Synthesis and some properties of poly-5-vinyl-N,N′-dimethyltetrazolium salts

  • Sergei V. Voitekhovich Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus https://orcid.org/0000-0002-7015-5062
  • Yuri V. Grigoriev Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus
  • Oleg A. Ivashkevich Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

Abstract

Poly-5-vinyl-N,N′-dimethyltetrazolium salts, the first representatives of ionic carbochain polymers with a positively charged tetrazole ring in the side chain, were synthesised using polymer-analogous transformations of polyacrylonitrile. The synthesis of salts involves the cycloaddition reaction of sodium azide to polyacrylonitrile to form poly-5-vinyltetrazole, the exhaustive alkylation of which with dimethyl sulfate leads to poly-5-vinyl-N,N′-dimethyltetrazolium methylsulfate. By treating the latter with aqueous solutions of tetrafluoroboric or perchloric acids, poly-5-vinyl-N,N′-dimethyltetrazolium tetrafluoroborate and perchlorate were obtained respectively. The high efficiency of using the resulting polymers for the selective extraction of palladium from model systems containing ions of other heavy and transition metals has been demonstrated.

Author Biographies

Sergei V. Voitekhovich, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

PhD (chemistry); leading researcher at the laboratory for chemistry of condensed systems

 

Yuri V. Grigoriev, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

PhD (chemistry), docent; head of the laboratory for chemistry of condensed systems

 

Oleg A. Ivashkevich, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

doctor of science (chemistry), academician of the National Academy of Sciences of Belarus; chief researcher at the laboratory for chemistry of condensed systems

 

References

  1. Gaponik PN, Ivashkevich OA. Tetrazole-containing polymers: synthesis and properties. Vestnik BGU. Seriya 2, Khimiya. Biologiya. Geografiya. 2013;1:3–29. Russian. EDN: SPKZRT.
  2. Kizhnyaev VN, Golobokova TV, Pokatilov FA, Vereshchagin LI, Estrin YI. Synthesis of energetic triazole- and tetrazole-containing oligomers and polymers. Chemistry of Heterocyclic Compounds. 2017;53(6–7):682–692. DOI: 10.1007/s10593-017-2109-6.
  3. Sukhanov GT, Bosov KK, Filippova YV, Sukhanova AG, Krupnova IA, Pivovarova EV. New 5-aminotetrazole-based energetic polymers: synthesis, structure and properties. Materials. 2022;15(19):6936. DOI: 10.3390/ma15196936.
  4. Klapötke TM, Sproll SM. Investigation of nitrogen-rich energetic polymers based on alkylbridged bis-(1-methyl-tetrazolylhydrazines). Journal of Polymer Science. Part A, Polymer Chemistry. 2010;48(1):122–127. DOI: 10.1002/pola.23767.
  5. Tarchoun AF, Trache D, Klapötke TM, Khimeche K. Tetrazole-functionalized microcrystalline cellulose: a promising biopolymer for advanced energetic materials. Chemical Engineering Journal. 2020;400:125960. DOI: 10.1016/j.cej.2020.125960.
  6. Grigoriev YV, Grigorieva IM, Voitekhovich SV, Ivashkevich OA. [Sorption extraction of Сu2+, Co2+, Ni2+ and Pb2+ from aqueous solutions by tetrazole polymers based on commercial acrylonitrile copolymer]. Doklady of the National Academy of Sciences of Belarus. 2016;60(6):59–63. Russian. EDN: XIESNX.
  7. Gharbi S, Zrida H, Hriz K, Chemek M, Wazzan N, Majdoub M. Synthesis of new tetrazole based-semiconducting polymers for optoelectronic application: study of the effect of anthracene group on photophysical properties. Journal of Molecular Structure. 2022;1250(2):131760. DOI: 10.1016/j.molstruc.2021.131760.
  8. Akdemir MS, Huber B, Simian M, Mutlu H, Theato P. Main chain 1,5-disubstituted-1H-tetrazole-based polymers via ugi-azidefour-multicomponent polymerization (UA-4MCP). ACS Applied Polymer Materials. 2023;5(8):6643–6650. DOI: 10.1021/acsapm.3c01231.
  9. Geiselhart CM, Mutlu H, Barner-Kowollik C. Passerini multicomponent reactions enabling self-reporting photosensitive tetrazole polymers. ACS Macro Letters. 2021;10(9):1159–1166. DOI: 10.1021/acsmacrolett.1c00280.
  10. Zuraev AV, Grigoriev YV, Ivashkevich LS, Lyakhov AS, Ivashkevich OA. Copper-polymer nanocomposite catalyst for synthesis of 1,4-diphenylbutadiyne-1,3. Journal of Inorganic and General Chemistry. 2017;643(19):1215–1219. DOI: 10.1002/zaac.201700213.
  11. Zuraev AV, Grigoriev YV, Budevich VA, Ivashkevich OA. Copper-polymer nanocomposite: an efficient catalyst for green Huisgen click synthesis. Tetrahedron Letters. 2018;59(16):1583–1586. DOI: 10.1016/j.tetlet.2018.03.028.
  12. Henkensmeier D, Duong NMH, Brela M, Dyduch K, Michalak A, Jankova K, et al. Tetrazole substituted polymers for high temperature polymer electrolyte fuel cells. Journal of Materials Chemistry A. 2015;3(27):14389–14400. DOI: 10.1039/C5TA01936B.
  13. Mohamed Zaki MT, Mohamed AES. Potentiometric determination of silver(I), palladium(II) and gold(III) in mixtures by use of an iodide-selective electrode. Mikrochimica Acta. 1991;103:191–198. DOI: 10.1007/BF01309025.
  14. Gaponik PN, Ivashkevich OA, Karavai VP, Lesnikovich AI, Chernavina NI, Sukhanov GT, et al. Polymers and copolymers based on vinyltetrazoles. 1. Synthesis of poly(5-vinyltetrazole) by polymer-analogous conversion of polyacrylonitrile. Die angewandte makromolekulare Chemie. 1994;219(1):77–88. DOI: 10.1002/apmc.1994.052190107.
  15. Gaponik PN, Karavai VP, Grigoriev YV. Synthesis of 1,4,5- and 1,3,5-trisubstituted tetrazolium salts by exhaustive alkylation of 5-monosubstituted tetrazoles with dimethyl sulfate. Doklady of the National Academy of Sciences of Belarus. 1997;41(5):66–68. Russian. EDN: HASMPJ.
Published
2024-02-28
Keywords: tetrazoles, polymers, palladium, sorption
Supporting Agencies The research was supported by the Ministry of Education of the Republic of Belarus (assignment 2.1.01.01 of the state programme of scientific research «Chemical processes, reagents and technologies, bioregulators and bioorgchemistry», state registration No. 20210515).
How to Cite
Voitekhovich, S. V., Grigoriev, Y. V., & Ivashkevich, O. A. (2024). Synthesis and some properties of poly-5-vinyl-N,N′-dimethyltetrazolium salts. Journal of the Belarusian State University. Chemistry, 1, 46-50. Retrieved from https://journals.bsu.by/index.php/chemistry/article/view/6043