History & Discovery

Acetone is a flammable, colorless liquid characterized by a pleasant odor, widely employed as an organic solvent within the chemical industry. Recognized as the simplest ketone, it is also referred to as dimethyl ketone (DMK). Initially named pyroacetic spirit due to its derivation from the destructive distillation of acetates and acetic acid, its chemical formula was accurately determined in 1832 by Justus von Liebig (1803–1873) and Jean-Baptiste André Dumas (1800–1884). The term "acetone" came into use in 1839, signifying the daughter of acetum, as it was obtained from acetic acid.

During the 19th and early 20th centuries, the conventional method of producing acetone involved distilling acetates, notably calcium acetate (Ca(C2H3O2)2). The onset of World War I heightened England's demand for gunpowder, explosives, and propellants like cordite, made using nitroglycerin and nitrocellulose. Facing a shortage of acetone due to German blockades, England sought alternative sources, leading to Chaim Weizmann's groundbreaking work in 1914. Weizmann, a prominent Russian-born scientist at Manchester University, developed the Weizmann process using Clostridium acetobutylicum bacteria to produce butyl alcohol and acetone.

Acknowledging England's urgent need for acetone during the war, Winston Churchill enlisted Weizmann to scale up the Weizmann process for industrial production. Large-scale plants were established in Canada, India, and the United States to supply the Allies with acetone for munitions. Weizmann, recognized as the "father of industrial fermentation," gained significant acclaim for his contributions during the war, leveraging his status to advocate for the establishment of a Jewish homeland. A leader in the Zionist movement, Weizmann played a pivotal role until the establishment of the nation of Israel in 1948, subsequently becoming its first president.

Preparation & Application

In the 1950s, the cumene oxidation process (Figure 2.1) supplanted fermentation and distillation techniques for acetone production. This method involves the oxidation of cumene to cumene hydroperoxide, subsequently decomposed with acid to yield acetone and phenol. Acetone is produced as a co-product in this primary method, with a yield ratio of approximately 0.6:1 for acetone to phenol.

Acetone can also be produced from isopropanol using several methods, but the main method is by catalytic dehydrogenation:

Acetone, a chemical extensively employed in the industry, boasts an annual consumption of nearly 2 million tons in the United States and close to 5 million tons globally. Its principal application lies in the production of acetone cyanohydrin, a precursor to methyl methacrylate (MMA). MMA is crucial for manufacturing polymethyl methacrylate, widely used in various plastic and resin applications such as skylights, Plexiglas, outdoor advertising signs, building panels, light fixtures, paints, lacquers, enamels, and coatings.

Another significant use of acetone in the chemical industry is in the production of bisphenol A (BPA) through the condensation reaction of acetone and phenol with a suitable catalyst. BPA finds application in polycarbonate plastics, polyurethanes, and epoxy resins, known for their toughness and durability. Polycarbonate plastics serve as substitutes for glass in products such as eyeglasses, safety glasses, bullet-proof "glass," beverage and food containers, helmets (bicycle, motorcycle), compact discs, and DVDs.

Beyond its role as a chemical feedstock and intermediate, acetone serves as a prevalent organic solvent in lacquers, varnishes, pharmaceuticals, and cosmetics. Notably, nail polish remover is a common consumer product containing acetone. Additionally, acetone plays a crucial role in stabilizing acetylene for transport (refer to Acetylene).

Furthermore, acetone and various ketones are naturally produced in the liver during fat metabolism. Ketone blood levels, typically at around 0.001%, may increase due to low carbohydrate intake, leading to a condition known as ketosis. Individuals on low-carbohydrate diets and those with diabetes may experience elevated ketone levels, characterized by the distinct smell of acetone on the breath.

Reference

Richard L. Myers (2009). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood Publishing Group. October 1, 2009. https://doi.org/10.1021/ed086p1182