CM134-1L: ORGANIC CHEMISTRY (LABORATORY)
1ST Quarter SY 2019-2020
Experiment 2
RECRYSTALLIZATION
Bares, Ma. Ella Glyze B. / Group No. 1
August 29, 2019
INTRODUCTION
Purification, in a chemical context, is the physical separation of a chemical substance of interest from
foreign or contaminating substances. Purification is done to reduce the concentration of contaminants in the
substance since these contaminants have significant effects on the physical properties of substances like
boiling point and melting point. There are various types of purification processes, these are simple
crystallization, fraction crystallization or recrystallization, sublimation, simple distillation, fractional distillation,
distillation under reduced pressure, steam distillation, azeotropic distillation and chromatography. Among the
types, recrystallization of fractional crystallization was the one utilized in this experiment.
Crystallization is the process by which a solid forms, where the atoms or molecules are highly
organized into a structure known as a crystal. Some of the ways by which crystals form are precipitating from
a solution, freezing, or more rarely deposition directly from a gas. In chemistry, fractional crystallization or
more widely known as recrystallization--- is a technique used to purify chemicals--- the process of separation
of different components mostly impurities in a mixture by repeated crystallizations. By dissolving both
impurities and a compound in an appropriate solvent, either the desired compound or impurities can be
removed from the solution, leaving the other behind. To acquire perfect recrystallization, we must determine
first the appropriate solvent. This is the heart of the experiment. The solute or substance must be insoluble
in cold solvent and soluble in hot solvent. Yes, solubility is the core of this experiment. Solubility increases
with increasing temperature that is why there is a need for the solution to not dissolve in cold solvent but
dissolve completely in hot solvent. If the solvent is not specified, there is a dramatic need to try variety of
solvents to determine which works the best with reference to the concept of insolubility in cold solvent and
solubility in hot solvent. Stirring or swirling is recommended to help the dissolution of the substance occur
faster. If the test sample dissolves at room temperature or with cold solvent, it must be discarded right away
for it does not satisfy the criterion. If the sample did not dissolve in cold solvent, it now enters the second
phase, dissolution in hot solvent. If it did not dissolve, again, it must be discarded right away, if it does not,
then it might be the appropriate solvent for that certain solution. After choosing the right solvent, the solution
now goes into series of procedures and is subjected for recrystallization. It will undergo filtration to separate
the impurities from the filtrate or the clear and pure solution. This is necessary because this is the reason
why such purification process is being conducted, to discard or separate impurities of foreign bodies which
increases the concentration of the substance. The solution being cooled down in an ice bath completes the
crystallization process.
All purification processes end with the calculation of percentage recovery. Percentage recovery
computes the percentage of an original substance that us recovered after a chemical reaction is completed,
in this case, recrystallization. Percentage recovery determines the efficiency of the experiment. It is mainly
applicable to reactions in which the identity of the substance to be purified remains the same before and after
the reaction. The formula to get the percentage recovery is as follows:
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑝𝑢𝑟𝑖𝑓𝑖𝑒𝑑 𝑚𝑎𝑡𝑒𝑟𝑖𝑎𝑙
% 𝑟𝑒𝑣𝑜𝑣𝑒𝑟𝑦 = ∗ 100
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑢𝑛𝑝𝑢𝑟𝑖𝑓𝑖𝑒𝑑 𝑚𝑎𝑡𝑒𝑟𝑖𝑎𝑙
Experiment 02 │ A10 │ Group No. 2 │ August 29, 2019
CM134-1L: ORGANIC CHEMISTRY (LABORATORY)
1ST Quarter SY 2019-2020
MATERIALS AND METHODS
Equipment and Glassware
Buchner funnel, hot plate, stemless funnel, funnel support, micro test tubes, test tube rack, Erlenmeyer flask,
beaker and oven
Test Compounds for Choice of Solvent Experiment
acetamide, acetanilide, aspirin, benzoic acid, naphthalene and sucrose
Solvents or Reagents for Choice of Solvent Experiment
benzene, distilled water, ethanol, ethyl acetate,
Test Compounds for Recrystallization of Impure Acetanilide
crude acetanilide
Methodology
a. Choice of Solvent
Test samples were all prepared in the balance room as we stepped in the laboratory. We weighed exactly
0.10 g of each test samples and dissolved them in 2 mL of cold water. We observed how it reacted upon
dissolution, we swirled and stirred for the reaction to occur faster than it should. We observed its reaction or
solubility behavior. If the test sample happen to not dissolve in cold water, it is subjected to sit in boiling water
for observation again.
The procedures first-stated were repeated using the rest of the solvents to test the solubility. Every
reaction or observation on the solution’s solubility were taken down and noted. The purpose of this
experiment is to categorize where the test samples are soluble and insoluble and what is the appropriate
solvent for each.
b. Recrystallization of Impure Acetanilide
We heated approximately 100 mL of distilled water and set it aside to be used later. We weighed the filter
paper that will be used to hold the crystals and exactly 3.50 g of crude oil. We dissolved it in 30 mL distilled
water and it was subjected to boiling. As the mixture or solution starts to boil, we added 2 mL of the preheated
water that was set aside earlier and maintained the boiling temperature at 90℃ as stated in the laboratory
manual. We kept on adding 2 mL of preheated water until the white solid completely dissolved. Since the
mixture was not colored, we did not use or utilize activated carbon. We filtered the mixture out using the hot
gravity filtration. We set aside the now clear solution and waited for it to be in equilibrium with room
temperature and placed it in an ice bath for 10-15 minutes. We vacuum filter it afterwards to get the crystals
and put it in the oven. We waited for a couple of hours for it to completely solidify so we will be able to get
the weight of pure crystals from 3.5 g of impure acetanilide.
Below are the illustrations for how the hot gravity filtration and vacuum filter were set up:
Figure 1. Vacuum Filter Set Up
Experiment 02 │ A10 │ Group No. 2 │ August 29, 2019
CM134-1L: ORGANIC CHEMISTRY (LABORATORY)
1ST Quarter SY 2019-2020
Figure 2. Hot Gravity Filtration Set Up
RESULTS AND DISCUSSION
a. Choice of Solvent
WATER ETHANOL BENZENE ETHYL ACETATE
COMPOUND
Cold Hot Cold Hot Cold Hot Cold Hot
acetamide S S S S I S I S
acetanilide I S S S I S S S
aspirin I I S S I S S S
benzoic acid I S I S I S I S
naphthalene I I I S S S S S
sucrose S S I S I I I I
Table 1. Solubility of Test Samples
Table 1 shows the data where the test samples or solutes were categorized based on their solubility.
Solubility is the ability of a solute, may it be in solid, liquid or gaseous form to dissolve in a solvent. Solubility
is largely influenced by temperature and pressure. In this experiment, the two factors were utilized. All the
solution were subjected to sit in an ice bath or boiling water to get their solubility. For many solids dissolved
in liquid water, solubility tends to correspond with increasing temperature. As water molecules heat up, they
vibrate more quickly and are better able to interact with and break apart the solute. However, on the gaseous
forms case, as temperature increases, their solubility decreases. Pressure, on the other hand, has a
negligible effect on the solubility of solid and liquid solutes, but it has a strong effect on solutions with gaseous
solutes. Since all the test samples were all solid type of solute, we can neglect pressure on this experiment
and utilize the effect of temperature on solubility by having two solvents, specifically a cold one and a hot to
try the solubility test which is very essential for recrystallization.
Acetamide is an organic compound, the simplest amide derived from acetic acid. It finds some use
as a plasticizer and as an industrial solvent. In literature, it is said to be soluble in water, alcohol, chloroform,
glycerol, hot benzene, and slightly soluble in ether. By comparison of the solubility of the solute stated from
the literature and from the result of the experiment, the results are actually the same. Since amides have low
molecular weight, they are very soluble in water. Since it is soluble in water, it is also soluble in ethanol since
ethanol has polar –OH group. Hydrogen bonds to water which makes ethanol soluble. Acetanilide is an
odorless solid chemical of leaf or flake-like appearance. It is also known as N-phenyl acetamide, acetenyl, or
acetanilide. In literature, it is slightly soluble in water, very soluble in ethanol and acetone and on ethyl ether
also. By comparison, the solubility of the solute from the literature and from the result of the experiment satisfy
each other, too. It can be observed from the results of the experiment that acetanilide has a much higher
Experiment 02 │ A10 │ Group No. 2 │ August 29, 2019
CM134-1L: ORGANIC CHEMISTRY (LABORATORY)
1ST Quarter SY 2019-2020
solubility in hot water than in cold water, this claim can be justified by the concept of solubility itself--- that
solubility increases with increasing temperature. This explains why some compounds are insoluble in cold
solvent but soluble in hot solvent and this is perfectly natural. Since more heat or increase is necessary to
break the bonds and to acquire the solubility of the substance. Aspirin or acetylsalicylic acid is a member of
the class of benzoic acids that is salicylic acid in which the hydrogen that is attach ed to the
phenolic hydroxy group has been replaced by an acetoxy group. In literature, aspirin is more soluble in basic
solutions. Basic solutions are those solutions that contain more hydroxide ions than hydronium ions.
However, in the experiment, it appears that aspirin is both insoluble in hot and cold water, the reason for this
is that aspirin is hydrophobic in nature, so it will not really dissolve. Benzoic acid is a compound comprising
a benzene ring core carrying a carboxylic acid substituent--- a monobasic aromatic acid, moderately strong,
white crystalline powder. By theory, it is very soluble in alcohol, ether, and benzene, but poorly soluble in
water. Comparing its solubility in result and in the theory, both are alike. Increase in temperature is necessary
for it to dissolve completely. Naphthalene is an aromatic hydrocarbon comprising two fused benzene rings.
It is a white, volatile, solid polycyclic hydrocarbon with a strong mothball odor. In literature, it is insoluble in
water but soluble in ethyl alcohol, ether and acetone. Comparing its solubility from the literature and from the
experiment, it shows that it is true that naphthalene is insoluble in water because it is a nonpolar substance
to begin with. Lastly, sucrose, a common sugar. It is a disaccharide, a molecule composed of two
monosaccharides: glucose and fructose. In literature, sucrose is soluble in water, ethanol, methanol,
propylene glycol, glycerol, acetone and pyridine. However, in the experiment, it shows that sucrose is
insoluble in benzene and ethyl acetate. It is insoluble in benzene because benzene do not contain any -OH
groups. Sucrose has very low solubility in ethyl acetate.
COMPOUND CANDIDATES APPROPRIATE SOLVENT
Benzene
acetamide ethyl acetate
ethyl acetate
water
acetanilide water
benzene
aspirin benzene benzene
water
benzoic acid ethanol water
benzene
naphthalene ethanol ethanol
sucrose ethanol ethanol
Table 2. Appropriate Solvent
Table 2 shows the list of appropriate solvents chosen carefully for each test sample or solute after
series of trials. The criterion in finding the right solvent for recrystallization is that the solution must not
dissolve or must not be soluble in cold solvent but it must dissolve in cold solvent. This idea sticks with the
concept that solubility increases with increasing temperature. Comparing Table 1 and Table 2, it is noticeable
that elimination process was conducted to narrow down the choices in finding the appropriate solvent for a
certain solute. Compounds that were already soluble or dissolved in cold solvent were automatically
discarded for they do not satisfy the criterion. However, those that satisfied the criterion were subjected for
studying their nature to determine which solvent works best for the particular compound. Polarity was taken
in consideration, their functional groups and molecule size were also noted to help us determine the
appropriate solvent for the compounds. Table 2 also shows the candidates of being the appropriate solvent,
these were the solvents that were insoluble in cold solvent and soluble in hot solvent making the
recrystallization process attainable. Ethyl acetate is the appropriate solvent for acetamide because it satisfied
the criterion. Benzene also satisfied the criterion, however, benzene is nonpolar and acetamide is polar
because of its functional groups. Actually, you can have the mixture if benzene and ethyl acetate as the
appropriate solvent for acetamide. A mixture of nonpolar and polar solvents could and might dissolve
acetamide. But since the aim of this experiment is to determine the appropriate solvent, we are ought to
single out the right solvent. In the case of acetanilide, water is the more appropriate solvent than benzene.
Benzene is nonpolar while acetanilide is polar. Like dissolves like, benzene is not a likely candidate as solvent
of acetanilide. Benzene is the appropriate solvent for aspirin for only it satisfied the criterion. For benzoic
acid, water is more likely to be the right solvent. Benzene is nonpolar so it is automatically eliminated,
however, between water and ethanol, the former is likely the right one since ethanol infinitely dissolves in
Experiment 02 │ A10 │ Group No. 2 │ August 29, 2019
CM134-1L: ORGANIC CHEMISTRY (LABORATORY)
1ST Quarter SY 2019-2020
water. Ethanol, on the other hand, is the appropriate solvent for both naphthalene and sucrose since
everything else were eliminated.
b. Recrystallization of Impure Acetanilide
mass of crude acetanilide 3.5 g
mass of filter paper 1.24 g
weight of pure acetanilide 1.01 g
volume of water used 36 mL
percent recovery 28.66 %
Table 3. Data Needed For Recrystallization of Impure Acetanilide
STEP OBSERVATION
Boiling of Crude Acetanilide visibility of impurities, white solids precipitate
Addition of Activated Carbon no activated carbon was added
Hot Gravity Filtration colorless filtrate
Cooling in An Ice Bath slow formation of crystals
Vacuum Filtration wet crystals
Table 4. Observation on the Phases of Recrystallization
Table 3 represents the data we needed to calculate for the pure acetanilide or its solids or crystals
per se. The mass of filter paper and pure acetanilide which was gotten off the oven was exactly 2.25 g,
subtracting the mass of filter paper which was 1.24 g yields us 1.01 g of pure crystals. The percent recovery
was 28.66% which was relatively small, however, this concludes that 3.5 g of crude acetanilide contains too
much impurities in it which decreased the chance of yielding a large percent recovery. On the other hand,
recrystallization is a very serious series of processes of boiling, sitting on an ice bath and filtrations, therefore
loss in the substance cannot be helped.
Table 4 shows the summary of our observation of the experiment conducted. In the boiling phase, the
gray solution of crude acetanilide dissolved in water turned cloudy as the black impurities in squishy texture
formed themselves together and settled below and the white solids formed as precipitate of the solution.
These white solids actually looked like crystals floating above the solution. As we boil the solution white solids
dissolved, however, we needed to add some preheated water to the solution to help the dissolution occur
faster. We added a total of 6 mL of preheated water from the initial 30 mL, it appears that the solvent was
insufficient to dissolve all the 3.5 g of crude acetanilide. When we filtered the solution using the hot gravity
filtration, the filtrate was very clear, it is colorless, it is in its purest form. All the impurities, including the white
solids that was dissolved earlier. As we let the clear solution sit in the ice bath for 10-15 minutes, crystals or
pure acetanilide started to form slowly. The solution being cooled down in the ice bath was actually semi-
foamy. When we vacuum filter the solution cooled down from the ice bath, wet crystals were spotted. It was
then sent in the oven to dry it or drain excess water.
CONCLUSION
In this experiment, the core of purification was carefully observed. Solubility, defined as the ability of
solute to dissolve in a solvent, plays a very significant role in purification processes, specifically, in this sense,
recrystallization process. This experiment was very strict to the criterion of recrystallization. Insoluble in cold
solvent and soluble in hot solvent was a very easy way of eliminating all the possible solvents needed for
recrystallization of a specific substance. The objectives of the experiments were both satisfied. We were able
to identify the appropriate solvent for the recrystallization technique. Choosing the right solvent is quite a hard
task for you have to try every solvent available only to single out the best that could be utilized in
recrystallization technique. However, as soon as the solute completely dissolves in cold solvent, it can be
discarded already which diminishes your big set of solvents to try on. In this part of experiment, since the test
samples were all solids and that pressure is automatically neglected because it only works on gases--- the
essence and effect of temperature was extremely emphasized. The probable source of error on choosing the
right solvent part of this experiment is human error. There could be error in Table 1 caused by impatience of
the student assigned to this part of this experiment.
The second objective was also satisfied through the second part of this experiment. From Table 2,
the said appropriate solvent of acetanilide is water, that was what we used in purifying impure or crude
Experiment 02 │ A10 │ Group No. 2 │ August 29, 2019
CM134-1L: ORGANIC CHEMISTRY (LABORATORY)
1ST Quarter SY 2019-2020
acetanilide. Benzene is also candidate to be the appropriate solvent, unfortunately, it s a nonpolar solvent
which will totally not react with acetanilide which is a polar substance. In this sense, polarity has become one
of the factors. As the recrystallization process continues, evident changes can be observed just like what was
stated in Table 4. There are no probable source of error in this experiment because we followed the laboratory
manual carefully. However, the small percent recovery can be justified by the substance itself, it has too
many impurities to begin with.
REFERENCES
Retrieved from https://courses.lumenlearning.com/introchem/chapter/solubility/
Retrieved from https://www.ausetute.com.au/aspirin.html
Retrieved from https://cpb-us-e1.wpmucdn.com/sites.ucsc.edu/dist/9/291/files/2015/12/Exp-1-
Recrystallization-of-Acetanilide.pdf
Retrieved from https://www.encyclopedia.com/science-and-technology/chemistry/organic-
chemistry/naphthalene
Retrieved from https://link.springer.com/chapter/10.1007/978-1-4615-2676-6_5
Retrieved from http://www.saralstudy.com/study-eschool-ncertsolution/chemistry/biomolecules/679-glucose-
or-sucrose-are-soluble-in-water-but-cycloh
Retrieved from https://en.wikipedia.org/wiki/Acetamide
Retrieved from https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/benzoic-acid
Retrieved from https://www.slideshare.net/sureshselvaraj108/seperation-and-purification-techniques
Retrieved from https://en.wikipedia.org/wiki/Crystallization
Experiment 02 │ A10 │ Group No. 2 │ August 29, 2019
