[rjb]

Hello,

Without wishing to appear too stupid, I am having a few difficulties trying to get my head around the reaction mechanism for the so called 'Woolwich' process used in the manufacture of 1,3,5-Trinitro-1,3,5-triazacyclohexane (a common military energetic also known as RDX). The process involves the direct nitration of methanamine (hexamethylenetetramine), but so far, not having been involved in organic chemistry (until recently) for a good few years, I can't quite get my head what's actually happening (from a purely mechanistic perpective) during the reaction. Can anyone explain the mechanism for this?

I wish to make it clear that I have no interest or desire in the actual synthesis of the compound, I am purely intesreted in the mechanism from a thoretical perspective.

Many thanks

Richard

[AWK]

_{but so far, not having been involved in organic chemistry (until recently) for a good few years}
and, probably never will not be involved. But, after inquisitive reading of any good university textbook on organic chemistry you can find mechanisms for all steps of this process.

[rjb]

AWK,

Many thanks, I have tried a number of textbooks without much luck. I can sort of work out what's going on, but what confuses me is that one of the secondary products of the reaction is cyclotetramethylene-tetranitramine a sort of 'tetramer' of a nitroamine. This is the bit that doesn't make sense me or fit with my thinking of what's going on during the reaction.

I'm sorry if the question is obvious, but I've not done any organic since my undergrad days and after working in molecular biology have lost any semblence of the knowledge I must once have had - That's my excuse anyhow

Many thanks

R

[AWK]

There is nothing confusing for me. You start from urotropine that contain 4 nitrogen atoms. You can imagine such a ring comes from the impurity of reagent or is formed under acidic condition or is a result of an rearrangement in the course of reaction. Looking at Wikipedia one can guess the third possibility is the most probable since in proper condition the yield of "tetramer" may be increased substantially.