Picric Acid from Tylenol(acetaminophen)

[Nihilist]

I was wondering whether you guys think this would be possible using at least a fairly similar method as the picric acid synth. with aspirin. I would think that considering the molecules are fairly similar a process could be developed to produce picric from tylenol. Also an interesting sidenote about the compound is that when heated it will produce oxides of nitrogen, though i'm not sure which oxide of nitrogen but if it's NO2 it could also be a good way to make nitric. Sorry if this is completely wrong, I could not find much information on the compound, all I could find was a chemical formula so I don't know the structure only the physical properties and the chemical forumula.

<small>[ February 18, 2003, 08:19 PM: Message edited by: Nihilist ]</small>

[Macgyver]

Sorry, but that won't work. Acetaminophen is a completely different chemical than the acetylsaliyic acid you need to make picric acid.

[imported_reodor_felgen]

Nihilist, you can find the structure at this page:
<a href="http://chemfinder.cambridgesoft.com/" target="_blank">http://chemfinder.cambridgesoft.com/</a>
(CAS: 103-90-2)

It's an exelent resource for finding chemical data, and you don't have to register or anything!

[mongo blongo]

Yea the molecule hasn't got the valency to start with.
Nice to see some new people with some brains by the way. :)

[Nihilist]

Thanks for the help, btw that site is an awesome resource for chemical info. However, what do you think about possibly using it as a method of synthesizing nitric, because on the msds sheet i read it says that when heated it will release oxides of nitrogen but it didn't specify which, if someone could figure that out it might be a really cheap and easy way to mass produce nitric. Later today I might try bubbling some of the fumes produced through water, I'll tell you all how it goes if I get around to doing it.

<small>[ February 19, 2003, 09:18 PM: Message edited by: Nihilist ]</small>

[Anthony]

"it might be a really cheap and easy way to mass produce nitric"

How?

I couldn't find an RRP price for it using google, but say 24 tablets cost $1 and each tab contains 500mg (similar to paracetamol).

that's 12gm for $1 or approx $83.33/kg.

How much of that would you get decomposed into NO2? A fraction. Then the efficiency of dissolving it in water to produce HNO3, again a fraction.

At this rate you're heading for multi-hundred dollar per litre nitric, as opposed to $2.50/kg for H2SO4 and $1/kg for KNO3 to do the same.

Plus the shop you're buying hundreds of packs of pain killers from would no doubt tip off the law.

Please correct if I'm wrong here...

[Nihilist]

hmm... you do seem to be right I didn't really think that one through sorry.

[Bo bo]

doesnt this substance start life as (OH)C6H4(NO2)?

[kabooom]

<a href="http://www.angelfire.com/rnb/pjff/acetaminophen_PJFF.GIF" target="_blank">click here</a>

[achmed]

if you take a look at those pictures you see that the CH3COO is splitted off by the HCl. If you use nitric instead the NO2-ion would bond to the nitrogen atom and you would get a nitramine group. Then you could treat the molecule with more nitric/sulphuric acid. What do think about that?

[Crystaline Green]

I believe that your idea, achmed, of using nitric acid to hydrolyze the acetaminophen and simultaneously using it to create the nitoramino group would work. I cannot, however, find any reference to nitroamines in my organic text book. I believe that it is very probable that the synthesis of a nitroamine is very similar to the synthesis of a nitrosamine which utilizes dilute nitrous acid to facilitate the nitrogen nitrogen bond. Your suggestion of using nitric acid I think would behave in a similar fashion, but the end result would be a nitroamine. It would be nice to find supporting work on this point, or supporting experiments. Either one would work.

Kaboom according to my text book (Organic Chemistry by Solomons & Fryhle 8th edition if you are interested) the oxidation of primary or secondary amines usually results in a multitude of different products and is usually a fairly useless reaction. Also the reaction with the methylamine I believe you are thinking of is a reductive amination which utilizes the ketone or aldehyde functional group not the hydroxyl group. I'm sorry but I don't think those two reaction you proposed would work.

[tapira1]

Your idea of getting PA from tylenol won't work. Once you try to oxidize the drug (without or after acid hydrolysis of the acetamido group to p-aminophenol), you will get a quinone (actually perhaps quinone-imine) and then this will get decomposed.
You should use a different starting material; for example, chlorobenzene may afford you phenol by caustic fusion and then TNP (PA) by nitration.