Rogeni Misaelle M.

Petinglay Date performed: February 13, 2017

Date submitted: February 27, 2017

Experiment No. 3
PURIFICATION AND MELTING POINT DETERMINATION

I. Summary of Results

Table 1. Recrystallization
Sample / Material Mass (g)
Naphthalene (C10H8) 0.5165
Pre-weighed filter paper 1.0629
Filter paper + Naphthalene Crystals 1.4558
Naphthalene Crystals 0.1058

Percent recovery of Naphthalene 20.48%

after recrystallization

Table 2. Sublimation of Benzoic Acid

Sample / Material Mass (g)
Crude Benzoic Acid (C6H5COOH) 0.10190
Pre-weighed Vial 30.2075
Vial + Benzoic Acid Crystals 30.2544
Benzoic Acid Crystals 0.04690

Percent recovery of pure benzoic acid 46.03 %

Table 3. Melting Point Determination of Benzoic Acid

Sample Lower Limit Melting Point ( C ) Upper Limit Melting Point ( C )
Pure Benzoic Acid 120 124
Crude Benzoic Acid 117 123

II. Discussion

Purification is the physicsl separation of a chemical substance of interest from

contaminating substances. Pure results of a successful purification process are termed
isolate. In this experiment, three methods of purification were used- crystallization,
sublimation and melting point determination.

Recrystallization

Recrystallization is a procedure for purifying an impure compound in a solvent.

The method of purification is based on the principle that the solubility of most solids
increases with increased temperature. The success of a recrystallization is based on the
amount of pure solid crystals that can be obtained using this technique. Crystal structures
refer to the relative arrangement of the atoms, not the macroscopic properties of the
crystal, although those are a result of the internal crystal structure

The recrystallization process consists of two major events- nucleation and crystal
growth. In nucleation solute molecules dispersed in the solvent start to gather in clusters
and the atoms arrange in a defined and periodic manner. Crystal growth is the subsequent
growth of the nuclei that succeed in achieving the critical cluster size.

The first step in using the technique is choosing a suitable recrystallization

solvent. In the experiment, a crude sample of naphthalene was used. Two setups were
made and compared. In test tube A, naphthalene and water were mixed while in test tube
B, naphthalene and 95% ethanol solution were mixed. As for the appearance of the
solutions, test tube A was cloudy-white with some tiny particles of naphthalene settling at
the bottom while in test tube B, the naphthalene completely dissolved in the solvent and
is colorless. It was observed that test tube A needed boiling for the naphthalene to
completely dissolve in water while in test tube B, the naphthalene dissolved only at room
temperature with minimal stirring. At the end of this part, water was the chosen solvent.

Several factors were considered in choosing water as a solvent. The crude sample
should be soluble in the solvent at a lower temperature and soluble at higher temperature.
It must have a lower boiling point than the melting point of the compound because if the
boiling point of the solvent is higher that the melting point of the compound, it will tend
to melt instead of dissolving.

The second step is dissolving the compound. A small amount of naphthalene was
added with water and placed in a test tube. For an easy purification, adding the minimum
amount of hot solvent is essential. The minimum amount is completely dependent on the
quantity of material and the solubility of that material in the solvent used. This was then
heated in a hot water bath while stirring until the entire sample was dissolved. The goal
when heating this mixture is to create a saturated solution in hot solvent. By creating a
completely saturated solution, the less soluble compound will crystallize upon cooling.
Filtration and/or treatment with activated carbon are only necessary when there are
insoluble or colored impurities present. Addition of activated carbon will remove the
impurities in the solution and will make it clear. After heating, the mixture was allowed
to cool at room temperature and was then placed in an ice- water bath, along with the test
tube of pure solvent. A few minutes after the mixture was cooled, it was filtrated. The
dried naphthalene crystals were then weighed and the percent recovery was calculated.
Only 20.48% naphthalene was recovered. A very low percentage was obtained; this
might be due to the delayed weighing of the sample. It was weighed after a couple of
days, so the sample might have evaporated.

Sublimation of Benzoic Acid and Caffeine

The transition of a substance from the solid phase to the gas phase without
passing through an intermediate liquid phase is called sublimation. It is a process used to
purify substances in small scale quantities because there is a little loss of the sample in
the process. Sublimate is a solid deposit of a substance that has sublimed; it is the product
of sublimation process.

In the experiment, about 0.1 grams of crude benzoic acid were obtained and
placed in a beaker. The beaker was covered with filter paper and was then taped in order
for the filter paper to be in place. The sand bath in a hot plate was heated and the beaker
was immersed in it. Under this reduced pressure, the crude benzoic acid volatilizes and
condenses as a purified compound on a cooled surface. After this, the sublimate was
scraped from the filter paper and the surface of the beaker and placed inside the pre-
weighed vial for the next experiment.

As a bonus experiment, the amount of caffeine extracted from tea was sublimed.
The caffeine sample required more heat. It decomposed to form brown parts and
produced fewer yields. Increasing the pressure would decrease the amount of heat
required, while producing a purer sample. Compared to the benzoic crystals formed, the
caffeine crystals were shorter and only a few crystals were obtained.

Melting Point Determination of Benzoic Acid

The melting point of a compound is the physical state from a solid phase to liquid
phase. Purity can be determined by evaluating the melting point range.

In the experiment, a small amount of recovered pure benzoic acid was pulverized;
from this about 1-2mm high was placed into a capillary tube (a glass capillary closed at
one end). The setup was assembled. In the setup oil was used instead of water because oil
has a higher boiling point than water. Upon melting, the sample of benzoic acid will not
evaporate easily. Hence, the melting point range can be determined. The steps were
repeated again using the crude benzoic acid instead of the pure one and the results were
compared.

Based on the results, the melting point range of the pure benzoic acid was from
120 C to 124 C while the melting point range of the crude benzoic acid was from 117
C to 123 C. The crude benzoic acid had a lower melting point than the pure benzoic
acid because when an impurity is soluble in the compound, the melting point will be
depressed. In the pure benzoic acid, there is a narrower melting point range compared to
the crude benzoic acid, which indicates that it is a better melting point range.

One of the biggest and most common mistakes when obtaining a melting point is
not allowing the sample to dry completely. Traces of solvent in the sample act just as any
other impurity. It will depress the melting point and broaden its range. Another common
mistake is to heat the sample too fast. In general, it is best to heat the sample slowly, no
faster than 2C per min in the range of the melting point.
III. Conclusion

This experiment successfully demonstrated how to recrystallize and sublime an

organic sample which is useful in the purification of organic compounds. Furthermore, it
recognized melting point as a physical property that can serve as an index of purity.

The principle behind recrystallization is that the amount of solute that can be
dissolved by a solvent increases with temperature. This technique includes selecting of
appropriate solvent, dissolving of the compound, removing of colored insoluble
impurities (if present), drying and cooling. In the experiment, the recovered naphthalene
was about 20.48% .

Sublimation occurs by applying reduced pressure where the vapor pressure of the
solid can reach the applied pressure.

In the melting point determination experiment, it was found that the melting point range
of crude benzoic acid was from 117 C to 123 C while the pure benzoic acid was from 120 C
to 124 C. The melting point of the substance changed according to the changes regarding its
purity. As the substance became increasingly impure, its melting point increased and its melting
point range broadened.

IV. References

OChem331- Sublimation. Retrieved February 16, 2017 at

https://ochem331.wikispaces.cm/Sublimation

University of Mugla Engineering Departmant: Crystallisation and Sublimation Experiment..

Retrieved February 16, 2017 at
https:/muglaengineering.blogspot.com/2011/12/crystallisation-andsublimation.html?m=1

Organic Chemistry, A Short Course (13th Ed.); Manual H. Hart & L. Craine. Laboratory Manual

V. Calculations
0.1058
% naphthalene = 0.5165 100% = 20.48%

0.0469
% benzoic acid =0.1019 100% = 46.03%