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Old 02-08-2010, 11:32 PM   #1 (permalink)
 
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Paracetamol Hydrolysis question (4-aminophenol)

Not after a parodinal formula.

I was wondering, how many mol to how many mol it takes for paracetamol to convert to 4-aminophenol, using potassium hydroxide.

edit: and the resulting amount of 4-aminophenol.

Last edited by Athiril; 02-09-2010 at 12:02 AM..
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Old 02-09-2010, 12:04 AM   #2 (permalink)
 
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It takes 151.17 grams of paracetamol (Tylenol) to make 109.13 grams of 4-aminophenol.
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Old 02-09-2010, 12:08 AM   #3 (permalink)
 
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The important part is how much potassium hydroxide does that take? Is it 1 mol to 1 mol?

If you get less 4-aminophenol than the weight of paracetamol and hydroxide together.. what are the byproducts?
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Old 02-09-2010, 10:53 AM   #4 (permalink)
 
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If you use paracetamol (insoluble) to make p-aminophenol (insoluble) how do you know the reaction has gone to completion and the result is not a mixture of the two?To get round this I make the aminophenolate which is soluble.I use sodium not potassium but the equation can be converted by replacing Na=23 by K=39.The by-products are sodium acetate and water.

C8H9NO2......+.....2NaOH...........->...C6H6NaNO....+C2H3NaO2.....+H2O
Paracetamol..Sodium Hydroxide....->.Sodium Aminophenolate...+...+..
151.17..................80...............->....131.12.......
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Old 02-09-2010, 02:25 PM   #5 (permalink)
 
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You probably want an excess of NaOH there too to drive the reaction and keep the pH up for the hydrolysis...
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