657 (2019).Search in Google Scholar

[25] M. Gazitua, R. A. Tapia, R. Contreras, P. R. Campodonico. New J. Chem.38, 2611 (2014).Search in Google Scholar

[26] H. Zhao, G. A. Baker. Front. Chem. Sci. Eng.9, 262 (2015).Search in Google Scholar

[27] S. A. Dharaskar, K. L. Wasewar, M. N. Varma, D. Z. Shende, C. K. Yoo. Proc. Eng.51, 416 (2013).Search in Google Scholar

[28] K. R. Balinge, A. G. Khiratkar, M. Krishnamurthy, D. S. Patle, K. K. Cheralathan, P. R. Bhagat. Resour. Effic. Technol.2, S105 (2016).Search in Google Scholar

[29] C. S. Pomelli, C. Chiappe, A. Vidis, G. Laurenczy, P. J. Dyson. J. Phys. Chem. B111, 13014 (2007).Search in Google Scholar

[30] C. Chiappe, C. S. Pomelli. Top. Curr. Chem.375, 52 (2017).Search in Google Scholar

[31] J. Pernak, F. Walkiewicz, M. Maciejewska, M. Zaborski. Ind. Eng. Chem. Res.49, 5012 (2010).Search in Google Scholar

[32] M. Maciejewska, F. Walkiewicz, M. Zaborski. Ind. Eng. Chem. Res.52, 8410 (2013).Search in Google Scholar

[33] M. Maciejewska, M. Zaborski. Polym. Bull.75, 4499 (2018).Search in Google Scholar

[34] N. P. Tarasova, Y. O. Mezhuev, A. A. Zanin, E. G. Krivoborodov. Dokl. Chem.484, 8 (2019). https://doi.org/10.1134/s0012500819010051.Search in Google Scholar

[35] J. M. Catala, M. Clauss. Macromolecules24, 2663 (1991).Search in Google Scholar

[36] A. V. Tobolsky. J. Polym. Sci. Part C Polym. Symp.12, 71 (2007).Search in Google Scholar

[37] S. Penczek, R. Slazak, A. Duda. Nature273, 738 (1978).Search in Google Scholar

[38] N. P. Tarasova, E. G. Krivoborodov, A. N. Egorova, A. A. Zanin, L. M. Glukhov I. Y. Toropygin Y. O. Mezhuev. Pure Appl. Chem.92, 1297 (2020).Search in Google Scholar

[39] A. V. Tobolsky, A. Eisenberg. J. Am. Chem. Soc.81, 780 (1959).Search in Google Scholar

[40] J. J. Griebel, R. S. Glass, K. Char, J. Pyun. Prog. Polym. Sci.58, 90 (2016).Search in Google Scholar

[41] O. Holloczki, D. S. Firaha, J. Friedrich, M. Brehm, R. Cybik, M. Wild, A. Stark, B. Kirchner. J. Phys. Chem. B117, 5898 (2013).Search in Google Scholar

[42] I. Chiarotto, L. Mattiello, F. Pandolfi, D. Rocco, M. Feroci. Front. Chem.6, 355 (2018).Search in Google Scholar

[43] A. F. Villamizar-Mogotocoro, J. M. Urbina-González. J. Anal. Pharm. Res.7, 463 (2018).Search in Google Scholar

Published Online: 2020-09-24
Published in Print: 2021-01-27

© 2020 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/

Downloaded on 25.4.2024 from https://www.degruyter.com/document/doi/10.1515/pac-2019-0804/html
Scroll to top button