A.

TITLE OF EXPERIMENT
Recrystallization and Synthesis of Aspirin

B. DATE OF EXPERIMENT
Tuesday, March 6th , 2018 at 10.20-14.20 a.m

C. PURPOSE OF EXPERIMENT
- Doing recrystallization well
- Determining a suitable solvent for recrystallization
- Perform aspirin preparation by acetylation of phenol groups
- Eliminate impurities through recrystallization
- Recrystallize aspirin synthesis well

D. BASIC THEORIES
Recrystallization

The principle behind recrystallization is that the amount of solute that can be
dissolved by a solvent increases with temperature. In recrystallization, a solution is
created by dissolving a solute in a solvent at or near its boiling point. At this high
temperature, the solute has a greatly increased solubility in the solvent, so a much smaller
quantity of hot solvent is needed than when the solvent is at room temperature. When the
solution is later cooled, after filtering out insoluble impurities, the amount of solute that
remains dissolved drops precipitously. At the cooler temperature, the solution is saturated
at a much lower concentration of solute. The solute that can no longer be held in solution
forms purified crystals of solute, which can later be collected. (Fessenden, 1989)
Actually recrystallization is simply a further process of crystallization. If
crystallization (in this case the result of crystallization) satisfactory recrystallization only
works when used in solvents at room temperature, but can be more soluble at higher
temperatures. It aims to be a pure substance can not break through the filter paper and left
was pure crystal. (Fessenden, 1989)
In chemistry, recrystallization is a procedure for purifying compounds. The most
typical situation is that a desired "compound A" is contaminated by a small amount of
"impurity B". There are various methods of purification that may be attempted (see
Separation process), recrystallization being one of them. There are also different
recrystallization techniques that can be used such as: (Laurence & Christopher, 1989:
127-132)
In chemistry, recrystallization is a technique used to purify chemicals. By
dissolving both impurities and a compound in an appropriate solvent, either the desired
compound or impurities can be coaxed out of solution, leaving the other behind. It is
named for the crystal soften formed when the compound precipitates out.
Alternatively, recrystallization can refer to the natural growth of larger ice crystals at the
expense of smaller ones.

In chemistry, recrystallization is a procedure for purifying compounds. The most

typical situation is that a desired "compound A" is contaminated by a small amount of
"impurity B". There are various methods of purification that may be attempted
(see Separation process), recrystallization being one of them. There are also different
recrystallization techniques that can be used such as:

1. Single-solvent recrystallization

Typically, the mixture of "compound A" and "impurity B" are dissolved in the
smallest amount of hot solvent to fully dissolve the mixture, thus making
a saturated solution. The solution is then allowed to cool. As the solution cools
the solubility of compounds in solution drops. This results in the desired compound
dropping (recrystallizing) from solution. The slower the rate of cooling, the bigger the
crystals form.

2. Multi-solvent recrystallization

This method is the same as the above but where two (or more) solvents are used.
This relies on both "compound A" and "impurity B" being soluble in a first solvent. A
second solvent is slowly added. Either "compound A" or "impurity B" will be insoluble in
this solvent and precipitate, whilst the other of "compound A"/"impurity B" will remain
in solution. Thus the proportion of first and second solvents is critical. Typically the
second solvent is added slowly until one of the compounds begins to crystallize from
solution and then the solution is cooled. Heating is not required for this technique but can
be used.

3. Hot filtration-recrystallization

Hot filtration can be used to separate "compound A" from both "impurity B" and
some "insoluble matter C". This technique normally uses a single-solvent system as
described above. When both "compound A" and "impurity B" are dissolved in the
minimum amount of hot solvent, the solution is filtered to remove "insoluble matter C".
This matter may be anything from a third impurity compound to fragments of broken
glass. For a successful procedure, one must ensure that the filtration apparatus is hot in
order to stop the dissolved compounds crystallizing from solution during filtration, thus
forming crystals on the filter paper or funnel.

One way to achieve this is to heat a conical flask containing a small amount of
clean solvent on a hot plate. A filter funnel is rested on the mouth, and hot solvent vapors
keep the stem warm. Jacketed filter funnels may also be used. The filter paper is
preferably fluted, rather than folded into a quarter; this allows quicker filtration, thus less
opportunity for the desired compound to cool and crystallize from the solution. (Laurence
& Christopher, 1989)
Aspirin can be produced in a one step chemical process by reacting salicylic
acid with acetyl chloride, according to the reaction:

(Anonymous, 2003)

Salicylic acid acetyl chloride acetylsalicylic acid hydrochloric acid aspirin.

Aspirin is a white solid that is almost completely insoluble in water. We will use this
physical property of our product to separate it from the final solution. If time allows,
we will synthesize methyl salicylate, which is another ester of salicylic acid. It occurs
in a wide range of plants and is known as ‘oil of wintergreen’. (Anonymous, 2003)

(Anonymous, 2003)

Aspirin, chemically known as acetylsalicylic acid, is the most commonly

used anti-inflammatory drug. It is effective in relieving symptoms of pain (analgesic)
due to headaches, injury, or arthritis, treating fever (antipyretic) and inflammation,
and preventing blood clots. It was extracted by the Native Americans from willow
and poplar tree bark about 2500 years ago. Native Americans used willow bark in
teas to reduce fever. In 1763, Reverend Edward isolated and identified one of the
compounds used to synthesize aspirin, which came to be known as salicylic acid.
Large quanti-ties of salicylic acid became available; however, it caused severe
stomach irritation. In 1893, German chemist Felix Hoffman synthesized an ester
derivative of salicylic acid, acetylsalicylic acid (“aspirin”). The acetyl group
cloaks the acidity when ingested. The drug then passes through the small intestine
where it gets convert-ed back to salicylic acid, and enters the blood-stream.
Although, weaker than salicylic acid, aspirin had medicinal properties without the
bitter taste and harsh stomach irritation. The company Bayer patented aspirin in
1899, which has made aspirin one of the most widely used and commer-cially
available drugs today.
Aspirin is a nonsteroidal anti-inflammatory drug (NSAID) which works to
reduce levels of prosta-glandins, chemicals released due to inflamma-tion, pain,
and fever. Prostaglandins are located on receptors of different cells types, thus
having multiple effects. Cyclooxygenase is the enzyme that makes prostaglandins.
NSAIDs inhibit the enzyme reducing the levels of prostaglandins, in turn reducing
inflammation, fever, and pain. Aspirin is not only anti-inflammatory, but also
analgesic and antipyretic. Prostaglandins carry out fever and pain by activating
the hypothalamus, the portion of the brain that controls autonomic and
endocrinal functions. Inhibiting prostaglan-dins suppresses fever and pain by
stopping nerve signals that are sent to the brain. Suppression of prostaglandins also
desensitizes the function of platelets and the ability of blood clots, thus aspirin’s
antithrombotic effects have been approved to prevent heart attacks and strokes. ( El-
Magrib, 2014 )

Synthesis Of Aspirin (Acetylsalicylic Acid) acetylsalicylic acid would weaken

the heart and that physicians would be reluctant to prescribe it. In 1899, Heinrich
Dreser, a top chemist with Friedrich Bayer and Co., gave acetylsalicylic acid the now
familiar name aspirin, but in 1897 Bayer didn't think aspirin had much of a future.
Little did they know what the future held for aspirin.

In the experiment, aspirin will be synthesized utilizing a reaction very similar

to the way it is manufactured industrially. Salicylic acid acting as an alcohol is reacted
with acetic anhydride acting as the acid in an esterification reaction to produce an
ester, acetylsalicylic acid (aspirin). Concentrated sulfuric acid is used as a catalyst.

COOH COOH
O
OH CH3
O O
C

C C
O
H3C O CH3
(s) + (aq)  (s)
 C7H6O3 C4H6O3 C9H8O4
Salicylic Acid Acetic Anhydride Acetyl Salicylic Acid

+ CH3COOH (aq)

C2H4O2
Acetic Acid

Synthesizing a compound in the laboratory usually requires the student to

compare the experimental yield of product with the amount that is theoretically
possible based on the amounts of materials used.
The first step in this process is to determine the molar ratio of the reactants actually
used relative to the stoichiometric molar ratio as defined in the balanced equation of
the reaction. In most laboratory courses one of the reagents has an insufficient number
of moles to react with the other reagent. This reagent is referred to the “limiting
Reagent,” while the other reagent is considered “in excess.” Thus, the limiting reagent
is totally consumed in the reaction and it dictates, on a molar equivalent basis, the
theoretical amount of product that can be expected from the reaction.
The % yield of the experiment is then determined from the ratio of the amount
of product actually obtained to this theoretical amount (mass or moles can be used for
the calculation).

mass of crystal aspirin∈experiment

% result = x 100%
mass of crystal aspirin∈theory

There are actually several ways to determine your product's purity: melting
point, chromatography, mass spectrometry, spectrophotometry, and others. Of course
that last one, spectrophotometry, should ring a bell since we used it previously to
determine the thickness of the copper clad on newer pennies. It turns out that salicylic
acid will react with iron (III) nitrate to Produce a complex that absorbs green light, but
aspirin does not. So you can use this to determine the amount of unreacted salicylic
acid that remains in your aspirin, and ultimately determine its purity.
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 ᵒC and the melting point
range of the salicylic acid starting material is 158-161 ᵒC. 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% ferric salicylate 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.
[ CITATION LAH \l 1033 ]
The laboratory synthesis of a compound usually requires the product to go
through a series of steps to isolate it from the reaction mixture and any soluble
impurities. The procedures used to accomplish these tasks in this experiment will be
(1) vacuum filtration and (2) recrystallization.
1. Vacuum filtration:
Vacuum (suction) filtration is a commonly used procedure to separate a solid from
a liquid. The apparatus used consists of a Buckner funnel, paper filter, single-hole
rubber stopper, ring stand and clamp, filter flask (sometimes called a Buckner
flask), and vacuum tubing connecting the flask to an aspirator (water or air). A
typical setup is shown in figure 1. [CITATION Geo15 \l 1033 ]
Figure 1: Vacuum Filtration System
 Source : [CITATION Geo15 \l 1033 ]
In a vacuum filtration, the solution to be filtered is drawn through the filter paper
by applying a vacuum to a filter flask with a side arm adaptor (also known as a
Buchner flask).Vacuum filtration is typically a fast and efficient way of filtering.
The crystals are collected by swirling the mixture of the solid and liquid and then
pouring quickly it into the filtration apparatus. This typically comprises a Buchner
funnel fitted with the appropriate size filter paper; a clamped filter flask with
conical filter adapter, and a vacuum applied to the side arm of the filter flask (see
left). If smaller quantities are to be filtered the Hirsch funnel and a small filter
paper should be used instead. If needed, the filter flask can be replaced by a test
tube with side arm. Again, the tube should be clamped and the vacuum applied at
the side arm using the thick walled vacuum tubing. When using vacuum filtration,
it is very important that the correct size of filter paper be used. The filter paper
should be flat (i.e. not folded up at the edges) and should coverall the holes in the
base of the funnel. It is also important that the apparatus be clamped since it is
very easily tipped over usually resulting in loss of the sample. To filter the crystals,
assemble the apparatus, ensuring that the funnel is sealed into the flask; turn the
aspirator tap full on; moisten the filter paper with a little cold solvent to adhere the
paper to the funnel, to prevent crystals from creeping under the paper and through
 the filter. The mother liquor containing the crystals may now be filtered. The
crystals should then be rinsed with a small portion of cold solvent. Allow the
crystals to remain exposed to the vacuum for a few minutes in order to dry them.
Disconnect the tubing before turning off the aspirator tap. Thick-Walled pressure
tube is used throughout the apparatus. A trap is used in conjunction with the water
aspirator. If the water pressure in the laboratory line drops suddenly, the pressure
in the filter flask may become less than that in the water aspirator. This would
cause water to be drawn from the aspirator stream into the filter flask and would
contaminate the filtrate. The trap stops this reverse flow. A similar reverse flow
would occur if the water flow at the aspirator were stopped before disconnecting
the tubing to the aspirator side-arm or opening the valve on the top of the water
trap. [ CITATION Uni \l 1033 ]

E. TOOLS AND MATERIALS

TOOLS :
- Erlenmeyer flask 2 pieces
- Side pipe erlenmeyer 1 piece
- Graduated cylinder 2 pieces
- Buchner funnel 1 piece
- Beaker glass 2 pieces
- Electric stove 1 piece
 - Thermometer 1 piece
- Spatula 1 piece
- Watch glass 1 piece
- Desicator 1 piece
- Evaporator 1 piece
- Pipettes 4 pieces
- Funnel paper 5 pieces
- Melting block 1 piece

MATERIALS :
- Salicylic acid 3,5 grams
- Aquadest until enough
- Acetic acid anhydrous 3,75 mL
- H2SO4 concentrated 3 drops
- Ethanol 96% 7,5 mL
- FeCl3 until enough

Measured 1 gram of Salicylic Acid

+ 15 mL aquadest

Put into Erlenmeyer

F. LANES WORK
Heated on spiritus burner until boiled and at the
1. Recrystallization
same time shaken
Added aquadest until the crystal dissolve
Calculate the required volume of aquadest

Mix solution

Filtered in a hot state with Buchner funnel

Filtrate Precipitate

Cooled until crystal formed

Filtered again with Buchner funnel

White crystal

Dried on the desiccator

Measure the mass
Compared the melting point with the first substance

White crystal
 2,5 g dry salicylic acid

Entered into Erlenmeyer flask 125 mL

Added with 3.75 g acetic acid anhydrous
Added with 3 drops of sulfuric acid concentrate
Stirred until homogenous
Heated in beaker glass until the temperature 50-
60 ◦C
Stirred until 5 minutes
Take from the electric stove and cooled in room
temperature, with stirred
Added 37.5 ml aquadest
2. Making Aspirin Filtered with Buchner funnel

Filtrate Residue

Entered into Erlenmeyer flask

Added with 7.5 mL ethanol
96% and 35 mL of aquadest
Heated in electric heater until
homogenous
Filtered in hot condition with
Buchner funnel

Filtrate Concentrate
Settled in room
temperature until
crystal formed
Filtered with
Buchner funnel
 Filtrate Concentrate (Crystal)
Dried with
exicator

Aspirin

Weighed Calculate the Dried with

melting point exicator

Mass Melting Purity

Point Test

Reaction:
 H2SO4

+ +

+ FeCl3 
 G. OBSERVATION RESULT
Exp. Experiment Result
Numbe Procedure Experiment Hypothesis/Reaction Conclusion
r Before After

1 Recrystallization - Salicylic acid - Salicylic acid - Melting point of salicylic - The solvent that
(s): white + water: acid: 158◦C-161◦C match for
powder insoluble (LAHC – Aspirin recrystallization
(turbid) Synthesis) is water.
- Aquadest:
colorless - +heated + 70 - Melting point of
mL water: salicylic acid is
soluble, 152◦C
salicylic
solution
- Salicylic - (s) +
solution +
H2O(l) 
filtered with
Buchner
funnel: crystal
of salicylic
acid formed
- Filtrate +
filtered + (aq)
heated:
colorless,
crystal half
dissolve
- +cooled:
crystal of
salicylic acid
formed
- Crystal +
 filtered: crystal
of salicylic
acid
- Mass of
crystal
salicylic:
- Melting point:
152◦C
2 Synthesis of Aspirin - Salicylic acid: - Salicylic acid - The melting
white crystal + acetic acid point of aspirin
anhydrous: is 132◦C
- Acetic acid
colorless
anhydrous: - The weight of
+
colorless - Salicylic acid Salicylic acid Acetic acid aspirin is 1.2
+ acetic acid + anhydrous gram
- Sulfuric acid:
H2SO4: H2SO4
colorless
colorless
- Aquadest:
- Heated until
colorless
50-60◦C:
colorless
- After filtered: +
white granule Aspirin
formed
- Residue +
ethanol + Acetic acid
aquadest:
colorless
- After heated:
homogenous
solution
- After filtered:
white crystal
formed
- Filtered again:
colorless
filtrate
- After dried:
dry aspirin
with shite color
- Weighed: 1.2
gram +
FeCl3 
- Melting point:
132◦C
- After added
FeCl3: brown
color
H. ANALYSIS AND EXPLANATIONS
1. Recrystallization
In this first experiment has purpose to recrystallization well, determining a
suitable solvent for recrystallization, perform aspirin preparation by acetylation of
phenol groups, eliminate impurities through recrystallization and recrystallize aspirin
synthesis well. First, measured 1 gram of salicylic acid which in the form of white
powder and 5 mL of water. Then, put the substances into erlenmeyer flask and mixed
it. After mixing, the solution yields a white mixture indicate that the mixture has not
been homogeneous. Then boiled the mixture over the electric stove until it begins to
boil and then the water is added in small amounts while stirring with the stirrer so that
the sediment dissolves and the solution becomes colorless and homogeneous. When
added the water do not added 70 mL aquadest directly, but added 10 mL first then 10
mL again until 70 mL of aquadest. It caused when added each 10 mL will make the
impurities dissolve in the solution. In this experiment we added 70 mL of aquadest
and the solution become colorless that indicate if the solution was homogenous. It
caused water can dissolve well salicylic acid in hot conditions, but slightly dissolve in
cold. Substances to be dissolved should be dissolved in a hot solvent with the least
volume possible, so it is estimated to be precisely around the saturation point. This
indicates that water is a suitable solvent in this recrystallization. Suitable solvents for
recrystallizing a sample of a particular substance are solvents which can dissolve
either the substance in a hot state, but slightly dissolve in a cold state.
After this filtered the colorless solution by Buchner funnel in hot condition.
The function filtering in hot conditions is to separate the impurities substances which
are insoluble or suspended in solution, such as sand dust and so on. For filtering to
run fast usually used Buchner funnel. From the results of this filtration obtained a
colorless filtrate and there is little white sediment, while the residue left in the filter
paper on the buchner funnel. Next, cooled the filtrate until the crystals was formed. In
this experiment the result of crystal that formed has yellow color as the result of
recrystallization, while based on theory the color of crystal that formed must be white
color. It caused there is yellow dirt in the buchner funnel when we filtered the
solution. The yellow dirt in that buchner funnel also dissolved when filtered the
solution, so it make the crystal became yellow. So, before doing experiment we must
cleaned up all the equipment that will we use.
After the crystal was formed, the solution was filtered by Buchner funnel. The
results are yellow crystal as residue and colorless solution as filtrate. Then, dried the
residue in the desicator for 1-2 days. In the bottom of desiccator there are many
 silicate gels. The silicate gels are natural mineral that can be used to absorb the water
that is still contained in the crystal. After the crystal dried, weighed the mass of
crystal and calculated the rendemen. We got the mass of salicylic crystal is 1,1 gram,
thus the rendemen percent of salicylic acid crystal is 110%. The mass of salicylic
dried should 1 gram same with the initially mass of salicylic acid or under 1 gram
because the crystal was dried, so the mass of water in the salicylic acid was decrease
it could make the mass of crystal decrease too. But in this experiment got mass of
salicylic dried more than the initially mass, it caused by many factors. One of them is
the crystals are still not fully dry or it’s mean still contain water in the crystal. And
also it could occur because when weighed the crystal the funnel paper still wet so it
can increase the mass of crystal. That is make the rendement become more than
100%.
After weighed the mass of dried crystal, the salicylic acid crystal was tested the
melting point. The theoretically melting point of salicylic acid is 158-161°C. While
the experimental melting point results at 152°C, so that the experimental melting
point of crystal almost approaching the theoretically melting point. So the experiment
result was suitable with the theory. The melting point in this experiment is under the
theoretically, it caused still there is the impurities in the salicylic acid crystal, so the
melting point was decrease.

2. Making of Aspirin
The second experiment is synthesis aspirin, the purpose of this experiment is
making aspirin with acetylase process to phenol group and can doing recrystallization
of aspirin well. The Acetylation refers to the process of introducing an acetyl group
(resulting in an acetoxy group) into a compound, namely the substitution of an acetyl
group for an active hydrogen atom. A reaction involving the replacement of the
hydrogen atom of a hydroxyl group with an acetyl group (CH3 CO) yields a
specific ester, the acetate. Acetic anhydride is commonly used as an acetylating agent
reacting with free hydroxyl groups.
First, weighing 2.5 gram of dried salicylic acid that have white color and
granule properties, put it into Erlenmeyer flask 125 ml. Then, added 3.75 gram acetic
acid anhydrate that colorless solution. Salicylic acid has a role as a alcohol, because it
have OH- group, and acetic acid anhydrate have function as a anhydrade acid. As a
esther, aspirin can formed with reacting alcohol and anhydrade acid. Using of
anhydrade acid because acetic acid anhydrade not contain of water and easy to adsorb
water, so the water that hydrolyzed aspirin become salicylic acid and acetic acid can
stayed away.
 Then, added 3 drops of sulphuric acid concentrate, that have function for
catallisator and as a hydrazing, to formed a turbid solution. And then, this solution
stirred until homogenous, and boiled in burner at (50-60) 0C about 5 minutes, the
temperature must saved at the certainly. The step is doing because reaction between
salicylic acid and acetic acid anhydrate will have a good result at this temperatureand
this heated doing to make reaction run fast.
After that, this solution has cooled and still stirred, then added 37.5 ml of
aquadest. Adding of aquadest have purpose when it cooled will formed a crystal,
because in cool temperature the particle of aspirin in solution will move slowly and in
the end become precipitate. The precipitate that formed is salicylic acetile acid
(aspirin). The acetile group (CH3COO-) is come from acetic acid anhydrade, while
the R-group come from salicylic acid.
This precipitate filtered with Buchner funnel that complited with suction flask
and filter paper. This reaction will have byproducts salicylic acid and anhydrade
acetic acid, the salicylic acid will hydrazed formed anhydrade acetic acid. The
anhydrade acetic acid will reacting again with salicylic acid to form aspirin and
acetate acid as a byproduct. So, this reaction will stop when all of the salicylic acid
reacted with sulphuric acid concentrate. This reaction are shown below :

Aspirin that getting is not pure, because this aspirin mixed with other
substance in making aspirin with byproduct is CH 3COOH. So important to make
aspirin more pure with recrystallization process. This recrystallization is done with
added 7.5 ml ethanol 96% that colorless and 25 ml of aquadest . Alcohol is a good
solvent for organic compound. After that heated the solution in burner until the
solution dissolved. Then, filtered it with Buchner funnel that competed with sunction
flask and filter paper. Filtered again and again until the solvent actually separated.
Dried the residue of aspirin about 3 days, dried it in desicator until the crystal of
aspirin actually dry. Then after 3 days, weigh the crystal and from this experiment is
get the mass of crystal 1.3 gram. After that calculate the melting point with melting
block, and from the experiment is getting the boiling point of aspirin is 132 0C, this
boiling point its matchs with range of (130-136)0C theory aspirin. Next, the aspirin
must be tested in purity test with FeCl3. This purity can indicate when FeCl3 is added
 in aspirin crystal, and the color change to brown purple, it indicate that the aspirin is
not pure, the brown purple is indicate that FeCl 3 react with salicylic acid that have
phenol group or OH and formed a complex with purple color, in theory when the
aspirin pure the color of FeCl3 is not change or yellow. The rendement of aspirin is
36.83%.

I. DISCUSSION
Recrystallization
In this experiment the result of crystal that formed has yellow color as the result of
recrystallization, while based on theory the color of crystal that formed must be white
color. It caused there is yellow dirt in the buchner funnel when we filtered the solution.
The yellow dirt in that buchner funnel also dissolved when filtered the solution, so it
make the crystal became yellow. So, before doing experiment we must cleaned up all the
equipment that will we use.
We got the mass of salicylic crystal is 1,1 gram, thus the rendemen percent of salicylic
acid crystal is 110%. The mass of salicylic dried should 1 gram same with the initially
mass of salicylic acid or under 1 gram because the crystal was dried. But in this
experiment got mass of salicylic dried more than the initially mass, it caused by many
factors. One of them is the crystals are still not fully dry or it’s mean still contain water in
the crystal. And also it could occur because when weighed the crystal the funnel paper
still wet so it can increase the mass of crystal. That is make the rendement become more
than 100%.
The theoretically melting point of salicylic acid is 158-161°C. While the experimental
melting point results at 152°C. The melting point in this experiment is under the
theoretically, it caused still there is the impurities in the salicylic acid crystal, so the
melting point was decrease.

J. CONCLUSION
From the experiment and the analyze of the result experiment, can get the conclsion are :

1. The solvent that match for recrystallization of aspirin is water.

2. Melting point of recrystallization aspirin is 1520C.

3. The mass of recrystallization aspirin is 1.1 gram with the rendement 110%.
 4. Aspiryn can synthesis from salicylic acid and acetic acid anhydrous with acetylation
process.

5. The boiling point of aspirin is 1320C.

6. The weight of aspirin that getting is 1.2 gram. With the rendement 36.83%.

K. REFERENCES
Anonymous. 2003. Chem, Chemistry Experiment : Synthesis of Aspirin, Experiment 11.
Page 111

Calgary, U. o. (n.d.). University of Calgary. Retrieved from FILTRATION METHODS:

http://www.chem.ucalgary.ca/courses/351/laboratory/filtration.pdf
Fessenden & Fessenden. 1989. Kimia Organik II. Jakarta : Erlangga.
El-Magrib, Mariam. 2014. Journal Of Chemical Education. The Synthesis and Analysis
of Aspirin. Washington : American University.
LAHC. (n.d.). Los Angeles Harbor College. Retrieved from Aspirin Synthesis :
http://www.lahc.edu/classes/chemistry/arias/Exp%205%20-%20AspirinF11.pdf

Tim Dosen Kimia Organik. 2017. Panduan Praktikum Kimia Organik I. Surabaya :
Jurusan Kimia FMIPA UNESA.
L. ATTACHMENT
1. ANSWER OF QUESTIONS
Recrystallization
1. Explain the basic principle of recrystallization!
Answer:
The basic principle of recrystallization is the most effective way to purify organic
substances in solid form

2. Mention the work sequences to be performed in the recrystallization work!

Answer:
 Selection of the right solvent
 Dissolving the compound into the hot solvent is as little as possible
 Filter the solution in a hot state to remove the insoluble impurities
 Cool filtrate
 Refine and dry crystals

3. What properties should a solvent have to be used to crystalize a particular organic

compound?
Answer:
The properties that the solvent must have to be used are those solvents which
can dissolve the substance well in hot conditions, but slightly dissolve in cold.
Usually a compound which is in polar state is recrystalized in a less polar solvent
and vice versa

4. What are at least two reasons why filtering with suction flask (Buchner) is
preferred in separating the crystals from the parent?
Answer:
The reason for using buchner funnel is preferably: The function of filtering
with a Buchner funnel equipped with a vacuum evaporator or vacuum pump is to
filter a solution on a particular compound to obtain maximum results, fast and
accurate. And the working principle used in this filtering is to minimize a pressure
within the system, so the pressure outside the system (environment) becomes
larger

5. Calculate the percentage of recovery of the recrystalized compound you did!

Answer:
- the initial mass = 1 gram
- the mass of crystals = 1.1 grams
- the mass of filter paper = 0.8 grams

crystal mass 1.1

Salicylic acid yield =
initial mass
x 100% = 1
x 100 =110

Synthesis of Aspirin
1. Write a complete aspirin-making reaction!
Answer:

+ +
+ CH3COOH(aq)

Salicylic acid acetic acid anhydride aspirin acetic acid

2. What is acetylation and what is the function of sulfuric acid?

Answer:

Acetylation is the process of introducing acetyl radicals into molecules of

organic compounds containing the -OH group, wherein we must react
between salicylic acid and acetic acid by using concentrated sulfuric acid as a
catalyst.

3. What is the FeCl3 function in the reaction and explain how to prove the
formation of aspirin?
Answer:
FeCl3 serves to prove the formation of aspirin. If aspirin has been formed then
after the drop the FeCl3 solution will be yellow. Meanwhile, if not formed
aspirant then after the solution FeCl3 will be purple. It memans that still
contains of fenolic group bond in aromatic if change become purple.
4. Calculate the rendement of the experimental results obtained!

Answer:

Making Aspirin

-mass of acetic acid = 3.75 grams

-Mr acetic acid = 102 gram / mol

- mass of salicylic acid = 2.5 gram

-Mr salicylic acid = 138,12 gram / mol

-mol salicylic acid = mx 2.5 grams

Mr. 138.12 grams / mol

= 0.0181 mol

-mol acetic acid = mx 3.75 grams

Mr. 102 gram / mol

 = 0.0357 mol

+ + CH3COOH(aq)

Salicylic Acid Acetic Acid Aspirin

Salicylic acid acetic acid aspirin

M: 0. 0181 mol 0,0357 mol -

-

R: 0. 0181 mol 0.0181 mol 0.0181 mol

S: - 0.0186 mol 0.0181 mol

Aspirin Mol = 0.0181 mol

Mass Aspirin theoretical = mole aspirin x Mr aspirin

= 0.0181 mol. 180 gram / mol

= 3.258 grams

experiment mass
Rendement of aspirin = x 100%
theoretical mass

1.2 grams
= x 100 =36.83
3.258 grams

2. CALCULATION
a. Recrystallization
- the initial mass = 1 gram
- the mass of crystals = 1.1 grams
- the mass of filter paper = 0.8 grams

crystalmass 1.1
Salicylic acid yield =
initial mass
x 100% = 1
x 100 =110

b. Making of Aspirin
mass of acetic acid = 3.75 grams
-Mr acetic acid = 102 gram / mol
- mass of salicylic acid = 2.5 gram
-Mr salicylic acid = 138,12 gram / mol
-mol salicylic acid = mx 2.5 grams
Mr. 138.12 grams / mol
= 0.0181 mol
-mol acetic acid = mx 3.75 grams
Mr. 102 gram / mol
= 0.0357 mol

+
+ CH3COOH(aq)

Salicylic Acid Acetic Acid Aspirin

Salicylic acid acetic acid aspirin

M: 0. 0181 mol 0,0357 mol - -
R: 0. 0181 mol 0.0181 mol 0.0181 mol
S: - 0.0186 mol 0.0181 mol

Aspirin Mol = 0.0181 mol

Mass Aspirin theoretical = mole aspirin x Mr aspirin
= 0.0181 mol. 180 gram / mol
= 3.258 grams

experiment mass
Rendement of aspirin = x 100%
theoretical mass
1.2 grams
= x 100 =36.83
3.258 grams
3. DOCUMENTASION
a. Recrystallization

Entered 1 gram salicylic acid into

Added 5 mL aquades and heated : the
erlenmeyer flask : white powder
mixture become turbid

Filtered with buchner funnel produce

Added 70 mL aquades and the mixture
filtrate and residue
was homogen : colorless

Cooled the filtrate until crystal formed : Filtered with buchner funnel
white yellowish crystal
Dried the residue : crystal white yellow Crystal entered into capiller pipe to
calculate the melting point

Calculate the melting point of salicylic After melting point

acid : 152°C

b. Making of Aspirin

Weighed 2,5 grams of salicylic acid :

white powder
Entered into erlenmeyer flask
Salicylic acid + 3,75 mL acetic acid
anhydrous + 3 drops H2SO4 Heated and stir until homogen :
concentrated : turbid solution colorless

Filtered with buchner funnel : residue

residue + 7,5 mL ethanol + 35 mL
(white) + filtrate turbid
aquades + heated : homogen

Filtered with buchner funnel : filtrate

The mixture become colorless and residue

 Filtered the filtrate again Dried Crystal of aspirin in desicator for
1-2 days

Weighed dried aspirin crystal : 1,2

Crystal of aspirin : white crystal and like
grams
pin

Calculate the melting point : 152°C Melting point of aspirin : 132°C

Aspirin in capiller pipe after calculate Entered dried aspirin into test tube
the melting point

Aspirin + FeCl3 : purple brownish