Submitted 8/2017

Oleic Acid from Napoleons Buttons

Patrick Spoor

1. Summary of Oleic Acid in Napoleons Buttons

1.1 History of Oleic Acid

The molecule is presented in its various uses (including as a food additive, for cosmetics, or for
soap), but the olive itself has roots that trace themselves much deeper.
1.1.1 The Olive
The oil that derives from the olive is considered one of the prime trading goods alongside others
such as spices, nutmeg, and pepper. This is because it is such a popular item that comes from a
very limited source, the Mediterranean, due to its specific climate. The olive tree, Olea europaea,
is likely to have derived from either Greece or Italy five to seven thousand years ago. The most
common estimate is that the cultivation of olives began in Crete around 2000 BCE where olive oil
became a massive export to nearby lands. The Romans are responsible for eventually spreading
the olive to around all the rest of Europe and making it into a super industry.
1.1.2 Uses and Importance
Olive oil was used to add flavor to food, to light lamps, to be rubbed onto the skin for bathing
(using olive oil and sand), to be massaged onto the skin for athletic rehabilitation, to make fragrant
scents, and to increase the longevity of hair. The leaves of the olive tree also happened to have
salicylic acid (now known as aspirin), making the tree of utter importance for medicinal purposes.
Additionally, the olive branch is notable today for its symbol of peace, usually as an olive branch
in the beak of a dove.
1.1.3 Soap
The origins of soap date back to Rome where women would wash clothes in the Tiber River due
to the combination of ash and animal fat that came from sacrificial fires atop Mount Sapo. Soap
grew in popularity until it was commercialized in Spain and France (eighth century CE), called
castile, using olive oil as the soaps base. However, soap became frowned upon as the bubonic
plague arrived (fourteenth century CE); people thought the disease could be spread through baths.
Despite the misconceptions, soap made from olive oil eventually was modernized by French
chemist Nicolas Leblanc in 1853, allowing for even the poor to make soap.
1.2 Chemistry of Oleic Acid
Oleic acid is an oil, and it comes from a triglyceride. A triglyceride is composed of two major
parts: the glycerol molecule and three (usually randomly distributed) chains of fatty-acid

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molecules with an acid group on one end (COOH). These chains connect to the glycerol by losing
an H2O (like how polysaccharides form). There are two main types of fatty-acids: saturated (where
every C on the chain is filled with hydrogens) and unsaturated (where there is at least one double
bond between two carbons). Within unsaturated fats are monounsaturated (where there is only one
double carbon bond) and polyunsaturated (where there are more than one double carbon bond).
Saturated fats tend to have a higher melting point than unsaturated because their straight fatty-acid
chains allow them to stick together, and it takes more energy to pull them apart. As for unsaturated,
their double bond forces them to have a cis shape, where the chain forms an angle on the same
side as the double bond.
1.2.1 Health and Shelf Life
Saturated fats are deemed unhealthy due to their links to heart disease; these fats are usually found
in animals. Oleic acid itself is an eighteen-carbon monounsaturated fatty acid and have a neutral
effect on cholesterol levels. Polyunsaturated fats do lower those levels, but they also increase the
amount of low-density lipoprotein (LDL), responsible for clogging up artery walls alongside
saturated fats. Monounsaturated fats increase the amount of high-density lipoprotein (HDL) which
unclogs those arteries. To increase shelf life, unsaturated fats are hydrogenated to remove some of
their double bonds (which increase oxidation, spoiling). This not only makes the cis bonds trans
but also begins to solidify the fatty acid.
1.2.2 Soap
Soap from oils is created by adding an alkali base to the fatty acid, splitting the molecules into a
glycerol and three soap molecule chains. Each chain has a charged end, soluble in water, and a
charged end, soluble in grease. The nonpolar ends can attach to grease while the polar ends repel
on each other negatively, causing the grease particle to be pulled along by the running water.

2. Impact of Oleic Acid

2.1 Exportation
Greece once had a massive amount of fertile land used to grow a vast variety of crops. Due to the
increase in local popularity of the olive (economically), Solon of Athens became a proprietor for
the selling of olives and made it so that olive oil was Greeces only export (sixth century BCE).
This inevitably brought a monoculture of olive trees, replacing all other crops, that decreased the
fertility of the soil over time causing a need for imports of other crops necessary for life. This led
to the dependency on other nations to provide food for Greece and eventually to their fall despite
their temporary wealth.

2.2 Soap
Soap was especially important during the eighteenth century when the Industrial Revolution was
lowering the quality of city life, and many people succumbed to dirt and disease. Nicolas Leblancs
innovation of producing soda ash from common salt allowed for the people to make their own
soap, increase their qualities of life, and decrease their infant mortality rate.

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3. Opinion on Impact of Oleic Acid Today

3.1 As an Oil
Olive oils use not only as a trading good but as a food additive touches us still today. It spurred
the Greek economy which in turn developed their government that inspired our civilizations today.
Additionally, olive oil is a healthy choice for diets today that could prove extremely useful on the
fight against heart disease (and by making food taste better at the same time). Without olive oil,
we may not have had a strong contender for our necessary healthy lifestyles, and we will learn to
incorporate the oil more and more in our daily lives as awareness increases.
3.2 As a Soap
Soap was a major pusher for human cleanliness since back in Rome. Due to the castile soap made
from olive oil, soap has been a part of our lives to push back common diseases and germs and to
increase our life expectancies as we go forward. Without soap, we may still have had life
expectancies of around forty, productivity would have decreased, and life as we know it may have
grinded to a slow halt.

4. Reflection

Surprisingly, most of the chemistry concepts throughout the entire book tend to make logical sense
and do not require more than around five or so minutes of concentrated thought. In the Oleic Acid
chapter, the difference between saturated and unsaturated fats was finally made clear in one
location, and this information is extremely valuable for getting rid of false notions that coconut
oil, an oil containing elevated levels of saturated fats, is somehow the healthy option. Additionally,
the influence of olives on history was never made so clear to me until now, and it is simply
astounding how one species of tree, one molecule can change the world in so many ways. The
writing itself is very clear, concise, and manages to capture the readers attention by focusing on
a topic just long enough to be thorough but still thought-provoking to even a casual reader. The
average length of each chapter, around twenty pages, is just enough to give a broad summary of
the history of a molecule (surprising enough that they span so many decades of history) and the
chemistry that makes these molecules run the world. Personally, chapters more focused on the
chemical aspect tend to be more engaging (such as Nitro Compounds or Wonder Drugs), but the
histories selected tie everything together in the end. I would recommend the book to anyone
seeking to understand the fundamentals of our society today at the chemical level just because of
how interesting it all really is.
References
Le Couteur, P.; Burreson, J. Oleic Acid. In Napoleons Buttons: 17 Molecules That Changed
History; Penguin Group (USA): New York, 2004, pp. 270-290.