METHYLATION OF 5-NITROTETRAZOLE SODIUM SALT UNDER PHASE-TRANSFER CATALYSIS CONDITIONS

Authors

  • Юлия Н. Павлюкова Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013
  • Ольга М. Нестерова Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013
  • Михаил А. Илюшин Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013
  • Владимир А. Островский Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013

DOI:

https://doi.org/10.1007/3849

Keywords:

1-methyl-5-nitrotetrazole, 2-methyl-5-nitrotetrazole, 5-nitrotetrazole sodium salt, tetrabutylammonium bromide, alkylation, phase-transfer catalysis, two-phase water – organic solvent mixtures

Abstract

The alkylation of 5-nitrotetrazole sodium salt with dimethyl sulfate was studied in a two-phase water–dichloromethane system in the presence of tetrabutylammonium bromide as a phase-transfer catalyst. The reaction produced a mixture of regioisomers – 1-methyl- and 2-methyl-5-nitrotetrazoles in 1:3 ratio. 2-Methyl-5-nitrotetrazole was obtained from this mixture as individual compound in 52% yield. The application of phase-transfer catalysis allowed to obtain 5-nitrotetrazole N-alkyl derivatives under conditions that did not require preliminary isolation of highly impact and friction sensitive 5-nitrotetrazole salts from aqueous solutions.

Authors: Yulia N. Pavlyukova, Olga M. Nesterova, Mikhail A. Ilyushin, Vladimir A. Ostrovskii*

 

Author Biography

Владимир А. Островский, Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg 190013

д.х.н., Кафедра химии и технологии органических соединений азота

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Published

2017-08-18

Issue

Vol. 53 No. 6/7 (2017): Heterocycle-based energetic materials

Section

Original Papers