[ Search Rogue Science ]




[ Search The Forum ]


Advanced Search


Synthesis of AMMO

AMMO, an acronym for azidomethylmethyloxetane, is an energetic plasticizer or binder. While not an explosive itself, AMMO is one of several of a new class of materials designed to replace inert plasticizers with energetic ones. AMMO finds use in propellants, plastic explosives, and in gas generating systems like airbags. AMMO will add extra energy to any explosive or propellant, whereas the traditional binders are inert, thus decreasing explosive energy from the intended application.


C5H9N3O
b.p. ? °C mass ? g/mol
m.p. ? °C CAS# 90683-29-7
den. ? g/mL v.det. ? m/s

3-(azidomethyl)-3-methyloxetane
3-(azidomethyl)-3-methyloxetane
3-(azidomethyl)-3-methyl-oxetane
azidomethylmethyloxetane
oxetane, 3-(azidomethyl)-3-methyl-


AMMO

AMMO

Synthesis 1:
Into a 5-L round-bottomed flask prepare a solution of 1062 g of sodium azide and 2450 g of 3-bromomethyl-3-methyloxetane in 1972 mL of water.  Heat this solution to reflux for 48 hours while stirring vigorously.  Allow the solution to cool to room temperature and the layers to separate.  Decant off the organic layer and wash it by mixing three times with 1000 mL of water.  The organic layer of pure AMMO can be dried by storing over molecular sieves.  Final yield is about 85%.
To polymerize the AMMO this procedure can be used:  Into a flame dried 5-L round-bottomed flask protected by an inert argon atmosphere prepare a mixture of 14.94 g of butanediol and 1.34 mL of dry methylene chloride.  Add to this mixture 11.77 g of borontrifluoride-etherate and let the reaction proceed for 1 hour at room temperature.  The flask is then cooled to -10 C and 937.78 g of AMMO is added.  The flask is allowed to warm to room temperature and is left for three days while the polymerization commences.  The reaction is quenched by adding 50 mL of saturated sodium chloride solution.  The organic layer is decanted off and shaken with 100 mL of 10% sodium bicarbonate solution in a separatory funnel.  The solvent is removed by aspiration and the resulting liquid is poured into 5 L of methyl alcohol to precipitate the polymerized AMMO.  Filter to collect the polymer crystals and dry them under vacuum at 30 C.

Synthesis 2:
Prepare a solution of 10.1 g of 3-chloromethyl-3-methyloxetane, 6.5 g of sodium azide, and 0.308 g of tetra-n-butylammonium bromide in 27 mL of water.  Reflux this solution at 96-103 C for 4.5 hours.  Allow the solution to cool to room temperature and extract it with 25 mL of methylene chloride in a separatory funnel.  The extract is poured through a column containing 10 g of aluminum oxide and the column is rinsed with additional methylene chloride.  The combined solvent is gently heated to evaporate it leaving crystals of AMMO behind.  Final yield is about 9.85 g or 93%.  The AMMO may be polymerized as in the procedure given above.

While a good faith effort has been made to ensure the accuracy of all scientific information presented on this page, the possibility exists that some errors have invaded the machine. Furthermore, there may be certain omissions of physical properties, reaction conditions, necessary equipment, storage and handling requirements, and critical safety data. As with any scientific endeavor, especially chemistry, the necessary safety precautions should be observed at all times.

I do not allow errors to persist on my website once they have been discovered, but I need your help to find them. If you observe an error in any procedure, or a critical omission of essential safety precautions, and you have a valid reference that I can independently verify to back up your claim, please contact me via the error reporting form. If there are omissions in this procedure, such as a missing boiling point, density, etc., please contact me if you can fill in the blanks. I am also interested in receiving any alternate methods, or improvements in the procedure to synthesize this compound. If you are interested in submitting your own information please use the user submission area.

If you have comments, additions, clarifications, or observations that you wish to add about this compound and its method of synthesis, post them on The Forum using the thread below . You must be a registered member of The Forum to make posts, which is free and easy to do. The rules of this commenting thread are different from the regular rules of The Forum. This thread is for additions to this page only, no questions or remarks are allowed that do not contribute to the scientific information of this compound are allowed. To that end all posts to this thread will be moderated.

Home     |     The Chem Lab      |     The Forum      |     Tools & Techniques      |     The Library      |     Contacts
Copyright © Rogue Science, 1997-2008