Acetone

It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.

Acetone is miscible with water and serves as an important organic solvent in industry, home, and laboratory.

About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics.

The prefix refers to acetone's relation to vinegar (acetum in Latin, also the source of the words "acid" and "acetic"), rather than its chemical structure.

[36][37] Johann Josef Loschmidt had presented the structure of acetone in 1861,[38] but his privately published booklet received little attention.

[40] With 1.56 million tonnes per year, the United States had the highest production capacity,[41] followed by Taiwan and China.

[46] In the presence of suitable catalysts, two acetone molecules also combine to form the compound diacetone alcohol (CH3)C=O(CH2)C(OH)(CH3)2, which on dehydration gives mesityl oxide (CH3)C=O(CH)=C(CH3)2.

[51] At its melting point (−96 °C) is claimed to polymerize to give a white elastic solid, soluble in acetone, stable for several hours at room temperature.

Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ketosis, in which acetone is formed in body tissue.

Certain health conditions, such as alcoholism and diabetes, can produce ketoacidosis, uncontrollable ketosis that leads to a sharp, and potentially fatal, increase in the acidity of the blood.

It is used for thinning polyester resin, cleaning tools used with it, and dissolving two-part epoxies and superglue before they harden.

[65][needs update] A variety of organic reactions employ acetone as a polar, aprotic solvent, e.g. the Jones oxidation.

[73] The chemical modifies peptides, both at α- or ε-amino groups, and in a poorly understood but rapid modification of certain glycine residues.

[73] In pathology, acetone helps find lymph nodes in fatty tissues (such as the mesentery) for tumor staging.

Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting.

[76] Acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations.

[77] It has been hypothesized that the high-fat low-carbohydrate ketogenic diet used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain.

[80] Even pouring or spraying acetone over red-glowing coal will not ignite it, due to the high vapour concentration and the cooling effect of evaporation.

[83] Acetone occurs naturally as part of certain metabolic processes in the human body, and has been studied extensively and is believed to exhibit only slight toxicity in normal use.

[79] Acetone can be found as an ingredient in a variety of consumer products ranging from cosmetics to processed and unprocessed foods.

Acetone has been rated as a generally recognized as safe (GRAS) substance when present in drinks, baked foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L.

[88] In 1995, the United States Environmental Protection Agency (EPA) removed acetone from the list of volatile organic compounds.

The companies requesting the removal argued that it would "contribute to the achievement of several important environmental goals and would support EPA's pollution prevention efforts", and that acetone could be used as a substitute for several compounds that are listed as hazardous air pollutants (HAP) under section 112 of the Clean Air Act.

[90] In making its decision EPA conducted an extensive review of the available toxicity data on acetone, which was continued through the 2000s.

Full structural formula of acetone with dimensions
Full structural formula of acetone with dimensions
Skeletal formula of acetone
Skeletal formula of acetone
Ball-and-stick model of acetone
Ball-and-stick model of acetone
Space-filling model of acetone
Space-filling model of acetone
Sample of acetone
Sample of acetone
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code