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Study on the Mechanism of the Acetolysis of Hexamethylenetetramine
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AbstractThe acetolysis of hexamethylenetetramine (hexamine) to give 3,7‐diacetyl‐1,3,5,7‐tetraaza‐[3.3.1]‐bicyclononane (DAPT), 1,3,5,7‐tetraacetyl‐1,3,5,7‐tetraazacyclooctane (TAT) and 1,3,5‐triacetyl‐1,3,5‐triazacyclohexane (TRAT) was studied. NMR tracing showed the courses of acetolysis, the effects of the reaction conditions on its directions, and the evidence that the methylene degraded from hexamine was the formaldehyde. Based on these results, the acetolysis mechanism was proposed. The comparison of the acetolysis with the nitrolysis of hexamine showed that the two reactions experienced the similar courses, which would be useful for searching out a way to improve the yield of 1,3,5,7‐tetranitro‐1,3,5,7‐tetraazacyclooctane (HMX) in Bachmann process.
Title: Study on the Mechanism of the Acetolysis of Hexamethylenetetramine
Description:
AbstractThe acetolysis of hexamethylenetetramine (hexamine) to give 3,7‐diacetyl‐1,3,5,7‐tetraaza‐[3.
3.
1]‐bicyclononane (DAPT), 1,3,5,7‐tetraacetyl‐1,3,5,7‐tetraazacyclooctane (TAT) and 1,3,5‐triacetyl‐1,3,5‐triazacyclohexane (TRAT) was studied.
NMR tracing showed the courses of acetolysis, the effects of the reaction conditions on its directions, and the evidence that the methylene degraded from hexamine was the formaldehyde.
Based on these results, the acetolysis mechanism was proposed.
The comparison of the acetolysis with the nitrolysis of hexamine showed that the two reactions experienced the similar courses, which would be useful for searching out a way to improve the yield of 1,3,5,7‐tetranitro‐1,3,5,7‐tetraazacyclooctane (HMX) in Bachmann process.
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