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1. Calculate the number of moles of methyl salicylate used.

2. Determine the number of moles of aspirin you synthesized.

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Week #11: Synthesis of Aspirin and Oil of Wintergreen


This will allow crystallization upon cooling.
CONVERSION OF SALICYLIC ACID INTO ASPIRIN
Salicylic Acid + Acetic Anhydride
+ Sulfuric Acid = Aspirin
ACETYLSALICYLIC ACID
METHYL SALICYLATE
SODIUM HYDROXIDE
Caustic Soda
Lye
Different industries: Cleaning, food, paper
ETHYL ACETATE
SULFURIC ACID
Often used as a cleaning agent
Highly corrosive
Strong odor
Used in the experiment as a mineral acid
PREPARATION OF SALICYLIC ACID
HYDROXAMIC ACID TEST
Useful for detecting esters
Red-violet (+)
Detects the presence of Acetylsalicylic acid
FERRIC CHLORIDE TEST
Abridged version of Hydroxamic acid test
Phenols: Purple, red, green
Enols: Red, tan, violet
Yellow (-)
Aspirin comes from Salicylic Acid, which comes from the bark of Willow trees.

Experiment: Synthesis of Aspirin – Bellevue College

A comprehensive review of the existing medical literature on methyl salicylate poisoning has determined that it is a relatively common source of pediatric exposures.[7] In younger children, most of these exposures are accidental. Intentional ingestions are much more common in adolescents.

alexleyenda's synthesis of salicylic acid from methyl ..

Synthesis of aspirin from oil of wintergreen

this is because Willow trees have salicin in them which is the glycoside of salicylic acid.
Where did Aspirin come from?
Aspirin
A known analgesic used as medication to relieve headaches, body pains, fever, and as an anti-inflammatory
Felix Hoffman
Wanted to find a medicine alternative to salicylic acid
Synthesized in the experiment
Oil of Wintergreen
Bengay
Treatment of joint and muscular pain
Flavoring
Common ester in wine
Used during the recrystallization of aspirin
Methyl Salicylate + NaOH + Heat + H2SO4 = Salicylic Acid
base-promoted ester hydrolysis.
Recrystallize then heat in oven
Background
Safe, inexpensive, available
Paved the way for other pain killers to be approved

consumption & health benefits
many dosages (60-650 mg)
tablets, capsules, caplets, liquid elixir
general pain or fever; rheumatic fever, gout, rheumatoid arthritis.


Precursor: Salicylic Acid
Aspirin takes away pain by inhibiting or preventing the growth of inflammation causing cells
History
Circa 1800: Salicylic Acid- discovered from bark of Willow tree
1853: primitive form of Aspirin
1897: synthesized by Felix Hoffman under Bayer
1899: Bayer mass produces
How to manufacture Aspirin:
-weighing of ingredients (Corn starch, water & lubricant -> binding agent and fillers, acetylsalicylic acid )
-mixing - mixes ingredients, takes out air w/ glen mixer -> "Slugs"
-drying-forcing mixture by hand on mesh or use of fitzpatrick mill
-compression
-testing and packaging
*lubricants-hydrogenated vegetable oil, stearic acid, talc, or aluminum stearate
Aspirin
Acetylsalicylic Acid
QUALITATIVE TESTS
Medicine
Relieves pain
Different reactions
Aspirin industry
Social Issue
When you use,
DON'T ABUSE!
similar drugs:
Ibuprofen - same potency but does not upset stomach as much
Naproxen - same potency, stays in the body 6 times longer.

Experiment 7A: Synthesis of Aspirin and Oil of …

Advise patients and their families that use or overuse of seemingly benign OTC medications is sometimes dangerous. The ready availability of aspirin and aspirin-containing products does not establish the safety of aspirin.

Compare your laboratory aspirin with several brands of commercial aspirin.[The laboratory synthesized aspirin should have an absorbance >0.5 at 540 nm.

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  • THE SYNTHESIS OF ASPIRIN (Acetylsalicylic Acid) ..

    Esterification: The Synthesis of Aspirin (ASA) Methyl salicylate, for example, is oil of wintergreen, ..

  • Synthesis of methy salicylate - Almedauniversity

    Synthesis of methy salicylate ..

  • Experiment 19 synthesis of aspirin and oil of wintergreen

    Synthesis of Aspirin and Methyl Salicylate

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3:44 Experiment 4 Synthesis of Aspirin.

According to the American Association of Poison Control Centers' National Poison Data System, 10,243 single exposures to acetylsalicylic acid, alone or in combination with other drugs, were reported in 2016, along with 6573 single exposures to methyl salicylate. About 4,500 of these exposures were intentional. Almost 200 exposures resulted in major outcomes, and 22 fatal cases were noted.[1]

aspirin lab - 315 Experiment 23 The Synthesis of Aspirin ..

Nausea and vomiting are the most common toxic effects. This can be caused by CNS toxicity or by direct damage to the gastric mucosa. Salicylates can disrupt the mucosal barrier and occasionally cause GI bleeding. Pylorospasm, decreased GI tract motility, and bezoar formation can occur with large doses. These slow elimination and cause greater amounts of salicylates to be absorbed from the GI tract.

315 Experiment 23 The Synthesis of Aspirin ..

The toxicity of salicylates does not always correlate well with serum levels, and the levels are often less helpful in patients with long term exposure. Serum salicylate levels may correlate only moderately with clinical manifestations. In acute ingestion, levels may sometimes be high without significant clinical signs, whereas levels in patients with chronic ingestion that are in the high therapeutic range may be associated with significant clinical toxicity. Therefore, levels must always be interpreted and correlated with the history and clinical findings.

Synthesis and Characterization of Aspirin - Odinity

Increased cellular metabolic activity due to uncoupling of oxidative phosphorylation may produce clinical hypoglycemia, although the serum glucose levels may sometimes be within the normal range. As intracellular glucose is depleted, the salicylate may produce discordance between levels of plasma and cerebrospinal fluid (CSF) glucose and symptoms of CNS hypoglycemia (eg, altered mental status) may occur even when blood glucose levels are within the reference range.

Synthesis of Aspirin and Oil of Wintergreen CHEM 131 ..

Historically, qualitative determination for the presence of salicylates was rapidly performed in the emergency department by adding a few drops of 10% ferric chloride (FeCl3) to 1 mL of urine. If salicylates are present, the solution changes to a brown/purple color. Positive results with the urine ferric chloride test only indicate that a salicylate is present; however, even very small amounts of a salicylate, such as a single ingested aspirin tablet, can give a positive test result. Most emergency departments no longer perform this test and instead obtain a plasma salicylate level because these results are now rapidly available from almost all hospital laboratories and are much more useful clinically.

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