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Acetone ( 2-propanone or dimethyl ketone) is an with the . It is the simplest and smallest (). It is a colorless, highly volatile, and liquid with a characteristic pungent odor.

Acetone is with water and serves as an important 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 , 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 . 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. It is normally present in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. that increase (acetone, β-hydroxybutyric acid and ) in the blood are used to counter in children who suffer from refractory epilepsy.


Name
From the 17th century, and before modern developments in organic chemistry nomenclature, acetone was given many different names. They included "spirit of Saturn", which was given when it was thought to be a compound of and, later, "pyro-acetic spirit" and "pyro-acetic ester".Mel Gorman, History of acetone (1600-1850), 1962

Prior to the name "acetone" being coined by the chemist , it was named "mesit" (from the Greek μεσίτης, meaning mediator) by , who also claimed that consisted of mesit and .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 and which were first synthesised from acetone.

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 with 2 carbons. The prefix refers to acetone's relation to ( acetum in , also the source of the words "acid" and "acetic"), rather than its chemical structure.


History
Acetone was first produced by in 1606 by distillation of lead(II) acetate.

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 and decided to name acetone by adding the suffix -one to the stem of the corresponding acid (viz, ) just as a similarly prepared product of what was then confused with 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 ;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, developed the process for industrial production of acetone (Weizmann Process). Chaim Weizmann chemistryexplained.com


Production
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 and . The largest producer of acetone is , owning 17% of the world's capacity, with also significant capacity (7–8%) by , and Shell in 2010. INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in (Belgium). 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


Current method
Acetone is produced directly or indirectly from . Approximately 83% of acetone is produced via the ; as a result, acetone production is tied to phenol production. In the cumene process, is with propylene to produce , which is by air to produce and acetone:
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.


Older methods
Previously, acetone was produced by the of , for example in ketonic decarboxylation.
Ca(CH3COO)2 -> CaO_{(s)}{} + CO2_{(g)}{} + (CH3)2CO v
After that time, during World War I, acetone was produced using acetone-butanol-ethanol fermentation with Clostridium acetobutylicum , which was developed by (later the first president of ) in order to help the British war effort, in the preparation of .
(2024). 9783527302895, Wiley-VCH.
This acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found.


Chemical properties
The flame temperature of pure acetone is 1980 °C.Haynes, p. 15.49

Like most ketones, acetone exhibits the keto–enol tautomerism in which the nominal structure of acetone itself is in equilibrium with the 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 . This product can further combine with another acetone molecule, with loss of another molecule of water, yielding and other compounds.

(2024). 9780824727291, Taylor & Francis.

Acetone is a weak Lewis base that forms adducts with soft acids like and hard acids like . Acetone also forms complexes with divalent metals.


Polymerisation
One might expect acetone to also form and (possibly ) of two types. In one type, units could be acetone molecules linked by bridges derived from opening of the double bond, to give a -like (PKA) chain . The other type could be obtained through repeated aldol condensation, with one molecule of water removed at each step, yielding a poly(methylacetylene) (PMA) chain .

The conversion of acetone to a polyketal (PKA) would be analogous to the formation of from , and of from . In 1960, Soviet chemists observed that the thermodynamics of this process is unfavourable for liquid acetone, so that it (unlike thioacetone and formol) is not expected to polymerise spontaneously, even with catalysts. However, they observed that the thermodynamics became favourable for crystalline solid acetone at the melting point (−96 °C). They claimed to have obtained such a polymer (a white elastic solid, soluble in acetone, stable for several hours at room temperature) by depositing vapor of acetone, with some as a catalyst, onto a very cold surface. In 1962, reported the synthesis of a similar product, from liquid acetone cooled to −70 to −78 °C, using or triethylaluminium as catalysts. He claimed that the absorption spectrum showed the presence of linkages but no groups. However, conflicting results were obtained later by other investigators.

The PMA type polymers of acetone would be equivalent to the product of polymerisation of , except for a keto end group.


Natural occurrence
Humans exhale several milligrams of acetone per day. It arises from decarboxylation of . Small amounts of acetone are produced in the body by the of . Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce , in which acetone is formed in body tissue. Certain health conditions, such as alcoholism and diabetes, can produce , uncontrollable ketosis that leads to a sharp, and potentially fatal, increase in the acidity of the blood. Since it is a byproduct of fermentation, acetone is a byproduct of the distillery industry.
(1998). 9781420048292, CRC Press.


Metabolism
Acetone can then be metabolized either by CYP2E1 via to and , and ultimately /energy, or by a different pathway via to , , (usable for energy) and .


Uses

Industrial
About a third of the world's acetone is used as a solvent, and a quarter is consumed as acetone cyanohydrin, a precursor to methyl methacrylate.


Solvent
Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning , cleaning tools used with it, and dissolving two-part and before they harden. It is used as one of the volatile components of some and . As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting or , and to remove rosin flux after soldering (to prevent adhesion of dirt and electrical leakage and perhaps corrosion or for cosmetic reasons), although it may attack some electronic components, such as polystyrene capacitors.
(2024). 9783030223656

Although itself , acetone is used extensively as a solvent for the safe transportation and storage of , which cannot be safely 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.

(1999). 9780824782108, Taylor & Francis. .
Acetone is also present as an in some pharmaceutical drugs. Inactive Ingredient Search for Approved Drug Products, FDA/Center for Drug Evaluation and Research


Chemical intermediate
Acetone is used to synthesize methyl methacrylate. It begins with the initial conversion of acetone to acetone cyanohydrin via reaction with (HCN):
(CH3)2CO + HCN -> (CH3)2C(OH)CN
In a subsequent step, the is to the unsaturated , which is :
(CH3)2C(OH)CN + CH3OH -> CH2=C(CH3)CO2CH3 + NH3
The third major use of acetone (about 20%) is synthesizing . Bisphenol A is a component of many polymers such as , , and . The synthesis involves the condensation of acetone with :
(CH3)2CO + 2 C6H5OH -> (CH3)2C(C6H4OH)2 + H2O
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.
2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3
Condensation with acetylene gives 2-methylbut-3-yn-2-ol, precursor to synthetic and .
(2024). 9780471443858, Wiley-Interscience.


Laboratory

Chemistry
A variety of employ acetone as a polar, . It is critical in the . Because acetone is cheap, volatile, and dissolves or decomposes with most laboratory chemicals, an acetone rinse is the standard technique to remove solid resides from laboratory glassware before a final wash. Despite common use, acetone dries only via bulk displacement and dilution. It forms no with water (see ). What is an Azeotrope?. Solvent—recycling.com. Retrieved on 2012-11-26.

Acetone freezes well below −78 °C. An acetone/dry ice mixture many low-temperature reactions.

(1998). 9780935702767


Physics
Under ultraviolet light, acetone fluoresces. Fluid flow experiments use its vapor as a tracer.


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

In , acetone helps find in fatty tissues (such as the ) for . The liquid dissolves the fat and hardens the nodes, making them easier to find.

Acetone also removes certain from .


Medical
Dermatologists use acetone with alcohol for acne treatments to dry skin. Common agents used today for chemical peeling are , , , 30% in , and trichloroacetic acid (TCA). Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting. Acetone, , or a combination of these agents was used in this process.
(2024). 9780387884950, Springer.

Acetone has been shown to have effects in animal models of , in the absence of toxicity, when administered in millimolar concentrations. It has been hypothesized that the high-fat low-carbohydrate 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.


Domestic and other niche uses
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.
(2024). 9780240818948, Focal Press.
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.

Acetone is often used for of printing artifacts on 3D-printed models printed with ABS plastic. The technique, called acetone vapor bath smoothing, involves placing the printed part in a sealed chamber containing a small amount of acetone, and heating to around 80 degrees Celsius for ten minutes. This creates a vapor of acetone in the container. The acetone condenses evenly all over the part, causing the surface to soften and liquefy. Surface tension then smooths the semi-liquid plastic. When the part is removed from the chamber, the acetone component evaporates leaving a glassy-smooth part free of striation, patterning, and visible layer edges, common features in untreated 3D printed parts. "Quality Finish 3D Prints with Acetone" instructables.com

Acetone efficiently removes felt-tipped pen marks from glass and metals.


Safety
Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a ; in larger amounts, fuel evaporation causes incomplete combustion and a . When hotter than acetone's of , air mixtures of 2.512.8% acetone (by volume) may explode or cause a . Vapors can flow along surfaces to distant ignition sources and flash back.

Static discharge may also 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.

(2024). 9783642409547
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 and mixtures.Haynes, p. 16.3 It may also explode when mixed with in the presence of a base.Haynes, p. 16.5 When oxidized without combustion, for example with hydrogen peroxide, acetone may form , a highly unstable primary explosive. Acetone peroxide may be formed accidentally, e.g. when waste peroxide is poured into waste solvents.

(2024). 9781621980261


Toxicity
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. There is no strong evidence of chronic health effects if basic precautions are followed. Basic Information on Acetone. Ccohs.ca (1999-02-19). Retrieved on 2012-11-26. It is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled. Acetone is not currently regarded as a , a , or a concern for chronic effects.

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.

Acetone is however an irritant, causing mild skin and moderate-to-severe eye irritation. At high vapor concentrations, it may depress the central nervous system like many other solvents. 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


Environmental effects
Although acetone occurs naturally in the environment in plants, trees, volcanic gases, forest fires, and as a product of the breakdown of body fat, Acetone, Agency for Toxic Substances and Disease Registry ToxFAQs, 1995 the majority of the acetone released into the environment is of industrial origin. Acetone evaporates rapidly, even from water and soil. Once in the atmosphere, it has a 22-day half-life and is degraded by UV light via (primarily into and .) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways.


EPA classification
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. In making its decision EPA conducted an extensive review of the available toxicity data on acetone, which was continued through the 2000s. It found that the evaluable "data are inadequate for an assessment of the human carcinogenic potential of acetone". Toxicological Profile for Acetone. U.S. Environmental Protection Agency June 2022 p. 7


Extraterrestrial occurrence
On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on 67P surface, measurements by the COSAC and Ptolemy instruments revealed sixteen , four of which were seen for the first time on a comet, including , acetone, methyl isocyanate, and .


Common sources


Further reading

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