I.

THEORETICAL BACKGROUND

The separation and purification of organic compounds in solution are critical in

chemistry. Many synthetic reactions produce mixtures of products. Therefore it is encouraged
that individuals, particularly students, must have a good understanding of how to separate and
purify mixtures of molecules. Almost all compounds of biochemical interest occur naturally as
components of very complex mixtures, out of which they can only be separated and purified with
incredible difficulty. Separations and purification can be achieved through differences in physical
characteristics, such as distinctions in boiling point, or through the chemical method, in which
chemical reactions accentuate variations in physical properties.

Purification of organic compounds is a necessary, though somewhat complex, step after

separation from a natural source or laboratory synthesis. The procedure entails removing
impurities from an organic compound. However, the method of purifying organic compounds is
largely determined by the nature of the substance and the impurities present. There are several
ways of purification of organic compounds involved in separating organic substances. The
condition causes the process to be time-consuming because, unlike inorganic compounds, a large
number of organic compounds decompose upon heating, while some are sensitive to specific
reagents and resist water solubility. It should be required that there must be a precise composition
whenever a product is produced. If there is an impurity in the reactant, there may be another
impurity in the result that will degrade its quality. That is one of the most significant reasons
organic compounds must be purified. The most common methods are sublimation, crystallization,
distillation, differential extraction, and chromatography. 

Sublimation and crystallization are two common methods for solid purification.
Sublimation is the process by which a compound changes its state from solid to liquid. The
method is used to separate sublime compounds from non-sublimate or nonvolatile substances.
These nonvolatile substances are typically solids with boiling points greater than 212°F (100°C)
that do not vaporize easily at room temperature and pressure. The most common method for
purifying solid organic compounds is crystallization. The method relies on variations in the
solubility of a given solvent and solute. Because most compounds are not soluble in water, other
solvents such as alcohol, acetone, chloroform, and ether are frequently used for the procedure.
The method utilizes heat, the solvent, and the compound to be purified. The solvent has to have a
low solubility. The solution is heated to obtain a saturated solution. After cooling, the obtained
crystals of the compounds are removed through filtration. Organic Chemistry at CU Boulder
stated that filtration is a process for removing solid contaminants from organic solutions or
isolating an organic solid. Gravity filtration and vacuum or suction filtration are the two most
prevalent methods of filtering employed in organic chemistry laboratories.

For the purification of liquids, distillation, differential extraction, and chromatography

are methods frequently utilized. Distillation is the process of converting a liquid to a gas and then
condensing the gas to a liquid. The idea behind the method is that liquids in a solution can be
separated due to differences in boiling points. Differential extraction is used for immiscible
liquids and can also be used for some solids in aqueous solutions. It is the removal of a substance
from its aqueous solution by shaking it with an organic solvent. The liquids are expected to
separate based on the liquids' specific gravities. Chromatography is a modern technique for
separating component particles of a mixture of substances, purifying compounds, and
determining the purity of organic compounds. The method is based on the idea that different
components of a mixture absorb to varying degrees by a given adsorbent.
 II. OBJECTIVE (TLO)
TLO#3: Differentiate the types of separation and purification of organic compounds, such as
Buchner filtration and sublimation using organic compounds. 

TLO#5: Demonstrate purification and separation by sublimation. Apply the limitations

encountered in the application of sublimation as a general method of purification.

III. PROCEDURES

FILTRATION: 
A. A mixture of organic substances (1 gram of benzoic acid and 0.5 gram of sugar) is divided into
five equal portions. (Three of these portions are to be saved for the next experiments). 
1. To one portion, add 25 ml of distilled water, shake vigorously and filter. Examine the residue
and compare it with samples of the two substances. 

2. To the second portion, add 10 ml of denatured alcohol, shake the mixture vigorously and filter
as before. Examine the residue, and compare it with samples of the two substances. 

B. Another mixture of organic substances (0.5 gram of benzoic acid and 0 5 gram of urea) is
divided into two equal portions. 
1. To one portion, add 25 ml of distilled water, shake vigorously and filter. Examine the residue
and compare it with samples of the two substances. 

2. To the second portion, add 10 ml of denatured alcohol, shake the mixture vigorously and filter
as before. Examine the residue, and compare it with samples of the two substances. 

SUBLIMATION: 
1. Obtain a clean, dry 250-m1 beaker and carefully weigh and record its weight. Obtain the
sample of the organic mixture (the remaining portion of the sugar benzoic acid mixture).
With the beaker still on the balance, carefully transfer the organic mixture and record the
weight of the beaker with its contents. Calculate the sample weight. 

EXPERIMENTAL SETUP:
 ICE

ORGANIC
MIXTURE

2. Prepare the laboratory set-up for sublimation as shown in the diagram, being careful not to get
any water on the underside of the evaporating dish or inside the beaker. Carefully heat the beaker
on low flame. (Avoid overheating which may cause charring of the sugar). After 5 minutes of
heating, remove the flame, carefully remove the evaporating dish from the beaker and scrape off
the sample of sublimed material from the evaporating dish. Drain away any water from the
evaporating dish and add ice to it, if necessary. Stir the contents of the beaker, return the
evaporating dish to the beaker and apply heat again until no more solid is collected. 

3. Calculate the weight of the sublimate and determine percentage recovery.  

IV. DATA AND RESULTS

A. FILTRATION
What are the relative solubilities of benzoic acid and sugar in water?
Benzoic acid is insoluble in water. On the contrary, sugar is highly soluble in water.
What are the relative solubilities of benzoic acid and sugar in denatured alcohol?
Benzoic acid is highly soluble in denatured alcohol. On the contrary, sugar is insoluble in
denatured alcohol.
What are the relative solubilities of benzoic acid and urea in water?
Urea dissolved much faster than benzoic acid, which needed a higher temperature to
dissolve in water.
What are the relative solubilities of benzoic acid and urea in denatured alcohol?
Benzoic acid dissolved much faster than urea, which needed a higher temperature to
dissolve in the denatured alcohol.

B. SUBLIMATION
Describe the appearance of the material remaining in the bottom of the beaker.
The material remaining in the bottom turned brown.
How does it compare with the material which was sublimed?
The sublimed material formed a transparent, crystalline, needle-like appearance and was
easily scraped off. The material in the bottom of the beaker quickly hardened but turned
liquid once heated again.
Weight of the sublimate and determine percentage recovery.

% recovery = weight of sublimate X 100

Weight of sample

% recovery = 0.07 g X 100 = 7.87%

0.89 g

V. DISCUSSION

The experiment involved separating and purifying organic compounds through filtration
and sublimation. The first procedure concerned the solubilities of benzoic acid, sugar, and urea in
different solvents, such as water and denatured alcohol. It was observed that benzoic acid
dissolved poorly in water. In contrast, sugar dissolved easier, associated with the energy released
by the slightly polar sucrose molecules when coming in contact with polar water molecules. The
experiment demonstrated how benzoic acid is insoluble in water and sugar is highly soluble in
water. On the other hand, benzoic acid can dissolve in denatured alcohol because it is a
monobasic aromatic acid that is a moderately powerful white crystalline powder which explains
how it is soluble in denatured alcohol (Soucy, 2014). In contrast, sugar does not readily dissolve
in denatured alcohol, even in oil, because alcohol is non-polar due to that being insoluble in
denatured alcohol. 

When it came to urea, urea dissolved faster than benzoic acid in water but dissolved
slower in denatured alcohol. The presence of urea is greatly diminished by monovalent alcohol’s
hydrophobic action at low temperatures and to a lesser amount at high temperatures which,
having the presence of the water molecules, urea suppresses inner hydrophobic interactions. As a
result, benzoic acid dissolved much faster than urea, which needed a higher temperature to
dissolve in the denatured alcohol.
 Lastly, the experiment on sublimation involved a sugar-benzoic mixture. It resulted in a
soft, fragile, needle-like sublimate. The sublimed material collected was 0.07 grams compared to
the 89 grams sample weight. The percent recovery calculated is 7.87%, which describes the
purification operation's efficiency.

VI. QUESTIONS

1. Explain the term, selective solubility. 

Selective solubility refers to a separation technique used to remove a compound from a
mixture. 

2. How could one recover the sugar in part A.1 above? 

The sugar in the experiment was mixed with benzoic acid and then divided into equal parts.
While the sugar dissolves in water, the benzoic acid remains precipitated. And, as a result of
the filtration, benzoic acid remains to precipitate on the filter paper, while sugar dissolves
in the filtrate. 

3. Name five solvents available to the organic chemists for use in the purification of organic
compounds. 
As inferred from the experiments that have been conducted thus far, the chemists may use
water, ethyl alcohol, chloroform, benzene, and ether.

4. Explain the term sublimation. 

Sublimation is the process wherein a substance in the solid phase directly transitions into
the gaseous phase without having to go through the liquid phase. This is usually done by
heating the substance under a vacuum in order to purify compounds.  

5. What limitations are encountered in the application of sublimation as a general method of

purification? 
Sublimation can only be done with a handful of substances as the process requires the
substance to have high vapor pressure and low boiling point. As observed in the experiment
conducted, sublimation requires a vacuum in a controlled environment for the process to go
smoothly. The equipment and set-up for sublimation may not be accessible for many.

6. Explain how a process of fractional sublimation might be applied to a mixture of two

substances which sublime closely together. 
The process of fractional sublimation, the method involves the purification of substances
that sublime when heated under lowered air pressure and are less than the increasing vapor
pressure. 
VII. CONCLUSION

The separation and purification of organic compounds are necessary for identifying
unknown components. In initiating chemical reactions and experiments, knowing the specific
composition of the compounds being dealt with is essential. In some cases, there may be
impurities that may obstruct the accuracy of an experiment or a quality of a product. Therefore,
methods such as filtration and sublimation may be used for separation and purification.

Filtration is used to separate insoluble solid components of a mixture from soluble

components in a given solvent. Solubility is an essential factor to consider in separating and
purifying solutions. The solubility of certain compounds must be considered in utilizing certain
solvents. The general idea is that organic solutes are better dissolved in organic solvents.
However, solubility can still vary, so knowing a compound's solubility in a solvent can help better
determine the best method for separating and purifying.

On the other hand, sublimation results in impurities being left behind while the
compound that evolved into gas gets collected in the solidified state on a cold surface. The
vaporized compound was collected at the bottom of the evaporating dish in this experiment. Most
of the time, final products contain many impurities. Hence, the sublimate is the purified product
obtained.
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