Synthesis of hexamethylenetriperoxidediamine

Preparation of hexamethylenetriperoxidediamine

Alternative Names: HMTD; 3,4,8,9,12,13-HEXAOXA-1,6-DIAZABICYCLO[4.4.4]TETRADECANE; Hexamethylenetriperoxidediamine; Hexamethylene triperoxide diamine; 3,4,8,9,12,13-Hexaoxa-1,6-diazabicyclo(4.4.4)tetradecane;

Preparation of hexamethylenetriperoxidediamine

Preparation of hexamethylenetriperoxidediamine

14 g of hexamethylenetetramine are dissolved in 45 g of 30% hydrogen peroxide solution which is stirred mechanically in a beaker standing in a freezing mixture of cracked ice with water and a little salt. To the solution 21 g of powdered citric acid is added slowly in small portions at a time while the stirring is continued and the temperature of the mixture is kept at 0° C or below. After all the citric acid has dis­solved, the mixture is stirred for 3 hours longer while its temperature is kept at 0° C. The cooling is then discontinued, the mixture is allowed to stand for 2 hours at room temperature, and the white crystalline product is filtered off, washed thoroughly with water, and rinsed with alcohol in order that it may dry out more quickly at ordinary tempera­tures. Hexamethylenetriperoxidediamine is almost insoluble in water and in the common organic solvents at room temperature.

Chemistry of Powder and Explosives, by T. L. Davis, 451, 1941

IUPAC Name

3,4,8,9,12,13-hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane

InChI

InChI=1S/C6H12N2O6/c1-7-2-11-13-5-8(4-10-9-1)6-14-12-3-7/h1-6H2

InChI Key

HMWPNDNFTFSCEB-UHFFFAOYSA-N

Canonical SMILES

C1N2COOCN(COO1)COOC2

MeSH Synonyms

hexamethylene triperoxide diamine, hexamethylenetriperoxidediamine, HMTD

Depositor-Supplied Synonyms

HMTD, 3,4,8,9,12,13-HEXAOXA-1,6-DIAZABICYCLO[4.4.4]TETRADECANE, Hexamethylenetriperoxidediamine, Hexamethylene triperoxide diamine, 283-66-9, 3,4,8,9,12,13-Hexaoxa-1,6-diazabicyclo(4.4.4)tetradecane, AC1L1UJ0, AC1Q1ID0, Ex145, CHEMBL346085, SCHEMBL3408654, CTK1A6758, HMWPNDNFTFSCEB-UHFFFAOYSA-N, Hexamethylene triperoxide diamine (dry), HE045017, HE331567, Hexamethylene triperoxide diamine (dry) [Forbidden]

Removed Synonyms

CID61101

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