Saponification soap making

Learning Goals:
Understand the concept of ester hydrolysis
Understand how the structure of a salt of a fatty acid helps a soap function
Illustrate how an ester carbonyl group acts as an electrophile
Introduction:
In this experiment you will make soap by hydrolyzing coconut oil. Fats and oils are composed
of a complex mixture of esters. One family of these esters is called triglycerides. Triglycerides
are composed of the esters of the three carbon triol (three hydroxyl groups) called glycerol and a
variety of long chain carboxylic acids containing between 8 and 24 carbons. These ester bonds
can be hydrolyzed under basic conditions to give salts of the carboxylic acids and glycerol.
O

R1 CO 2

R1

Na

Na

Na

HO

NaOH
R 2CO2

H2O

R 3 CO 2

R2

HO

HO
R3

Vegetable oils such as coconut oil contain mixtures of triglycerides that when hydrolyzed will
give many different fatty acids. These mixtures of fatty acids, which vary in the length of the R
group and number of double bonds, give soap its characteristics (water solubility, ability to
lather, etc.) Coconut oil contains triglycerides that when hydrolyzed give mainly lauric acid
(C12H24O2), a water soluble fatty acid that easily lathers and has little smell. Dyes, scents, and
other additives give soaps their unique color and smell.
Fatty acid soaps have two domains that are important to their function of cleaning things. The
first domain is the carboxylate, which is an ion and therefore very soluble in water (hydrophilic).
The second domain is the long chain hydrocarbon tail of the fatty acid, which is insoluble in
water (hydrophobic) but very soluble (lipophilic) in oils. As a result
Na

Na

Na
Na

of

long chain
fatty acid salts

dirt

micelle (in water)

charge and sodium ions not shown

these two

opposite domains, long chain fatty acid salts form complexes called micelles in which the
carboxylate group is on the outside (next to the water) and the hydrocarbon tails are on the inside
(next to each other).
Objects are dirty usually because dirt has become trapped in oil that is absorbed to the object.
The soap micelles dissolve this oil. The water soluble micelle-oil complexes and dirt are then
removed with water and the object is clean.
On the web:
http://www.alcasoft.com/soapfact/history.html
http://chemistry.about.com/library/weekly/aa081301a.htm
Procedure:
Obtain a hotplate from the stockroom. Attach your thermometer to a heat block and heat to 110
C. Add about 15 g of coconut oil to a 50 mL beaker and heat. Once the oil has melted, begin
stirring with a glass rod. Meanwhile, under the hood, combine 5 mL of water and 2.2 g of
sodium hydroxide in a 10mL Erlenmeyer flask (Caution: 1. sodium hydroxide is very basic: if
spilled, wash with water immediately; 2. dissolving sodium hydroxide in water is an exothermic
process (HOT) and produces aerosolized sodium hydroxide). Swirl the flask until the sodium
hydroxide has completely dissolved. Slowly add the solution of sodium hydroxide to the melted
oil. Stir this mixture on for 10 minutes while maintaining a temperature of 110 C. The mixture
should slowly turn cloudy. Turn off the heat to the hotplate and continue to stir for an additional
10 minutes. If you choose, add color or scent at this time. When the solution cools to room
temperature, place the beaker in an ice bath until the solution begins to thicken. If your solution
does not thicken, you have not completely hydrolyzed your esters (reheat for 10 minutes more).
Pour the thickened solution into the plastic cup and place it in your drawer. It may take up to
two weeks for your soap to cure (non-technical word which means to assume its final form- ie
to become rigid).
Post Lab:
Include what is required in the Lab Expectations handout
In your post lab address the following questions:
1. Draw the mechanism for saponification.
2. What is the nucleophile in this reaction?
3. Why doesnt sodium acetate act as soap?
4. Detergents contain compounds that have a sulfonate group instead of a carboxylate.
Why do detergents work better than soaps at all pH ranges?
5. Why wouldnt you want to put your banana oil (isopentyl acetate) from last weeks
lab into this reaction?