Skoči na glavni sadržaj

Chemical and Biochemical Engineering Quarterly, Vol. 28 No. 2, 2014.

Izvorni znanstveni članak

https://doi.org/10.15255/CABEQ.2013.1936

Synthesis of 5-phenyltetrazole and its N-methyl Derivatives in a Microreactor

E. A. Popova ; Saint-Petersburg State University, Chemical Faculty, Universitetskii pr. 26, 198504, Saint-Petersburg, Petrodvorets, Russia
R. Sh. Abiev ; St. Petersburg State Institute of Technology (Technical University), 26 Moskowskii Pr., 190013, St. Petersburg, Russia
L. A. Lappalainen ; St. Petersburg State Institute of Technology (Technical University), 26 Moskowskii Pr., 190013, St. Petersburg, Russia
S. D. Svetlov ; St. Petersburg State Institute of Technology (Technical University), 26 Moskowskii Pr., 190013, St. Petersburg, Russia
T. V. Andreeva ; St. Petersburg State Institute of Technology (Technical University), 26 Moskowskii Pr., 190013, St. Petersburg, Russia
R. E. Trifonov ; Saint-Petersburg State University, Chemical Faculty, Universitetskii pr. 26, 198504, Saint-Petersburg, Petrodvorets, Russia
V. A. Ostrovskii ; St. Petersburg State Institute of Technology (Technical University), 26 Moskowskii Pr., 190013, St. Petersburg, Russia

Puni tekst: engleski pdf 338 Kb

str. 241-246

preuzimanja: 1.183

citiraj

Sažetak

Azidation of benzonitrile with dimethylammonium azide yielding 5-phenyltetrazole dimethylammonium salt was performed under microreactor conditions. The kinetics of azidation of benzonitrile in DMF was investigated at the range 80–95 °С. The reaction rate constants were determined:kII·104(L mol–1 s–1): 0.79, 0.97, 1.19, 1.51, at 80, 85, 90, and 95 °С, respectively. It was found that the reaction rate constants obtained in a microreactor are comparable to ones for a batch-type reactor. The thermodynamic parameters
of azidation under the microreactor conditions correspond to the mechanism of the 1,3-dipolar cycloaddition of azides to nitriles. It was established that the excessive pressure in the microreactor notably accelerates the process. The alkylation of 5-phenyltetrazole with methyl iodide in microreactor was performed in dichloromethane-aqueous sodium hydroxide system. The accumulation of regioisomers of N1- and N2-methyl-5-phenyl tetrazole in the microreactor under the conditions of slug flow of the reaction mixture occurs considerably faster than in the batch-type reactor in the conditions of phase-transfer catalysis.

Ključne riječi

azidation of nitriles; tetrazoles; synthesis; alkylation; rate constants; microreactor

Hrčak ID:

120555

URI

https://hrcak.srce.hr/120555

Datum izdavanja:

5.5.2014.

Posjeta: 1.884 *