Revision 804795468 of "Acetone" on enwiki

{{distinguish|Acetoin}}
{{Chembox
| Watchedfields = changed
| verifiedrevid = 477239274
| Reference = <ref>''[[The Merck Index]]'', '''15th Ed.''' (2013), p. 13, [http://www.rsc.org/Merck-Index/monograph/mono1500000065 Acetone Monograph] '''65''', O'Neil: [[The Royal Society of Chemistry]].{{subscription needed}}</ref>
| ImageFileL1 = Acetone-CRC-MW-ED-dimensions-2D.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSizeL1 = 136
| ImageNameL1 = Full structural formula of acetone with dimensions
| ImageFileR1 = Acetone-2D-skeletal.svg
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageSizeR1 = 101
| ImageNameR1 = Skeletal formula of acetone
| ImageFileL2 = Acetone-3D-balls.png
| ImageFileL2_Ref = {{chemboximage|correct|??}}
| ImageSizeL2 = 131
| ImageNameL2 = Ball-and-stick model of acetone
| ImageFileR2 = Acetone-3D-vdW.png
| ImageFileR2_Ref = {{chemboximage|correct|??}}
| ImageSizeR2 = 106
| ImageNameR2 = Space-filling model of acetone
| ImageFile3 = Sample of Acetone.jpg
| ImageName3 = Sample of acetone
| PIN = Propan-2-one <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
| OtherNames = {{plainlist|
* Acetone
* Dimethyl ketone<ref name = "Acetone">{{cite web|url = http://webbook.nist.gov/cgi/cbook.cgi?ID=67-64-1|title = Acetone|work = NIST Chemistry WebBook|location = USA|publisher = [[National Institute of Standards and Technology]]}}</ref>
* Dimethyl [[carbonyl]]
* β-Ketopropane<ref name = "Acetone" />
* Propanone<ref>{{Cite book
| isbn = 978-0-444-51994-8
| pages = 92–94
| last = Klamt
| first = Andreas
| title = COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design
| year = 2005
| publisher = Elsevier
}}</ref>
* 2-Propanone<ref name = "Acetone" />
* Dimethyl formaldehyde<ref>{{Cite book
| title = Handbook of preservatives
| last1 = Ash
| first1 = Michael
| last2 = Ash
| first2 = Irene
| page = 369
| year = 2004
| publisher = Synapse Information Resources, Inc.
| isbn = 1-890595-66-7
}}</ref>
* Pyroacetic spirit (archaic)<ref>{{cite book |title = The 100 Most Important Chemical Compounds: A Reference Guide |last = Myers |first = Richard L. |year = 2007 |publisher = Greenwood |isbn = 978-0-313-08057-9 |pages = 4–6}}</ref>
* Ketone propane<ref name=NIOSH/>
}}
|Section1={{Chembox Identifiers
| Abbreviations = DMK
| CASNo = 67-64-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 180
| ChemSpiderID = 175
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 1364PS73AF
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 200-662-2
| UNNumber = 1090
| KEGG = D02311
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Acetone
| ChEBI = 15347
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 14253
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = AL3150000
| Beilstein = 635680
| Gmelin = 1466
| 3DMet = B00058
| SMILES = CC(=O)C
| StdInChI = 1S/C3H6O/c1-3(2)4/h1-2H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C3H6O/c1-3(2)4/h1-2H3
| StdInChIKey = CSCPPACGZOOCGX-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = CSCPPACGZOOCGX-UHFFFAOYAF
}}
|Section2={{Chembox Properties
| C=3 | H=6 | O=1
| Appearance = colorless liquid
| Odor = pungent, irritating, floral, cucumber like
| Density = 0.7845 g/cm<sup>3</sup> (25 °C)
| MeltingPtC = −94.7
| MagSus = −33.78·10<sup>−6</sup> cm<sup>3</sup>/mol| MeltingPt_ref=<ref name=CRC>David R. Lide (ed), ''CRC Handbook of Chemistry and Physics, 84th Edition''. CRC Press. Boca Raton, Florida, 2003; Section 3, Physical Constants of Organic Compounds.</ref>
| BoilingPtC = 56.05
| BoilingPt_ref=<ref name=CRC/>
| LogP = −0.042
| VaporPressure = 9.39 kPa (0&nbsp;°C)<br> 30.6 kPa (25&nbsp;°C)<br> 374 kPa (100&nbsp;°C)<br> 2.8 MPa (200&nbsp;°C)<ref name=nist>{{nist|name=Acetone|id=C67641|accessdate=2014-05-11|mask=FFFF|units=SI}}</ref>
| pKa = 19.2
| pKb = −5.2 (for conjugate base)
| Solubility = miscible
| SolubleOther = miscible in [[benzene]], [[diethyl ether]], [[methanol]], [[chloroform]], [[ethanol]]<ref name=chemister />
| RefractIndex = 1.3588 (''V''<sub>D</sub> = 54.46)
| Viscosity = 0.295 mPa·s (25&nbsp;°C)<ref name=chemister>[http://chemister.ru/Database/properties-en.php?dbid=1&id=27 Properties of substance: acetone]. chemister.ru.</ref>
}}
|Section3={{Chembox Structure
| Coordination = Trigonal planar at C2
| MolShape = Dihedral at C2
| Dipole = 2.91 D
}}
|Section4={{Chembox Thermochemistry
| DeltaHf = −250.03–(−248.77) kJ/mol
| DeltaHc = −1.772 MJ/mol
| Entropy = 200.4 J/(mol·K)
| HeatCapacity = 125.45 J/(mol·K)
}}
|Section5={{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|225|319|336}}
| PPhrases = {{P-phrases|210|261|305+351+338}}
| NFPA-F = 3
| NFPA-H = 1
| NFPA-R = 0
| FlashPtC = −20
| AutoignitionPtC = 465
| ExploLimits = 2.6–12.8%<ref>[http://www.americanchemistry.com/s_acc/sec_solvents.asp?CID=1488&DID=5735 Working with modern hydrocarbon and oxygenated solvents: a guide to flammability] {{webarchive|url=https://web.archive.org/web/20090601224141/http://www.americanchemistry.com/s_acc/sec_solvents.asp?CID=1488&DID=5735 |date=2009-06-01 }} [[American Chemistry Council]] Solvents Industry Group, pg. 7, January 2008</ref>
| PEL = 1000 ppm (2400 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0260}}</ref>
| REL = TWA 250 ppm (590 mg/m<sup>3</sup>)<ref name=NIOSH/>
| IDLH = 2500 ppm<ref name=NIOSH/>
| TLV-TWA = 1185 mg/m<sup>3</sup>
| TLV-STEL = 2375 mg/m<sup>3</sup>
| LD50 = 5800 mg/kg (rat, oral)<br/>3000 mg/kg (mouse, oral)<br/>5340 mg/kg (rabbit, oral)<ref name=IDLH>{{IDLH|67641|Acetone}}</ref>
| LC50 = 20,702 ppm (rat, 8&nbsp;h)<ref name=IDLH/>
| LCLo = 45,455 ppm (mouse, 1&nbsp;h)<ref name=IDLH/>
}}
|Section6={{Chembox Related
| OtherCompounds = [[Butanone]]<br> [[Isopropanol]] <br> [[Urea]] <br> [[Carbonic acid]] <br> [[Carbonyl fluoride]] 
}}
}}

'''Acetone''' (systematically named '''propanone''') is the [[organic compound]] with the [[chemical formula|formula]] (CH<sub>3</sub>)<sub>2</sub>CO.<ref>{{cite journal|doi=10.1039/TF9524800991|title=The molecular structure of acetone|journal=Transactions of the Faraday Society|volume=48|pages=991|year=1952|last1=Allen|first1=P. W.|last2=Bowen|first2=H. J. M.|last3=Sutton|first3=L. E.|last4=Bastiansen|first4=O.}}</ref> It is a colorless, volatile, flammable liquid, and is the simplest [[ketone]].

Acetone is [[miscibility|miscible]] with [[properties of water|water]] and serves as an important [[solvent]] in its own right, typically for cleaning purposes in the laboratory. About 6.7 million [[tonne]]s were produced worldwide in 2010, mainly for use as a solvent and production of [[methyl methacrylate]] and [[bisphenol A]].<ref name=r1>[http://www.sriconsulting.com/WP/Public/Reports/acetone/ Acetone], World Petrochemicals report, January 2010</ref><ref name=Ullmann>Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref> It is a common building block in [[organic chemistry]]. Familiar household uses of acetone are as the active ingredient in [[Nail polish#Nail polish remover|nail polish remover]], and as paint thinner.

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with [[diabetes]] produce it in larger amounts. Reproductive toxicity tests show that it has low potential to cause reproductive problems. Pregnant women, nursing mothers and children have higher levels of acetone.<ref name=acc>American Chemistry Council, Acetone VCCEP Submission, September 10, 2003, page 9.</ref> [[Ketogenic diet]]s that increase acetone in the body are used to counter [[Epilepsy|epileptic]] attacks in infants and children who suffer from recalcitrant [[refractory disease|refractory]] epilepsy.

==History==
Acetone was first produced by alchemists during the late Middle Ages via the dry distillation of metal acetates (e.g., [[lead acetate]], which produced "spirit of Saturn" (since the alchemical symbol for lead was also the astrological symbol for the planet Saturn)).<ref>{{cite journal|author1=Gorman, Mel  |author2=Doering, Charles  |lastauthoramp=yes |year=1959|title=History of the structure of acetone|journal=Chymia|volume=5|pages= 202–208|jstor=27757186}}</ref>

In 1832, French chemist [[Jean-Baptiste Dumas]] and German chemist [[Justus von Liebig]] determined the [[empirical formula]] for acetone.<ref>Dumas, J. (1832) [https://books.google.com/books?id=nilCAAAAcAAJ&pg=PA208 "Sur l'esprit pyro-acétique"] (On pyro-acetic spirit), ''Annales de Chimie et de Physique'', 2nd series, '''49''' :  208–210.</ref><ref>Liebig, Justus (1832) [https://books.google.com/books?id=nilCAAAAcAAJ&pg=PA146 "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).</ref>  In 1833, the French chemist [[Antoine Bussy]] named acetone by adding the suffix ''-one'' to the stem of the corresponding acid (viz, [[acetic acid]]).<ref>Bussy, Antoine  (1833) [http://babel.hathitrust.org/cgi/pt?id=hvd.hx3dwq;view=1up;seq=404 "De quelques Produits nouveaux obtenus par l’action des Alcalis sur les Corps gras à une haute température"]{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }} (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 [http://babel.hathitrust.org/cgi/pt?id=hvd.hx3dwq;view=1up;seq=415 footnote on p. 409]{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }}, continued from p. 408.</ref>  By 1852, English chemist [[Alexander William Williamson]] realized that acetone was methyl [[acetyl]];<ref>Williamson, A. W. (1852) [https://books.google.com/books?id=cqAwAAAAYAAJ&pg=PA229#v=onepage&q&f=false "On Etherification,"] ''Journal of the Chemical Society'', '''4''' :  229–239 ; see especially pp. 237–239.</ref> the following year, the French chemist [[Charles Frédéric Gerhardt]] concurred.<ref>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 ; [http://babel.hathitrust.org/cgi/pt?id=hvd.hx3dyg;view=1up;seq=343 see p. 339.]{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>  In 1865, the German chemist [[August Kekulé]] published the modern structural formula for acetone.<ref>Kekulé, Auguste (1865) [http://babel.hathitrust.org/cgi/pt?id=osu.32435053454401;view=1up;seq=108 "Sur la constitution des substances aromatiques,"]{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }} ''Bulletin de la Société chimique de Paris'', '''1''' :  98–110 ; [http://babel.hathitrust.org/cgi/pt?id=osu.32435053454401;view=1up;seq=120 see especially p. 110.]{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref>Kekulé, Auguste  (1866) "Untersuchungen über aromatischen Verbindungen" (Investigations into aromatic compounds), ''Annalen der Chemie und Pharmacie'', '''137''' :  129–196 ; [http://babel.hathitrust.org/cgi/pt?id=uiug.30112025843977;view=1up;seq=158 see especially pp. 143–144.]{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref>Johann Josef Loschmidt had presented the structure of acetone in 1861, but his privately published booklet received little attention.  See:  J. Loschmidt, [https://books.google.com/books?id=ksw5AAAAcAAJ&pg=PP5#v=onepage&q&f=false ''Chemische Studien''] (Vienna, Austria-Hungary:  Carl Gerold's Sohn, 1861).</ref> During WWI, [[Chaim Weizmann]] developed the process for industrial production of acetone (Weizmann Process).<ref>http://www.chemistryexplained.com/Va-Z/Weizmann-Chaim.html</ref>

==Metabolism==
{{See also|Ketosis}}

===Biosynthesis===
Small amounts of acetone are produced in the body by the [[decarboxylation]] of [[ketone bodies]]. 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.  Since it is a byproduct of fermentation, acetone is a byproduct of the distillery industry.

===Metabolic use===
Although some biochemistry textbooks and current research publications<ref name="Vujasinović2007">{{cite journal|doi=10.1177/0960327107087794|title=Poisoning with 1-propanol and 2-propanol|journal=Human & Experimental Toxicology|volume=26|issue=12|pages=975|year=2007|last1=Vujasinovic|first1=M|last2=Kocar|first2=M|last3=Kramer|first3=K|last4=Bunc|first4=M|last5=Brvar|first5=M}}</ref> indicate that acetone cannot be metabolized, there is evidence to the contrary, some dating back thirty years.  Acetone can be produced from the oxidation of ingested [[isopropanol]], or from the spontaneous/[[acetoacetate decarboxylase|enzymatic]] breakdown of [[acetoacetic acid|acetoacetate]] (a ketone body) in ketotic individuals. It can then be metabolized either by [[CYP2E1]] via [[methylglyoxal]] to [[lactic acid|<small>D</small>-lactate]] and [[pyruvic acid|pyruvate]], and ultimately [[glucose]]/energy, or by a different pathway via [[propylene glycol]] to [[pyruvate]], [[lactic acid|lactate]], [[acetate]] (usable for energy) and [[propionaldehyde]].<ref name=Glew2010>{{cite journal|url=http://www.bioline.org.br/request?np10002|author=Glew, Robert H|title=You Can Get There From Here: Acetone, Anionic Ketones and Even-Carbon Fatty Acids can Provide Substrates for Gluconeogenesis|journal=Nig. J. Physiol. Sci. |volume=25|year=2010|pages= 2–4}}</ref><ref>{{cite journal | author = Miller DN, Bazzano G | year = 1965 | title = Propanediol metabolism and its relation to lactic acid metabolism | journal = Ann NY Acad Sci | volume = 119 | pages = 957–973 | bibcode = 1965NYASA.119..957M | last2 = Bazzano | doi = 10.1111/j.1749-6632.1965.tb47455.x | pmid = 4285478 | issue = 3}}</ref><ref>{{cite journal | author = Ruddick JA | year = 1972 | title = Toxicology, metabolism, and biochemistry of 1,2-propanediol | journal = Toxicol App Pharmacol | volume = 21 | pages = 102–111 | doi = 10.1016/0041-008X(72)90032-4}}</ref>

==Production==
In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year.<ref name=CEH>{{cite web|url=http://www.sriconsulting.com/CEH/Private/Reports/604.5000//|title=CEH Marketing Research Report: ACETONE|author1=Greiner, Camara |author2=Funada, C|date=June 2010|work=Chemical Economics Handbook|publisher=SRI consulting|accessdate=2 September 2016}}{{paywall}}</ref> With 1.56 million tonnes per year, the United States had the highest production capacity,<ref>{{cite web | publisher = ICIS.com | title = Acetone Uses and Market Data | url = http://www.icis.com/v2/chemicals/9074858/acetone/uses.html | date = October 2010 | accessdate = 2011-03-21}}</ref> followed by [[Taiwan]] and [[mainland China]]. 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 [[Royal Dutch Shell|Shell]] in 2010.<ref name=CEH/> 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.<ref name=icispricing_132>[http://www.icispricing.com/il_shared/Samples/SubPage132.asp Acetone (US Gulf) Price Report – Chemical pricing information]. ICIS Pricing. Retrieved on 2012-11-26.</ref>

===Current method===
Acetone is produced directly or indirectly from [[propylene]]. Approximately 83% of acetone is produced via the [[cumene process]];<ref name = Ullmann/> as a result, acetone production is tied to phenol production. In the cumene process, [[benzene]] is [[alkylated]] with propylene to produce [[cumene]], which is [[oxidation|oxidize]]d by air to produce [[phenol]] and acetone:
:[[File:Cumene-process-overview-2D-skeletal.png|320px|Overview of the cumene process]]
Other processes involve the direct oxidation of propylene ([[Wacker-Hoechst process]]), or the [[hydration reaction|hydration]] of propylene to give [[2-propanol]], which is oxidized to acetone.<ref name = Ullmann/>

===Older methods===
Previously, acetone was produced by the [[dry distillation]] of [[acetate]]s, for example [[calcium acetate]] in [[ketonic decarboxylation]].
: Ca(CH<sub>3</sub>COO)<sub>2</sub> →  CaO<sub>(s)</sub> + CO<sub>2(g)</sub> + (CH<sub>3</sub>)<sub>2</sub>CO (v)
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,<ref name=Ullmann/> in the preparation of [[Cordite]].<ref>{{cite book|last=Wittcoff|first=M.M. Green ; H.A.|title=Organic chemistry principles and industrial practice|year=2003|publisher=Wiley-VCH|location=Weinheim|isbn=3-527-30289-1|page=4|edition=1. ed., 1. reprint.}}</ref> This acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found.<ref name=Ullmann/>

==Uses==
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]].<ref name=r1/>

===Solvent===
Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning [[fiberglass|polyester]] resin, cleaning tools used with it, and dissolving two-part [[epoxy|epoxies]] and [[superglue]] before they harden. It is used as one of the volatile components of some [[paint]]s and [[varnish]]es. As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting. It is also useful for high reliability [[soldering]] applications to remove [[Flux (metallurgy)#Rosin fluxes|rosin]] flux after soldering is complete; this helps to prevent the [[rusty bolt effect]].

Acetone is used as a solvent by the [[pharmaceutical industry]] and as a [[Denaturation (food)|denaturant]] in [[denatured alcohol]].<ref>{{Cite book
| isbn =978-0-8247-8210-8
| page = 32
| last = Weiner
| first = Myra L.
| author2 = Lois A. Kotkoskie
| title = Excipient Toxicity and Safety
| year = 1999
}}</ref>
Acetone is also present as an [[excipient]] in some [[pharmaceutical drug]]s.<ref>[http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm Inactive Ingredient Search for Approved Drug Products], FDA/Center for Drug Evaluation and Research</ref>

Although itself [[flammable]], acetone is used extensively as a solvent for the safe transportation and storage of [[acetylene]], which cannot be safely [[pressurization|pressurized]] as a pure compound. 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 at a pressure of 10 bar.<ref>[http://www.msha.gov/alerts/hazardsofacetylene.htm Mine Safety and Health Administration (MSHA) – Safety Hazard Information – Special Hazards of Acetylene]. Msha.gov. Retrieved on 2012-11-26.</ref><ref>[http://www.aga.com/web/web2000/com/WPPcom.nsf/pages/History_Acetylene_1 History – Acetylene dissolved in acetone]. Aga.com. Retrieved on 2012-11-26.</ref>

===Chemical intermediate===
Acetone is used to [[organic synthesis|synthesize]] [[methyl methacrylate]]. It begins with the initial conversion of acetone to [[acetone cyanohydrin]]:
:(CH<sub>3</sub>)<sub>2</sub>CO + [[hydrogen cyanide|HCN]] → (CH<sub>3</sub>)<sub>2</sub>C(OH)CN
In a subsequent step, the [[nitrile]] is [[hydrolysis|hydrolyzed]] to the unsaturated [[amide]], which is [[ester]]ified:
:(CH<sub>3</sub>)<sub>2</sub>C(OH)CN + CH<sub>3</sub>OH → CH<sub>2</sub>=(CH<sub>3</sub>)CCO<sub>2</sub>CH<sub>3</sub> + NH<sub>3</sub>
The third major use of acetone (about 20%)<ref name=r1/> is synthesizing [[bisphenol A]]. Bisphenol A is a component of many polymers such as [[polycarbonate]]s, [[polyurethane]]s, and [[epoxy resin]]s. The synthesis involves the [[condensation reaction|condensation]] of acetone with [[phenol]]:
:(CH<sub>3</sub>)<sub>2</sub>CO + 2 C<sub>6</sub>H<sub>5</sub>OH → (CH<sub>3</sub>)<sub>2</sub>C(C<sub>6</sub>H<sub>4</sub>OH)<sub>2</sub> + H<sub>2</sub>O
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]].<ref name=Ullmann/>
:2 (CH<sub>3</sub>)<sub>2</sub>CO → (CH<sub>3</sub>)<sub>2</sub>C(OH)CH<sub>2</sub>C(O)CH<sub>3</sub>

===Laboratory===
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 critical for the [[Jones oxidation]]. It does not form an [[azeotrope]] with water (see [[azeotrope (data)]]).<ref>[http://www.solvent--recycling.com/azeotrope_1.html What is an Azeotrope?]. Solvent—recycling.com. Retrieved on 2012-11-26.</ref> It is a common solvent for rinsing [[laboratory glassware]] because of its low cost and volatility. Despite its common use as a supposed [[Desiccant|drying agent]], it is not effective except by bulk displacement and dilution. Acetone can be cooled with [[dry ice]] to −78&nbsp;°C without freezing; acetone/dry ice baths are commonly used to conduct reactions at low temperatures. Acetone is fluorescent under ultraviolet light, and its vapor can be used as a fluorescent tracer in fluid flow experiments.<ref>{{Cite journal|title = Acetone: a tracer for concentration measurements in gaseous flows by planar laser-induced fluorescence|journal = [[Exp. Fluids]]|volume = 13|pages = 369–376|year = 1992|doi = 10.1007/BF00223244| issue = 6|bibcode = 1992ExFl...13..369L |last1 = Lozano|first1 = A.|last2 = Yip|first2 = B.|last3 = Hanson|first3 = R.K.}}</ref>

===Medical and cosmetic uses===
Acetone is used in a variety of general medical and cosmetic applications and is also listed as a component in [[food additives]] and food packaging and also in nail polish remover.
Dermatologists use acetone with alcohol for acne treatments to peel dry skin.

Acetone is commonly used in [[chemical peel]]ing. Common agents used today for chemical peels are salicylic acid, [[glycolic acid]], 30% [[salicylic acid]] in [[ethanol]], and [[trichloroacetic acid]] (TCA). Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting. Acetone, [[Septisol]], or a combination of these agents is commonly used in this process.{{Citation needed|date=August 2011}}

===Domestic and other niche uses===
Acetone is often the primary component in cleaning agents such as [[nail polish]] remover. Acetone is a component of [[superglue]] remover and easily removes residues from glass and porcelain. [[Make-up artist]]s use acetone to remove skin adhesive from the netting of wigs and moustaches by immersing the item in an acetone bath, then removing the softened glue residue with a stiff brush.

Acetone is often used for [[vapor polishing]] 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 10 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.<ref>[http://www.instructables.com/id/Quality-Finish-3D-Prints-with-Acetone/?ALLSTEPS "Quality Finish 3D Prints with Acetone"]. instructables.com</ref>

Low-grade acetone is also commonly used in academic laboratory settings as a glassware rinsing agent for removing residue and solids before a final wash.<ref>{{Cite web|url=http://bnorthrop.faculty.wesleyan.edu/files/2009/09/CleaningGlassware.pdf|title=Cleaning Glassware|date=September 2009|website=Wesleyan University|access-date=July 7, 2016}}</ref>

==Safety==

===Flammability===
The most hazardous property of acetone is its extreme flammability. At temperatures greater than acetone's [[flash point]] of {{convert|-20|C|F}}, air mixtures of between 2.5% and 12.8% acetone, by volume, may explode or cause a flash fire. Vapors can flow along surfaces to distant ignition sources and flash back. [[Static electricity|Static]] discharge may also ignite acetone vapors, though acetone has a very high ignition initiation energy point and therefore accidental ignition is rare. Even pouring or spraying acetone over red-glowing coal will not ignite it, due to the high concentration of vapour and the cooling effect of evaporation of the liquid.<ref name="msds">[http://hazard.com/msds/mf/baker/baker/files/a0446.htm Acetone MSDS]. Hazard.com (1998-04-21). Retrieved on 2012-11-26.</ref> It [[auto-ignition temperature|auto-ignites]] at {{convert|465|C|F}}. Auto-ignition temperature is also dependent upon the exposure time, thus at some tests it is quoted as 525&nbsp;°C. Also, industrial acetone is likely to contain a small amount of water which also inhibits ignition.

===Acetone peroxide===
{{Main|acetone peroxide}}
When oxidized, acetone forms acetone [[peroxide]] as a byproduct, which is a highly [[Chemical stability|unstable]], [[primary explosive|primary]] [[high explosive]] compound. It may be formed accidentally, e.g. when waste [[hydrogen peroxide]] is poured into waste solvent containing acetone.  Due to its instability, it is rarely used, despite its simple chemical synthesis.

===Health information===
Acetone has been studied extensively and is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled.<ref name= sids >{{cite journal | title = SIDS Initial Assessment Report: Acetone | publisher = Environmental Protection Agency | url = http://www.inchem.org/documents/sids/sids/67641.pdf}}</ref>  Acetone is not currently regarded as a [[carcinogen]], a [[mutagen]]ic chemical or a concern for chronic [[neurotoxicity]] effects.<ref name="msds" />
The materials safety data sheet for Acetone lists the following as Potential Health Effects. <br>

Inhalation: Inhalation of vapors irritates the respiratory tract. May cause coughing, dizziness, dullness, and headache. Higher concentrations can produce central nervous system depression, narcosis, and unconsciousness. <br>

Ingestion: Swallowing small amounts is not likely to produce harmful effects. Ingestion of larger amounts may produce abdominal pain, nausea and vomiting. <br>
Aspiration into lungs can produce severe lung damage and is a medical emergency. Other symptoms are expected to parallel inhalation. <br>

Skin Contact: Irritating due to defatting action on skin. Causes redness, pain, drying and cracking of the skin. <br>

Eye Contact: Vapors are irritating to the eyes. Splashes may cause severe irritation, with stinging, tearing, redness and pain. <br>

Chronic Exposure: Prolonged or repeated skin contact may produce severe irritation or dermatitis. <br>

Aggravation of Pre-existing Conditions: Use of alcoholic beverages enhances toxic effects. Exposure may increase the toxic potential of chlorinated hydrocarbons, such as chloroform, trichloroethane.<ref name="msds" />

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 beverages, baked foods, desserts, and preserves at concentrations ranging from 5 to 8&nbsp;mg/L.<ref name= sids/>

====Toxicology====
Acetone is believed to exhibit only slight toxicity in normal use, and there is no strong evidence of chronic health effects if basic precautions are followed.<ref>[http://ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/basic_ace.html Basic Information on Acetone]. Ccohs.ca (1999-02-19). Retrieved on 2012-11-26.</ref>

At very high vapor concentrations, acetone is irritating and, like many other solvents, may depress the [[central nervous system]]. It is also a severe irritant on contact with eyes, and a potential [[pulmonary aspiration]] risk. In one documented case, ingestion of a substantial amount of acetone led to systemic toxicity, although the patient eventually fully recovered.<ref>{{cite web|url=http://ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/health_ace.html|title=Health Effects of Acetone|accessdate=2008-10-21|author=Canadian Centre for Occupational Health and Safety| archiveurl= https://web.archive.org/web/20081017104151/http://www.ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/health_ace.html| archivedate= 17 October 2008 <!--DASHBot-->| deadurl= no}}</ref> Some sources estimate [[median lethal dose|LD<sub>50</sub>]] for human ingestion at 0.621 g/kg; LD<sub>50</sub> inhalation by mice is given as 23 g/m<sup>3</sup>, over 4 hours.<ref>[http://msds.chem.ox.ac.uk/PR/propanone.html Safety (MSDS) data for propanone]. Msds.chem.ox.ac.uk. Retrieved on 2012-11-26 {{dead link|date=September 2014}}</ref>

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|vauthors=Likhodii SS, Serbanescu I, Cortez MA, Murphy P, Snead OC, 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|pmid=12891674}}</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"/>
* EPA EPCRA Delisting (1995). EPA removed acetone from the list of "toxic chemicals" maintained under Section 313 of the Emergency Planning and Community Right to Know Act (EPCRA). In making that decision, EPA conducted an extensive review of the available toxicity data on acetone and found that acetone "exhibits acute toxicity only at levels that greatly exceed releases and resultant exposures", and further that acetone "exhibits low toxicity in chronic studies".
* [[Genotoxicity]]. Acetone has been tested in more than two dozen in vitro and in vivo assays. These studies indicate that acetone is not genotoxic.
* [[Carcinogenicity]]. EPA in 1995 concluded, "There is currently no evidence to suggest a concern for carcinogenicity". (EPCRA Review, described in Section 3.3). NTP scientists have recommended against chronic toxicity/carcinogenicity testing of acetone because "the prechronic studies only demonstrated a very mild toxic response at very high doses in rodents".
* [[Neurotoxicity]] and Developmental Neurotoxicity. The neurotoxic potential of both acetone and [[Isopropyl alcohol|isopropanol]], the metabolic precursor of acetone, have been extensively studied. These studies demonstrate that although exposure to high doses of acetone may cause transient central nervous system effects, acetone is not a neurotoxicant. A guideline developmental neurotoxicity study has been conducted with isopropanol, and no developmental neurotoxic effects were identified, even at the highest dose tested. (SIAR, pp.&nbsp;1, 25, 31).
* Environmental. When the EPA exempted acetone from regulation as a [[volatile organic compound]] (VOC) in 1995, EPA stated that this exemption would "contribute to the achievement of several important environmental goals and would support EPA's pollution prevention efforts". 60 Fed. Reg. 31,634 (June 16, 1995). 60 Fed. Reg. 31,634 (June 16, 1995). EPA noted 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 (United States)|Clean Air Act]].

==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,<ref name="atsdr">[http://www.atsdr.cdc.gov/toxfaqs/tfacts21.pdf Acetone], Agency for Toxic Substances and Disease Registry ToxFAQs, 1995</ref> 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 [[photolysis]] (primarily into [[methane]] and [[ethane]].<ref>{{cite journal|doi=10.1021/j100841a010|title=The Photolysis of Acetone|year=1960|last1=Darwent|first1=B. deB.|last2=Allard|first2=M. J.|last3=Hartman|first3=M. F.|last4=Lange|first4=L. J.|journal=Journal of Physical Chemistry|volume=64|issue=12|pages=1847–1850}}</ref>) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways.<ref name=atsdr/>  The [[median lethal dose|LD<sub>50</sub>]] of acetone for fish is 8.3 g/L of water (or about 1%) over 96 hours, and its environmental half-life in water is about 1 to 10 days. Acetone may pose a significant risk of oxygen depletion in aquatic systems due to the microbial consumption.<ref>[http://jmloveridge.com/cosh/Acetone.pdf Safety Data Sheet Acetone] {{webarchive|url=https://web.archive.org/web/20090320150055/http://jmloveridge.com/cosh/Acetone.pdf |date=2009-03-20 }}. jmloveridge.com. Retrieved on 2012-11-26.</ref>

==Extraterrestrial occurrence==
On 30 July 2015, scientists reported that upon the first touchdown of the ''[[Philae (spacecraft)|Philae]]'' lander on [[comet]] [[67P]]{{'s}} surface, measurements by the COSAC and Ptolemy instruments revealed sixteen [[organic compound]]s, four of which were seen for the first time on a comet, including [[acetamide]], acetone, [[methyl isocyanate]], and [[propionaldehyde]].<ref name="wapo20150730">{{cite news |url=https://www.washingtonpost.com/world/philae-probe-finds-evidence-that-comets-can-be-cosmic-labs/2015/07/30/63a2fc0e-36e5-11e5-ab7b-6416d97c73c2_story.html |title=Philae probe finds evidence that comets can be cosmic labs |work=The Washington Post |agency=Associated Press |first=Frank |last=Jordans |date=30 July 2015 |accessdate=30 July 2015}}</ref><ref name="esa20150730">{{cite web |url=http://www.esa.int/Our_Activities/Space_Science/Rosetta/Science_on_the_surface_of_a_comet |title=Science on the Surface of a Comet |publisher=European Space Agency |date=30 July 2015 |accessdate=30 July 2015}}</ref><ref name="SCI-20150731">{{cite journal |last1=Bibring |first1=J.-P. |last2=Taylor |first2=M.G.G.T. |last3=Alexander |first3=C. |last4=Auster |first4=U. |last5=Biele |first5=J. |last6=Finzi |first6=A. Ercoli |last7=Goesmann |first7=F. |last8=Klingehoefer |first8=G. |last9=Kofman |first9=W. |last10=Mottola |first10=S. |last11=Seidenstiker |first11=K.J. |last12=Spohn |first12=T. |last13=Wright |first13=I. |title=Philae's First Days on the Comet – Introduction to Special Issue |url=http://www.sciencemag.org/content/349/6247/493.short |date=31 July 2015 |journal=[[Science (journal)|Science]] |volume=349 |issue=6247 |page=493 |doi=10.1126/science.aac5116 |accessdate=30 July 2015 |bibcode=2015Sci...349..493B |pmid=26228139}}</ref>

==References==
{{reflist|30em}}

==External links==
{{Commons category|Acetone}}
* {{ICSC|0087|00}}
* [https://www.cdc.gov/niosh/npg/npgd0004.html NIOSH Pocket Guide to Chemical Hazards]
* [http://sdsdata.org/244731 Acetone Safety Data Sheet (SDS)]
* [http://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~EQIVt8:1 Hazardous substances databank entry at the national library of medicine]
* {{SIDS|name=Acetone|id=67641}}
* Calculation of [http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Acetone vapor pressure], [http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Acetone liquid density], [http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Acetone dynamic liquid viscosity], [http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Acetone surface tension] of acetone

{{Cholesterol and steroid intermediates}}
{{GABAAR PAMs}}
{{Molecules detected in outer space}}

{{Authority control}}

[[Category:Household chemicals]]
[[Category:Cosmetics chemicals]]
[[Category:Biotechnology products]]
[[Category:Dialkylketones]]
[[Category:Ketone solvents]]
[[Category:Fuel additives]]
[[Category:Excipients]]
[[Category:Commodity chemicals]]
[[Category:GABAA receptor positive allosteric modulators]]
[[Category:Anticonvulsants]]