Made two new peroxy compounds.
I made some hydroxy acetone from bromoacetone and a dilute solution of lead nitrate. This reacted a solution of ammonia, probably making
amino-acetone.
CH3C(O)CH2OH <--> CH3C(OH)CHO
A typical nitration was performed in an icebath, and a highly explosive compound was obtained. Only limited H2SO4 was used. The compound was only
fairly sensitive. A hammer blow would set it off. I am unsure exactly what the product was, but I believe it may have been
CH3CH(ONO2)CH2N(NO2)CH2CH(ONO2)CH3
or
O2NCH2C(O)CH2NHNO2
The second reaction done, also involved CH3COCH3.
H2O2, then a small ammount of NaBr was added. Slowly, dilute HNO3 was added. A brown color would appear, then dissapear after stirring, then reappear
after more HNO3 solution was added. Eventually, addition of HNO3, or even more H2O2, stopped making a brown color. There were no bromide ions left in
solution at this point. After 30min a white precipitate began appearing at the top, and floating in the water; this precipitate appeared to be
heavier, and a portion appeared to mix in the solution differently than acetone perxoide. The precipitate was removed 3 hours later, and allowed to
react with AgNO3 in toluene. AgBr obviously precipitated. The toluene was left to evaporate. The precipitate had crystallized somewhat, and, like
Acet.perox. still made a fireball on ignition. This was somewhat disappointing, since it would be expected that adding a nitrate would make it less
volatile, and explode with a bang instead. This is an interesting example of an organic mixed nitrate ester and peroxide. The extra nitrate was hoped
to allow actual combustion that could also utilize the oxygen in the peroxide to burn. In normal acet. perox. , the oxygen balance is too poor to
allow a burn, and the explosion is all entropic; O2 and acetone are basically the only decomposition products.
Bromoacetone can be made by simply mixing a solution of bromine into acetone. I used NaBr, H2O2, and dilute HNO3 to make the bromine.
from wikipedia: "Bromoacetone is a versatile reagent in organic synthesis. It is, for example, the precursor to hydroxyacetone "
Let me clarify the uniqueness of using hydroxyacetone.
NH4OH will not, to any substancial degree, condense with acetone or an alcohol. But it will condense with acetaldehyde CH3CHO (making a hexamine like
compound with extra methyl groups). HydroxyAcetone has equilibrium with an aldehyde, and can react as such. But the ketone dominates, so the end
carbon only bonds with one nitrogen atom, not two as CH2O would. Note: anhydrous NH3 is NOT required, that is a completely separate dehydration
reaction.
CH3C(OH)CHO + NH4OH --> CH3C(OH)CH(OH)(NH2) + H2O
CH3C(OH)CH(OH)(NH2) --> CH3C(O)CH2NH2 + H2O
This is an easy way to put an amine on acetone, that can be used to make the nitramine.
[Edited on 2-7-2010 by Anders Hoveland]
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