Contribution to the Synthesis of 4,10-Dinitro-2,6,8,12-
tetraoxa-4,10-diazatetracyclo[ 5,9 0 3,11 ]dodecane (TEX)

and Svatopluk ZEMAN

University of Pardubice, Faculty of Chemical Technology,
Institute of Energetic Materials,
Studentská 95, CZ-532 10, Pardubice, Czech Republic

Abstract: The infuence of the reaction conditions on 4,10-dinitro-2,6,8,12-tetraoxa-
4,10-diazatetracyclo[,9 03,11 ]dodecane (TEX) yield was studied. TEX was
prepared by the reaction of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine with glyoxal
in nitric acid. The infuence of the acidity of reaction mixture and ratios of starting
materials on the yield of TEX was examined and synthesis was optimised. The
highest yield (37%) was obtained at 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine/
nitric acid molar ratio 67 and sulfuric acid/nitric acid molar ratio around 0.15. Starting
material 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine was prepared from formamide
and glyoxal using triethylamine or other tertiary amines to adjust suitable basicity.
The best yield (84%) of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine was reached
at molar ratio triethylamine/formamide equal to 0.1.

Keywords: 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracy-
clo[ 5,9 0 3,11 ]dodecane, TEX, 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine,
tertiary amines, insensitive explosives