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Acetone

physical science Maturity 9-11 Next article →

Acetone is a colorless, highly volatile organic compound. It is also known as 2-propanone or dimethyl ketone. In the world of chemistry, it is classified as the smallest and simplest ketone. A ketone is a specific type of organic molecule. Acetone is famous for its pungent, characteristic odor. It is also very flammable and evaporates quickly. Because it can dissolve many other substances, it is a vital industrial solvent.

Acetone KetoEnol
Acetone KetoEnol

Chemists produce acetone through several different industrial methods. The most common method is called the cumene process. This process accounts for about 83% of all acetone production. In this method, benzene is alkylated with propylene to create cumene. This cumene is then oxidized by air. This reaction results in two products: acetone and phenol.

Cumene-process-overview-2D-skeletal
Cumene-process-overview-2D-skeletal

Other methods include the Wacker-Hoechst process, which uses the direct oxidation of propylene. Another way is the hydration of propylene to make 2-propanol, which is then oxidized. In the past, scientists used the dry distillation of acetates. During World War I, Chaim Weizmann developed a fermentation process using Clostridium acetobutylicum bacteria. This helped the British war effort by providing materials for Cordite.

Acetone serves many different roles in modern industry. About one third of the world's acetone is used directly as a solvent. A quarter of it is used to create acetone cyanohydrin. This chemical is a precursor to methyl methacrylate, a building block for plastics. Another 20% of acetone is used to synthesize bisphenol A. This substance is a key component in polycarbonates and epoxy resins. Acetone is also used to make methyl isobutyl alcohol and methyl isobutyl ketone. Furthermore, it is used as a safe way to transport acetylene. Acetone can dissolve about 250 liters of acetylene per liter of acetone.

Cumene-process-overview-2D-skeletal
Cumene-process-overview-2D-skeletal

Understanding acetone required centuries of scientific discovery. In 1606, Andreas Libavius first produced it via distillation. For a long time, it had many different names. People called it "spirit of Saturn" or "pyro-acetic spirit." In 1834, Carl Reichenbach called it "mesit." Later, in 1832, Jean-Baptiste Dumas and Justus von Liebig determined its empirical formula. In 1833, Antoine Bussy and Michel Chevreul created the modern name. They added the suffix "-one" to the stem of acetic acid. By 1865, August Kekulé published the modern structural formula. This helped scientists finally understand how the atoms were arranged.

Acetone KetoEnol
Acetone KetoEnol

Global production of acetone is massive. In 2010, the world produced about 6.7 million tonnes. The United States led the world with 1.56 million tonnes of capacity. Taiwan and China were also major producers. One company, INEOS Phenol, owns 17% of the world's capacity. They also own the largest production site in Beveren, Belgium. This site produces 420,000 tonnes every year. In the summer of 2011, the spot price in the U.S. was between 1100 and 1250 USD per tonne.

Acetone is also a natural part of biology. The human body produces it through normal metabolic processes. Small amounts are found naturally in human blood and urine. It is created through the decarboxylation of ketone bodies. Some dietary patterns, like high-fat or low-carbohydrate diets, can increase these levels. This state is known as ketosis. In certain medical conditions like diabetes, people may experience ketoacidosis. This is a dangerous increase in blood acidity. Interestingly, doctors use medical ketogenic diets to help children with treatment-resistant epilepsy. These diets increase ketone bodies to help suppress epileptic attacks.

Finally, acetone has unique chemical behaviors. It exhibits keto-enol tautomerism. This means the keto structure and the enol isomer exist in an equilibrium. In acetone vapor, only about 2.4% of molecules are in the enol form.

Acetone KetoEnol
Acetone KetoEnol

Acetone is also a weak Lewis base. It can form complexes with divalent metals. Under ultraviolet light, acetone will fluoresce. It can even be used to dissolve superglue or thin polyester resin. Because it is so useful, it remains a fundamental building block in organic chemistry.

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File:Cumene-process-overview-2D-skeletal.png
Cumene-process-overview-2D-skeletal.png
File:Acetone KetoEnol.svg
Acetone KetoEnol.svg
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