EXP9 - 1 Layla Fijany Chem 12A T/TH 5-10pm 9/5/2011...

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1 Layla Fijany Chem 12A T/TH 5-10pm 9/5/2011 Experiment 9: Acetaminophen Purpose : to prepare acetaminophen by treating an amine with and acid anhydride to form an amide Introduction: Crystallization (or recrystallization) is a common method used to purify solid compounds, in this case it will be acetaminophen. The drug acetaminophen is a pain reliever (an analgesic) and a fever- reducing agent. It is found in over-the-counter medicines such as Tylenol and Excedrin. It is widely used to treat both chronic and acute pain and is considered to have a pain-relieving potency similar to that of other over-the-counter analgesics, such as aspirin and ibuprofen. Crystallization techniques will be used to isolate the crude acetaminophen with vacuum filtration to collect the crystals. Crude, Solid acetaminophen has dark impurities, which are formed from oxidation of the starting phenol. A decolorization agent, such as sodium dithionite, will be used to produce a colorless substance. Recrystallization will then be used to purify the acetaminophen. Calculating the percent yield and determining the melting point will be useful in comparing the isolated product to crude acetaminophen. Hypothesis: The greatest percent yield will be attained by cooling the mixture in the most effective way possible (slow-long cooling period) and by adding the right amount of solvent best for crystallization. Also, the more pure the isolated acetaminophen, the closer it will be the literature melting point value. Reaction: List of Reagents FW (g/mol) BP (˚C) MP (˚C) Density (g/cm 3 ) Other (hazards, uses, etc)
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2 Methyl Alcohol (CH 4 O) : 32.05 64.7 -98 0.7918 - reacts violently with acids, reducing agents, highly flammable; colorless, volatile, poisonous Acetaminophan ( C 8 H 9 N O 2 ):151.17 ----- 169 1.26 - aka Tylenol, used as over the counter pain reliever and fever reducer; overdoses may cause liver damage and may be heightened by alcohol consumption; white crystalline powder; stable under ordinary conditions p-aminophenol (C 6 H 7 NOH): 109.13 284 188 1.13 - white fine powder, used as a developer in black and white films, crystals darken when exposed to light; possible mutagen and teratogen Acetic anhydride (C 4 H 6 O 3 ): 102140 -73 1.08 -clear liquid, smells strongly of acetic acid, versatile reagent for acetlyations; irritant and flammable, vapors are harmful Sodium dithionite (Na 2 S 2 O 4 ): 174.1 decomposes 52 2.19 -white crystalline powder with weak sulfurous odor, stable under most conditions, but will decompose in hot water and acid solutions; very soluble in water; skin, eye, throat irritant
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This note was uploaded on 02/26/2012 for the course OCHEM 12A taught by Professor Alston during the Fall '11 term at Saddleback.

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EXP9 - 1 Layla Fijany Chem 12A T/TH 5-10pm 9/5/2011...

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