PAPER

Organic Chemistry
“Soap”

Arranged by:

ANDI RIA INDAHSARI ASIK

1913442004

CHEMISTRY EDUCATION OF ICP

DEPARTMENT OF CHEMISTRY
FACULTY MATHEMATIC AND NATURAL SCIENCE
STATE UNIVERSITY OF MAKASSAR
2020
 CHAPTER 1
INTRODUCTION

A. BACKGROUND
Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a
domestic setting, soaps are surfactants usually used for washing, bathing, and other types
of housekeeping. In industrial settings, soaps are used as thickeners, components of
some lubricants, and precursors to catalysts.When used for cleaning,
soap solubilizes particles and grime, which can then be separated from the article being
cleaned. In hand washing, as a surfactant, when lathered with a little water, soap
kills microorganisms by disorganizing their membrane lipid bilayer and denaturing their
proteins. It also emulsifies oils, enabling them to be carried away by running water.
The lipid bilayer (or phospholipid bilayer) is a thin polar membrane made of two layers
of lipid molecules. These membranes are flat sheets that form a continuous barrier around
all cells. The cell membranes of almost all organisms and many viruses are made of a lipid
bilayer, as are the nuclear membrane surrounding the cell nucleus, and membranes of
the membrane-bound organelles in the cell. The lipid bilayer is the barrier that
keeps ions, proteins and other molecules where they are needed and prevents them from
diffusing into areas where they should not be. Lipid bilayers are ideally suited to this role,
even though they are only a few nanometers in width, because they are impermeable to most
water-soluble (hydrophilic) molecules. Bilayers are particularly impermeable to ions, which
allows cells to regulate salt concentrations and pH by transporting ions across their
membranes using proteins called ion pumps.
Soap is created by mixing fats and oils with a base, as opposed to detergent which is
created by combining chemical compounds in a mixer.Humans have used soap for millennia.
Evidence exists of the production of soap-like materials in around 2800 BC in
ancient Babylon.

B. PURPOSE
1. To know the history of soap
2. To know the types of soap
3. To know soap-making
4. To know the mecanism of soap
 CHAPTER 2
INTRODUCTION

A. HISTORY
1. Ancient Middle East
The earliest recorded evidence of the production of soap-like materials dates back to
around 2800 BC in ancient Babylon. A formula for soap consisting of water, alkali,
and cassia oil was written on a Babylonian clay tablet around 2200 BC. The Ebers
papyrus (Egypt, 1550 BC) indicates the ancient Egyptians bathed regularly and combined
animal and vegetable oils with alkaline salts to create a soap-like substance. Egyptian
documents mention a similar substance was used in the preparation of wool for weaving.
In the reign of Nabonidus (556–539 BC), a recipe for soap consisted of uhulu (ashes),
cypress (oil) and sesame (seed oil) "for washing the stones for the servant girls". In ancient
Israel, the ashes from barilla plants, such as species of Salsola, saltwort (Seidlitzia rosmarinus)
and Anabasis, were used in soap production, known as potash. Soap made from potash (a
concentrate of burnt wood or vegetable ashes mixed with lard or olive oil) is alkaline. If
animal lard were used, it was heated and kept lukewarm (not boiling hot; neither cold). Lard,
collected from suet, needed to be rendered and strained before being used with ashes (with
the recommended consistency of 1 cup of lard to 3/8 cup of concentrated ash water).
Traditionally, olive oil was used instead of animal lard throughout the Levant, which was
boiled in a copper cauldron for several days. As the boiling progresses, alkali ashes and
smaller quantities of quicklime were added, and constantly stirred. In the case of lard, it
required constant stirring while kept lukewarm until it began to trace. Once it began to
thicken, the brew was poured into a mold and left to cool and harden for 2 weeks. After
hardening, it was cut into smaller cakes. Aromatic herbs were often added to the rendered
soap to impart their fragrance, such as yarrow leaves, lavender, germander, etc. The ancient
method here described is still in use in the production of Nabulsi soap.
2. Roman Empire
The word sapo, Latin for soap, likely was borrowed from an early Germanic language and
is cognate with Latin sebum, "tallow". It first appears in Pliny the Elder's account, Historia
Naturalis, which discusses the manufacture of soap from tallow and ashes, but the only use
he mentions for it is as a pomade for hair; he mentions rather disapprovingly that the men of
the Gauls and Germans were more likely to use it than their female counterparts. The Romans
avoided washing with harsh soaps before encountering the milder soaps used by the Gauls
around 58 BC. Aretaeus of Cappadocia, writing in the 2nd century AD, observes among
"Celts, which are men called Gauls, those alkaline substances that are made into balls
called soap". The Romans' preferred method of cleaning the body was to massage oil into the
skin and then scrape away both the oil and any dirt with a strigil. The Gauls used soap made
from animal fat. Zosimos of Panopolis, circa 300 AD, describes soap and
soapmaking. Galen describes soap-making using lye and prescribes washing to carry away
impurities from the body and clothes. The use of soap for personal cleanliness became
increasingly common in the 2nd century AD. According to Galen, the best soaps were
Germanic, and soaps from Gaul were second best.
3. Ancient China
A detergent similar to soap was manufactured in ancient China from the seeds of Gleditsia
sinensis. Another traditional detergent is a mixture of pig pancreas and plant ash
called zhuyizi (simplified Chinese: 猪 胰 子 ; traditional Chinese: 豬 胰 子 ; pinyin: zhūyízǐ).
True soap, made of animal fat, did not appear in China until the modern era.[23] Soap-like
detergents were not as popular as ointments and creams.
4. Islamic Middle East
Hard toilet soap with a pleasant smell was produced in the Middle East during the Islamic
Golden Age, when soap-making became an established industry. Recipes for soap-making
are described by Muhammad ibn Zakariya al-Razi (854–925), who also gave a recipe for
producing glycerine from olive oil. In the Middle East, soap was produced from the
interaction of fatty oils and fats with alkali. In Syria, soap was produced using olive oil
together with alkali and lime. Soap was exported from Syria to other parts of the Muslim
worldand to Europe. A 12th-century Islamic document describes the process of soap
production. It mentions the key ingredient, alkali, which later becomes crucial to modern
chemistry, derived from al-qaly or "ashes". By the 13th century, the manufacture of soap in
the Islamic world had become virtually industrialized, with sources in Nablus, Fes, Damascus,
and Aleppo.
5. Medieval Europe
Soapmakers in Naples were members of a guild in the late sixth century (then under the
control of the Eastern Roman Empire), and in the eighth century, soap-making was well
known in Italy and Spain. The Carolingian capitulary De Villis, dating to around 800,
representing the royal will of Charlemagne, mentions soap as being one of the products the
stewards of royal estates are to tally. The lands of Medieval Spain were a leading soapmaker
by 800, and soapmaking began in the Kingdom of England about 1200. Soapmaking is
mentioned both as "women's work" and as the produce of "good workmen" alongside other
necessities, such as the produce of carpenters, blacksmiths, and bakers. In Europe, soap in the
9th century was produced from animal fats and had an unpleasant smell. Hard toilet soap with
a pleasant smell was later imported from the Middle East.
6. 15th–18th centuries
In France, by the second half of the 15th century, the semi-industrialized professional
manufacture of soap was concentrated in a few centers of Provence Toulon, Hyères, and
Marseille which supplied the rest of France. In Marseilles, by 1525, production was
concentrated in at least two factories, and soap production at Marseille tended to eclipse the
other Provençal centers. English manufacture tended to concentrate in London.
Finer soaps were later produced in Europe from the 16th century, using vegetable oils
(such as olive oil) as opposed to animal fats. Many of these soaps are still produced, both
industrially and by small-scale artisans. Castile soap is a popular example of the vegetable-
only soaps derived from the oldest "white soap" of Italy. In 1634 Charles I granted the newly
formed Society of Soapmakers a monopoly in soap production who produced certificates
from ‘foure Countesses, and five Viscountesses, and divers other Ladies and Gentlewomen of
great credite and quality, besides common Laundresses and others’, testifying that ‘the New
White Soap washeth whiter and sweeter than the Old Soap’.
Industrially manufactured bar soaps became available in the late 18th century, as
advertising campaigns in Europe and America promoted popular awareness of the
relationship between cleanliness and health. In modern times, the use of soap has become
commonplace in industrialized nations due to a better understanding of the role of hygiene in
reducing the population size of pathogenic microorganisms.
7. 19th century
Until the Industrial Revolution, soapmaking was conducted on a small scale and the
product was rough. In 1780, James Keir established a chemical works at Tipton, for the
manufacture of alkali from the sulfates of potash and soda, to which he afterwards added a
soap manufactory. The method of extraction proceeded on a discovery of Keir's. In
1790, Nicolas Leblanc discovered how to make alkali from common salt. Andrew
Pears started making a high-quality, transparent soap in 1807 in London. His son-in-
law, Thomas J. Barratt, opened a factory in Isleworth in 1862.
During the Restoration era (February 1665 – August 1714) a soap tax was introduced in
England, which meant that until the mid-1800s, soap was a luxury, used regularly only by the
well-to-do. The soap manufacturing process was closely supervised by revenue officials who
made sure that soapmakers' equipment was kept under lock and key when not being
supervised. Moreover, soap could not be produced by small makers because of a law which
stipulated that soap boilers must manufacture a minimum quantity of one imperial ton at each
boiling, which placed the process beyond reach of the average person. The soap trade was
boosted and deregulated when the tax was repealed in 1853.
William Gossage produced low-priced, good-quality soap from the 1850s. Robert Spear
Hudson began manufacturing a soap powder in 1837, initially by grinding the soap with
a mortar and pestle. American manufacturer Benjamin T. Babbitt introduced marketing
innovations that included sale of bar soap and distribution of product samples. William
Hesketh Lever and his brother, James, bought a small soap works in Warrington in 1886 and
founded what is still one of the largest soap businesses, formerly called Lever Brothers and
now called Unilever. These soap businesses were among the first to employ large-
scale advertising campaigns.

B. TYPES OF SOAP
Since they are salts of fatty acids, soaps have the general formula (RCO2−)nMn+ (Where R
is an alkyl, M is a metal and n is the charge of the cation). The major classification of soaps is
determined by the identity of Mn+. When M is Na or K, the soaps are called toilet soaps, used
for handwashing. Many metal dications (Mg2+, Ca2+, and others) give metallic soap. When M
is Li, the result is lithium soap (e.g., lithium stearate), which is used in high performance
greases.
1. Non-toilet soaps
Soaps are key components of most lubricating greases and thickeners. Greases are usually
emulsions of calcium soap or lithium soap and mineral oil. Many other metallic soaps are
also useful, including those of aluminium, sodium, and mixtures thereof. Such soaps are also
used as thickeners to increase the viscosity of oils. In ancient times, lubricating greases were
made by the addition of lime to olive oil. Metal soaps are also included in modern artists' oil
paints formulations as a rheology modifier.
Most metal soaps are prepared by neutralization of purified fatty acids:
2 RCO2H + CaO → (RCO2)2Ca + H2O
2. Toilet soaps
In a domestic setting, "soap" usually refers to what is technically called a toilet soap, used
for household and personal cleaning. When used for cleaning, soap solubilizes particles and
grime, which can then be separated from the article being cleaned. The insoluble oil/fat
molecules become associated inside micelles, tiny spheres formed from soap molecules with
polar hydrophilic (water-attracting) groups on the outside and encasing a lipophilic (fat-
attracting) pocket, which shields the oil/fat molecules from the water making it soluble.
Anything that is soluble will be washed away with the water.

Structure of a micelle, a cell-like structure formed by the aggregation of soap subunits

(such as sodium stearate): The exterior of the micelle is hydrophilic (attracted to water) and
the interior is lipophilic (attracted to oils).
Production of toilet soaps
The production of toilet soaps usually entails saponification of triglycerides, which are
vegetable or animal oils and fats. An alkaline solution (often lye or sodium hydroxide)
induces saponification whereby the triglyceride fats first hydrolyze into salts of fatty acids.
Glycerol (glycerin) is liberated. The glycerin can remain in the soap product as a softening
agent, although it is sometimes separated.
The type of alkali metal used determines the kind of soap product. Sodium soaps,
prepared from sodium hydroxide, are firm, whereas potassium soaps, derived from potassium
hydroxide, are softer or often liquid. Historically, potassium hydroxide was extracted from
the ashes of bracken or other plants. Lithium soaps also tend to be hard. These are used
exclusively in greases.
For making toilet soaps, triglycerides (oils and fats) are derived from coconut, olive, or
palm oils, as well as tallow. Triglyceride is the chemical name for the triesters of fatty acids
and glycerin. Tallow, i.e., rendered beef fat, is the most available triglyceride from animals.
Each species offers quite different fatty acid content, resulting in soaps of distinct feel. The
seed oils give softer but milder soaps. Soap made from pure olive oil, sometimes
called Castile soap or Marseille soap, is reputed for its particular mildness. The term "Castile"
is also sometimes applied to soaps from a mixture of oils, but a high percentage of olive oil.
C. PREPARATION OF SOAP
When the chemists are formulating antibacterial soaps, they must keep all of these factors
in mind when establishing the chemical structure of benzalkonium chloride (BAC) repeatable
and dependable formula for a finished product. While the exact nature of the formula will
vary depending on the company in question, deionized (distilled) water will always be the
primary and most abundant ingredient in soap. In fact, it may comprise roughly 40-80% of
the soap’s composition.

Water is used because it is an excellent carrier molecule and solvent for the other
ingredients prescribed in the formula. More specifically, deionized water is useful, because it
lacks any ions or molecules that may bond with/disrupt the actual needed substances in the
soap. Of course, using just the hydrogen bonds in water will not remove any hydrophobic,
also known as water-hating, gunk or bacteria from your hands. You’ll need something much
more capable of emulsifying and mixing all of the nasty debris on the skin so that it can be
carried away by the water. This is accomplished by the usage of animal or vegetable oils and
an aqueous strong-base solution (such as sodium or potassium hydroxide) called lye. These
oils are primarily triglycerides, which often times are are what comes to mind when one
mentions lipids in a biological and chemical context. A triglyceride contains three fatty acids,
which are just carboxylic acid chains attached to a single glycerol molecule. A glycerol
molecule simply contains 3 Carbons, 8 Hydrogens, and 3 Oxygens. In the production of soap,
the triglyceride molecules will be added to water in order to hydrolyze the three fatty acids
off. Then the next step in the production process is to bond the lye to the three fatty acids. To
form the crude soap structure.
In large scale industrial production, this is done in stainless steel tanks that can hold as
much 3,000 Gallons of soap. At these early steps in production, highly precise changes in
temperature must occur at specific times to ensure that the reactions can occur at the desired
rate and that the solution does not become to emulsified. A basic chemical equation that
demonstrates the combination of fatty acids and a lye is,

(C18H35O2)3C3H5 + 3 NaOH → C3H5(OH)3 + 3 C18H35O2Na

With this basic mixture of water, oils, and lye combined in these massive containers, the
next step is to actually make the soap antibacterial, and to make it smell, appear, and feel like
the soap we are used to pumping into our hands several times a day. Here is a shredded
sample of sodium hydroxide lye. It is important to notice the chalky texture that contributes
to the hydrophobic properties of soap. In order to create a bacteria slaying household item,
chemists use specialized organic molecules, filled with an abundance of carbon, hydrogen,
and more specifically chlorine, which is deadly to these tiny creatures, but relatively safe for
us if used in appropriate amounts. Specifically, the favorite molecules of use are, 3,4,4'-
trichlorocarbanilide (commonly called triclocarban) and 2-hydroxy-2',4,4'-triclorodiphenyl
ether (commercially known as triclosan). These molecules are also known as aromatic
molecules. This means that they are cyclic and planar molecules with conjugated (alternating)
double bonds within the rings. This allows the carbons to be numbered in a sequence. These
numbers are then utilized to show where atoms such as chlorine protrude off of.
What makes these molecules workable within soaps is that they are soluble in basic
solutions. If we remember one of the base components of soap, lye, a strong base such as
sodium hydroxide that easily dissociates in water to form highly basic solutions, then this
works perfectly in helping dissolve these molecules. Next when taking a look at the
antibacterial soap making process, the next major step is adding the appropriate ingredients to
make the soap smell and feel pleasant. This way, there is a shredded sample of sodium
hydroxide lye. More incentive to wash one’s hands, but you should be doing that anyways!
The first challenge is the scent or the aroma of the soap. The lye and oil solutions do not
necessarily combine to form the most pleasant odor, so companies and chemists must find
certain chemicals to make the soap smell better without hindering its function. This is
accomplished by the addition of fragrance oils. Many of these oils can be synthetic, but often
come from plant and animal parts, such as the leaves of lavender flowers. The exact chemical
composition of these fragrance oils varies greatly, but they all function as oils within the
chemical mixture to help ensure the soap solution stays basic and can emulsify hydrophobic
substances on the hand.
Another key identifying aspect of soap is its ability to form bubbles. The bubbles of soap
themselves are caused by a spherical layer of soap film encapsulating the water in the
solution. The film consists of a thin sheet of water sandwiched between two layers of soap
molecules. One end of each soap molecule is hydrophilic, or attracted to water. The other end
consists of a hydrophobic hydrocarbon chain that tends to avoid water. The hydrophobic ends
of the soap molecules crowd to the surface, trying to avoid the water, and stick out away from
the layer of water molecules. As a result, water molecules separate from each other. The
increased distance between the water molecules causes a decrease in surface tension,
enabling bubbles to form. The primary agent in making soap produce more bubbles is a
carbon compound called Glycerin (C3H5(OH)3). The hydrogen bonds formed with water by
this molecule make it slightly more difficult for the water to evaporate in the bubble forming
process. So, the soap and water solution becomes frothier for longer.

D. PRINCIPLE OF SOAP WORK

What are we trying to clean with soap? Some examples include dried food burnt onto
dishes or dust/mud covered on your skin; the examples are endless, but these all have a
common factor… they are all infused with oil. This grime is hard to wash off with water,
simply because water molecules are more attracted to one another than they are to oil. Oil and
water don't mix; thus, they separate into two. We have been taught this since elementary
school, with lots of demonstrations. Oil molecules are large and awkward; they are not polar,
so water, a very polar molecule, can’t bond with it. This is why when you have dirt on your
hands, and try to use only water to wash it off, it does not work. Or, when you try to wash a
greasy pan with only water, it just runs off without removing the dirt and grime because the
oily particles can’t bond with water. Soap isn’t new by any means; thousands of years ago,
people figured out how to make a substance that overcame the deep hatred between oil and
water, thus, creating soap. Today, soap is a major business; it looks a lot nicer and smells
better, too. Nonetheless, it's the same product.
Soap works by breaking up the oil into
smaller drops, so it can mix with the water. The
principle of soap works because soap is made
up of molecules with two very different ends.
One is hydrophilic, and it is this end of the soap
molecule that loves water. This is the "salt" end
of the soap; it is ionic and soluble in water. The
hydrophobic end does not mix with water, and
is therefore repelled by it. Since soap molecules
have both properties of non-polar and polar
molecules, the soap acts as an emulsifier, or something that is capable of diffusing one liquid
into another unmixable liquid. When you mix soap and water, the soap molecules position
themselves into micelles, or tiny clusters. The hydrophilic part of the soap molecules points
out, whereas the hydrophobic parts group together on the inside. The hydrophobic parts don't
come into contact with the water at all, due to the repulsion. These collect the oil particles in
the center, as shown in the figure. The oil is trapped in the soap, and then when water is
washed over your hands, the hydrophilic parts are attracted to water taking the soap, and the
grime connected to the soap with it.

CHAPTER 3
CLOSING

A. CONCLUSION
Soap is a mixture of sodium salts of various naturally occurring fatty acids. Air bubbles
added to a molten soap will decrease the density of the soap and thus it will float on water. If
the fatty acid salt has potassium rather than sodium, a softer lather is the result. Soap is
produced by a saponification or basic hydrolysis reaction of a fat or oil. Currently, sodium
carbonate or sodium hydroxide is used to neutralize the fatty acid and convert it to the salt.
The cleansing action of soap is determined by its polar and non-polar structures in
conjunction with an application of solubility principles. The long hydrocarbon chain is of
course non-polar and hydrophobic (repelled by water). The "salt" end of the soap molecule is
ionic and hydrophilic (water soluble). When soap is added to water, the ionic-salt end of the
molecule is attracted to water and dissolved in it. The non-polar hydrocarbon end of the soap
molecule is repelled by water. A drop or two of soap in water forms a monolayer on the water
surface as shown in the graphics on the left. The soap molecules "stand up" on the surface as
the polar carboxyl salt end is attracted to the polar water. The non-polar hydrocarbon tails are
repelled by the water, which makes them appear to stand up.