1.

Abstract
This experiment is conducted to prepare soap and compare its properties to that of a synthetic detergent. There are three procedures involved in this experiment which is the first procedure is to prepare the soap. Then followed by the second procedure, to compare the soap and the synthetic detergent properties by observing the precipitation and emulsification formed. Finally, the third procedure is to test the cleaning ability of the soap and synthetic detergent by washing the dirty cloth strip that that containing tomato sauce. In the second procedure (section 6.2), both of the cleaning agent was tested using the solution that contain 1% CaCl2, 1% MgCl2, and 1% FeCl2 to represent as the hard water which contain Ca2+, Mg2+ and Fe 3+ ions. In this process, we can see the precipitation and emulsification formed. We can see that the syndets can be used in the hard water compare to the stock soap that weve made in the first procedure (section 6.1). For the third procedure (section 6.3), our soap has higher clean ability since there are no tomato sauce left at the cloth strip after the washing process. But, maybe there are scientific reason can be explained in this process because the syndets usually has higher cleaning ability than the stock soap. This will be explained in the discussion section.

2. Introduction
Soap is a generic term for the sodium or potassium salts of long-chain organic acids (fatty acids) made from naturally occurring esters in animal fats and vegetable oils. All organic acids contain the RCO2H functional group, where R is shorthand notation for methyl, CH3-, ethyl CH3CH2-, propyl, CH3CH2CH2-, or more complex hydrocarbon chains called alkyl groups. Chemists use the R shorthand notation because these groups can be very large and the hydrocarbon chain has little effect on the compound's chemical reactivity. All esters contain the RCO2R functional group. The R groups in soaps are hydrocarbon chains that generally contain 12 to 18 carbon atoms. Sodium fatty acids such as lauric (vegetable oil), palmitic (palm oil), and stearic (animal fat) acids are just a few examples of soaps. CH3(CH2)10COONa CH3(CH2)16COONa sodium laurate sodium stearate

The hydrocarbon chain in soaps may contain saturated (no double bonds) or unsaturated (contains double bonds) chains. Sodium salts are usually solid therefore; most bars of soap are of sodium salts. Potassium salts are the basis of liquid soaps, shaving creams, and greases. Fats and vegetable oils are triglycerides. Triglycerides are esters derived from three fatty acids. A triglyceride made from three lauric acid molecules is shown in Figure 7-1.

Saponification is the basic hydrolysis of an ester producing a carboxylic acid salt and an alcohol (Eq.7-1). A lone pair of electrons on the OH- is attracted to the partially positively charged C atom in the C=O bond in the ester (Eq.3-1). The C-OR' bond breaks generating a carboxylic acid (RCO2H) and an alcohol (R'OH). In the presence of NaOH carboxylic acids are converted to their sodium salts (RCO2-Na+). When a triglyceride is saponified, three fatty acid salts (soaps) and glycerol are produced as shown in Equation 7-2. The R groups in the triglyceride may or may not have the same chain length (same number of carbons). Thus, different types of soaps may be produced from the saponification of a particular triglyceride.

Figure 0-1: A Triglyceride molecule made from lauric acid and glycerol

(Equation 0-1)

(Equation 0-2)

3. Objectives of the Experiment

To prepare a soap and compare its properties to that of a synthetic detergent.

4. Theory
Soap is the salt of a weak acid. Most organic acids arc weak acids. Consequently, hydrolysis occurs to
some extent when soap dissolves in water. Soap solutions tend to be slightly alkaline (basic) due to partial hydrolysis of the acid (Eq. 3).

(Equation 0-1) The cleansing action of soaps results from two effects. Soaps are wetting agents that reduce the surface tension of water, allowing the water molecules to encounter the dirty object. They are also emulsifying agents. "Dirt" frequently consists of a grease or oil along with other organic species. In general, organic compounds are nonpolar. Water is a polar species. These two substances will not dissolve in each other because of their dissimilar characteristics (the "Like Dissolves Like" rule). Soaps cross the boundary between polar and nonpolar because they contain a polar hydrophobic (water-hating) end and a polar hydrophilic (water loving) end as shown in Figure 7-2.

Figure 0-1: a) A molecular line drawing and b) a skeletal representation of sodium stearate.

Soaps have both polar and nonpolar molecular regions, hence they are soluble in both polar and nonpolar species. The hydrophobic (nonpolar) portion of soap is soluble in non polar compounds like

grease and oils and the hydrophilic (polar) end dissolves in water. Soap molecules surround grease and oils and break them up into microscopic droplets, which can remain suspended in water. These suspended microscopic droplets are called micelles (Figure 7-3). Micelles contain very small amounts of oil or grease in their center. Thus oil or grease dissolved in water forms an emulsion; a form of suspension in water.

Figure 0-2: Formation of micelle

Water supplies in certain areas are acidic as a result of acid rain or pollution, or "hard" due to dissolved mineral content. Both acidic and "hard" water reduce the cleansing action of soap. Soap is the salt of a weak acid and in the presence of a stronger acid, the sodium salt is converted to an insoluble organic acid (Equation 7-4).

"Hard water" contains dissolved Ca , Mg and Fe

2+

2+

3+

(Equation 0-2) ions from the minerals that the water passes over.

Normally, soaps made from sodium and potassium fatty acid salts are soluble in water. However, in the presence of these metal ions, the Na+ and K+ convert to insoluble Ca2+, Mg2+ and Fe 3+ salts (Equation 75).

(Equation 0-3)

In either acidic or "hard" water, the soluble soaps form insoluble salts which leave scummy rings on bathtubs and black areas on shirt collars. The cleansing ability of soap is reduced because soap molecules are removed from solution. There are several techniques used to circumvent the problems generated by hard water. Water can be "softened" via removing hard water ions from solution using ion exchange techniques or by adding water-softening agents, such as sodium phosphate (Na3PO4) or sodium carbonate (Na2CO3). Water-softening agents react with the Ca2+, Mg2+ and Fe 3+ removing them from water (Equations 7-6 and 7-7) and preventing the reaction of these ions with soap (Equations 7-4 and 7-5).

(Equation 0-4)

(Equation 0-5)

Thus Syndets were developed to overcome the soap hard water problem. Syndets differ from soaps in that the nonpolar fatty acids groups are replaced with alkyl or aryl sulfonic acids (ROSO3H). The alkyl or aryl sulfonic acids have long hydrophobic carbon chains and a hydrophilic sulfonate end. The difference in polar groups is one of the key distinctions between a soap and a synthetic detergent. Syndets form micelles and cleanse in the same manner as soaps. Two examples of synthetic detergents are shown in Figure 7-4.

Figure 0-3: Examples of synthetics detergents

Sulfonic acids are stronger than carboxylic acids, hence Syndets do not precipitate in acidic solutions. Furthermore, alkyl and aryl sulfonates do not form insoluble salts in the presence of typical hard water ions. Thus, synthetic detergents remain soluble in both acidic and "hard" water.

5. Apparatus and Materials

Reagent Vegetable oil Ethanol Sodium Hydroxide Saturated Sodium Chloride (NaCl) Synthetic detergent Mineral oil 1% CaCl2 1% MgCl2 1% FeCl2 Tomato Sauce Distilled water Apparatus Stirrer Magnetic flea 250-mL Erlenmeyer flask Vacuum Filtration Apparatus Beaker Test tube Cloth strip

6. Methodology
6.1 Soap preparation
1. 25 mL of vegetable oil was placed in a 250-mL Erlenmeyer flask. 20 mL of ethanol and 25 mL of 6M sodium hydroxide solution were added into the flask. The mixture was stirred using the stirring bar to mix the contents of the flask. 2. The 250-mL flask was heated in a 600 mL boiling-water bath. 3. The mixture was stirred continuously during the heating process to prevent the mixture from foaming. If the mixture should foam to the point of nearly overflowing, remove the flask from the boiling-water bath until the foaming subsides, then continue heating. The mixture was heated for about 20-30 minutes until the alcohol odor is no longer detectable. 4. The paste-like mixture was removed from the water bath and then the flask was cooled in an ice bath for about 10-15 minutes.

5. The vacuum filtration apparatus was assembled during the cooling process, shown in Figure 7-5. The vacuum flask was secured to a ring stand with a utility clamp to pre-vent the apparatus from toppling over.

Figure 0-1: Vacuum Filtration apparatus 6. The mass of a piece of filter paper to the nearest 0.001g was recorded. The filter paper was placed inside the Buchner funnel. The paper was washed with water to fits the flush in the bottom of the funnel. 7. Once the flask has cooled, 150 mL of saturated sodium chloride (NaCl) solution was added to the flask to "salt out" the soap. 8. Slowly turn on the water at the aspirator. The mixture was poured from the flask into the Buchner funnel. Once all of the liquid has filtered through the funnel, the soap was washed with 10 mL of ice-cold water. Then, continue the suction filtration until a11 of the water is removed from the soap. 9. The soap was removed from the funnel and dried it by pressing it between two paper towels. The filter paper and dried soap was weighed and the mass was recorded to the nearest 0.001 g. The mass of the soap was calculated by difference and the mass was recorded.

6.2 Comparison of soap and detergent properties precipitation and emulsification

1. Stock soap solution was prepared by dissolving 2g of soap in the first procedure in 100 mL of boiling, distilled water. Stir the mixture until the soap has dissolved and allow the solution to cool. 2. Step 1 was repeated by using 2 g of synthetic detergent. When both solutions are cool, the pH of each solution was determined using the pH probe.

3. Three test tubes were labeled as test tube 1, 2, and 3 to avoid error occurs during experimental procedure. 4 drops of mineral oil was added to each test tube. About -5 mL of distilled water was added to test tube 1. For test tube 2, about-5 mL of stock soap solution was added. Finally, about -5 mL of stock synthetic detergent was added to test tube 3. 4. Each solution was mixed by shaking and leaved for three to five minutes. Note which of the solutions, if any, emulsifies the oil by forming a single layer. 5. The mixtures were poured into the Waste Container. The three test tubes was washed and stored in the drying channel. 6. Three more test tubes were labeled as test tube 1, 2, and 3. 2 mL of stock soap solution was poured in each of the three test tubes. 2 mL of 1% CaCl2, 2 mL of 1% MgCl2, and 2 mL of l% FeCl2 solutions were poured to test tube 1, 2, and 3. Each test tube was shaked to mix the solutions. The observation was recorded. 7. 4 drops of mineral oil was added to each of the test tubes in Step 6. Each test tube was shaked to mix the solutions and leaved the solutions for three to five minutes. Note which of the solutions, if any, emulsifies the oil by forming a single layer. 8. Steps 6-7 was repeated using -2 mL of stock detergent solution. The observation was recorded. 9. Note which of the solutions, if any, emulsifies the oil by forming a single layer. 10. The mixtures were poured into the Waste Container. The test tube was washed and stored in the drying channel. 11. 5 ml of stock soap solution was added in cine clean test tube and 5 mL of stock detergent solution in a second test tube. 1 M HCl one drop was added at a time to both solutions until the pH in each test tube is equal to 3. (Determined by using a pH probe). The number of drops of acid added to each mixture was counted and the data was recorded. 12. 1 drop of mineral oil was added to each test tube in Step 11. Shake each test tube to mix the solution.

6.3 Comparison of the cleaning abilities of a soap and detergent

1. Three beakers were cleaned, dried, and labeled. 20 mL of stock soap solution (from Step 1 in section 6.2) was placed in the 1st beaker. 20 mL of stock detergent solution (from Step 2 in section 6.2) was placed in the 2nd beaker. 20 mL of a commercial liquid was placed in a third beaker. 2. Three cloth test strips that have been soaked were obtained in tomato sauce and one strip was placed in each of the beakers. One cloth strip was placed in beaker 1 (from above), one cloth

strip in beaker 2, and one cloth strip in beaker 3. Repeatedly stir each solution with a stirrer bar for 5 minutes. 3. The cloth strips was removed from the soap and detergent solution and squeeze out the excess water. Each cloth strip was compared to determine their relative cleanliness. The observations were recorded.

7. Results and Calculations

7.1 Soap preparation
Mass of Filter (g) Mass of filter paper + soap + Petri dish (g) Mass of soap recovered (g) 0.3568 68.1490 22.8757

7.2 Comparison of soap and detergent properties

Brand name of synthetic detergent pH of soap solution pH of synthetics detergent solution Dynamo 11.871 8.670

System Distilled water Soap detergent

Emulsification Occurred YES NO NO

7.3 Hard and acidic

Precipitate System Soap CaCl2 MgCl 2 FeCl3 Acidic YES YES YES YES Synthetic detergent NO NO NO NO Soap NO NO NO YES Synthetic detergent NO NO NO NO Oil emulsified

7.4 Cleaning comparison of a soap and detergents

Cleaning Agents Soap Syndets Obsevation High cleaning ability Red spot observed

8. Discussion
This experiment was performed successfully and the objective was achieved. The objective of this experiment is to prepare soap and compare its properties to that of a synthetic detergent. We have conducted three of the procedure (6.1, 6.2, and 6.3) in this experiment. The first procedure was conducted on 24 March 2011. Then the experiment was completed on 31 March 2011 followed by the second and third experimental procedure. In making the soap, the experiment was conducted by combining 4 groups that are assigned by our lab instructor. The second procedure was conducted to compare the soap properties with the synthetic detergent by observing the precipitation and emulsification that occurs. For this process, we are using the soap produced in the first procedure (section 6.1). In this process, there are 4 tests for two of the cleaning agents (soap and syndets). The first three tests, it represents the water condition is in hard water which contains Ca2+, Mg2+ and Fe 3+ ions. The
experiment was conducted using 3 different test tubes. By using our soap, precipitate form in three of the test tubes. This is because the metal ions from the hard water will cause the soap to form an insoluble salt. Thats why the water does not mix with the soap forming precipitate.

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Then, mineral oil was added to all of the three mixtures. In this process, the precipitate that forms in the three of our test was dissolved for the soap test. The hydrocarbon is hydrophobic and soluble with grease or oil; micelles will still be form even though the metal ions causing the soap to be insoluble with water. For the syndets tests, there are no precipitates and oil emulsifications formed. Means, the syndet are suitable to be used in the hard water, so as the function to remove any grease or oil from cloth, since the formation micelles occur.

In the final test (fourth test), both of the cleaning agent are tested in the acidic water condition. For this test, both precipitate and oil emulsification occur in the soap tests. But for the syndets tests, there are no precipitates and oil emulsifications formed. Thus, from our result that
weve obtained, we can conclude that the syndets can also bu used in acidic solution. But in the third procedure (section 6.3), soap are more effective than the syndets. This is because the water used to wash to cloth strip is distilled water and soap is very volatile, thus, will create more shear stress causing the cloth strip to be cleaner.

9. Conclusion
From this experiment, we can conclude that: The pH value of the soap produced are higher that the synthetic detergent. Thus, this shows that the soap is more alkali. Soap and synthetic detergent are soluble in water due to the presents of Hydrophilic polar end of the atomic structure. Thats why, no emulsification occur if water is added. Soap is not suitable to be used in hard water. It is because the presents of metal ions making the soap become insoluble in water. By using soap in hard water, micelles will still occur due to the Hydrocarbon of the soap structure. Soap is not suitable to be used in acidic water. The syndets are suitable to be used in hard water and also acidic water since the syndets are remains soluble in the solution.

10. Experimental Precaution

We must wear the glove when conduct the experiment to avoid any error occurs because the tip of our fingers is acidic. Avoid the parallax reading by putting the paper to the same level of solution at the back of measuring cylinder and flask while filling the solution of mixture. Make sure the apparatus in the stable position. Before conduct the experiment, make sure all apparatus in good condition especially the pH electrode and pH meter. All steps in the procedure should follow without miss any detail in order to obtain an accurate reading.

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Make sure that pH probe was rinsed completely before used it to read the other pH of the solution. Repeat the experiment for a few times to get a better and accurate result.

11. References
Engineering Chemistry Lab (CHE 485). Chemistry The Central Science 11th edition, Pearson International Edition (2009); BROWN, LeMAY, BURSTEN, MURPHY.

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