LAB 6 - CHE485

SOAPS AND DETERGENT

1.1 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 RC0
2
H functional group, where R is a shorthand notation for methyl, CH
3
-,
ethyl CH
3
CH
2
-, Propyl, CH
3
CH
2
CH
2
-, 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 RC0
2
R functional group.
The R groups in soaps are hydrocarbon chains that generally contain 12 to18 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 sodium laurate
CH3(CH2)16COONa sodium stearate
The hydrocarbon chain in soaps may contain saturated (no double bond) or unsaturated
chains (contains double bonds). 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 in an ester derived from three fatty
acids. A triglyceride made from three lauric acid molecules is shown in Figure 6-1.
Saponification is the basic hydrolysis of an ester producing a carboxylic acid salt and an
alcohol (Eq.3-1) .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.6-1). The C-OR' bond breaks generating a
carboxylic acid (RC0
2
H) and an alcohol (R'OH). In the presence of NaOH, carboxylic are
converted to their sodium salts (RCO
2
-
Na
+
).
When a triglyceride is saponified, three fatty acid salts (soaps) and glycerol are produced as
shown in Equation 6-2. The R groups in the triglyceride may or may not have the same
chailength (same number of carbons).Thus, different types of soaps may be produced from
the saponification of a particular triglyceride.

Figure 6-1: A Triglyceride molecule made from lauric acid and glycerol

(Equation 6-1)

(Equation 6-2)



1.2 Objectives
To prepare soap and compare its properties to that of a synthetics detergent.
1.3 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 6-3)
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 6-2.

Figure 6-2: Molecular structure, a) a line drawing, b) of sodium stearate. In a line drawing, all carbon and
hydrogen atoms are omitted at the intersection of each line as a shorthand method of drawing molecule. It
is understood that the C and H atoms are part of the molecule.
Because soaps have both polar and nonpolar region in the molecule, they are soluble in both
polar and nonpolar species. The hydrophobic (nonpolar) portion of soap is soluble in non polar
compound like grease and oils. The hydrophilic (polar) end dissolves in water. Soap
molecules surround the grease and oils and break them up into microscopic droplets can
remain suspended in the water. These suspended microscopic droplets are called micelles
(Figure 6-3). Micelles contain very small amounts of oil or grease in their center. Thus the oil
or grease has been dissolved in water forming an emulsion, one form of a suspension in
water.

Figure 6-3: Formation of micelle
Water supplies in certain areas are acidic as a result of acid rain or pollution, or "hard" due to
the dissolved mineral content. Both acidic and "hard" water reduce the cleansing action of
soap. Soap is the salt of a weak acid. In the presence of a stronger acid, the sodium salt is
converted to an insoluble organic acid (Eq. 3-4).
(Equation 6-4)
"Hard water" contains dissolved Ca
2+
, Mg
2+
, and Fe
3+
, 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
+
soluble salts convert to
insoluble Ca
2+
, Mg
2+
, and Fe
3+
salts (E q. 3-5).
(Equation 6-5)
In either acidic or "hard" water, the soluble soaps form insoluble salts that becomes a
scummy ring 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 (Na
3
PO
4
) o rsodium carbonate (Na
2
CO
3
). Water-
softening agents react with the Ca
2+
, Mg
2+
, and Fe
3+
, removing them from water (Eq. 6-6
and 6-7) and preventing the reaction of these ions with soap (Eq. 6-4 and 6-5).
(Equation 6-6)
(Equation 6-7)
Thus Syndets was design to overcome the soap problem with hard water. Syndets differ
from soaps in that the nonpolar fatty acids groups are replaced with alkyl or aryl sulfonic
acids (ROS03H). The alkyl or aryl sulfonic acids have long chains of carbon atoms giving the
hydrophobic (nonpolar) end. The salt of the sulfonic acid (sulfonate) group forms the
hydrophilic end of the molecule. 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 6-4.

Figure 0-4: Examples of synthetics detergents
Because sulfonic acid is a stronger acid than carboxylic acids, Syndets do not precipitate in
acidic solutions. Furthermore, alkyl and aryl sulfonates do not form insoluble salts in the
presence of the typical hard water ions. Thus, synthetic detergents remain soluble in both
acidic and "hard" water.
1.4 Procedure
1.4.1 Soap preparation
1. Place 25 mL of vegetable oil in a 250-mL Erlenmeyer flask. Add 20 mL of
ethanol and 25 mL of 6 M sodium hydroxide solution to the flask. Stir the mixture
with d stirring rod to mix the contents of the flask.
2. Heat the 250-mL flask in a boiling-water bath inside of a 600-mL beaker.
3. Stir the mixture 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. Heat the mixture for 20-30 minute or until the alcohol odor is no
longer detectable.
4. Remove the paste-like mixture from the boiling-water bath and cool the flask in
an ice bath for 10-15 minutes.
5. While the flask is cooling assemble the vacuum filtration apparatus shown in
Figure 3-5. Secure the vacuum flask to a ring stand with a utility clamp to pre-
vent the apparatus from toppling over.

Figure 6-5: Vacuum Filtration apparatus
6. Weigh a piece of filter paper to the nearest 0.001 g and record the mass. Place
the filter paper inside the Buchner funnel. Moisten the paper with water so that it
fits flush in the bottom of the funnel.
7. Once the flask has cooled, add 150 mL of saturated sodium chloride (NaCl)
solution to the flask to "salt out" the soap.
8. Slowly turn on the water at the aspirator. Pour the mixture from the flask into
the Buchner funnel. Once all of the liquid has filtered through the funnel, wash
the soap with 10 mL of ice-cold water. Continue the suction filtration until a11 of
the water is removed from the soap.
9. Remove the soap from the funnel and press it between two paper towels to dry
it. Weigh the filter paper and dried soap, and record the mass to the nearest 0.001
and determine the mass of the soap by difference and record the mass.
1.4.2 Comparison of soap and detergent properties- precipitation and
emulsification
1. Prepare a stock soap solution by dissolving 2g of your prepared soap in 100 mL
of boiling, distilled water. Stir the mixture until the soap has dissolved and allow
the solution to cool.
2. Repeat step 1 using 2 g of synthetic detergent (e.g., Dynamo). When both
solutions are cool, determine the pH of each solution using pH paper.
3. Label three test tubes as test tube 1, 2, and 3. Add 4 drops of mineral oil to each
test tube. Add -5 mL of distilled water to test tube 1. Add -5 mL of stock soap
solution to test tube 2. Add -5 mL of stock synthetic detergent to test tube 3.
4. Mix each solution by shaking and let stand for three to five minutes. Note
which of the solutions, if any, emulsifies the oil by forming a single layer.
5. Pour the mixtures into the Waste Container. Clean and dry the three test tubes.
6. Label three test tubes as test tube 1, 2, and 3. Place 2 mL of stock soap solution
in each of the three test tubes. Add 2 mL of 1% CaCl2 solution to test tube 1. Add
2 mL of 1% MgC12 solution to test tube 2. Add 2 mL of l% FeCl2 solution to test
tube 3. Shake each test tube to mix the solutions. Record your observation.
7. Add 4 drops of mineral oil to each of the test tubes in Step 6. Shake each test
tube to mix the solutions and let the solutions stand for three five minutes. Note
which of the solutions, if any, emulsifies the oil by forming a single layer.
8. Repeat Steps 6-7 using -2 mL of stock detergent solution. Which solutions form
a precipitate?
9. Note which of the solutions, if any, emulsifies the oil by forming a single layer.
10. Pour the mixtures into the Waste Container. Clean and dry the test tube.
11. Place 5 ml, of stock soap solution in cine clean test tube and 5 rnL of stock
detergent solution in a second test tube. Add 1 M HC1 one drop at a time to both
solutions until the pH in each test tube is equal to 3. (Use pH paper to
measure).Count the number of drops of acid added to each mixture. Does a
precipitate form in either mixture?
12. Add 1 drops of mineral oil to each test tube in Step 11. Shake each test tube to
mix the solution. Is the oil emulsified in either mixture?.
1.4.3 Comparison of the cleaning abilities of a soap and detergent.
1. Clean, dry, and label three beakers. Place 20 mL of stock soap solution (from
Step 1 in section 3.4.3) in the 1
st
beaker. Place 20 mL of stock detergent solution
(from Step 2 in section 6.4.4) in the 2nd beaker. Place 20 mL of a commercial
liquid Dynamo.
2. Obtain three cloth test strips that have been soaked in tomato sauce and place
one strip in each of the beakers. Place one cloth strip in beaker 1 (from above),
one cloth strip in beaker 2, and one cloth strip in beaker 3. Repeatedly stir each
solution with a stirring rod for 5 minutes.
3. Remove the cloth strips from the soap and detergent solution and squeeze out
the excess water. Visually compare each cloth strip to determine their relative
cleanliness. Record your observations.

1.5 Result & Calculations
1.5.1 Soap preparation
Mass of Filter (g)

Mass of filter paper
+ soap (g)

Mass of soap
recovered (g)


1.5.2 Comparison of soap and detergent properties.
Brand name of
synthetics
detergent

pH of soap
solution

pH of synthetics
detergent
solution


Answer yes or no in the space provided below
System Emulsification
Occurred
Distilled water
Soap
detergent

Hardness and acidic







1.5.3 Cleansing comparison of a soap and detergents
Visually compare each cloth strip to determine their relative cleanliness. Record
your observations.
Compare the cleansing ability of the two detergents.








System Precipitate Oil emulsified
Soap x Soap x
CaCl2
MgCl 2
FeCl3
Acidic