Chemistry Everyday for Everyone
Secondary School Chemistry
Synthesis of Exotic Soaps in the Chemistry Laboratory
Otto Phanstiel IV,* Eric Dueno, and Queenie Xianghong Wang
Department of Chemistry, University of Central Florida, Orlando, FL 32816
History of Soap
The earliest accounts of soap production date back more
than 5000 years (1). Indeed, historical studies have revealed
that soap was utilized in both ancient Egypt and Babylonia
(1 ). Several millennia ago crude mixtures of animal fats and
alkaline plant ash were found to generate crude soaps, which
lathered and cleaned efficiently. Modern soaps most likely
evolved from further experimentation with these mixtures.
How soaps clean and the influence of cleanliness on devel-
oping society has been discussed by several authors (2– 4).
What Is Soap?
Soap-making has remained virtually unchanged for
several thousand years. The procedure involves the basic
hydrolysis (saponification) of a fat or oil. Most fats and oils
(triglycerides or triacylglycerols) are triesters comprising three
long-chain aliphatic carboxylic acids appended to a single
glycerol molecule. The process of saponification involves heat-
ing either animal fat or vegetable oil in an alkaline solution.
Lye (sodium hydroxide) is the primary source of alkali. As
shown in the following generalized reaction scheme, the al-
kaline solution hydrolyzes the triglyceride to its component
parts—salts of long-chain carboxylic acids (general structure,
RCOO᎑ Na+) and glycerol:
O
O Fats and oils are supplied by the students. The fats used
O-Na+
x O NaOH HO
x (listed in Table 1) range from an exotic Vietnamese garlic oil
O
O to the grill sludge from a local restaurant. Five grams of so-
O H 2O HO + y
O-Na+
y
O "alkali" HO O 95% ethanol mixture. CAUTION: Aqueous sodium hydroxide
z
O z
O-Na+
triglyceride or fat glycerol carboxylate salts
The carboxylic acid salts are frequently precipitated from so-
lution by a “salting out” process involving aqueous sodium chlo-
ride. The precipitated soap is then isolated by filtration. The
carboxylates tend to be structurally diverse, typically having
linear chain lengths ranging from 8 to 18 carbons. Even-
numbered carbon chains predominate (especially C14, C16,
and C18). Some of these chains contain sites of unsaturation.
The degree of unsaturation and the number of carbon atoms
present in the chain (x, y, and z in the reaction scheme) depend
on the triglyceride source.
The Problem
Many students entering chemistry labs for the first time
lack confidence in manipulating matter at a molecular level.
*Corresponding author.
612 Journal of Chemical Education • Vol. 75 No. 5 May 1998 • JChemEd.chem.wisc.edu
A key aspect of their laboratory training is to develop their
ability to observe changes with their senses. Therefore, a quali-
tative experiment was needed to start them on their journey
of discovery. The new experiment needed to test their obser-
vation skills and their understanding of at least one aspect of
chemistry.
The Plan
The synthesis of soap via the hydrolysis of animal fat is
a typical experiment encountered in a high school or college
organic chemistry laboratory and has been described in many
soap-making articles in this Journal (5–14 ). The standard
experiment hydrolyzes vegetable shortening and gives a reli-
able white soap (15). We recognized that different fats should
give different soaps. Since the physical characteristics of a soap
are derived from its fat source, a “designer” soap experiment
using a vast array of triglycerides met our earlier criteria for
experimentation. This paper describes the exotic soap experi-
ment and presents actual class feedback after its implemen-
tation. The assignment for my organic chemistry laboratory
class was to read the following experimental procedure and
to bring in their own “unique” triglyceride source, which
would be saponified into a “designer” soap.
Experimental Procedure
dium hydroxide was dissolved in 40 mL of a 50/50 water–
solution is corrosive and it is very dangerous to the eyes. Skin
burns are possible. Appropriate safety precautions must be ob-
served. Students should be supervised by the chemistry teacher
when carrying out this procedure. This alkaline solution was
combined with 10 g of the fat source in a 250-mL beaker.
The mixture was heated by partially submerging the 250-
mL beaker in a larger beaker of boiling water for 45 min.
During this heating period the mixture was stirred frequently
and 40 mL of additional water–95% ethanol solution was
added to make up for evaporation of the solution. The sa-
ponification mixture was poured directly into a cooled solu-
tion of 25 wt % aqueous sodium chloride. The mixture was
stirred vigorously and allowed to cool to room temperature.
The precipitated soap was collected by vacuum filtration and
washed with ice-cold water. The solid was allowed to air-dry
and was then inspected for color, texture, and smell. The re-
sults are listed in Table 1. Each soap generated suds when
dispersed in water.
Quantification is problematic, as diverse mixtures of tri-
glycerides are often present in natural sources of fat. It is
 Chemistry Everyday for Everyone

Table 1. Designer Soap Experimental Data

Fat Source (Color) Color of Soap Texture Smells like...

Butter (yellow) beige waxlike, hard waxy
Peanut butter (tan) cream, brown specs smooth burnt peanuts
Peanut oil (light yellow) white flaky oatmeal
Sunflower oil (yellow) vanilla white smooth, creamy bread dough
Walnut oil (brown) cream, beige smooth, creamy oily
Vietnamese garlic oil (brown) yellow thick paste strong, oily
Sesame oil (caramel) yellow large granules faint sesame
Olive oil #1 (yellow) ivory crumbly grains wax crayons
Olive oil # 2 (light yellow) white flaky paper maché
Vegetable oil (yellow) creamy white powderlike potato chips
Corn oil (light yellow) beige sandy Playdough
Local restaurant grill sludge (brown) brown chunky plastic
Bacon grease (beige) white fluffy flakes rancid, burnt butterscotch
Provolone cheese (white) white paste sweet butter
Steak drippings (white) white chunky milk

virtually impossible for students to calculate the exact moles
of starting triester and to purify each unique carboxylate salt
product. In addition, the precise fatty acid makeups of the
more exotic triglyceride sources are unknown. Therefore,
students do not quantify the yields from each fat source, but
use their powers of observation to deduce the properties of
their own unique soap.
Results and Discussion
Product evaluation via sensory inspection not only hones
observation skills but allows the student to proceed without
fear of the “dreaded” low yield or low product purity con-
straints. The outcome of each designer experiment is unique.
Since the physical characteristics of the soap product are
directly related to the fat source selected, students were in
control of their own destiny. In a sense, their fate was sealed
by their choice of fat. Because students were held account-
able for explaining their results, many important questions
were asked, such as:
1. Why does my soap not smell like what I started with?
2. Why does my soap crumble, whereas my neighbor’s
soap is hard?
3. Why is one soap yellow and another white or brown?
4. Why does my soap stink and the one at home smells
so good?
Students were directed to consult the following table
(Table 2) in explaining their results.
These questions led to class discussions of how chemi-
cal changes such as esters being converted to carboxylate salts
(soaps) often result in changes of texture, color, and odor. At
first glance, texture differences seem to be related to units of
unsaturation (compare Tables 1, 3). For example, butter has
a high percentage of saturated fats and gives a very hard waxy
soap, presumably due to the presence of large amounts of
saturated carboxylate salts. This is in contrast to the oils listed
in Table 3, which contain higher percentages of unsaturated
fats and give more flaky, easily crumbled soaps. It is possible
that the observed soap textures may also be influenced by
occluded impurities. Further studies are necessary to be con-
clusive.
Surprisingly, there was no obvious relationship between
triglyceride unsaturation and soap color in these samples
(Tables 1, 3). Sunflower oil, with nearly 90% unsaturated
fat, gave a vanilla-white soap. Butter, with only 35% unsat-
urated fat, gave a beige soap. A priori one may have expected
yellowing of the unsaturated carboxylate salts after air dry-

Table 2. Fatty Acid Composition of Selected Fats and Oils

Weight % of Total Fatty Acids
Fat or Oil Saturated Monounsaturated Polyunsaturated
< C10 C12 – C16 C18 Other C16,C18 Other C18 Other
Butter 9.2 41.0 12.5 2.5 30.1 1.2 3.4 0.1
Beef tallow 0.1 28.9 21.6 3.0 42.1 1.1 2.8 0.4
Bacon 0.1 26.4 12.3 0.9 48.2 1.6 10 0.5
Olive oil – 13.7 2.5 0.9 72.3 – 10.6 –
Corn oil – 12.2 2.2 0.1 27.6 – 57.9 –
Sunflower oil – 7.5 4.7 0.4 18.7 – 68.7 –
Peanut oil – 11 2.3 0 51.0 – 30.9 4.8
N OTE: Data are from ref 16.

JChemEd.chem.wisc.edu • Vol. 75 No. 5 May 1998 • Journal of Chemical Education 613

Chemistry Everyday for Everyone

ing. As the yellowing process may be time dependent, future Table 3. Saturated and Unsaturated Fatty Acid
studies will monitor soap color changes during further aging. Content of Fats and Oils
Odor changes were perhaps the most striking finding Saturated Unsaturated
Fat or Oil Ratio, S/U
for the students. Only one of the soaps (sesame) smelled like (%) (%)
the starting fat or oil. As shown in Table 1, student descrip- Butter 65 35 1.86
tions ranged from smells like “burnt peanuts” and “milk” to Beef tallow 54 46 1.17
“plastic” and “crayons”. While their descriptors may not be
Bacon 40 60 0.67
precise, they were certainly diverse. Olfactory comparisons
of the product and starting material revealed differences, Olive oil 17 83 0.20
which reflected the fact that odor changes are related to Corn oil 15 85 0.18
changes in chemical structure. Another possibility is that the Sunflower oil 13 87 0.15
initial odor was lost during the isolation of the soap. Olfac- Peanut oil 13 87 0.15
tory inspection of the filtrates, however, did not support this
N OTE: Data are from ref 16.
premise. It was also mentioned that many esters smell nice,
whereas acids are often more pungent and acrid. Since most
of the soaps had unappealing smells, the students concluded
3. Magner, L. N. A History of Medicine; Dekker: New York, 1992;
correctly that commercial soap vendors must add fragrances pp 260–267.
to mask the true odor of their products. This assumption was 4. Ainsworth, S. J. Chem. Eng. News 1996, 74(4), 32–54.
confirmed by reading the labels on household bars of soap. 5. Preston, W. C. J. Chem. Educ. 1925, 2, 1035, 1130.
In conclusion, this experiment was deemed the favorite 6. Lowman, O. E. J. Chem. Educ. 1932, 9, 1809.
lab of many who took the course. Moreover, the freedom to 7. Evans, D.C. J. Chem. Educ. 1937, 14, 534.
choose their own starting material introduced a well-received 8. Cook, G. A. J. Chem. Educ. 1938, 15, 161.
component of flexibility into an often rigid curriculum. In 9. Preston, W. C. J. Chem. Educ. 1940, 17, 476.
10. Snell, F. J. Chem. Educ. 1942, 19, 172–180.
addition, the lab increased student awareness of the organic 11. Nelson, A. F. J. Chem. Educ. 1948, 25, 379.
chemistry of soaps and sharpened their observation skills. 12. Bossert, R. G. J. Chem. Educ. 1950, 27, 10.
Additional experiments are needed to further define the rela- 13. Mangold, M. C. J. Chem. Educ. 1951, 28, 266.
tionship between soap texture and the unsaturation levels of 14. Hill, J. W.; Soldberg, S. J.; Hill, C. S. J. Chem. Educ. 1982, 59, 788.
their component fatty acid salts. 15. Pavia, D. L.; Lampman, G. M.; Kriz, G. S. Introduction to Organic
Laboratory Techniques; Saunders College Publishing: Orlando, FL,
Literature Cited 1988; pp 112–114.
16. Food Fats and Health; Task Force Report No. 118; Council for
1. Levey, M. J. Chem. Educ. 1954, 31, 521–524. Agricultural Science and Technology: Ames, IA, December 1991;
2. Mettler, C. C.; Mettler, F. A. History of Medicine; Blakiston: Phila- pp 6, 58.
delphia, 1947; pp 245–248, 363.

614 Journal of Chemical Education • Vol. 75 No. 5 May 1998 • JChemEd.chem.wisc.edu