SUBLIMATION

Pamela Estrada, Carlo Falconi, Shina Go, Joana Gozon, Monica Hamtig, and Caitlin Hao.
Group 4 2F Medical Technology Organic Chemistry Laboratory

ABSTRACT
This experiment was performed so as to purify benzoic acid using sublimation, to determine and compare the melting points of the product
with a standard, and to be able to calculate the percentage recovery. An evaporating dish filled with 5.00g of impure benzoic acid that is
covered with a perforated paper and an inverted watch glass was heated using a hot plate, and cooled with a wet tissue paper
simultaneously for 10-15 minutes. After this part of the procedure, the set-up was allowed to cool. All the sublimate that were adhering to
the watch glass and perforated paper were collected and weighed to be able to compute for the percentage recovery. The sublimate was
then grounded into a fine powder and was compared with a pure benzoic acid by determining the melting point range through the use of an
oil bath so as to distinguish the purity of the product.

INTRODUCTION
Benzoic Acid is a white, crystalline organic
compound that belongs to the family of
carboxylic acids[1]. It is slightly soluble in water
and has a melting point of 122 degrees
Celsius[2].
Sublimation is the direct vaporization of a solid
by heating without passing through the liquid
state[3]. In order to purify the impure benzoic
acid, the process of sublimation was used in this
experiment. The impurities in the benzoic acid
contain amino compounds that can be found at a
greater limit and must be taken away because of
phenyl and benzyl compounds that extremely
affect the product of the reaction. This process
occurs when the vapor pressure of the
substances is greater than that of the
atmospheric pressure at the melting point. The
purification process involved in sublimation is
more applicable for impurities with low vapor
pressure or non-volatile than pure substances or
compounds[4].
The melting point of an organic compound is
one of several physical properties by which it is
identified, so one way to test the purity of a
substance is by determining its melting point. A
pure substance generally has a melting range of
one or two degrees. This is the difference
between the temperature at which the sample
starts to melt and the temperature at which the
sample
completely
melted.
The
samples
impurities tend to depress and broaden the
melting range so the purified sample should have
a higher and smaller melting range than the
original, impure sample[5].
The objectives of this experiment are:
(1) To purify the impure benzoic acid through
sublimation.
(2) To calculate the percentage recovery of
the benzoic acid after sublimation.
(3) To identify the melting points of the
sublimate and the pure benzoic acid
through the use of an oil bath.

EXPERIMENTAL
A. Compounds tested (or Samples used)

Figure 1. Structural
Formula of Benzoic Acid

The
tested in

compound
this
experiment
is
only
benzoic
acid but
the group
made use
of its pure
and
impure
forms. The pure benzoic acid was the standard while the
impure benzoic acid was experimented on. Benzoic acid is
a white, crystalline organic compound[1], which has a
melting point of 122C and has a boiling point of 249C at
760 mmHg or 1 atm. Its molecular formula is C 7H6O2
and it has a -COOH functional group, making it a
carboxylic acid[6].
B. Procedure
1. Sublimation
To start, 5.00g of impure benzoic acid was placed in an
evaporating dish, and covered with a perforated bond
paper and an inverted watch glass. All openings were
secured with masking tape so as not to allow the vapor to
escape from the set-up. This set-up was then heated
using a hot plate for 10-15 minutes until most of the
sample were vaporized, as the center top of the set-up
was cooled with a wet tissue paper that is kept moist with
water. After heating, the set-up was allowed to cool, and
the sublimate, in the form of crystals, adhering to the
surface of the watch glass and paper was carefully
collected and weighed. The weight of the sublimate and
the weight of the sample were used to calculate the
percentage recovery.
2. Melting Point Determination
To determine the melting point of the product, the
sublimate was first pulverized into a fine powder, and then
placed in a capillary tube that is sealed on one end. The
sublimate was then packed at the bottom of the capillary

tube by repetitively dropping the closed end of the

capillary tube through a glass tubing. This was also done
with a pure benzoic acid to use as a standard for
comparison with the product. The amount of the
sublimate and the standard were of the same height in
the capillary tube, assuming both are well-packed and
properly labeled. Then, both were aligned with and
attached to the mercury bulb of the thermometer. This
set-up was then immersed in an oil bath and heated. The
initial temperature at which the sublimate and the
standard start to melt and the final temperature at which
the sublimate and the standard completely melted were
recorded.

Thermometer

Oil Bath
Capillary tubes

Distilled water to
keep the tissue
paper moist

Gas Source

Bunsen Burner
Wet tissue paper
over the watch glass

Evaporating dish with

impure benzoic acid covered
with perforated paper and
inverted watch glass

3. Computations
After the sublimate was weighed, computations were
done. The percentage recovery of the benzoic acid was
then calculated using the formula below.
Percentage recovery:

Hot Plate

w
weight of sublimate
yield benzoic acid=
100
w
weight of sample
w
3.28 grams
yield benzoic acid=
100
w
5.00 grams
w
yield benzoic acid=65.6
w
Also, the initial temperature at which the first
crystals started to melt, and the final
temperature at which all the crystals completely
melted were recorded. The difference between
the final and initial temperatures determines the
melting point range and the purity of the
substance.
Melting point range:

Melting point range=final tempinitial temp

M . P .range of . =126 deg C124 deg C

M . P .range of 2 deg C

M . P .range of std .=125 deg C124 deg C

M . P .range of 1 deg C

RESULTS AND DISCUSSIONS

The weight of the sublimate (i.e. benzoic acid)
and the watch glass were measured in order to
determine the weight of the product. This data
was used to calculate the percentage recovery
with reference to the 5.00-gram impure benzoic
acid sample. The weight of the watch glass and
the sublimate is 55.87g while the weight of the
watch glass alone is 52.49g, so the weight of the
product is 3.28g. The percentage recovery of the
benzoic acid sublimate was calculated by using
the weight of the sublimate divided by the weight
of the sample, then the quotient is multiplied by
100. The computations show that there is a
65.6% recovery of the benzoic acid in the impure
sample.
Table 1. Data of sample used and calculated
percentage recovery of benzoic acid sublimate
Data determined
Weight of the impure
benzoic acid
Weight of the watch
glass and sublimate
Weight of watch glass
Weight of sublimate
Percentage recovery

5.00 grams
55.87 grams
52.49 grams
3.28 grams
65.6%

Aside from weighing and calculating the

percentage recovery of the benzoic acid, the
initial and final temperatures of the sublimate
and the standard at which they started to melt
and completely melted were recorded so as to
compare the purity of both compounds. Both
compounds started to melt at 124 oC. The
standard was the first one to completely melt at
125oC, and the sublimate completely melted next
at 126oC. Thus, the melting range of the standard
is 1oC and the sublimate is 2oC.
Table 2. Temperatures and Melting Points
Sublimate
Standard

Initial
Temp
124oC
124oC

Final
Temp
126oC
125oC

Melting
pt. range
2oC
1oC

The key compound in this experiment is

benzoic acid. The benzoic acid was extracted
from its impurities using the process of
sublimation, a purification technique. In the
experiment, the evaporating dish filled with
impure benzoic acid was sealed to secure the
vapor of the benzoic acid that will consequently
solidify when the center top is cooled. This
technique presented a relatively high percentage

recovery, considering there are impurities in the

sample. The collected sublimate formed crystals
and were pulverized into a fine powder so as to
fit in a capillary tube. The pure benzoic acid was
also pulverized and placed in another capillary
tube to use as a comparison with the benzoic acid
sublimate. Both capillary tubes were attached to
the mercury bulb tip of the thermometer and the
initial and the final temperatures at which each of
the compounds started and ended melting,
respectively, were recorded. Since a pure
substance has a melting range of only 1 or 2
degrees Celsius, the sublimate that was collected
can be considered as nearly as pure as the
standard.
Sources:
[3] Helmenstine, A. (2015)
Retrieved 10/10/15
http://chemistry.about.com/od/chemistry
glossary/a/sublimationdef.htm
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Laboratory Manual in Organic Chemistry:
Revised Edition (p. 37-39). C&E Publishing
Inc.
[5] Yoder, C. (2015)
Retrieved 10/10/15
http://www.wiredchemist.com/chemistry/i
nstructional/laboratorytutorials/determination-of-melting-point
[2] Haynes, W. (2010).
CRC Handbook of Chemistry and Physics
(91st ed. ed., pp. 3-3). Boca Raton, FL:
CRC Press.
[1] Encyclopdia Britannica. (2015).
Retrieved October 11, 2015, from
http://www.britannica.com/science/benzoi
c-acid
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National Center for Biotechnology
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