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Optimization of the Synthesis of 2,4,6,8,10,12‐Hexaallyl‐ 2,4,6,8,10,12‐Hexaazaisowurtzitane
Author(s) -
Adamiak Joanna,
Maksimowski Paweł
Publication year - 2009
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.200800027
Subject(s) - glyoxal , allylamine , yield (engineering) , formic acid , catalysis , chemistry , acetonitrile , solvent , condensation , aminosalicylic acid , nuclear chemistry , organic chemistry , materials science , polyelectrolyte , physics , metallurgy , thermodynamics , polymer , medicine , pharmacology
2,4,6,8,10,12‐Hexaallyl‐2,4,6,8,10,12‐hexaazaisowurtzitane (HALLIW) was obtained in a condensation reaction of glyoxal with allylamine in the presence of a protonic acid as a catalyst. Optimization of the synthesis was accomplished by means of a mathematical experiment planning theory with the steepest descent method. The effect of the following parameters was examined: process temperature, amount of the catalyst, amount of the solvent, glyoxal addition time, reaction time, and the ratio of the substrates. As a result of the study an improved yield was achieved from 20 to 66.5%. The highest yield for the reaction was found for the conditions (mole ratios relative to glyoxal): catalyst (formic acid) 0.1 : 1; solvents: acetonitrile 9.35 : 1, water 0.18 : 1; allylamine 2.2 : 1; temperature 15 °C; glyoxal addition time 15 min, reaction time 60 min. The studies were conducted on a small laboratory scale where the yield and purity of the product obtained were examined. A method was developed for purification of HALLIW. NMR, IR spectroscopy, DSC, and TG analyses were employed in the study and their results are reported.