View source for Acetone

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{{Chembox new
|   Name = Acetone<ref>''Merck Index'', 11th Edition, '''58'''.</ref>
|   ImageFileL1 = Acetone-skeletal.png
| ImageSizeL1 = 100px
|   ImageNamel1 = Acetone
|   ImageFileR1 = Acetone-3D-balls.png
| ImageSizeR1 = 100px
|   ImageNameR1 = Ball-and-stick model of acetone
|   ImageFile2 = Acetone-3D-vdW.png
| ImageSize2 = 150px
|   ImageName2 = Space-filling model of acetone
|   IUPACName = Propanone
|   OtherNames = β-ketopropane<br />Dimethyl ketone,

| Section1 = {{Chembox Identifiers
|   SMILES = CC(=O)C
|   CASNo = 67-64-1
|   RTECS = AL31500000
|   InChI=1/C3H6O/c1-3(2)4/h1-2H3
  }}
| Section2 = {{Chembox Properties
|   Formula = CH<sub>3</sub>COCH<sub>3</sub>
|   MolarMass = 58.08 g/mol
|   Appearance = Colorless liquid
|   Density = 0.79 g/cm³, liquid
|   Solubility = [[miscible]]
|   MeltingPt = −94.9 °C (178.2 K)
|   BoilingPt = 56.53 °C (329.4 K)
|   Viscosity = 0.32 c[[Poise|P]] at 20 °C
  }}
| Section3 = {{Chembox Structure
|   MolShape = trigonal planar at C=O
|   Dipole = 2.91 [[Debye|D]]
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS =
|   EUClass = [[Flammable]] ('''F''')<br />Irritant ('''Xi''')
|   NFPA-H = 1
|   NFPA-F = 3
|   NFPA-R = 0
|   RPhrases = {{R11}}, {{R36}}, {{R66}}, {{R67}}
|   SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S26}}
|   FlashPt = -18 °C
|   Autoignition = 465 °C
  }}
| Section8 = {{Chembox Related
|   Function = [[ketone]]s
|   OtherFunctn = [[Butanone]]
|   Function = [[solvent]]s
|   OtherFunctn = [[water (molecule)|Water]]<br />[[Ethanol]]<br />[[Isopropanol]]<br />[[Toluene]]
  }}
}}
'''Acetone''' (also known as '''propanone''', '''dimethyl ketone''', '''2-propanone''', '''propan-2-one''' and '''β-ketopropane''') is a colorless, mobile, flammable liquid. It is the simplest example of the [[ketone]]s. Acetone is [[miscible]] with [[water (molecule)|water]], [[ethanol]], [[diethyl ether|ether]], etc., and itself serves as an important [[solvent]].  The most familiar household use of acetone is as the active ingredient in [[nail polish remover]] and [[paint thinner]].  Acetone is also used to make [[plastic]], fibers, drugs, and other chemicals.  In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body.

==Production==
Acetone is produced primarily in the [[cumene process]]. Previously, acetone was produced by the [[dry distillation]] of [[acetate]]s, for example [[calcium acetate]]. During [[World War I]] a new process of producing acetone through [[bacterium|bacterial]] [[Fermentation (biochemistry)|fermentation]] was developed by [[Chaim Weizmann]], later the first president of [[Israel]], in order to help the British war effort. This [[Clostridium acetobutylicum|Acetone Butanol Ethanol process]] was abandoned due to the small yield of Acetone [[Butanol]] compared to the organic waste.

==Biosynthesis==
{{seealso|ketosis}}
Small amounts of acetone are produced in the body by the [[decarboxylation]] of [[ketone bodies]].

==Uses==
===Cleaning fluid===
Acetone is often the primary (or only) component in [[nail polish|nail polish remover]]. [[Ethyl acetate]], another organic solvent, is sometimes used as well. Acetone is also used as a [[superglue]] remover. It can be used for thinning and cleaning fiberglass resins and epoxies. It is a strong solvent for most plastics and synthetic fibres.

It is ideal for thinning fiberglass resin, cleaning fiberglass tools and dissolving two-part [[epoxy|epoxies]] and [[superglue]] before hardening. A heavy-duty degreaser, it is useful in the preparation of metal prior to painting; it also thins polyester resins, vinyl and adhesives. It easily removes residues from glass and porcelain. In biological research contexts, buffers that contain acetone (such as citrate-buffered formalin) use the acetone to [[lysis|lyse]] cells for further experimentation.

Additionally, acetone is extremely effective when used as a cleaning agent when dealing with permanent markers.

===Solvent===
Acetone can also dissolve many plastics, including those used in [[Nalgene]] bottles made of polystyrene, polycarbonate and some types of polypropylene.<ref>[http://www.nalgenelabware.com/techdata/chemical/ NALGENE Labware - Technical Data<!-- Bot generated title -->]</ref>

In the laboratory, acetone is used as a [[chemical polarity|polar]] [[aprotic solvent]] in a variety of [[organic reaction]]s, such as [[SN2 reaction|S<sub>N</sub>2 reactions]]. The use of acetone solvent is also critical for the successful [[Jones oxidation]]. Technical grade acetone is inexpensive. Because of acetone's medium polarity, it dissolves a wide range of compounds. Thus, it is commonly loaded into squeeze bottles and used as a general solvent in rinsing [[laboratory glassware]].

Acetone is also used extensively for the safe transporting and storing of [[acetylene]]. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One liter of acetone can dissolve around 250 liters of acetylene.

===Feedstock===
An important industrial use for acetone involves its reaction with [[phenol]] for the manufacture of [[bisphenol A]]. Bisphenol A is an important component of many polymers such as [[polycarbonate]]s, [[polyurethane]]s and [[epoxy resin]]s. Acetone has also been used in the manufacture of [[cordite]].

===Automotive fuel additive===
Some automotive enthusiasts add acetone at around 1 part in 500 to their fuel, following claims of dramatic improvement in fuel economy and engine life.<ref>{{cite web|author=Louis LaPonte|url=http://www.lubedev.com/smartgas/additive.htm|title=Acetone in Fuels (A Study of Dimethylketone or Propanone)|accessdate=2007-06-06|date=2007-02-13|publisher=[http://smartgas.net Smartgas.net]}}</ref> This practice is controversial as the body of systematic testing shows that acetone has no measurable effect or may in fact reduce engine life by adversely affecting fuel system parts.<ref>{{cite web|url=http://addacetone.com|title=Acetone as a Fuel Additive|publisher=[http://www.peswiki.com Pure Energy Systems Wiki]|accessdate=2007-06-06}}</ref><ref>{{cite web|url=http://www.helenair.com/articles/2006/01/21/automotive/c01012106_03.txt|publisher=[[Independent Record]]|date=2006-01-21|title=Click and Clack Talk Cars|author=Tom and Ray Magliozzi|accessdate=2007-06-06}}</ref><ref>{{cite web|url=http://msgboard.snopes.com/message/ultimatebb.php?/ubb/get_topic/f/20/t/000594/p/1.html|title=Can adding Acetone to fuel increase mpg by 15 to 35%?|publisher=[[Snopes|Snopes.com]] Message Board|accessdate=2007-06-06}}</ref> Debates on this subject and the perrenial claims of a "Big Oil" cover-up intensified when the practice was addressed on the popular American TV show [[MythBusters]] in 2006, and shown to have negative effect in the televised fuel economy test.<ref>[[MythBusters]] ([[MythBusters (season 4)#Episode 53 - "Exploding Pants"|Season 4, Episode 53]])</ref>.  The jury is still out though, the only negatives to using acetone would be the result of exceeding the recommended blending calculation (one ounce of acetone to five gallons of gasoline).   Even common paint thinner (which contains acetone, and other chemicals, some of which have been used to boost octane and fuel Formula One race cars, such as toluene and xylene) has been used as a gasoline and diesel fuel additive, point being that the chemical surface tension of the gasoline will be reduced to allow a more efficient combustion process to occur, thus resulting in better economy and performance.  Conversely, alcohol based octane boosters, such as ethanol and methanol, actually increase the chemical surface tension of common gasoline, and this is precisely why less economy, less miles per gallon, occurs when using alcohol as an additive in gasoline.

===Other uses===
Acetone is also used as a [[desiccant|drying agent]], due to the readiness with which it mixes with water, and its volatility.

It can be used as an artistic agent; when rubbed on the back of a laser print or photocopy placed face-down on another surface and burnished firmly, the toner of the image is allowed to transfer to the destination surface.

==Safety==
===Acetone peroxide===
{{main|acetone peroxide}}
When oxidized, acetone forms acetone peroxide as a by-product, which is a highly unstable compound. It may be formed accidentally, e.g. when waste [[hydrogen peroxide]] is poured into a carboy containing waste acetone solvent. Acetone peroxide is more than ten times as friction and shock sensitive as [[nitroglycerin]]. Due to its instability, it is rarely used, despite its easy chemical synthesis.

===Toxicology===
Acetone is an irritant and inhalation may lead to [[hepatotoxic]] effects (causing liver damage). The vapors should be avoided. In no circumstance should it be consumed directly or indirectly. Always use goggles when handling acetone; it can cause permanent eye damage ([[corneal clouding]]).

Small amounts of acetone are metabolically produced in the body, mainly from fat. In humans, fasting significantly increases its endogenous production (see [[ketosis]]). Acetone can be elevated in [[diabetes]]. Contamination of water, food (e.g. milk), or the air (acetone is volatile) can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Relatively speaking, acetone is not a very toxic compound; it can, however, damage the [[mucosa]] of the [[mouth]] and can irritate and damage skin. Accidental intake of large amounts of acetone may lead to unconsciousness and death.

The effects of long-term exposure to acetone are known mostly from animal studies. [[Kidney]], [[liver]], and [[nerve]] damage, increased [[birth defect]]s, and lowered reproduction ability of males (only) occurred in animals exposed long-term. It is not known if these same effects would be exhibited in humans.  Pregnant women should avoid contact with acetone and acetone fumes in order to avoid the possibility of birth defects, including brain damage.

Interestingly, acetone has been shown to have [[anticonvulsant]] effects in animal models of [[epilepsy]], in the absence of toxicity, when administered in millimolar concentrations.<ref name="Likhodii">{{cite journal | author = Likhodii SS, Serbanescu I, Cortez MA, Murphy P, Snead OC 3rd, Burnham WM | title = Anticonvulsant properties of acetone, a brain ketone elevated by the ketogenic diet | journal = [[Ann Neurol.]] | year = 2003 | volume = 54 | issue = 2 | pages = 219–226 | doi = 10.1002/ana.10634}}</ref> 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.<ref name="Likhodii"/>

==References==
<references/>

==External links==
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc00/icsc0087.htm International Chemical Safety Card 0087]
* [http://www.npi.gov.au/database/substance-info/profiles/3.html National Pollutant Inventory – Acetone]
* [http://www.cdc.gov/niosh/npg/npgd0004.html NIOSH Pocket Guide to Chemical Hazards]

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[[Category:Household chemicals]]
[[Category:Cosmetic chemicals]]
[[Category:Biotechnology products]]
[[Category:Ketones]]
[[Category:Ketone solvents]]
[[Category:Fuel additives]]
[[Category:DEA List II chemicals]]

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