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University of Santo Tomas Faculty of Pharmacy

Physical Pharmacy Laboratory
DETERMINATION OF BENZOIC ACID’S SOLUBILITY IN WATER

Lagarteja, M.C.B.
1
; Lim, H.G.N.
1
; Lizo, K.J.R.
1
; Macalino, M.D.L.
1
, Macapala, C.M.
1
1
3D-Pharmacy, Faculty of Pharmacy, University of Santo Tomas

Abstract
Solubility is one of the most fundamental physicochemical properties in the Pharmacy field
particularly in discovering new drugs. In relation to this, experiment was conducted in order to
determine the solubility of benzoic acid, a chemical present in some drug products, in water. In an
Erlenmeyer flask a corn grain amount of benzoic acid was placed. The solution was agitated for
15 minutes, and then filtered. Five milliliters of the filtrate was placed in the two tared
evaporating dishes, and allowed to dry in the oven. The evaporating dishes were weighed again
and the solubility of the sample was computed. Based on the computation, 20 mL of water is
needed in order to dissolve one gram of benzoic acid, and therefore the description is soluble. The
incomplete drying of the filtrate contributed to error in the experiment. The principle behind is as
the nonpolar portion of hydrocarbon increases, the solubility of carboxylic acids in water
decreases. Benzoic acid is an unsaturated six membered ring with carboxylic acid attached to it.

Background of the Study
Solubility is one of the most
fundamental physicochemical properties. It
is remarkably useful for a wide variety of
applications important in the different
industries especially in the field of
Pharmacy. Accurate solubility data are
needed for process and product design,
including production and purification of
chemical compounds, separation,
precipitation processes, crystallization,
chemical reaction systems and other
processes involved [2].
Solubility of a substance is the
maximum amount of solute that will
dissolve in a given amount of solvent. If
water is going to be used as the solvent, the
temperature must at least be 25ºC but if the
solvent is volatile, the temperature must be
15.56ºC. Other temperatures used for
solubility may range depending on the
solvent used. The traditional concentration
terms such as molarity, molality, mole
fraction, and percentage provide and
accurate, quantitative account of the drug’s
property. For semiquantitative assessment of
drug solubility, the United States
Pharmacopoeia, USP describes the solubility
of drugs as the parts of a solvent needed to
dissolve one part of the solute with units
gram and/ or milliliters, and also the USP
adopts a number of descriptive terms [1].
Table 1. United States Pharmacopeial
Designation of Solubility Ranges [1].

There are several factors that affect
a substance’s solubility. The first is the
forces between particles. The nature of the
intermolecular forces or interionic forces in
both the solute and the solvent affects the
Description
Part of solvent that
dissolves 1 part of
solute
Very soluble <1
Freely soluble 1-10
Soluble 10-30
Sparingly soluble 30-100
Slightly soluble 100-1,000
Very slightly soluble 1,000-10,000
Practically insoluble >10,000
solubility. When one substance dissolves in
another, the attractive forces in both must be
overcome. The dissolving solute must be
able to break up the aggregation of
molecules in the solvent, meaning the
hydrogen bonds between molecules or the
dispersion forces between molecules in a
nonpolar solvent, and the molecules of the
solvent must have sufficient attraction for
the solute particles to remove them one by
one from their neighbors in the undissolved
solute. A general rule is that like dissolves
like [5].
Another factor is temperature.
Usually, the solubility of both liquid and
solid increase as the temperature increases,
but solubility of gases decreases with
increasing temperature [5].
Other factors are pressure and
particle size [1], although pressure may have
very little effect on the solubility of liquids
and solids, but has an enormous effect on the
solubility of gases. As partial pressure of a
gas in the atmosphere above the surface of a
solution increases, the solubility of that gas
increases which explains carbonated
beverages and how carbon dioxide is
dissolved [5].

The objective of this experiment
was to determine the solubility of a chemical
compound, which is benzoic acid, in the
sample.

Methods

The laboratory apparatuses used in
this experiment were Erlenmeyer flask,
funnel, 10 mL-serological pipette, stirring
rod, small evaporating dish, and Memmert
oven. The sample used was benzoic acid.
A corn grain amount of benzoic acid
was placed in an Erlenmeyer flask
containing 20 mL of distilled water. The
solution was shaken continuously for 15
minutes; since the benzoic acid did not
dissolve, addition of the sample was not
needed. After filtering the solution two
portions of 5 mL of the filtrate were pipetted
and placed in separate tared evaporating
dish. The two evaporating dishes containing
the filtrate were placed in the Memmert
oven set at 105 C for almost two hours. The
cooled oven dried evaporating dishes were
weighed again in order to get the weight of
the benzoic acid present after drying.

Results and Discussions
After getting the two evaporating
dishes inside the oven, very small amount of
residue was observed. Each evaporating dish
was weighed again in order to get the weight
of benzoic acid present on it. The first
evaporating dish weighs 114.15g;
subtracting it from its original weight, which
is 114.11 g, the weight of benzoic acid is 0.4
g. The second evaporating dish weighs
108.16 g; subtracting it from its weighed
when empty which is 108.15g, the weight of
the benzoic acid is 0.1 g. The average
weight of the two samples was 0.25 g. The
average weight of the sample was used in
the computation of benzoic acid’s solubility
in water. Solubility was computed using
ratio and proportion.


= 20 mL
Based on the computation, 20 mL
of water could dissolve 1 g of the sample.
Since 20 is in the range of 10-30 in the
United States Pharmacopeial designation of
solubility ranges, the description is soluble,
but the solubility of benzoic acid and
derivatives are very low [3], so this means
that there were factors contributed to the
result of the experiment and this might be
the incomplete drying of the filtrate.
Furthermore, carboxylic acids are
soluble in water because its molecules
interact with water molecules by hydrogen
bonding through both the C=O and O-H
groups. Carboxylic acids of four carbon
atoms or fewer are soluble in water in all
proportions [4].
Conclusion
Carboxylic acids are soluble in
water because its molecules and water
molecules interact with each other by
hydrogen bonding, but this rule is applicable
to carboxylic acids with four carbons or
fewer. As the nonpolar portion of
hydrocarbon increases, the solubility of
carboxylic acids in water decreases [4], like
in the case of benzoic acid wherein the six
membered ring with unsaturated
hydrocarbon is attached to carboxylic acid
References
[1] Ma, J., & Hadzija, B. (2013). Basic
physical pharmacy (Philippine Edition ed.,
pp. 80-82). Burlington, MA: Jones &
Bartlett Learning.
[2] Niti S., et al. (2013). Determination and
modeling of aqueous solubility of 4-position
substituted benzoic acid compounds in a
high-temperature solution, Fluid Phase
Equilibria, Volume 338, 25 January 2013,
Pages 217-223, retrieved from
http://dx.doi.org/10.1016/j.fluid.2012.11.023
.
(http://www.sciencedirect.com/science/articl
e/pii/S037838121200547X)
[3] Qing-Zhu, J., et al. (2006). The effect of
temperature on the solubility of benzoic acid
derivatives in water, Fluid Phase Equilibria.
Volume 250(Issues 1–2), Pages 165-172.
Retrieved form
http://www.sciencedirect.com/science/article
/pii/S0378381206004420
[4] Rodriguez, E. (1997). Basic Principles of
Organic Chemistry (p. 217, 386). Quezon
city: Open University.
[5] Rogers, E., et al. (2000). Solubility.
Retrieved from
http://www.chem.wisc.edu/deptfiles/genche
m/sstutorial/Text11/Tx112/tx112.html