2,4,6-trinitrophenol

Materials Required

• Concentrated sulfuric acid (>90%)
• Acetylsalicylic acid (aspirin, moron)
• Nitrate salt

• 19 g of purified aspirin was added to 50 ml of concentrated sulfuric acid.
• The aspirin had some trouble dissolving; it had also formed a cakey mass which is difficult to see due to my shitty abilities as a photographer.
• The sulfuric acid was heated to about 100*C and was allowed to react for 30 minutes. Once the sulfuric acid had heated to about 70-80*C all of the aspirin had dissolved.
• By this point the color of the solution had gotten very dark, so dark infact, you can't distinguish whether or not it is the reacting solution or a load of shit I just injected into the flask. Fucking camera.
• 30 g of NH₄NO₃ was added in small portions to the solution slowly. Mad foaming, much heat generated. Wish I had a decent photo to show you all.
• It took about 30 minutes to add all of the NH₄NO₃, dunking it occasionally in a cold water bath when the heat got out of hand.
• Look at all the beautiful NO₂ vapors. If my shit would fume, that would be the color. Uh oh, the temperature's getting out of hand. What's this white vapour? Oh, must be acetic acid. Since it boils at about 118*C, must be REALLY FUCKING HOT in there. Bath it, but only after filling the room with acetic acid and NO₂, we are trying to lead a healthy life, yes?
• By now the solution should be a nice orangey color. What's that? Piece of shit camera?
• Let it react a bit. You should probably go and get some fresh air at this point, while you let it cool off.
• Dumped about 350 ml's of cold water into the solution. It was done in portions and I suggest doing the same, shaking it after each addition and maybe letting it cool off a bit. Lots of NO₂ generated, but it subsides.
• After pouring it into water you can really see the true color of the picric acid.
• Put it in the fridge overnight.
• Filter the crystals. Rub them on yourself and have people address you as the Joker, you yellowing mutant freak.
• Dry them, mass it. 15 g, 63% yield.
• Recrystallize with
• Store under water, don't let it dry out otherwise you can lose a limb, possibly your happy flappy. This would be devestating.

• This isn't the original reaction I carried out. Originally I had used 5 g of aspirin in 20 ml of sulfuric acid, which I then decided was too little acid and I added more to 40 ml. I added about 9 g of NH₄NO₃. My yield was poor, about 40% or so. So I posted this one as I recieved better results using a less acid:aspirin ratio.
• NO₂ is not healthy, it's listed as a poison. It's really acrid smelling, reminds me of HCl, but it has it's own twisty fruity taste to it (no, I'm not being serious). Don't sniff too much of it, please.
• Acetic acid is formed from the ester hydrolysis of the aspirin.
• The water's added to crash the TNP from the solution, as it isn't very soluble in water.
• Store the TNP in at least 10% water to ensure it doesn't dry out, or unhappy flappy..
• I am in no way the original Joker, nor do I, or anybody else, have any right to use the proposed title. Mutation is a serious afflication, and it is in my deepest desire that everybody who are reading this far are condemned to the fate of the Joker. We love you Jack.

• This reaction undergoes a series of steps towards the desired product.
• First, the aspirin hydrolsed to give acetic acid and salicylic acid:
• C₆H₄(OCOCH₃)(COOH) + H₂O --H₂SO₄--> C₆H₄(OH)(COOH) + CH₃COOH
• Then the salicylic acid is decarboxylized to form phenol:
• C₆H₄(OH)(COOH) --H₂SO₄--> C₆H₄(OH) + CO₂
• The sulfonate electrophile is formed in situ via the concentrated H₂SO₄:
• H₂SO₄ --H₂SO₄--> S⁺O₃H + H₂O
• Which reacts with the phenol to form either the ortho or para hydroxybenzenesulphonic acid:
• C₆H₄(OH) + S⁺O₃H ---> C₆H₄(OH)(SO₃H)
• The nitro electrophile is created via concentrated H₂SO₄ in situ:
• NO₃^- + 2H₂SO₄ ---> NO₂⁺ + H₂O
• The nitro electrophile then reacts three times with the o/p-hydroxybenzenesulphonic acid to form 2,4,6-trinitrophenol. The last step is the removal of the S⁺O₃H group which is replaced by NO₂:
• C₆H₄(OH)(SO₃H) + 3NO₂⁺ ---> C₆H₄(OH)(3NO₂) + S⁺O₃H
• The overall reaction:
• C₆H₄(OCOCH₃)(COOH) + 3NH₄NO₃ --H₂SO₄--> C₆H₄(OH)(3NO₂) + CH₃COOH + CO₂ + 4H₂O + S⁺O₃H
  
  
• The mechanism:
• Formation of salicylic acid
• Formation of phenol and sulphonate electrophile
• Formation of 2-hydroxybenzenesulphonic acid and nitro electrophile
• Formation of 2,4,6-trinitrophenol

• In 1917 on the coast of Halifax a terrible accident had occured which killed many people. A ship called the Mont Blanc was travelling towards Europe carrying ammunition/explosives to be used for WWI. Well the ship collided with some other ship and spilled some flammable chemical (benzol - coming soon ;) ). This ignited and set the boat aflame. On the boat (and this is the frightening part), was about 6 T of gun cotton, 225 T of TNT, and 2300 T of the very chemical I just synthesized in my basement. After 20 minutes of burning, the explosives went off and over 2.5 km² of Halifax was destroyed. They found the anchor 5 km away from the site. 1635 people died and 9000 injured. The damage was estimated at 30 million dollars, and these were back in the days when comic books and whores were $0.10. Shit
• On the brighter side of things, TNP is also used as a dye. Just try it yourself, put your hand in it and wait a week for it to disappear! Even sex isn't this good!