Hayden Alford
3/5/15
CH-396X-01
Help Received: See references
Acetone
Acetone, also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane, is
the simplest the simplest representation of the group of chemical compounds known as ketones. Regardless of its
simplistic structure, acetone has had an increasing impact on civilizations worldwide since its discovery at the end
of the Middle Ages because of its wide array of application. This molecule has many interesting chemical
properties that have facilitated the growth of its popularity since its discovery nearly seven centuries ago.
Acetone belongs to the ketone group because of the carbonyl group in its structure. Its chemical formula
is C3H6O and has a molar mass of 58.08 grams per mole. Acetone is a colorless liquid with a very pungent, floral
odor. The boiling and melting points of acetone are 56°C and -95°C, respectively. The density of acetone is 0.791
g/cm3. Acetone is a polar molecule with similar dielectric constant to water, which makes it very soluble in water.
Because of acetone’s polarity, it is able to hydrogen bond with water. Other solvents acetone is miscible in are
benzene, diethyl ether, methanol, ethanol, and chloroform. Copper has an MSDS of two for health, three for fire,
and zero for reactivity. Acetone can be hazardous to one’s health if ingested as well as an irritant to the skin and
eyes. Pregnant women should avoid contact with Acetone and its fumes, to avoid the possibility of birth defects,
including brain damage. Acetone is a highly flammable molecule. The products of its combustion are carbon
monoxide and carbon dioxide. The most common form of instrumental analysis for acetone is infrared
spectroscopy. According to infrared spectroscopy, acetone displays an absorption band at approximately 1715cm1
, which is indicative the C=O group, and there is sp3 C-H stretches around 3000cm-1. Also, bending appears as a
medium-intensity peak in the range of 1300-1100cm-1 for acetone. The chemical properties previously discussed
are the reasons behind why acetone is such a useful molecule in society(1,2,3).
It is thought that acetone was first produced in the Middle Ages, but its first documented use was in 1610
by Jean Beguin. Beguin, who established a school of pharmacy in Paris in the early seventeenth century, provided
a description of the preparation of acetone in a textbook, Tyrocinium Chymicum, that was privately published in
1610. The discovery of acetone did not initially peak the interest of the scientific community because its
publication was relatively secret in nature, and those who were aware of its existence did not fully understand its
potential to be a useful tool in the advancement of society(4).
The production of acetone has both synthetic and biological origins. In the human body, acetone is one of
three ketone bodies that can be found. Under normal conditions, acetone is generated primarily in the liver as well
as to some extent the in the lungs and kidneys. Ketone bodies are excreted into the blood stream and transported
to all tissues and organs in the body. Once the ketone bodies are distributed, they can be used in various metabolic
processes as an energy source. Excess amounts of acetone are eliminated from the body either by excretion in
urine or exhaled air. Synthetically, there are a large variety of techniques that have been used to produce acetone.
One of the firsts methods used to prepare acetone was by the dry distillation of acetates. An example of this
ketonic decarboxylation of calcium acetate. The reaction process is Ca(CH3COO)2 → CaO(s) + CO2(g) +
(CH3)2CO. During World War I, Chaim Weizmann prepared acetone using acetone-butanol-ethanol fermentation
with Clostridium acetobutylicum bacteria to help the British with the war effort in the preparation of cordite, a
smokeless propellant used as a substitute for gunpowder. Eventually, Weizmann’s procedure was replaced with
newer methods that had higher yields. The most common method used today is known as the cumene process.
The cumene process is responsible for eighty-three percent of acetone production. The cumene process is C6H6 +
C3H7 + O2 →C3H6O + C6H5OH. Annually, the world produces approximately 6.7 million tons of acetone. The
United States is responsible for largest amount production with nearly 1.6 million tons per year followed by
Taiwan and China. INEOS Phenol, a privately owned chemical company, is the largest producer of acetone with
1.2 million tons of annual production. INEOS Phenol has production sites in Mobile, Alabama; Antwerp,
Belgium; Gladbeck, Germany; and Nanjing, China. Currently, the price of acetone is 47.50 cents per pound,
which equates to $950 per ton. Acetone’s high yielding production methods in conjunction with its lost cost is a
key factor in why it is such a popular chemical compound in today’s society(5,6,7).
Acetone has a wide variety of applications in the twenty-first century. Upon its discovery, Beguin
explored the medicinal applications of acetone, but at the time it was not of much use in the medical field. As of
today, the most popular use of acetone is as solvent for chemical processes in order to produce other chemical
compounds. Acetone is used in the manufacture of methyl methacrylate and bisphenol-A. Acetone is commonly
used in the skin rejuvenation process and is thought such processes were used in ancient Egypt. A product is
applied, sometimes as a skin peel, with the purpose of cleaning and removing excess fat, a process referred to as
defatting. Even though most uses of acetone are considered chemical or industrial, there are a small percentage of
applications in the workplace and home. Acetone is often used in laboratories to clean glass containers and
utensils. Acetone is consistently the primary component in cleaning agents such as nail polish remover.
Electricians are known to use acetone as a degreaser. Acetone is a component of superglue remover and it easily
removes residues from glass and porcelain. Another use of acetone is as a denaturation agent in denatured alcohol.
Additionally, hazardous spills of oil, gas or paint can be dissolved with a solvent such as acetone as a means to
help eliminate any threat to people or the environment(8).
The strategic importance of acetone lies with its impact on industrial chemistry. The vast majority of all
acetone produced is consumed by the industrial chemistry sector. Its ability to be used as a solvent for numerous
reactions is what makes such a strategically important compound to the scientific community. The low cost of
acetone is beneficial to chemical companies because it allows for reaction costs to be minimized. With lower
reaction costs, the products of these chemical companies can be manufactured cheaper. In regards to the
consumers, this is good because lower production costs results in lower prices in stores making various
chemically produced products available to a larger demographic.
To surmise, acetone is a simplistic molecule in regards to its structure, but its unique chemical properties
are what have made it a staple in a wide variety of sectors across the globe. Since the time of its discovery,
acetone has evolved in the ways it has been used to serve many purposes. Although the primary use of acetone in
today’s society is for solvent purposes, there are still many applications of acetone outside of the laboratory that
contribute in the continuation of its popularity. Acetone has had an immeasurable effect on the development and
advancement of civilizations stretching from North America to Europe to Asia, and it still continues to facilitate
the growth within the chemistry community each and every day.
References:
1. http://pubchem.ncbi.nlm.nih.gov/compound/acetone accessed 4 March, 2015.
2. http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ref/ch13ir.html accessed 4
March, 2015.
3. http://www.sciencelab.com/msds.php?msdsId=9927062 accessed 4 March, 2015.
4. http://www.jstor.org/stable/27757220?seq=1#page_scan_tab_contents accessed 4 March, 2015.
5. http://www.essentialchemicalindustry.org/chemicals/phenol.html accessed 4 March, 2015.
6. http://www.ineos.com/businesses/ineos-phenol/ accessed 4 March, 2015.
7. http://www.iaquk.org.uk/ResourcesAcetone.html accessed 4 March, 2015.
8. http://www.wisegeek.com/what-are-the-different-uses-of-acetone.htm accessed 4 March, 2015.