Fantasma4500
International Hazard
Posts: 1677
Registered: 12-12-2012
Location: Dysrope (aka europe)
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Mood: dangerously practical
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Dioxirane amine oxidation
DMDO oxidation of amines into nitrocompounds
im finding various sources on this reaction but its all pretty vague
i found one explaining KMnO4 and acetone for making DMDO, then reacting that with alanine to make nitroethane- but alanine is quite expensive and i
wanna make other nitrocompounds too. ive tried a bit with KHSO5 and acetone just completely guessing my way around in small amounts, cooling it down
and what not but im not even sure how to detect for any yield, ive tried flametest, nitrocompounds tend to give a kinda white flame- all negatives.
there is a reaction but i think its rather delicate as amine undergoes.... a handful of reactions to end up as the corresponding nitrocompound and
most likely can be overoxidized into CO2 and other useless stuff
https://erowid.org/archive/rhodium/chemistry/nitroethane.htm...
amines are doable to make by decarboxylation of aminoacids, theanine gave me decent yield but it was rather expensive. alanine is not as easy to get a
decent yield out of. glycine could possibly make methylamine- however thats much easier by reduction of nitromethane in race fuel or hexamine, NH4Cl
and HCl refluxed
the link explains a solution of DMDO, which is normally made from acetone and KHSO5 stirred, cooled- but nothing on how to prepare a specific
molarity, what yields etc you get? DMDO isnt otc, its made in the lab. some hints have explained using NaHCO3, which neutralizes the KHSO5- and breaks
it down making it unable to really make DMDO? a compound is listed as being able to titrate- but digging further into this just adds complexity to a
supposedly simple reaction. - has anyone in amateur setting used this successfully? why is there no writings on this very OTC reagent
if one were to make nitromethane, one of the most easy methods would be reacting methyl bromide with silver nitrite- a hazard i personally wouldnt
wanna try.
the link gets more confusing as the reference doesnt really mention anything relating to DMDO but rather the typical alkyl halide with silver nitrite
ive neither found any mentions of whether the acid salts such as methylamine*HCl would be possible to react with oxidizing agents to produce the nitro
compound- methylamine without acid cation is decently volatile.
this is all the more important since nitrite is very difficult to acquire lately
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medchemist
Harmless
Posts: 15
Registered: 10-7-2015
Member Is Offline
Mood: No Mood
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DMDO appears to be liable to overoxidise to the carbonyl. (find a pdf of the Wiley Encyclopedia of Reagents for Organic Synthesis, DOI:
10.1002/047084289X and have a look in there)
In theory you could add a single equivalent but the yield would depend on if the DMDO is more reactive with the starting amine or the resulting nitro
group. if it's the latter then it's unlikely to work. In any case you'd have to work out a way to titrate your starting solution of DMDO.
Personally I'd be looking for other synthetic routes at this point...
Good Luck
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