SONG, You Kyoung Locker 30 A

Experiment 1: Recrystallization of Benzoic Acid Feb. 15, 2020

Data Tables

Table 1: Obtained and Derived Data

Data Table
Crude Benzoic Acid sample (g) 2.01g
Wet Benzoic Crystals (g) 1.77g
Dry Benzoic Crystals (g) 1.42g
Percent Recovery (%) 70.65%
Melting Point (℃) 122-123℃

Discussion

Benzoic Acid, which can be found naturally in plants, is an important precursor for the
synthesis of many organic substances. It is industrially used to manufacture a wide variety of
perfumes, dyes, insect repellents, and topical medications. Sodium benzoate, a salt of benzoic
acid is commonly used as a pH regulator and preservative in food such as soft drinks. By
changing the internal pH to an acidic state, it becomes incompatible for microorganism to grow
or survive. (1)

The solid state of benzoic acid is a white, crystalline powder with a faint pleasant odor.
The pure compound has a melting point of 122.4℃. A compound mixed with impurities
however, melts at a lower temperature due to the disruption of the crystal lattice structure and
weakened intermolecular bonds which allow the solid to easily change state to liquid. Using
this knowledge, it can be assumed that a melting point, which is a physical property of a
substance, can be used to analyze the purity of a known substance, and the identity of an
unknown substance. (2)

This experiment uses a method called crystallization, which is a slow process of

molecules arranging into a defined crystal lattice structure in order to minimize the energetic
state. It is when solid crystals are formed from another phase, typically a liquid solution or
melt. Precipitation on the other hand, may be another word for crystallization, but occurs very
quickly through chemical reaction and may not be pure, nor have crystal lattice structure like
crystals. (3) The benzoic acid product from this experiment are sharp and needle-like clear
crystals formed by crystallization. (AtQ1)

In this experiment, 2.01g of crude benzoic sample was used to obtain 1.42g of dry
benzoic crystals which had a melting point of 122-123℃. The crude benzoic acid sample was
in the form of white powder with visible impurities. When dissolved, the solution was clear
with only a slight tint of blue. Hence, less than a dip of decolorizing charcoal was added to
reduce product loss, since it was not necessary to add more than a light dip. If excess charcoal
was added, it would absorb the benzoic acid along with the impurities, yielding less product.
If the liquid was deep blue and the charcoal added was lacking, the solution will still contain
colored impurities that make it slightly blue. (AtQ2) To trouble shoot, more decolorizing
charcoal can be added to treat the solution.
 When boiling, a little frothing was observed alongside with slight overflow of solution
due to the large bubbles as the heat was too immense. Immediately, the fire was lowered, and
the large bubbles subsided. The resulting solution was misty gray, due to the added charcoal
which was to be filtered out using gravity filtration. During the gravity filtration, it was a
struggle to tilt the hot flask with tongs and tissue. While searching for a better method to pour
the hot flask over the filter paper, the solution was slightly cooled. When poured over the filter
paper, it began to form premature crystals. To trouble shoot, hot distilled water was added to
dissolve the crystals back to liquid form. This repetitive trouble shooting led to another problem
– the mother liquor became too much to evaporate off in a few minutes before the hour
necessary to slowly cool the solution in room temperature before the ice bath. To urgently
reduce the solution to less than a 100mL, it was heated above the Bunsen burner at a relatively
large fire, but not large enough to make it overflow. The cooling at room temperature began as
soon as the flask reached the 100mL mark to allow enough time for the crystallization process.

The solution was cooled for one hour before bathing in ice. Once the flask was in
equilibrium with the ice-water bath, it was poured over the suction filtration. To wash the
remaining crystals off the flask, cold water was added then poured again over the suction
filtration. The water used to wash the crystals needed to be cold so that the crystals will not
dissolve and be sucked in along with the water, leading to major product loss. (AtQ3) The
accumulated product was then collected in a vial covered with tissue then left to dry for a week.
The dry crystals were weighed, then put in the melting point apparatus in a capillary tube. The
crystals began to move and break at 122℃ and was completely melted by the latter seconds of
123℃. Any impurity in the compound would disrupt the crystal lattice structure and thus lower
the melting point due to the fact that the intermolecular bonds are no longer strong and compact.
In addition, the impurities may have melting points of their own, which could possibly be
mistaken as the melting of benzoic acid in the apparatus. (AtQ4) Given that the researched
melting point of benzoic acid is 122.4℃, the melting point of the product of this experiment
was accurate enough to say that the product was pure based on its physical states of appearance
and melting point.

The percent yield recovery acquired from the experiment was 70.65%, due to product
loss in certain processes. First, when boiling the solution, there was overflow of solution due
to the large bubbles. Second, a large part of the sample was unable to dissolve through the filter
paper during the gravity filtration. As stated above, the flask was too hot to be poured with
hands, and too risky for it to be poured using tongs. Hence, while trying alternative methods,
the solution cooled, and began forming premature crystals on the filter paper which hindered
the solution from passing through. Although the premature crystals were bathed in hot distilled
water several times, there was not enough time to dissolve every crystal left on the filter paper.
Hence, the recovery of actual yield is 70.65%. It is important to note, however, that it is nearly
impossible to get a yield of 100% since benzoic acid is slightly soluble in water even at 0℃.
".$% '.&*%
Given 2.0g of benzoic acid in 60mL water with the solubility of &''() at 100℃ and &''() at
0℃, the maximum theoretical yield would be 94.9%, as shown in the calculations below:
0.17𝑔 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑 𝑥 𝑔 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑
=
100𝑚𝐿 𝑤𝑎𝑡𝑒𝑟 60𝑚𝐿 𝑤𝑎𝑡𝑒𝑟

x = 0.102g benzoic acid dissolved in 0℃

2.00g sample – 0.102g dissolved = 1.90g product
&.$A$%
B.''%
𝑥100 = 94.90% (AtQ5)
 In conclusion, the objectives which were to isolate pure compounds of contaminated
benzoic acid by crystallization, and to determine the purity of benzoic acid using the melting
point apparatus were met. Moreover, this experiment allowed students to learn important lab
techniques such as gravity filtration, suction filtration, recrystallization, and melting point
determination. Aside from techniques, the concepts of crystallization and melting points were
rediscovered in another depth.

Sample Calculations

Mass of Vial + Crude Benzoic Acid: 68.43g

Mass of Vial: 66.42g

Crude Benzoic Acid sample (g): = 68.43g – 66.42g

= 2.01g

Mass of Vial + Wet Crystals: 53.91g

Mass of Vial: 52.14g

Wet Benzoic Crystals (g): = 53.91g – 52.14g

= 1.77g

Mass of Vial + Dry Crystals: 53.56g

Mass of Vial: 52.14g

Dry Benzoic Crystals (g): = 53.56g – 52.14g

= 1.42g

CDEE FG HIJ KLMNFOP QIJERDSE

Percent Recovery (%) = CDEE FG QITUL KLMNFOP VPOU ED(WSL 𝑥100
&.XB%
= B.'&% 𝑥100
= 70.65%

References

(1) Benzoic Acid [Internet]. Canada: MSDSonline – VelocityEHS; 2015. Available from:
https://www.msdsonline.com/2015/02/16/benzoic-acid-uses-and-safety/
(2) Kirsop, A. Why do impure solids melt at lower temperatures? [Internet]. United
Kingdom: KirsopLabs project; 2019. Available from: https://kirsoplabs.co.uk/lab-
aids/impure-solids-melt-lower-temperatures/
(3) Mettler-Toledo. Crystallization and Precipitation. [Internet]. Ohio, United States:
Mettler-Toledo; 2020. Available from:
https://www.mt.com/us/en/home/applications/L1_AutoChem_Applications/L2_Cryst
allization.html