SYNTHESES OF SOAP AND DETERGENT

Romualdez, A., Sado, F., Sagum, I., San Juan, N., Sandoval, A., Savella, A.*

ABSTRACT Soap is the sodium or potassium of a fatty acid. A soap molecule consists of a lone hydrocarbon chain with a carboxylic acid group on one end, which is ionic-bonded to a metal ion. The hydrocarbon end is non-polar and is soluble in non-polar substances, whereas the ionic end is soluble in water. Detergents are structurally similar in soaps, but differ in water-soluble portion. The experiment aims to synthesize soap and detergent and compare their reaction in hard water. Soap and detergent were synthesized and were put on some tests like glycerol test and hard water behavior test. In the behavior in hard water, 1%CaCl2 and 1%MgCl2 were used as reagents. Soap has white gelatin appearance and is insoluble in CaCl2 and MagCl2. Detergent has white, pasty powder appearance and is soluble in CaCl2 and MgCl2. Soap reacts with calcium and magnesium ions, which are present in hard water. In the test for glycerol, only soap had a positive result, which is the odor of burned fat.

INTRODUCTION Soaps and detergents are used frequently in our daily day our life. We use them in many kind of ways such as wash hand, clean clothes, bathing and other. Soaps are carboxylate salts with very long hydrocarbon chains. Soap can be made from the base hydrolysis of a fat or an oil. This hydrolysis is called saponification, and the reaction has been known for centuries. Traditionally, soaps were made from animal fat and lye (NaOH). (Lye was traditionally made by pouring water through wood ashes.)

much more soluble in water than the corresponding uncharged fatty acids. Since the carboxylate salts also each have a long nonpolar tail, they are also compatible with nonpolar greases and oils. Soap can emulsify fats and oils by forming micelles around oil droplets. The soap molecules surround an oil droplet so that their nonpolar tails are embedded in the oil and their charged head groups are on the exterior of the droplets, facing the water. If the oil droplets are small enough and if there are enough soap molecules to surround them, the oil droplets become dispersed in the water and can then easily be washed away. Therefore, using lots of soap, hot water, and agitation can help clean greasy dishes. Hot water can melt solid fats, and agitation can help break up the fats and oils into smaller droplets. Using lots of soap makes it more likely that there will be enough soap molecules to surround and emulsify all of the fat droplets. Soaps are less effective in hard water, which is water that contains a significant 2+ 2+ concentration of Mg and Ca ions. These ions form precipitates with soap molecules, and this precipitate is often seen as a gray line on a bathtub or sink and is often called soap scum. Since soap forms a precipitate with these ions, it means that many of the soap molecules are no longer present in the solution. Therefore, soap will form fewer suds in hard water. Soft water is water that contains very few or no ions that precipitate with soap. Soap will therefore be much more effective in soft water than in hard water.

Figure 1. Example of Saponification Reaction Fats and oils are triesters of glycerol and three fatty acids. Esters can be hydrolyzed to their alcohol and carboxylic acid components in the presence of acid or base. Fats, oils, and fatty acids are insoluble in water because their hydrophobic tails are so long. If a base is used for hydrolysis, the fatty acids produced are deprotonated and are present as the corresponding carboxylate salts. Because these product carboxylate salts are charged, they are

Detergents are similar to soaps in that they have a charged head group and a long nonpolar tail group, but they are not prepared from natural fats or oils. Detergents are useful because they do not form precipitates with magnesium or calcium ions, which means that they work in both soft and hard water.

METHODOLOGY A. Preparation of Soap Prepare a mixture of 30 mL of 6M NaOH and 50 mL of water. Transfer into a 500 mL beake then heat using a small flame, stir frequently. Add in portions of 15 mL of coconut oil to the mixture. Heat for 15-20 minutes with frequent stirring and replace the water lost by evaporation. Test for complete saponification by adding a drop of the mixture to 1mL of water. If no trace of oil is observed, saponification is complete. If saponificaiton is insomplete, continue heating for another 15-20 monutes with frewuent stirring, replace the water lost by evaporation. When saponificaiton is complete, stir until the misture is homogenoeous. Pour the hot solution with vigorous stirring into 50 mL of a cold, saturated solution of NaCl. Filter the precipitated soap through cheesecloth. Remove the filtrate for the extraction and test for glycerol. Wash the collected soap twice with 5 mL portions of ice-cold water. Squeeze the cheesecloth to remove excess water from the soap. Place the pressed soap in a large evaporating dish. Add 10-20 mL water to completely dissolve the soap. Evaporate it to a jelly consistency. Cool the soap partially and pour into an appripriate molder. Use this soap to test for its behavior in hard water. B. Extraction of Glycerol Neutralize the filtrate with diluted HCl. Filter if it is not clear then evaporate the filtrate to a small volume or to a syrupy consistency. Allow it to cool. Extract the residue with 10 mL of 95% ethanol. Filter then evaporate the alcholic extract in a water bath. The residue contains the glycerol. Perform the test for glycerol. C. Test for Glycerol To the residue containing the glycerol, add a pinch of powdered potassium bisulfate. Heat the mixture strongly then observe the odor. D. Preparation of Detergent A synthetic detergent, a sodium alkyl sulfate called sofium dodecylsulfate, can be prepared by reacting dodecyl alcohol with sulfuric acid. The resulting dodecylsulfate is converted to the sodium salt by a reaction with sodium hydroxide. Place 5 mL of dodecanol into

Figure 2. Detergent Molecule After detergents started being widely used, it was discovered that they were not broken down in sewage treatment plants. Many streams and lakes became contaminated with detergents and large amounts of foam appeared in natural waters. Biodegradable detergents were then developed.

Figure 3. Sodium Laurylbenzenesulfonate (a biodegradable detergent) Many commercial detergents also contain phosphate compounds. This can be a problem, because phosphate is a nutrient for plants. Too much phosphate in a pond, lake, or stream accelerates the growth of algae, which consumes too much of the dissolved oxygen in the water. This disturbs the ecosystem in the pond, and some organisms will die. Therefore, you will see some detergents these days that are labeled phosphate free. These are better for the environment than phosphate-containing detergents.[1] The experiment aims to synthesize soap and detergent and to compare the behavior of soap and detergent in hard water. [2]

a 100-mL beaker, easure 2 mL of concentrated H2SO4 in a 10-ml graduated cylinder. With stirring, slowly add the concentrated H2SO4 to the dodecanol in the beaker. Continue stirring for 1 minute after addition of the H2SO4 is complete. Let the mixture stand for 10 minutes. Mix 5 mL of 6M NaOH with 1 mL of water in a small beaker. Mix well, then add 4 drops of phenolphthalein. The pink color of the phenolphthalein may begin to fade in the presence of the strongly basic solution. After 10 minutes carefully pour the NaOH solution into the dodecanol-sulfuric acid mixture. Stir until the pink color disappers. A large amount of solid detergent should form. Fill a 250-mL beaker one-third of ice. Add about 10 g of NaCl and mix thoroughly. Add water to bring the total colume to themixture to 75 mL. Pour the detergent mixture into the ace-salth bath. Stir the mixture well to break up large lumps of detergent. Filter the precipitated detergent mixture through 2-3 layers of cheesecloth in a funnel mounted on a ring stand. Wash the collected detergent twice with 10-mL portions of ice-cold water. Remove the cheesecloth from the funnel. Squeeze excess water from the solid detergent, and save the detergent to test for its behavior in hard water.

E. Behavior in Hard Water The sodium and potassium salth of most carboxylic acids ae water solble. However, the calcium, magnesium and iron salths are not. Thus, when soaps are places in hard water that contains such ions, an insoluble, curdy solid forms. The calcium, magnesium, and iron forms of most detergents are more soluble inw ater than the correspongding soap compounds. Consequently, detergents function almost as well in hard water as they do in soft water. Place 5 mL of the soap solution in each of two test tubes. Place 5 mL of the detergent solution in each of two test tubes. Add 2 mL of 1% CaCl2 into one soap-containing tube and another 2 mL into a detergent-containing tube. Repeat this process using 1% MgCl2. Mix the contents of eac test tube several times. Do not shake vigorously. Note whether or not a precipitate forms and how much very large, large, little or none if it does. Add 4 drops of cooking oil to each tube. Stopper and shake the mixture vigorously. Observe and record the emulsifying ability of the soap or detergent in each tube, as indicated primarily by the amount of suds formed (heavy suds, light suds, few or no suds). RESULTS AND DISCUSSIONS Observation of Properties of Soap and Detergent Table 1. Properties of samples Soap White gelatin Insoluble Insoluble Slightly emulsified (less suds) Detergent White, pasty powder Soluble Soluble MgCl2: produced more bubbles CaCl2: has bubbles Emulsified (more suds)

Color and appearance Solubility in 1% CaCl2 Solubility in 1% MgCl2 Emulsifying ability

Figure 4. Synthesis of Detergent

As shown in the table, soap has white gelatin appearance white detergent has white, pasty powder. Soap is insoluble in calcium chloride and magnesium chloride and it has slight emulsifying ability while detergent is soluble in both calcium chloride and magnesium chloride and has more emulsifying ability.

The sodium and potassium salts of most carboxylic acids are water-soluble. However, the calcium, magnesium, and iron salts are not. Thus, when soaps are placed in hard water that contains such ions, an insoluble, curdy solid forms. The calcium, magnesium, and iron forms of most detergents are more soluble in water than the corresponding soap compounds. Consequently, detergents function almost as well in hard water as they do in soft water. [3] Soaps ill react ith metal ions in the ater and can form insoluble precipitates. The precipitates can be seen in the soap ater and are referred to as soap scum . This soap scum can form deposits on clothes causing them to be gray or yellow in color. To eliminate the metal ions in water, washing aids such as washing soda (sodium carbonate) and borax (sodium tetraborate) were added to the wash water. These compounds would precipitate the metal ions, eliminating most of the soap scum. With the discovery of synthetic detergents, much of the need for washing aids was reduced. A detergent works similar to soap, but does not form precipitates with metal ions, reducing the discoloration of clothes due to the precipitated soap. Modern laundry detergents are mixtures of detergent, water softeners, optical brighteners, stain removers, and enzymes. As for the test of glycerol, burned fat odor indicates the presence of glycerol. Only soap contained the said odor because of the reagent used in the synthesis, which is a product of hydrolysis of fatty acids. REFERENCES [1] Retrieved on September 28, 2013 from http://www.laney.edu/wp/chelifossum/files/2012/01/13-Saponification.pdf [2] Bayquen, A., Cruz, C., de Guia, R., Lampa, F., Pea, G., Sarile, A., & Torres, P. (2009). Laboratory Manual in Organic Chemistry. Quezon City: C&E Publishing, Inc.. [3] Seager, S. & Slabaugh, M. (2008). SafetyScale Laboratory Experiments for Chemistry for Today, 8th ed. United States: Brooks/Cole Publishing Company