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Investigation 1.6.

3 - Saponification

Submitted By: Shane Rollit, Nicolas Casadiego,

Joey Bucci Penney
Submitted To: Mr. Romano
Submitted On: November 26, 2015
Course Code SCH 4UP - 02

Refer to textbook Nelson: Chemistry 12U, page 67-68, Investigation 1.6.3-Making Soap.
Refer to textbook Nelson: Chemistry 12U, page 67-68, Investigation 1.6.3-Making Soap.
Stearic acid, butanoic acid, methanol, a separatory funnel, a funnel rack, hot hands, PH strips, an
evaporating dish, and all materials listed in Nelson: Chemistry 12U, page 66-67,
Investigation 1.6.2 Synthesizing Esters excluding 2 test tubes, 2 test tube holders, a wax
pencil, a petri dish, 2-propanol, 1-pentanol, and ethanoic acid were added to the experiment.
A heat resistant mat and beaker tongs were not used during the experiment.
Refer to textbook Nelson: Chemistry 12U, page 67-68, Investigation 1.6.3-Making Soap.
Stearic acid was added to the soap mixture before the salt water was added.
Hot hands were used to handle all hot apparatus instead of tongs.

Following the use addition of vinegar to the soap mixture, PH strips were used to determine if the
alkalinity of the mixture was safe.
Methyl butanoate was produced following the procedure listed on Nelson: Chemistry 12U, page
66-67, Investigation 1.6.2 Synthesizing Esters. Using a separatory funnel held in place by
a funnel rack, the ester was added to the soap following the end of the base procedure.
The final soap product was in many ways different from a commercially obtainable
soap. In terms of its texture, the soap that was produced during this reaction was much more
coarse in comparison to the smooth varieties that are sold. It also lacked the adhesion
required in order to become a single object, instead existing as grain-like clumps. While it
was able to produce a lather when exposed to water, the amount and quality of suds produced
was dismal in comparison to the vigorous lather created by commercial products. In terms of
colour, the soap produced was largely off-white, but became pink once exposed to food
colouring. However, the colour was not uniform throughout the substance, unlike the pure
colours found in commercial soaps.
Aqueous sodium hydroxide + 1,3-Di(dodecanoyl oxy)propan-2-yl dodecanoate --->
propane-1,2,3-triol + sodium dodecanoate
The reaction described in the above word equation is a saponification reaction,
producing glycerol and a soap from sodium hydroxide and a triglyceride.
Adding vinegar to the soap mixture was intended to reduce the alkalinity of the
original mixture, especially in regards to any unreacted sodium hydroxide.
The reaction that takes place here is a neutralization reaction, and occurs as follows:
HC2H3O2 (aq) + NaOH (aq) ---> H2O + CH3COO- Na+
Within the filtrate one would expect to find waste glycerol from the saponification
reaction, excess vinegar used in the neutralization reaction, additional food colouring, water,
sodium chloride, and also some sodium dodecanoate molecules that were not precipitated out
by the salt water.
Esterification reactions and saponification reactions are almost reverse reactions. The
only thing separating these two processes from having this relationship is the introduction of
a metal ion during saponification. Ignoring that, esterification reacts a carboxylic acid with an
alcohol and produces an ester and water. Saponification begins with an ester and a hydroxide
compound and produces an alcohol and a carboxylic acid salt. In essence, saponification and
esterification are simply the same reaction starting at different ends.
Soap molecules have both polar and nonpolar properties, with the carboxyl/salt end of
the molecule being polar, while the rest of the hydrocarbon chain being non-polar. The fact
that soaps can dissolve parts in both polar and non-polar substances is very useful in the
removal of oils or greases from surfaces. The soap acts as a medium between the non-polar

oil and polar water, allowing the two to influence each other through the soap. Because of
this, when soap is used on oil, one would be able to wash away the solution with water, which
would be much more difficult to do using solely water.
In historic soap production, animal fats were mixed with strong bases, most
commonly lye. While the animal fat came from animals, such as pigs. Lye was instead
produced through leaching ashes, though simply using ashes as an ingredient was common as
well. As with handling any strong alkaline substance, there existed the danger of corrosion
from bases. This danger was amplified through the use of taste testing to determine if
saponification had occurred in reactions where heat was added to speed up the reaction. Soap
and generally the importance of hygiene entered large-scale usage during the 18th century,
and with that came great increases in the health of the general population. Soap has had
tremendous effects on increasing the cleanliness of humans, and through that increased
lifespans and reduced the spread of disease within populations.
Within this experiment students produced a simple soap through saponification
reactions with a naturally occurring oil and sodium hydroxide. The aqueous soap was then
precipitated out from a water solution through the addition of salt water. The resulting soap
was then neutralized through the addition of acetic acid before being separated from the
solvent it was produced in. An ester was also created through an esterification reaction, and
was then added to the soap so as to scent it.
Through this procedure, students were able to undergo a small-scale simulation of
industrial production of a common product, and through that understand how soap, a
commonly used good, is produced.
Systematic error within this procedure stems from the use of pellets instead of
weighed masses of sodium hydroxide. In addition to that, the balance used to measure masses
of fats and sodium chloride was not as precise as it could have been. Finally, the use of
largely guesswork instead of an measurable standard to determine when the saponification
reaction had concluded leaves the possibility of unreacted fats and sodium hydroxide
remaining within the mixture.
Random error with in this procedure include contamination from left over water or
other chemicals from previous labs in the lab aparati. Also, due to the rather lengthy
procedure of this lab, chemicals were left out overnight, giving air contaminates the
possibility of entering the lab chemicals.