UNIVERSIDAD AUTÓNOMA DE NUEVO LEÓN

CENTRO DE INVESTIGACIÓN Y DESARROLLO DE

EDUCACIÓN BILINGÜE

Chemical Phenomena in the Environment

Stage 4° Organic Compounds

Ms. Leilania Gómez Ruíz

Lab Report:

Aspirin Synthesis

Group: 318

Cristina Ascencio Espinosa 2000201

Diego Montes Ríos 1993582

Jesús Alejandro Navarro Hernández 2003791

Gabriel de Jesús Uribe Torres 1994994

Rosario de Jesús Zamora Martínez 1995297

Monterrey, Nuevo León, November 27th, 2020

Creation of aspirin (acetylsalicylic acid)

 Background

The aspirin, also known as acetylsalicylic acid, has a key ingredient that is salicylic acid, that
can be found: in jasmine, beans, peas, clover, and certain grasses and trees, the common
natural source where is found salicylic acid is the willow bark that was used as a remedy of
headaches and pains. To prepare aspirin, salicylic acid is reacted with an excess of acetic
anhydride. A small amount of a strong acid is used as a catalyst which speeds up the
reaction. In this experiment, we will use as catalyst phosphoric acid. First, we will quench
the excess acetic acid 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 chemical reaction of
the synthesis of aspirin is:

Aspirin is used to reduce fever and relieve mild to moderate pain from conditions such as
muscle aches, toothaches, common cold, and headaches. It also may be used to reduce
pain and swelling in conditions such as arthritis. Taking a low dose of aspirin can prevent
blood clots. This effect reduces the risk of stroke and heart attack. Low doses (typically 75 to
81 mg/day) are sufficient to reverse acetylated serine 530 of cyclooxygenase (COX)-1. This
effect inhibits platelet generation of thromboxane A2, resulting in an antithrombotic effect.
Intermediate doses (650 mg to 4 g/day) inhibit COX-1 and COX-2, blocking prostaglandin
(PG) production, and have analgesic and antipyretic effects. The side effects that can occur:
upset stomach and heartburn may occur, easy bruising, difficulty hearing, ringing in the ears,
signs of kidney problems, persistent or severe nausea, unexplained tiredness, dizziness,
dark urine, yellowing eyes.

Objective

The objective of this practice is to synthesize aspirin, learning what materials and
reagents are needed and the procedure. Through this experiment, we will learn more
about organic compounds, that they can be synthesized in a laboratory, and also
some of their properties.

Hypothesis

If we can make and replicate the indicated chemical reaction, then we are going to
be able to synthesize our own aspirin.
Variables
Independent variable: The quantity of the reactants.

Dependent: The quantity of aspirin produced.

Control variables: The time of the water bath, the addition of cold water after the
water bath, the porosity of the paper filter, the time and temperature the mix spends
in the oven.

Materials

❖ Cold water (H2O)

❖ Concentrated sulfuric acid (H₂SO₄)
❖ Dropper
❖ Graduated cylinder (100 mL)
❖ Funnel
❖ Filter paper
❖ Water bath
❖ Erlenmeyer flask (125 mL)
❖ Heating plate
❖ Digital scale
❖ Beaker (600 mL)
❖ Beaker (100 mL)
❖ Corning tubes (50 mL)
❖ Laboratory oven
❖ Spatula
❖ Petri dish

Reactants

❖ Salicylic acid (C7H6O3)

❖ Acetic acid (CH₃COOH)

Methods

Step 1: Put water in a beaker and place it on a laboratory hot plate

for the temperature bath.
Step 2: Pour the salicylic acid into a 125 mL E. flask (make sure
nothing remains).
Step 3: Later, pour the acetic acid into the same flask.
Step 4: Add five drops of sulfuric acid and swirl the flask to mix.
Step 5: Place the flask inside the beaker previously placed on the
heat plate.
Step 6: Heat the mixture in a temperature bath for 15 minutes.
Step 7: Once the mixture is hot, add cold water. The mixture will
crystallize.
Step 8: Add more cold water to make the mixture runny.
Step 9: Place a filter paper in a 100 mL cylinder and pour the
mixture. Make sure to put as much substance as possible.
Step 10: Take the filter paper and squeeze it so that it has no
water.
Step 11: Dry the filter paper in a laboratory oven for 24 hours at
35°C.
Step 12: Calculate the mass of the total aspirin with a digital scale
(weigh empty filter paper and then the filter paper with aspirin,
subtract the values).

Results

Physical Properties

White color - Crystalline - Melting point of 136 C° - Boiling point of 140 C°

Solid - Bitter taste - Colorless powder

Experimental grams: 1.79 g of Aspirin

Total grams of Aspirin obtained= 2.69 g (Filter paper and aspirin grams) – 0.90 g
(Only filter paper grams) = 1.79 g of Aspirin

Theoretical grams: 1.8 g of Acetylsalicylic Acid

Percentage Yield: 99.44%

When we add cold water to the solution of salicylic

acid and sulfuric acid, it crystallizes immediately

After we let the solution dry with the filter paper in

the oven, we obtained aspirin.

Discussion and analysis

One of the most important things that we have to notice is that the mole ratio of
salicylic acid and acetylsalicylic acid is equal to one. This means that for each mol of
salicylic acid, we will have one mol of acetylsalicylic acid and the same in the other
way. This is an important factor because it will allow us to calculate the theoretical
grams of acetylsalicylic acid or aspirin, but first, we have to see the experimental
grams.
The experimental grams that we obtained were 1.79 g, but that was the final product.
In the beginning, we had the acetylsalicylic acid in a filter paper, and it weighed 2.69
g. But we only wanted to know the grams of the acetylsalicylic acid, so we weighed
the mass of the filter paper, and then we subtract it from the total mass, and the
result was the 1.79 g of aspirin mentioned anteriorly.
Then the theoretical mass, the formula to obtain it is:
theoretical mass= (Salicylic Acid (g)/ MW Salicylic Acid (g/mol))= (Acetylsalicylic Acid
(g)/ MW Acetylsalicylic Acid (g/mol)). If we solve this formula for Acetyl Salicylic Acid
grams, we will do the next procedures. First, we transform the grams of salicylic acid
into moles. We had 1.5g of salicylic acid and, in 1 mol of salicylic acid, 138 g. If we
do the conversion, we obtain that our amount of salicylic acid is equal to 0.010
moles, and based on the mol ratio, the amount of moles is the same as the
acetylsalicylic acid, and after that, we only transform the number of moles of
acetylsalicylic acid in grams. In one mol of acetylsalicylic acid is 180 g. If we perform
the conversion, we obtain a final result of 1.8 g.
Finally, we have to find the yield percentage, which is a way to check the efficiency
of our process. Its formula is:
Yield percentage= (Experimental grams/ Theoretical grams)*100.
If we substitute the values in the equation will be: (1.80 g/ 1.79 g)*100
If we operate, the final result will be 99.44%.
The reason for the lack of matter is because it's an experiment performed by humans
and, even if they are professionals, they aren't perfect. For example, they could
leave a minimal amount of salicylic acid in the recipient for an accident, or they could
leave some grams of acetylsalicylic acid in the Erlenmeyer flask, or even an amount
of the product could pass through the filtration paper, little accidents that can affect a
little in the final result.
In our case, the hypothesis is correct because the experiment followed the
instructions perfectly. In the final, we obtained aspirin.
As the practice was virtual, we couldn't do the practice. We didn't make any mistakes
but, a better way to study this experiment is to experiment on our own, even if that
means that we can make some mistakes.
Our experiment is similar to the experiment made by the North Carolina School of
Science and Mathematics, 2011. In the experiment, they use another quantity.
Specifically, they use 2.027 g of salicylic acid and also, they use another method of
filtration and, for that reason, they add warm water a second time and, also they add
cold water again and, after that, they made a second filtration and, after it, they made
the same process of weighing the filter paper, which had a mass of .354g to subtract
its mass from the final result of aspirin in the filter paper which was 2.711 g.
In their experiment, the experimental grams were: 2.357 g
In their case, the theoretical grams was: 2.643 g
And their yield percentage: (2.357 g/ 2.643 g)*100= 89.17%

Conclusion

In this experiment, we were able to observe the process of Synthesization of the

aspirin using Salicylic acid (C7H6O3) and Acetic acid (CH ₃COOH) as the reactants.
We could see a chemical reaction where one of the processes involved was
crystallization was present. We also could say that with this practice, we learn more
about the different characteristics of the chemical reaction and we could also test our
experience from previous stages like calculate the molar mass and the stoichiometry
involved in the chemical reaction and also we saw the synthesis of a useful medicine
that is the aspirin. Finally, we can say that our hypothesis is perfectly acceptable
because we were able to see a chemical reaction that we can replicate to synthesize
more aspirin.
 References

LAHC. (n.d.). Aspirin Synthesis. Los Angeles Harbor College. Retrieved November 23, 2020,
from https://www.lahc.edu/classes/chemistry/arias/exp%205%20-%20aspirinf11.pdf

Monnier, A., Mora, E.,& Gutiérrez, G. (2015). Conect@ Entornos, Química. Ciudad de
México, México: Ediciones SM.

Morales, G., Monsiváis, D., & Rodríguez, V. (2020). Chemical Phenomena in the
Environment (First Edition). TDyIS.

Timberlake, K. C. (2018). General, Organic, and Biological Chemistry: Structures of Life (6th
ed.). Harlow, United Kingdom: Pearson Education.

WebMD. (n.d.). Drugs & Medications. Retrieved November 23, 2020, from
https://www.webmd.com/drugs/2/drug-1082-3/aspirin-oral/aspirin-oral/details

North Carolina School of Science and Mathematics. (2011). Synthesis of Aspirin Lab
[YouTube Video]. Retrieved from https://www.youtube.com/watch?v=Y4NMpO1xI8U