Experiment 9 Saponification

4/17/18

Purpose
The purpose of this experiment is to create a soap from a commercial oil by performing a
saponification reaction.The emulsifying properties of the soap will be tested.

Introduction
Saponification is the alkaline hydrolysis of a fat or oil which leads to the formation of soap. In
order for saponification to work, the three ester bonds in the triglyceride (oil or fat) must
be broken using heat exposure under basic conditions. A carboxylic acid and alcohol will be
formed from the bond breaking. Lastly, a carboxylic acid is deprotonated therefore, the negative
charge on the oxygen will be attracted to positively charged ions in the sodium solution, which
results in a soap.

Procedure
 1. Turn on sand bath
 2. Add 2.5mL of deionized water and 2.5mL of ethanol to 15 mL round bottom flask
 3. Add 0.7 grams of sodium hydroxide to flask
 4. Add 1 mL of grape seed oil and boiling chips, reflux for 45 minutes.
 5. Let cool
 6. Add 4.0 grams of sodium chloride to 10 mL of water and dissolve
 7. Add hot reflux mixture to sodium solution.
 8. Vacuum filtrate to collect soap
 9. Add a small pellet of soap to 1.5 mL of ethanol in a test tube then adding two drops of
phenolphthalein. Observe reaction
 10. Dissolve 0.35 g of soap in 25 mL of distilled water
 11. Add 2.5 mL of solution in 2 clean test tube and shake
 12. Add 3 drops of 5% calcium chloride to one tube. Observe
 13. Add 3 drops of 5% magnesium chloride to the other tube. Observe
 14. Add 0.3g of sodium carbonate to the soap test tube
 15. Fill tube with detergent and repeat steps 11-13.
 16. Add 2 drops of oil into 3 clean test tubes
 17. Add distilled water,soap,and detergent between the 3 tubes . Observe.
 18. Add sulfuric acid to the remaining soap solution until it turns acidic (pH 1)
 19. Repeat step 18 using detergent.Observe
Data
Residual Activity Test:
Soapy solution turned bright pink

Magnesium and Calcium Salts Test:

Detergent
CaCl2-cloudy white color with no precipitate MgCa-cloudy white color with no precipitate

Oil Test:
Tube 1(oil and distilled water)-clear with bubbles Tube 2(oil and soap)-mostly clear with a few white particles and foam Tube 3(oil and detergent)-light pink on the bottom with bubbles

Dilute Acid Test:

Conclusion
To start the experiment, 0.7 grams of sodium hydroxide was added to a deionized water and
ethanol mixture in a round bottom flask. The flask began to heat after the addition of the sodium
hydroxide. Grapeseed oil was chosen for this experiment and 1 mL of the oil was added to the
flask. The solution was refluxed for 45 minutes to allow the triglyceride ester bonds to break and
carboxylic acid and alcohol to form. Next, 4.0 grams of sodium chloride was dissolved in 10 mL
of water. The hot reflux mixture was added to the sodium solution, which is a good solution for
the negative oxygen from the carboxylic acid to find positive ions. After the solution cooled , the
liquid was clear with yellow clumps throughout. Vacuum filtration was used to collect the soap
pieces from the solution.
A series of test were performed using the fresh soap. Residual alkalinity was tested first by
dissolving a small pellet of soap in 1.5 mL of ethanol then by adding two drops of
phenolphthalein.The solution turned bright pink indicating it was basic with a lot of residual
alkalinity, which can be harmful to the skin. This is where an error occurred. The
phenolphthalein left a residue in the syringe turning everything it came in contact with pink.
Next time, the syringe would be cleaned more thoroughly in between to avoid cross
contamination. The second test focused on the effects of calcium and magnesium salts on soaps
and detergents. In a beaker, 0.35 grams of soap was dissolved in 25 mL of distilled water. Next,
2.5 mL of the solution was placed in 2 test tubes and shaken. After adding 3 drops of CaCl2 to
the first tube,all the foam disappeared and a white precipitate formed. In the second tube, 3 drops
of MgCl2 were added and the solution became milky white with a white precipitate.Once 0.3
grams of sodium carbonate was added, a white and faint pink foam solution formed.After a
minute, the solutions were pink on the top and clear on the bottom. In another 2 test tubes, a
detergent solution was added and the test were repeated.The tubes with CaCl2 and MgCl2 had
the same reaction, a cloudy white color with no precipitate. The next test performed was to show
effects of oil in different environments. To start, 2 drops of oil were placed into 3 test tubes. In
the first tube, distilled water and oil were mixed and the solution was just clear with small
bubbles. In the second tube, soap and oil were inside and the solution was mostly clear with a
few white particles and foam on the top. In the third tube , oil and detergent were inside and the
solution turned light pink on the bottom with bubbles. The last test was used to observe the effect
of dilute acid. Sulfuric acid was added to the remaining soap solution until it turned acidic (pH 1)
, which it turned after about 2 drops. When the sulfuric acid was added to the detergent, it took
about 10-12 drops to make it acidic. They required a different amount of drops because of their
 effects with hard water. When soap comes in contact with hard water it loses its negative charge,
no longer allowing to dissolve and attach itself to dirt.

References
Auburn University Department of Chemistry,Organic Chemistry 1I Laboratory
Manual,2018;Hayden -McNeil, LLC: Plymouth,MI,2018

Making Soap - Saponification (Experiment)

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Objectives

The objective of this laboratory is to make lye soap via the saponification reaction.

Soap making has remained unchanged over the centuries. The ancient Roman tradition called for
mixing rain water, potash and animal tallow (rendered form of beef or mutton fat). Making soap
was a long and arduous process. First, the fat had to be rendered (melted and filtered). Then,
potash solution was added. Since water and oil do not mix, this mixture had to be continuously
stirred and heated sufficiently to keep the fat melted. Slowly, a chemical reaction
called saponification would take place between the fat and the hydroxide which resulted in a
liquid soap. When the fat and water no longer separated, the mixture was allowed to cool. At this
point salt, such as sodium chloride, was added to separate the soap from the excess water. The
soap came to the top, was skimmed off, and placed in wooden molds to cure. It was aged many
months to allow the reaction to run to completion.

All soap is made from fats and oils, mixed with alkaline (basic) solutions. There are many kinds
of fats and oils, both animal and vegetable. Fats are usually solid at room temperature, but many
oils are liquid at room temperature. Liquid cooking oils originate from corn, peanuts, olives,
soybeans, and many other plants. For making soap, all different types of fats and oils can be used
– anything from lard to exotic tropical plant oils.

Figure 12.112.1: Saponification
Reactions: Fat + Lye → Soap + Glycerol
Procedure
Safety

Be sure to exercise caution when dispensing the 9 M NaOH. If the chemical comes into contact
with your skin, immediately rinse with water for a minimum of fifteen minutes and notify your
instructor.

Personal Protective Equipment (PPE) required: safety goggles, lab coat, closed-toe shoes

Materials and Equipment

Materials: warm olive oil (preheated by instructor), 9 M sodium hydroxide solution, food
coloring, assorted fragrances, stearic acid
Equipment: tall 250 mL beaker, PLASTIC stirring rod, glass pipets and pipet bulbs

1. Your instructor has a beaker of olive oil, preheated to 35°C, at the front bench. Pour 10
ml of the warm oil into a tall 250 mL beaker.
2. Prior to beginning the reaction, choose your fragrance. You may choose one of the
following: holiday candy, island coconut, yuzu, energy, lavender, white tea & ginger,
fresh cut grass, plumeria, lilac, oatmeal milk & honey, sandalwood, relaxing, cedarwood,
cinnamon, amyris, vanilla.
3. Add 1-2 drops of desired fragrance, using the pipet provided at front bench; do not mix
fragrances.
4. Add 3 ml of 9 M sodium hydroxide solution to the beaker. This is approximately two full
dropper squirts.
5. Use the plastic stirring rod to mix. You must stir for 20-45 minutes; you may choose to
take turns with your lab partner. The mixture will slowly become smoother and more
opaque; it should thicken to a pudding-like consistency.
6. After approval by your instructor, add 2-3 drops of desired food coloring. Stir.
7. Add a dash (approximately 1/8 teaspoon) of stearic acid. This will serve as a hardener for
the liquid soap. Stir.
8. Pour into chosen mold shape. Label with your names and lab section number.
9. After pouring into the mold, the process will continue on its own. The soap will heat up
and liquefy again, then cool off slowly, harden and dry. So, the soap must be left
undisturbed for at least 12 hours. You will pick up your finished soap in lab next week.

Report
Experimental Observations

You may make observations after the soap has dried; it will be returned in lab section or lecture.

1. Does it smell like any soap that you have used?

Now rinse your hands thoroughly just in case your soap contains any unreacted sodium
hydroxide.

Questions

1. The saponification reaction occurs between an acid and a base, shown in the figure in the
procedure. In the reaction you performed, what is the acid and what is the base?
2. The base used in the saponification reaction must always contain a hydroxide ion. What
bases are most commonly used for this reaction?
3. The products of the reaction are glycerol and a crude soap. The chemical formula of the
soap is CH3(CH2)14COO−Na+CH3(CH2)14COO−Na+. Draw the line-angle
structure.
4. One the above structure, circle the portion of the molecule that is water-soluble. Why is
this portion water-soluble?
5. On the above structure, box the portion of the molecule that is fat-soluble. Why is this
portion fat- soluble?
6. On the above structure, add interactions to water molecules: positive ion to hydrogen
dipole and negative ion to oxygen dipole.
7. During lab section, why did the saponification reaction require the long period of
stirring?
8. After lab section, why did the soap have to “cure” in the molds?
9. Do you think that the type of fat used will make a difference in the product? Why or why
not?