2. Acetone

CHEMICAL NAME = 2-propanoneCAS NUMBER = 67–64–1MOLECULAR FORMULA = C3H6OMOLAR MASS = 58.1 g/molCOMPOSITION = C(62.0%) H(10.4%) O(27.6%)MELTING POINT = –94.9°CBOILING POINT = 56.3°CDENSITY = 0.79 g/cm3

Acetone is a fl ammable, colorless liquid with a pleasant odor. It is used widely as an organic

solvent and in the chemical industry. It is the simplest ketone, which also goes by the name

dimethyl ketone (DMK). Acetone was originally referred to as pyroacetic spirit because it was

obtained from the destructive distillation of acetates and acetic acid. Its formula was correctly

determined in 1832 by Justus von Liebig (1803–1873) and Jean-Baptiste André Dumas (1800–

1884). In 1839, the name acetone began to be used. Acetone was derived by adding the ending

“one” meaning “daughter of” to the root of acetum (acetic acid) to mean daughter of acetum

because it was obtained from acetic acid.

Th e traditional method of producing acetone in the 19th century and the beginning of

the 20th century was to distill acetates, particularly calcium acetate, Ca(C2H

3O

2)

2. World

War I placed an increase demand on England to produce gunpowder, explosives, and propel-

lants such as cordite. Cordite is a propellant made using nitroglycerin and nitrocellulose, and

nitrocellulose is a principal component of smokeless gunpowder. Cordite is made by dissolv-

ing nitrocellulose in acetone, mixing it with nitroglycerin, then baking off the acetone. One

of England’s suppliers of calcium acetate before the war was Germany, and the loss of this

source and lack of other sources because of German blockades meant that it was imperative

to fi nd another source of acetone. One of these was from the fermentation of sugars. One

of England’s leading scientists working on bacterial fermentation was Chaim Weizmann

(1874–1952), a Russian-born Jew who was a professor at Manchester University. Weizmann

had been working on methods to make butyl alcohol in order to produce synthetic rubber.

Weizmann discovered a process to produce butyl alcohol and acetone from the bacterium

Clostridium acetobutylicum in 1914. With England’s urgent demand for acetone, Winston

Churchill (1874–1965) enlisted Weizmann to develop the Weizmann process for acetone

production on an industrial scale. Large industrial plants were established in Canada, India,

and the United States to provide the allies with acetone for munitions. Weizmann, who is

considered the “father of industrial fermentation,” obtained signifi cant status from his war

contributions and used this to further his political mission of establishing a Jewish homeland.

Weizmann was a leader of the Zionist movement and campaigned aggressively until the nation

of Israel was established in 1948. He was the fi rst president of Israel.

Fermentation and distillation techniques for acetone production were replaced starting in

the 1950s with the cumene oxidation process (Figure 2.1). In this process, cumene is oxidized

to cumene hydroperoxide, which is then decomposed using acid to acetone and phenol. Th is

is the primary method used to produce phenol, and acetone is produced as a co-product in

the process, with a yield of about 0.6:1 of acetone to phenol.

Figure 2.1 Acetone production using cumene.

Acetone can also be produced from isopropanol using several methods, but the main method

is by catalytic dehydrogenation:

Catalytic dehydrogenation

Acetone is used in the chemical industry in numerous applications. Its annual use in the

United States approaches 2 million tons and worldwide its use is close to 5 million tons. Th e

primary use of acetone is to produce acetone cyanohydrin, which is then used in the pro-

duction of methyl methacrylate (MMA). MMA polymerizes to polymethyl methacrylate.

MMA is used in a variety of applications involving plastics and resins. It is used extensively

in the production of skylights, Plexiglas, outdoor advertising signs, building panels, and

light fi xtures. It is also incorporated into paints, lacquers, enamels, and coatings.

Another use of acetone in the chemical industry is for bisphenol A (BPA). BPA results

form the condensation reaction of acetone and phenol in the presence of an appropriate

catalyst. BPA is used in polycarbonate plastics, polyurethanes, and epoxy resins. Poly-

carbonate plastics are tough and durable and are often used as a glass substitute. Eyeglasses,

safety glasses, and varieties of bullet-proof “glass” are made of polycarbonates. Additional

Acetone | 5

6 | Th e 100 Most Important Chemical Compounds

uses include beverage and food containers, helmets (bicycle, motorcycle), compact discs,

and DVDs.

In addition to its use as a chemical feedstock and intermediate, acetone is used exten-

sively as an organic solvent in lacquers, varnishes, pharmaceuticals, and cosmetics. Nail polish

remover is one of the most common products containing acetone. Acetone is used to stabilize

acetylene for transport (see Acetylene).

Acetone and several other ketones are produced naturally in the liver as a result of fat

metabolism. Ketone blood levels are typically around 0.001%. Th e lack of carbohydrates in a

person’s diet results in greater fat metabolism, causing ketone levels in the blood to increase.

Th is condition is called ketosis. People on low-carbohydrate diets and diabetics may have

problems with ketosis because of a greater amount of fat in the diet. An indicator of ketosis is

the smell of acetone on a person’s breath.