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Chemistry Project
Chemistry Project
Chemistry Project
Acknowledgement
IUPAC ID:
2-Acetoxybenzoic acid
Formula: C₉H₈O₄
Molar mass: 180.158 g/mol
Protein binding: 80–90%
AHFS/Drugs.com: Monograph
Discovery:
In 1897, Felix Hoffman, a German chemist working for the Bayer
company, was able to modify salicylic acid to create acetylsalicylic acid,
which was named aspirin (Fig. 1). The following year, Heinrich Dreser
at Bayer dismissed the market potential of aspirin on the ground that it
had an “enfeebling” action on the heart (“The product has no value”).
His real reason for ignoring aspirin was his preoccupation with the sales
potential of another new drug—heroin (first synthesized in the Bayer
laboratory in 1897)—which Bayer was about to launch as a cough
remedy.6 Arthur Eichengruen (whose job it was to originate new
products at Bayer) refused to accept Dreser's rejection of acetylsalicylic
acid and continued to press for its development.6 Eventually, Dreser
reneged and tested aspirin on himself and on his rabbits, confirming its
therapeutic properties. Subsequently, aspirin was found to be more
tolerable to the stomach than salicylic acid.7 Felix Hoffmann's
innovation led to the widespread modern use of aspirin for pain relief.
His acetylation of salicylic acid also proved fortunate in another way,
because the modification is important to aspirin's ability to prevent
cardiovascular events.
Fig. 1 Acetylsalicylic acid (aspirin) retains the carboxyl group (COOH) of salicylic acid and
makes a substitution in the hydroxyl group (OH). The drug was developed at Bayer by Felix
Hoffmann. Acetylation made aspirin more tolerable to the gastrointestinal tract, which led to
widespread use.
Physical properties
Aspirin, an acetyl derivative of salicylic acid, is a white,
crystalline, weakly acidic substance, with a melting point of
136 °C (277 °F), and a boiling point of 140 °C (284 °F) Its acid
dissociation constant (pKa) is 3.5 at 25 °C (77 °F).
ASPIRIN
Production:
i. Abstract
In this experiment you will synthesize aspirin and determine the yield or
fraction of the theoretical amount which can be made. The purity of the
product is confirmed by measuring its melting point range.
Aspirin is the common name for the compound acetylsalicylic acid,
widely used as a fever reducer and as a pain killer. Salicylic acid, whose
name comes from Salix, the willow family of plants, was derived from
willow bark extracts. In folk medicine, willow bark teas were used as
headache remedies and other tonics. Nowadays, salicylic acid is
administered in the form of aspirin which is less irritating to the stomach
than salicylic acid.
To prepare aspirin, salicylic acid is reacted with an excess of acetic
anhydride. A small amount of strong acid is used as a catalyst which
speeds up the reaction. In this experiment, phosphoric acid will be used
as the catalyst. The excess acetic acid will be quenched with the addition
of water. The aspirin product is not very soluble in water so the aspirin
product will precipitate when water is added. The synthesis reaction of
aspirin is shown below:
Since acetic acid is very soluble in water, it is easily separated from the
aspirin product. The aspirin isolated in this step is the “crude product”.
A “purified product” can be obtained through recrystallization of the
crude product in hot ethanol. In this experiment, the crude product will
be the desired product. The percent yield of the crude product will be
determined for this reaction. The purity of the product will also be
analyzed. The product will be analyzed by three different methods:
melting point, titration, and spectroscopic assay. The melting point range
of pure aspirin is 138-140 C and the melting point range of the salicylic
acid starting material is 158-161 C. If impurities are present in your
crude sample, the melting point range for your product will be lower
than the range of pure aspirin. Also, your melting point range may be
greater than 2 degrees. From the titration of your sample, the moles of
acetylsalicylic acid present can be determined assuming that there is not
a large percentage of an acid impurity present in your crude sample.
The spectroscopic analysis of aspirin will involve the complexing of
iron(III) to the deprotonated form of salicylic acid (salicylate ion) to give
a purple solution. Only the salicylate ion complexes to iron(III). Your
aspirin product as well as a commercial aspirin tablet will be compared
to a standard 0.15% ferricsalicylate solution. In the presence of moisture,
aspirin may decompose (hydrolysis) into salicylic acid and acetic acid.
This reaction is the reverse of the synthesis reaction. The maximum
allowable amount of free salicylic acid in an aspirin sample is 0.15%
salicylic acid.
iii. Procedure:
1. Weigh out 3.0 g of salicylic acid and place in a 250 ml Erlenmeyer
flask.
2. Measure out 6.0 ml of acetic anhydride and add this to your flask. Be
sure to do this in the hood and wear your goggles.
Don't let the acetic anhydride contact your skin and don't get the vapors
in your eyes.
3. Carefully add 5 to 10 drops of 85% phosphoric acid, a catalyst, to the
flask and swirl to mix everything thoroughly.
4. Still in the hood, heat the mixture for about 10 min. in a beaker of
warm water (70-80 oC).
5. After heating, cautiously add 20 drops of distilled water.
6. Next add 20 ml of distilled water and cool in an ice bath. You can do
this at your bench. If crystals do not appear, you can scratch the walls of
the flask with a stirring rod to induce crystallization.
7. Filter the solid aspirin through a piece of pre-weighed filter paper
using a Buchner funnel and the aspirator. Wash the crystals with 2-3 ml
of chilled water. The liquid is mostly water and can be washed down the
sink. Allow the air to be drawn through the solid and filter paper for 15
minutes. Be sure to record the filter paper weight in your notebook.
8. Place the filter paper with the product in a watch glass and put it in the
oven at 100 oC for about 30 min. until dry.
9. Put the dry aspirin and the filter paper into a pre-weighed plastic bag
and weigh again.
10. Measure the melting point range with the Meltemp Apparatus (your
instructor will demonstrate) and compare to the value for pure aspirin of
138-140 oC.
11. Calculate the weight of your product by subtracting the weight of the
paper and bag from the total. The theoretical (maximum) yield is 3.9
grams. What percent of this did you get? This is your percent yield.
Record it in your notebook and turn in your product to the Stockroom.
iv. Report:
Report the theoretical yield and the percent yield of the aspirin product.
Compare the melting point of you aspirin product to the theoretical
melting point (138-140 C). Is the crude product above of below this
mark?Explain why this is the case.
Determine the moles of aspirin from the titration and calculate the
percent purity of the crude aspirin product from the titration analysis.
Plot a Beer’s Law graph of the standard 0.15% salicylic acid solution
(C) on excel with Absorbance (yaxis) vs % salicylic acid (x-axis). To
make a Beer’s Law plot, enter % Salicylic Acid into one column on the
excel spread sheet (0 and 0.15) and absorbance into the next column (0
and the absorbance 5 reading).
Highlight the data and select insert, and scatter (w/ only markers). Right
click a data point and select add trend line. Now set the y-intercept to 0
and check the display equation box. To add titles to the plot, select
layout, axis titles, and then chart titles.
The % concentration for samples A and B can be determined by
plugging in the absorbance readings for those samples into the linear
equation and solving for x. Clearly state if the samples are below the
maximum allowable limit for percent salicylic acid (0.15 %).
Application:
Aspirin is a salicylate (sa-LIS-il-ate). It works by reducing substances in
the body that cause pain, fever, and inflammation.
Warnings:
You should not use aspirin if you have a bleeding disorder such as
hemophilia, a recent history of stomach or intestinal bleeding, or if you
are allergic to an NSAID (non-steroidal anti-inflammatory drug) such as
Advil, Motrin, Aleve, Orudis, Indocin, Lodine, Voltaren, Toradol,
Mobic, Relafen, Feldene, and others.
You should not use aspirin if you are allergic to it, or if you have:
Aspirin can pass into breast milk and may harm a nursing baby. You
should not breastfeed while using this medicine.
If you need surgery, tell the surgeon ahead of time that you are using this
medicine. You may need to stop using it for a short time.
Do not use aspirin if you smell a strong vinegar odor in the bottle. The
medicine may no longer be effective.
Procedure to avoid :
Avoid drinking alcohol while you are taking aspirin. Heavy drinking can
increase your risk of stomach bleeding.
If you are taking this medicine to prevent heart attack or stroke, avoid
also taking ibuprofen (Advil, Motrin). Ibuprofen may make this
medicine less effective in protecting your heart and blood vessels. If you
must use both medications, ask your doctor how far apart your doses
should be.
Stop using this medicine and call your doctor at once if you have:
Research
Psychiatry
In psychiatric research, aspirin has been investigated as an add-on
treatment for different disorders in the context of drug
repurposing strategies, considering the role of inflammation in the
pathogenesis of severe mental illnesses.
Bipolar disorder
Aspirin has been repurposed as an add-on treatment for depressive
episodes in subjects with bipolar disorder. However, meta-analytic
evidence is based on very few studies and does not suggest any efficacy
of aspirin in the treatment of bipolar depression. Thus, notwithstanding
the biological rationale, the clinical perspectives of aspirin and anti-
inflammatory agents in the treatment of bipolar depression remain
uncertain.
Infectious diseases
Several studies investigated the anti-infective properties of aspirin for
bacterial, viral and parasitic infections. Aspirin was demonstrated to
limit platelet activation induced by Staphylococcus
aureus and Enterococcus faecalis and to reduce streptococcal adhesion
to heart valves. In patients with tuberculous meningitis, the addition of
aspirin reduced the risk of new cerebral infarction [RR = 0.52 (0.29-
0.92)]. A role of aspirin on bacterial and fungal biofilm is also being
supported by growing evidence.
Cancer prevention
Conclusion
Aspirin, the original wonder drug, has long been a go-to medicine for
millions, a Jack-of-all trades remedy that is readily available and cheap.
Championed for its ability to relieve pain, fever and inflammation,
aspirin has been a staple in home medicine cabinets and first-aid kits for
more than a century.
Widespread reports that aspirin can help prevent heart attacks, strokes
and colorectal cancer have prompted many people to swallow either a
regular or low-dose (baby) aspirin every day without first consulting
their doctors or taking their susceptibility to complications into account.
People who rely solely on aspirin’s preventive abilities or advice from
friends and family may use it inappropriately, tipping the balance more
toward risks than benefits.
Bibliography
1. www.teachersfirst.com/lessons/forensics/ink-lab.html
2. www.reachoutmichigan.org/funexperiments/quick/csustan/mrsketch.htm
3. https://en.wikipedia.org/wiki/Mechanism_of_action_of_aspirin
4. https://en.wikipedia.org/wiki/Aspirin
5. https://www.drugs.com/aspirin.html
6. https://www.nytimes.com/2020/03/09/well/live/aspirin-the-original-wonder-
drug.html
7. https://g.co/kgs/a2Mtj7
8. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1894700/