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Acetone ( 2-propanone or dimethyl ketone) is an organic compound with the chemical formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odor. (2025). 9780313337581, Greenwood Press. ISBN 9780313337581
Acetone is miscibility with water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million 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 . Acetone, World Petrochemicals report, January 2010Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. It is a common building block in organic chemistry. It serves as a solvent in household products such as nail polish remover and paint thinner. It has volatile organic compound (VOC)-exempt status in the United States.
Acetone is produced and disposed of in the human body through normal metabolic processes. Small quantities of it are present naturally in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. Medical that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to suppress Epilepsy in children with treatment-resistant epilepsy.
Prior to the name "acetone" being coined by France chemists, it was named "mesit" (from the Greek μεσίτης, meaning mediator) by Carl Reichenbach, who also said that methyl alcohol consisted of mesit and ethyl alcohol.C. Reichenbach (1834) "Ueber Mesit (Essiggeist) und Holzgeist" (On mesit (spirit of vinegar) and wood spirits), Annalen der Pharmacie, vol. 10, no. 3, pages 298–314. Names derived from mesit include mesitylene and mesityl oxide which were first synthesised from acetone.
In 1839, the name "acetone" began to be used and the term was composed of "daughter of" and acetum (acetic acid) because it was obtained from acetic acid. Unlike many compounds with the acet- prefix which have a 2-carbon chain, acetone has a 3-carbon chain. That has caused confusion because there cannot be a ketone with 2 carbons. 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.
In 1832, French chemist Jean-Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone.Dumas, J. (1832) "Sur l'esprit pyro-acétique" (On pyro-acetic spirit), Annales de Chimie et de Physique, 2nd series, 49 : 208–210.Liebig, Justus (1832) "Sur les combinaisons produites par l'action du gas oléfiant et l'esprit acétique" (On compounds produced by the action of ethylene and acetic spirit), Annales de Chimie et de Physique, 2nd series, 49 : 146–204 ( especially 193–204). In 1833, French chemists Antoine Bussy and Michel Chevreul decided to name acetone by adding the suffix -one to the stem of the corresponding acid (viz, acetic acid) just as a similarly prepared product of what was then confused with margaric acid was named margarone.Bussy, Antoine (1833) "De quelques Produits nouveaux obtenus par l'action des Alcalis sur les Corps gras à une haute température" (On some new products obtained by the action of alkalies on fatty substances at a high temperature), Annales de Chimie et de Physique, 2nd series, 53 : 398–412; see footnote on pp. 408–409. By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl;Williamson, A. W. (1852) "On Etherification," Journal of the Chemical Society, 4 : 229–239; ( especially pp. 237–239). the following year, the French chemist Charles Frédéric Gerhardt concurred.Gerhardt, Charles (1853) "Researches sur les acids organiques anhydres" (Research on anhydrous organic acids), Annales de Chimie et de Physique, 3rd series, 37 : 285–342; see p. 339. In 1865, the German chemist August Kekulé published the modern structural formula for acetone.Kekulé, Auguste (1865) "Sur la constitution des substances aromatiques," Bulletin de la Société chimique de Paris, 1 : 98–110; ( especially p. 110).Kekulé, Auguste (1866) "Untersuchungen über aromatischen Verbindungen" (Investigations into aromatic compounds), Annalen der Chemie und Pharmacie, 137 : 129–196; ( especially pp. 143–144). Johann Josef Loschmidt had presented the structure of acetone in 1861,Loschmidt, J. (1861) Chemische Studien Vienna, Austria-Hungary: Carl Gerold's Sohn. but his privately published booklet received little attention. During World War I, Chaim Weizmann developed the process for industrial production of acetone (Weizmann Process). Chaim Weizmann chemistryexplained.com
Other processes involve the direct oxidation of propylene (Wacker-Hoechst process), or the hydration of propylene to give 2-propanol, which is oxidized (dehydrogenated) to acetone.
Previously, acetone was produced by the dry distillation of , for example calcium acetate in ketonic decarboxylation.
After that time, during World War I, acetone was produced using acetone-butanol-ethanol fermentation with Clostridium acetobutylicum bacteria, which was developed by Chaim Weizmann (later the first president of Israel) in order to help the British war effort, (2025). 9780313337581, Greenwood Press. ISBN 9780313337581 in the preparation of Cordite. (2025). 9783527302895, Wiley-VCH. ISBN 9783527302895 This acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found.
In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year. With 1.56 million tonnes per year, the United States had the highest production capacity, followed by Taiwan and PRC. The largest producer of acetone is INEOS Phenol, owning 17% of the world's capacity, with also significant capacity (7–8%) by Mitsui, Sunoco and Shell in 2010. INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in Beveren (Belgium). Spot price of acetone in summer 2011 was 1100–1250 USD/tonne in the United States. Acetone (US Gulf) Price Report – Chemical pricing information . ICIS Pricing, Retrieved on 2012-11-26
Like most ketones, acetone exhibits the keto–enol tautomerism in which the nominal ketone structure of acetone itself is in equilibrium with the enol isomer ( prop-1-en-2-ol). In acetone vapor at ambient temperature, only 2.4% of the molecules are in the enol form.
In the presence of suitable , two acetone molecules also combine to form the compound diacetone alcohol , which on dehydration gives mesityl oxide . This product can further combine with another acetone molecule, with loss of another molecule of water, yielding phorone and other compounds.
Acetone is a weak Lewis base that forms adducts with soft acids like iodine and hard acids like phenol. Acetone also forms complexes with divalent metals.
Under ultraviolet light, acetone fluoresces.
The flame temperature of pure acetone is 1980 °C.Haynes, p. 15.49
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. To do so, a vapor of acetone is co-condensed with magnesium as a catalyst onto a very cold surface.
Acetone can then be metabolized either by CYP2E1 via methylglyoxal to lactic acid and pyruvic acid, and ultimately glucose/energy, or by a different pathway via propylene glycol to pyruvate, lactic acid, acetate (usable for energy) and propionaldehyde.
In a subsequent step, the nitrile is hydrolysis to the unsaturated amide, which is :
The third major use of acetone (about 20%) is synthesizing bisphenol A. Bisphenol A is a component of many polymers such as , , and . The synthesis involves the condensation of acetone with phenol:
Many millions of kilograms of acetone are consumed in the production of the solvents methyl isobutyl alcohol and methyl isobutyl ketone. These products arise via an initial aldol condensation to give diacetone alcohol.
Condensation with acetylene gives 2-methylbut-3-yn-2-ol, precursor to synthetic and . (2025). 9780471443858, Wiley-Interscience. ISBN 9780471443858
Although itself flammable, acetone is used extensively as a solvent for the safe transportation and storage of acetylene, which cannot be safely pressurization as a pure compound. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One litre of acetone can dissolve around 250 of acetylene at a pressure of . Mine Safety and Health Administration (MSHA) – Safety Hazard Information – Special Hazards of Acetylene . Msha.gov. Retrieved on 2012-11-26. History – Acetylene dissolved in acetone . Aga.com, Retrieved on 2012-11-26
Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol. Acetone is also present as an excipient in some pharmaceutical drugs. Inactive Ingredient Search for Approved Drug Products, FDA/Center for Drug Evaluation and Research
Because acetone is cheap, volatile, and dissolves or decomposes with most laboratory chemicals, an acetone rinse is the standard technique to remove solid residues from laboratory glassware before a final wash. Despite common desiccant use, acetone dries only via bulk displacement and dilution. It forms no with water (see azeotrope tables). What is an Azeotrope?. Solvent—recycling.com. Retrieved on 2012-11-26. Acetone also removes certain staining from .
Acetone freezes well below −78 °C. An acetone/dry ice mixture cooling bath many low-temperature reactions. (1998). 9780935702767 ISBN 9780935702767
use acetone to remove skin adhesive from the netting of wigs and mustaches by immersing the item in an acetone bath, then removing the softened glue residue with a stiff brush. (2025). 9780240818948, Focal Press. ISBN 9780240818948 Acetone is a main ingredient in many nail polish removers because it breaks down nail polish. It is used for all types of nail polish removal, like gel nail polish, dip powder and acrylic nails.
In pathology, acetone helps find lymph nodes in fatty tissues (such as the mesentery) for tumor staging. The liquid dissolves the fat and hardens the nodes, making them easier to find.
Acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations. 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. Because of their higher energy requirements, children have higher acetone production than most adults – and the younger the child, the higher the expected production. This indicates that children are not uniquely susceptible to acetone exposure. External exposures are small compared to the exposures associated with the ketogenic diet.
Static discharge may ignite acetone vapors, though acetone has a very high ignition initiation energy and accidental ignition is rare. Acetone's auto-ignition temperature is the relatively high ; moreover, auto-ignition temperature depends upon experimental conditions, such as exposure time, and has been quoted as high as 535 °C. 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.
Acetone should be stored away from strong oxidizers, such as concentrated nitric acid and sulfuric acid mixtures.Haynes, p. 16.3 It may explode when mixed with chloroform in the presence of a base.Haynes, p. 16.5 When oxidized without combustion, for example with hydrogen peroxide, acetone may form acetone peroxide, a highly unstable primary explosive. Acetone peroxide may be formed accidentally, e.g. when waste peroxide is poured into waste solvents. (2025). 9781621980261 ISBN 9781621980261
Acetone can be found as an ingredient in a variety of consumer products ranging from cosmetics to processed and unprocessed foods. The United States Food and Drug Administration rates acetone as a generally recognized as safe (GRAS) substance when present in food and drink at concentrations from 5 to 8 mg/L.
Acetone is an irritant, causing mild skin and moderate-to-severe eye irritation. Like many other solvents, acetone may depress the central nervous system at high vapor concentrations. Acute toxicity for mice by ingestion (LD50) is 3 g/kg, and by inhalation (LC50) is 44 g/m3 over 4 hours. Safety (MSDS) data for propanone sciencelab.com/msds Retrieved on 2018-03-19
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