Preparing Soap

PREPARING SOAP
PURPOSE: PURPOSE To prepare a soap from an oil and a fat and to understand how a soap cleans. CAUTION: Handle solid sodium hydroxide and sodium hydroxide solutions with care. Sodium hydroxide is a corrosive material BACKGROUND

M A T E R I A L S NE E D E D

Soaps are commonly prepared from lipids, which are generally animal or vegetable fats or oils. Fats and oils are esters derived from glycerol and a variety of fatty acids. Because glycerol has three hydroxy groups, fats and oils are triesters called triglycerides. In addition to the three-carbon glyceride skeleton, the other components of the triester are long-chain aliphatic carboxylic acids, commonly referred to as fatty acids. These compounds predominantly contain an even number of carbon atoms, ranging from 4 to 30. Some of the more common fatty acids are stearic, palmitic, oleic, and linoleic acids. Saturated or Unsaturated? Animal fats such as tristearin and tripalmitin are solids at room temperature. Vegetable or plant oils such as triolein are liquids at room temperature. Why is tristearin a solid but triolein a liquid? Tristearin is an ester of glycerol and stearic acid. The carbons are attached to four atoms, either carbon or hydrogen. This portion of the molecule is said to be saturated. Stearic acid, therefore, is a saturated acid. Tristearin and glycerides containing predominantly saturated fatty acids are usually solids. Triolein is an ester of glycerol and oleic acid. Oleic acid has one carbon-to-carbon double bond. Hence, oleic acid is said to be unsaturated. Triolein and

fat - 68 g olive oil - 30 g deionized water sodium hydroxide - 12.5 g perfume oil colorant PAM or some spray nonstick coating container for ice bath hot plate beakers, 2 (150 ml), 250 ml large beaker for water bath thermometer stir rods ice container for ice bath soap mold - not metal cover for soap mold balance

Preparing Soap

glycerides that contain a large percentage of unsaturated fatty acids are usually oils. An unsaturated glyceride can also be saturated by a process called catalytic hydrogenation. Hydrogen gas under pressure and at elevated temperature in the presence of a catalyst, adds to the unsaturated centers in the glyceride. The plant or vegetable oil becomes saturated and is converted into a solid fat. This process, called hardening, is used to form solid shortenings such as Crisco and food such as margarine and peanut butter. Making soap A fat or an oil can react with either sodium or potassium hydroxide and form soap. The fat, a glyceride, is saponified. The word saponify is derived from the Latin sapo (soap) and facere (to make). Saponification, a soap-making process, is one of the oldest reactions of applied chemistry and was reported by Pliny in the first century A.D. In saponification one mole of triglyceride reacts with three moles of sodium hydroxide to form one mole of glycerol and three moles of fatty acid. When the glyceryl oleopalmitostearate reacts with three moles of aqueous sodium hydroxide, one mole each of sodium palmitate, sodium stearate and sodium oleate are formed. Many soaps are made from beef fat by melting it at a low enough temperature to avoid charring. This rendering process produces tallow. By filtering the tallow through wire gauze the proteinaceous material is separated from the tallow, which is then saponified. Today companies hydrolyze the beef tallow with steam, separate the glycerol from the fatty acids, and neutralize the acids with alkali to obtain soap. The use of sodium hydroxide produces a solid soap, while the use of potassium hydroxide forms a liquid soap. Cleansing Power The cleansing power of a soap solution is associated with the ability of a small amount of soap to lower the surface tension of water. The soap solution is able to wet an object more easily, emulsify the oil or grease and disperse the suspension in the aqueous medium. Because of waters surface tension, it does not spread on a greasy surface but forms almost spherical drops. The presence of a surface-active agent such as soap lowers the surface tension of water. The water in such a solution can penetrate into the small holes and crevices on the surface of a soiled fabric.

Preparing Soap

When we add a few drops of oil to water, the oil has a lower specific gravity than water and floats on the surface. When we shake the oil and water vigorously, the oil forms very small droplets which disperse uniformly throughout the water. When we stop shaking, the oil rises to the surface, forming a separate layer again. When we add oil to water containing a small amount of soap and shake vigorously, the oil droplets disperse throughout the solution, as before. However, when we allow this mixture to stand, the oil droplets do not readily coalesce to form two layers as before. Instead, we have formed an emulsion. What does the soap do to the oil droplets? When we add a soap such as sodium stearate (C17H35COONa) to water, the solution forms stearate ions (C17H35COO-) and sodium ions. The charged end of the stearate ion (-COO-] dissolves in water, while the hydrocarbon end (C17H35-) interacts with the nonpolar oil. The hydrocarbon end of the stearate ion is attached to an oil droplet, with the ionic end projecting out from the droplet into the water. The oil droplet has been emulsified by the soap solution. If we look at the emulsified oil droplet In the solution, we essentially see only the ionic ends of the soap ions. Emulsified oil droplets have a negative charge on the surface of the cluster. These droplets tend to repel each other and are prevented from coalescing. When we remove a grease stain from a fabric with a soap solution, the grease is emulsified and removed from the fabric. At the same time, some of the dirt originally sticking to the grease and fabric is dislodged. By rinsing the fabric thoroughly, we remove the grease and dirt. The fabric becomes clean. Effect of Hard Water Unfortunately soap form insoluble salts with calcium, magnesium and iron(III) ions. These ions are present in hard soapy water, and the insoluble salts are commonly seen as bathtub rings. On the other hand synthetic detergents do not form insoluble calcium, magnesium, and iron(III) salts. These detergents have the same emulsifying properties as soaps and work very well as cleaning agents in hard water because they do not form a scum. In this experiment, you will dissolve olive oil in melted fat, to which you will add a warm solution of sodium hydroxide. When the mixture becomes viscous, you will pour it into a mold to age. The glycerol will remain in the soap imparting useful properties. During aging carbon dioxide from the air will react with the excess NaOH in the soap forming sodium carbonate.

Preparing Soap

PROCEDURE 1. Lightly coat your soap molds with PAM or some other nonstick material. Tare a 250 ml beaker. Add 30.0 g of olive oil to the beaker. Tare a 250 ml beaker. Add 68.0 g of fat to the beaker. Place about 100 ml of tap water in a 600 ml beaker to use as a water bath for melting the fat. Place the beaker with the fat in the water bath. Heat the water bath on a hot plate until all the fat has melted. Remove the beaker containing the melted fat from the water bath. While stirring, slowly add the olive oil to the melted fat. Set this mixture in an ice bath to cool to 45 C. Do not let it cool much below this temperature. Tare a clean, dry 150 ml beaker. Weigh 12.5 g of NaOH in the beaker. While stirring rapidly, add 32.0 ml of deionized water to the solid NaOH. Continue stirring until the solid dissolves completely. If you use NaOH pellets, make sure you move each pellet with the stirring rod. If a pellet sticks to the beaker, it will dissolve slowly, even with rapid stirring. CAUTION: Handle the hot beaker with care. The dissolution of NaOH is highly exothermic. 9. After all the NaOH has dissolved, place the beaker containing the solution in an ice bath and cool to 45 C. Do not let it cool much below this temperature.

2. 3. 4.

5.

6.

7.

8.

10. Make sure the oil and NaOH solutions are close to the same temperature, approximately 45 C. Slowly pour the NaOH solution into the liquid oil mixture. 11. Add 40-50 drops of soap perfume oil and one or two drops of coloring to the mixture. Stir thoroughly.

Preparing Soap

12. Continue to stir until the mixture has the consistency of thick pea soup. This may take awhile. 13. Remove the stirring rod. When the mixture drops from the rod onto the surface and traces a pattern on the surface of the mixture, pour the soap into the mold. Do not wait too long before pouring the mixture into the mold. The mixture will become too viscous to be poured. 14. Do not allow the mixture to cool too rapidly, since saponification is not yet complete. 15. Immediately cover the mold. Leave the mold covered until you are leaving the laboratory, then uncover the mold. 16. Leave the soap in the mold until the next laboratory period. Remove the soap from the mold by turning the mold upside down onto several layers of paper towels. Lean the soap against the mold so that most of the surface of the soap is exposed to the atmosphere. If the soap doesn't come out of the mold, you may need to take it home and place it in the freezer for 2 to 3 hours, then the soap should come out. 17. Let the soap age for 3 weeks. Scrape off the thin, sodium carbonate layer. Now you have soap to use. Questions 1. Write out the esterification reaction between glycerol and stearic acid to form tristearin. Write out the saponification reaction between sodium hydroxide and triolein. Why does butter have a greater possibility of becoming rancid than margarine? Draw a picture of a micelle formed by soap and a grease droplet. Describe the difference between a saturated and an unsaturated fatty acid. Which one is usually solid at room temperature.

2.

3.

4.

5.