Wartime research on RDX: A false hypothesis is better than no hypothesis

Abstract

In 1899, Henning (/) obtained a compound CyHgNeOe by treating hexamethylenetetramine (hexamine) (1) with nitric acid and, in an action revealing much about the practices of industry, patented it as a urinary antiseptic, Hexamine hydrolyzes slowly to formaldehyde and ammonia at physiological pH and had already been used as a urinary antiseptic, whence its alternative name of urotropine; however, we now know that Henning's compound is completely useless for this purpose, being much too stable to hydrolysis.More than two decades later, Herz (2) recognized that Henning's compound had the structure 2 and was a powerful high explosive. In 1925 Hale (3) of Edgewood Arsenal, New Jersey, published a detailed account of its preparation in 99.8% nitric acid. After this, the military research establishments of several countries began to study its manufacture and military applications, giving it various trivial names such as RDX, cyclonite, hexogen, etc. Most of this work was secret. With the coming of World War II many academic

The decomposition of aliphatic N-nitro amines in aqueous sulfuric acid. Bisulfate as a nucleophile

“…Little information is available in the open literature concerning this functional group, probably because military explosives are often alkylnitramines, the two best known being RDX and HMX (2). In contrast, the parent molecule nitramide, NH2N02, has been widely studied, and the results have contributed greatly to the theory of acid-base catalysis (3).…”

Investigation of a new promising process for the RDX synthesis via 1,3,5‐triacetyl‐1,3,5‐triazinane (TRAT)

“…Its explosive properties and structure were not recognized until more than two decades later and arouse the interest of the military research establishments of several nations in the 1930s. With the start of World War II research in its production proliferated and the compound received various trivial names [2]. In the United Kingdom it was referred to as RDX, in the USA as cyclonite, in Germany as Hexogen and in Italy as T4 [3,4].…”