Acetone

{{short description|Organic compound ((CH3)2CO); simplest ketone}} {{distinguish|Acetoin|Acetate}} {{for|the musical instrument company|Ace Tone}} {{other uses}} {{Chembox | Watchedfields = changed | verifiedrevid = 477239274 | IUPACName = Acetone<ref>ChemSpider lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.</ref> | 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 required}}</ref> |ImageFileL1 = Acetone-CRC-MW-ED-dimensions-2D-Vector.svg |ImageClassL1 = skin-invert |ImageFileL1_Ref = {{chemboximage|correct|??}} |ImageSizeL1 = 136 |ImageNameL1 = Full structural formula of acetone with dimensions |ImageFileR1 = Acetone-2D-skeletal.svg |ImageClassR1 = skin-invert |ImageFileR1_Ref = {{chemboximage|correct|??}} |ImageSizeR1 = 130 |ImageNameR1 = Skeletal formula of acetone |ImageFileL2 = Acetone-3D-balls.png |ImageClassL2 = bg-transparent |ImageFileL2_Ref = {{chemboximage|correct|??}} |ImageSizeL2 = 131 |ImageNameL2 = Ball-and-stick model of acetone |ImageFileR2 = Acetone-3D-vdW.png |ImageClassR2 = bg-transparent |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<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 723 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |SystematicName = 2-Propanone |OtherNames = {{plainlist| * Acetonum ({{IPA|la|aˈkeːtonum}}) * Dimethyl ketone<ref name=nist>{{nist|name=Acetone|id=C67641|access-date=2014-05-11|mask=FFFF|units=SI}}</ref> * Dimethyl carbonyl * Ketone propane<ref name=NIOSH /> * β-Ketopropane<ref name=nist /> * 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> * 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 = [https://archive.org/details/100mostimportant0000myer/page/4 4–6] |url = https://archive.org/details/100mostimportant0000myer/page/4}}</ref> * Spirit of Saturn (archaic)<ref name=gorman1962 /> }} |Section1 = {{Chembox Identifiers |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 = Colourless liquid |Odour = Pungent, fruity, dry<ref name=smell /> |Density = 0.7845 g/cm3 (25 °C)<ref name=h1 /> |MeltingPtC = −94.9 |MeltingPt_ref=<ref name=h1>Haynes, p. 3.4</ref> |MagSus = −33.8·10−6 cm3/mol<ref>Haynes, p. 3.576</ref> |BoilingPtC = 56.08 |BoilingPt_ref=<ref name=h1 /> |CriticalTP = 508 K (235 °C), 48 bar |RefractIndex = 1.3588 (20 °C)<ref name=h1 /> |LogP = −0.24<ref>Haynes, p. 5.173</ref> |VaporPressure = {{Unbulleted list | 9.39{{nbsp}}kPa (0 °C) | 30.6{{nbsp}}kPa (25 °C) | 374{{nbsp}}kPa (100 °C) | 2.8{{nbsp}}MPa (200 °C)<ref name=nist /> }} |pKa = {{Unbulleted list |19.16 (H2O)<ref>{{cite journal |last1=Chiang |first1=Yvonne |last2=Kresge |first2=A. Jerry |last3=Tang |first3=Yui S. |last4=Wirz |first4=Jakob |title=The pKa and keto-enol equilibrium constant of acetone in aqueous solution |journal=Journal of the American Chemical Society |date=1984 |volume=106 |issue=2 |pages=460–462 |doi=10.1021/ja00314a055|bibcode=1984JAChS.106..460C }}</ref> |26.5 (DMSO)<ref name=Bordwell>{{cite journal |last1=Bordwell |first1=Frederick G. |title=Equilibrium acidities in dimethyl sulfoxide solution |journal=Accounts of Chemical Research |date=1988 |volume=21 |issue=12 |pages=456–463 |doi=10.1021/ar00156a004|s2cid=26624076 }}</ref> }} |Solubility = Miscible<ref name=h1 /> |SolubleOther = Miscible in benzene, diethyl ether, methanol, chloroform, ethanol<ref name=h1 /> |Viscosity = 0.4013 mPa·s (0 °C) 0.3311{{nbsp}}mPa·s at 20 °C 0.306{{nbsp}}mPa·s (25 °C)<ref>Haynes, p. 6.243</ref> 0.2562{{nbsp}}mPa·s at 50 °C<ref>''Lange's Handbook of Chemistry'', 10th ed. pp 1669-1674</ref> |ThermalConductivity = 0.161{{nbsp}}W/(m·K) (25 °C)<ref>Haynes, p. 6.254</ref> }} |Section3 = {{Chembox Structure |Coordination = Trigonal planar at C2 |MolShape = Dihedral at C2 |Dipole = 2.88 D<ref>Haynes, p. 9.60</ref> }} |Section4 = {{Chembox Thermochemistry |Thermochemistry_ref=<ref>Haynes, pp. 5.3, 5.67</ref> |DeltaHf = −248.4{{nbsp}}kJ/mol (liquid) −218.5 kJ/mol (gas) |DeltaHc = −1.79{{nbsp}}MJ/mol |DeltaHfus = +5.7{{nbsp}}kJ/mol |DeltaHvap = +30.3{{nbsp}}kJ/mol |Entropy = 199.8{{nbsp}}J/(mol·K) (liquid) 295.35{{nbsp}}J/(mol·K) (gas) |HeatCapacity = 126.3{{nbsp}}J/(mol·K) (liquid) 75{{nbsp}}J/(mol·K) (gas) 96{{nbsp}}J/(mol·K) (solid)<ref name="Maass1925">Maass, O.; Walbauer, L.J., The specific heats and latent heats of fusion of ice and of several organic compounds, J. Am. Chem. Soc., 1925, 47, 1-9.</ref> }} |Section5 = {{Chembox Hazards |MainHazards= Highly flammable |GHSPictograms = {{GHS02}} {{GHS07}} |GHSSignalWord = '''DANGER''' |HPhrases = {{H-phrases|225|302|319|336|373}} |PPhrases = {{P-phrases|210|235|260|305+351+338}} |NFPA-F = 3 |NFPA-H = 1 |NFPA-R = 0 |FlashPtC = −20 |FlashPt_ref = <ref name=ig /> |AutoignitionPtC = 465<ref name=ig>Haynes, p. 15.13</ref> |ExploLimits = 2.5–12.8%<ref name=ig /> |PEL = 1000{{nbsp}}ppm (2400{{nbsp}}mg/m3)<ref name=NIOSH>{{PGCH|0004}}</ref> |REL = TWA 250{{nbsp}}ppm (590{{nbsp}}mg/m3)<ref name=NIOSH /> |IDLH = 2500{{nbsp}}ppm<ref name=NIOSH /> |TLV-C = 500 ppm<ref name=da /> |TLV-STEL = 250 ppm<ref name=da>Haynes, p. 16.34</ref> |LD50 = {{Unbulleted list | 5800{{nbsp}}mg/kg (rat, oral) | 3000{{nbsp}}mg/kg (mouse, oral) | 5340{{nbsp}}mg/kg (rabbit, oral)<ref name=IDLH>{{IDLH|67641|Acetone}}</ref> }} |LC50 = 20,702{{nbsp}}ppm (rat, 8 h)<ref name=IDLH /> |LCLo = 45,455{{nbsp}}ppm (mouse, 1 h)<ref name=IDLH /> }} | Section6 = {{Chembox Related |OtherCompounds = {{Unbulleted list | Butanone | Isopropyl alcohol | Formaldehyde | Urea | Carbonic acid }} }} }}

'''Acetone''' ('''2-propanone''' or '''dimethyl ketone''') is an organic compound with the formula {{chem2|(CH3)2CO}}.<ref>{{cite journal|doi=10.1039/TF9524800991|title=The molecular structure of acetone|journal=Transactions of the Faraday Society|volume=48|page=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 the simplest and smallest ketone ({{chem2|R\sC(\dO)\sR'}}). It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odor.<ref name="Myers">{{cite book |last1=Myers |first1=Richard Leroy |title=The 100 Most Important Chemical Compounds: A Reference Guide |date=2007 |publisher=Greenwood Press |isbn=978-0-313-33758-1 |page=4-6}}</ref>

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.<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. 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.<ref>{{Cite web|url=https://www.paint.org/voc-exempt/|title=Update: U.S. EPA Exempt Volatile Organic Compounds|date=2018-01-30|website=American Coatings Association|access-date=2019-03-20|archive-date=2021-02-08|archive-url=https://web.archive.org/web/20210208171107/https://www.paint.org/voc-exempt/}}</ref>

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 ketogenic diets that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to suppress epileptic attacks in children with treatment-resistant epilepsy.<ref name=Freeman2007>{{cite journal | last1 = Freeman | first1 = JM | last2 = Kossoff | first2 = EH | last3 = Hartman | first3 = AL | date = Mar 2007 | title = The ketogenic diet: one decade later | journal = Pediatrics | volume = 119 | issue = 3| pages = 535–43 | doi = 10.1542/peds.2006-2447 | pmid = 17332207 | s2cid = 26629499 }}</ref>

== 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 lead and, later, "pyro-acetic spirit" and "pyro-acetic ester".<ref name=gorman1962>Mel Gorman, History of acetone (1600–1850), 1962</ref>

Prior to the name "acetone" being coined by French 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.<ref>C. Reichenbach (1834) [https://books.google.com/books?id=P0s9AAAAcAAJ&pg=PA298 "Ueber Mesit (Essiggeist) und Holzgeist"] (On mesit (spirit of vinegar) and wood spirits), ''Annalen der Pharmacie'', vol. 10, no. 3, pages 298–314.</ref><ref name=gorman1962 /> Names derived from mesit include mesitylene and mesityl oxide which were first synthesised from acetone.

In 1839, the name "acetone" began to be used, because it was obtained from acetic acid.<ref name="Myers" /> 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 can not 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.<ref name=chemtymology />

== History == Acetone was first produced by Andreas Libavius in 1606 by distillation of lead(II) acetate.<ref>{{cite book |last1=Libavius |first1=Andreas |title=Alchymia |date=1606 |publisher=printed by Joannes Saurius, at the expense of Peter Kopff |location=Frankfurt, Germany |page=123 |url=https://archive.org/details/BIUSante_00180/page/n141/mode/2up |language=la}}</ref><ref>{{Cite web|url=http://www.chemgapedia.de/vsengine/vlu/vsc/de/ch/6/ac/bibliothek/_vlu/aceton.vlu/Page/vsc/de/ch/6/ac/bibliothek/aceton/synthese.vscml.html|title=Aceton|work= Chemgapedia}}</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 ([https://books.google.com/books?id=nilCAAAAcAAJ&pg=PA193 especially 193–204]).</ref> 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.<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"] (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=414 footnote on pp. 408–409].</ref><ref name="chemtymology">{{cite web | url=https://chemtymology.co.uk/2018/09/28/acetone | title=Acetone | date=28 September 2018 }}</ref> By 1852, Alexander William Williamson, an English chemist, realized that acetone was methyl acetyl;<ref>Williamson, A. W. (1852) [https://books.google.com/books?id=cqAwAAAAYAAJ&pg=PA229 "On Etherification,"] ''Journal of the Chemical Society'', '''4''' : 229–239; ([https://books.google.com/books?id=cqAwAAAAYAAJ&pg=PA237 especially pp. 237–239]).</ref> the following year, the French chemist Charles Frédéric Gerhardt concurred.<ref>Gerhardt, Charles (1853) [http://babel.hathitrust.org/cgi/pt?id=hvd.hx3dyg;view=1up;seq=289 "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.]</ref> In 1865, a 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,"] ''Bulletin de la Société chimique de Paris'', '''1''' : 98–110; ([http://babel.hathitrust.org/cgi/pt?id=osu.32435053454401;view=1up;seq=120 especially p. 110]).</ref><ref>Kekulé, Auguste (1866) [http://babel.hathitrust.org/cgi/pt?id=uiug.30112025843977;view=1up;seq=143 "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=157 especially pp. 143–144]).</ref> Johann Josef Loschmidt had presented the structure of acetone in 1861,<ref>Loschmidt, J. (1861) [https://books.google.com/books?id=ksw5AAAAcAAJ&pg=PP5 ''Chemische Studien''] Vienna, Austria-Hungary: Carl Gerold's Sohn.</ref> but his privately published booklet received little attention. During World War I, Chaim Weizmann developed the biochemical process for industrial production of acetone (Weizmann Process).<ref>[http://www.chemistryexplained.com/Va-Z/Weizmann-Chaim.html Chaim Weizmann] chemistryexplained.com</ref>

== Production ==

Acetone is produced directly or indirectly from propene. 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 oxidized by air to produce acetone and phenol:

:class=skin-invert-image|590px|Overview of the cumene process

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.<ref name = Ullmann /> Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate in ketonic decarboxylation.

:{{chem2|Ca(CH3COO)2 -> CaO(s) + CO2(g) + (CH3)2CO}}

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 /><ref>{{cite book |last1=Myers |first1=Richard Leroy |title=The 100 Most Important Chemical Compounds: A Reference Guide |date=2007 |publisher=Greenwood Press |isbn=978-0-313-33758-1 |page=5}}</ref> in the preparation of Cordite.<ref>{{cite book|last1=Wittcoff|first1=M.M. |last2=Green|first2=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 />

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|access-date=2 September 2016}}{{subscription required}}</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 | access-date = 2011-03-21 | archive-url = https://web.archive.org/web/20090515133058/http://www.icis.com/v2/chemicals/9074858/acetone/uses.html | archive-date = 2009-05-15 }}</ref> followed by Taiwan and 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 Shell in 2010.<ref name=CEH /> INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in Beveren, Belgium. The 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] {{Webarchive|url=https://web.archive.org/web/20130516023618/http://www.icispricing.com/il_shared/Samples/SubPage132.asp |date=2013-05-16}}. ICIS Pricing, Retrieved on 2012-11-26</ref>

==Occurrence==

Humans exhale several milligrams of acetone per day and it arises from the decarboxylation of acetoacetate.<ref name=drug /><ref>{{cite journal |doi=10.1088/1752-7155/8/3/034001 |title=The human volatilome: Volatile organic compounds (VOCs) in exhaled breath, skin emanations, urine, feces and saliva |date=2014 |last1=Amann |first1=Anton |last2=Costello |first2=Ben de Lacy |last3=Miekisch |first3=Wolfram |last4=Schubert |first4=Jochen |last5=Buszewski |first5=Bogusław |last6=Pleil |first6=Joachim |last7=Ratcliffe |first7=Norman |last8=Risby |first8=Terence |journal=Journal of Breath Research |volume=8 |issue=3 |article-number=034001 |pmid=24946087 |bibcode=2014JBR.....8c4001A |s2cid=40583110 }}</ref> 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.<ref name=drug>{{cite book | last=Karch | first=Steven B. | title=Drug abuse handbook | publisher=CRC Press | publication-place=Boca Raton, Fla. | date=1998 | isbn=978-1-4200-4829-2 | oclc=61503700 | page=369}}</ref>

Acetone is naturally occurring. It is produced by terrestrial vegetation, undefined ocean processes, incomplete combustion of biomass, or oxidation of hydrocarbons in the atmosphere.<ref name=":02">{{Cite journal |last=Franco |first=B. |last2=Clarisse |first2=L. |last3=Stavrakou |first3=T. |last4=Müller |first4=J.-F. |last5=Pozzer |first5=A. |last6=Hadji-Lazaro |first6=J. |last7=Hurtmans |first7=D. |last8=Clerbaux |first8=C. |last9=Coheur |first9=P.-F. |date=2019 |title=Acetone Atmospheric Distribution Retrieved From Space |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2019GL082052 |journal=Geophysical Research Letters |language=en |volume=46 |issue=5 |pages=2884–2893 |doi=10.1029/2019GL082052 |issn=1944-8007}}</ref><ref name=":12">{{Cite journal |last=Jacob |first=Daniel J. |last2=Field |first2=Brendan D. |last3=Jin |first3=Emily M. |last4=Bey |first4=Isabelle |last5=Li |first5=Qinbin |last6=Logan |first6=Jennifer A. |last7=Yantosca |first7=Robert M. |last8=Singh |first8=Hanwant B. |date=2002 |title=Atmospheric budget of acetone |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2001JD000694 |journal=Journal of Geophysical Research: Atmospheres |language=en |volume=107 |issue=D10 |pages=ACH 5–1–ACH 5-17 |doi=10.1029/2001JD000694 |issn=2156-2202}}</ref><ref name=":22">{{Cite journal |last=Fischer |first=E. V. |last2=Jacob |first2=D. J. |last3=Millet |first3=D. B. |last4=Yantosca |first4=R. M. |last5=Mao |first5=J. |date=2012 |title=The role of the ocean in the global atmospheric budget of acetone |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2011GL050086 |journal=Geophysical Research Letters |language=en |volume=39 |issue=1 |doi=10.1029/2011GL050086 |issn=1944-8007 |pmc=7983863 |pmid=33758438}}</ref><ref name=":3">{{Cite journal |last=Gierczak |first=Tomasz |last2=Burkholder |first2=James B. |last3=Bauerle |first3=Stefan |last4=Ravishankara |first4=A. R. |date=1998-06-01 |title=Photochemistry of acetone under tropospheric conditions |url=https://www.sciencedirect.com/science/article/pii/S0301010498000068 |journal=Chemical Physics |volume=231 |issue=2 |pages=229–244 |doi=10.1016/S0301-0104(98)00006-8 |issn=0301-0104}}</ref>

== Chemical properties == Acetone is reluctant to form a hydrate:<ref name="Lemal2004">{{cite journal |doi=10.1021/jo0302556 |title=Perspective on Fluorocarbon Chemistry |year=2004 |last1=Lemal |first1=David M. |journal=The Journal of Organic Chemistry |volume=69 |pages=1–11 |pmid=14703372 |issue=1}}</ref> :{{chem2|(CH3)2C\dO + H2O <-> (CH3)2C(OH)2}} K = 10−3 M−1

Like most ketones, acetone exhibits the keto–enol tautomerism in which the nominal keto structure {{chem2|(CH3)2C\dO}} of acetone itself is in equilibrium with the enol isomer {{chem2|(CH3)C(OH)\d(CH2)}} ('''prop-1-en-2-ol'''). In acetone vapor at ambient temperature, only 2.4{{e|-7}}% of the molecules are in the enol form.<ref name=hine1976>{{cite journal | last1 = Hine | first1 = Jack | last2 = Arata | first2 = Kazushi | year = 1976 | title = Keto-Enol Tautomerism. II. The Calorimetrical Determination of the Equilibrium Constants for Keto-Enol Tautomerism for Cyclohexanone and Acetone | journal = Bulletin of the Chemical Society of Japan | volume = 49 | issue = 11| pages = 3089–3092 | doi = 10.1246/bcsj.49.3089 | doi-access = free}}</ref> :class=skin-invert-image|300px

In the presence of suitable catalysts, two acetone molecules also combine to form the compound diacetone alcohol {{chem2|(CH3)C\dO(CH2)C(OH)(CH3)2}}, which on dehydration gives mesityl oxide {{chem2|(CH3)C\dO(CH)\dC(CH3)2}}. This product can further combine with another acetone molecule, with loss of another molecule of water, yielding phorone and other compounds.<ref>{{cite book | last=Sowa | first=John R. | title=Catalysis of organic reactions | publisher=Taylor & Francis | publication-place=Boca Raton | date=2005 | isbn=978-0-8247-2729-1 | oclc=67767141 | page=363}}</ref>

Acetone is a weak Lewis base that forms adducts with soft acids like I2 and hard acids like phenol. Acetone also forms complexes with divalent metals.<ref>{{cite journal|author1= Driessen, W.L. |author2= Groeneveld, W.L. | year= 1969|title= Complexes with ligands containing the carbonyl group. Part I: Complexes with acetone of some divalent metals containing tetrachloro-ferrate(III) and -indate(III) anions |doi=10.1002/recl.19690880811|journal=Recueil des Travaux Chimiques des Pays-Bas|volume=88|issue= 8 |pages=77977–988}}</ref><ref>{{cite journal|author1=Kilner, C. A. |author2= Halcrow, M. A. |year= 2006|title= An unusual example of a linearly coordinated acetone ligand in a six-coordinate iron(II) complex |journal= Acta Crystallographica C |volume=62|issue= 9 |pages=1107–1109|doi= 10.1107/S0108270106028903|pmid= 16954630 |bibcode= 2006AcCrC..62M.437K |doi-access= free}}</ref>

Under ultraviolet light, acetone fluoresces.<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.|s2cid = 121060565}}</ref> The flame temperature of pure acetone is 1980 °C.<ref>Haynes, p. 15.49</ref> 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.<ref name="karg1960">{{cite journal|author1=Kargin, V. A.|author2= Kabanov, V. A.|author3= Zubov, V. P.|author4= Papisov, I. M. |year=1960|title=Polymerisation of acetone|journal=Doklady Akademii Nauk SSSR|volume =134| issue =5|pages =1098–1099|url=http://mi.mathnet.ru/eng/dan24153}}</ref><ref name="kawa1962">{{cite journal | last1 = Kawai | first1 = Wasaburo | year = 1962 | title = Polymerization of Acetone | journal = Bulletin of the Chemical Society of Japan | volume = 35 | issue = 3| page = 516A | doi = 10.1246/bcsj.35.516a | doi-access = free }}</ref><ref name="cata1996">{{cite journal | last1 = Cataldo | first1 = Franco | year = 1996 | title = Synthesis of ketonic resins from self-polymerization of acetone, 1 Action of protic and Lewis acids on acetone | journal = Die Angewandte Makromolekulare Chemie | volume = 236 | issue = 1| pages = 1–19 | doi = 10.1002/apmc.1996.052360101 }}</ref>

===Photochemistry=== The outcome of irradiation of acetone is wavelength dependent. At short wavelengths (<290 nm), carbon monoxide and methyl radicals are produced in high quantum yield:<ref name=":3"/> :{{chem2|(CH3)2CO -> 2 CH3 + CO}} At wavelengths >290 nm, the acetyl radical is produced: :{{chem2|(CH3)2CO -> CH3 + CH3CO}} The latter process is relevant to the atmospheric chemistry of acetone.

===Catabolism=== Acetone can then be metabolized either by CYP2E1 via methylglyoxal to D-lactate and pyruvate, and ultimately glucose/energy, or by a different pathway via propylene glycol to pyruvate, lactate, acetate (usable for energy) and propionaldehyde.<ref name=Glew2010>{{cite journal |url=http://www.bioline.org.br/request?np10002 |last=Glew |first=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 |access-date=2013-09-01 |archive-url=https://web.archive.org/web/20130926031021/http://www.bioline.org.br/request?np10002 |archive-date=2013-09-26 }}</ref><ref>{{cite journal |last1=Miller |first1=DN |last2=Bazzano |first2=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 | doi = 10.1111/j.1749-6632.1965.tb47455.x | pmid = 4285478 | issue = 3|s2cid=37769342 }}</ref><ref>{{cite journal |last=Ruddick |first=JA | year = 1972 | title = Toxicology, metabolism, and biochemistry of 1,2-propanediol | journal = Toxicol Appl Pharmacol | volume = 21 |issue=1 | pages = 102–111 | doi = 10.1016/0041-008X(72)90032-4|pmid=4553872|bibcode=1972ToxAP..21..102R }}</ref>

==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 />

===Chemical intermediate=== Acetone is used to synthesize methyl methacrylate. It begins with the initial conversion of acetone to acetone cyanohydrin via reaction with hydrogen cyanide (HCN): :{{chem2|(CH3)2CO + HCN -> (CH3)2C(OH)CN}}

In a subsequent step, the nitrile is hydrolyzed to the unsaturated amide, which is esterified: :{{chem2|(CH3)2C(OH)CN + CH3OH -> CH2C(CH3)CO2CH3 + NH3}}

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 polycarbonates, polyurethanes, and epoxy resins. The synthesis involves the condensation of acetone with phenol: :{{chem2 |(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.<ref name=Ullmann /> :{{chem2 |2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3}}

Condensation with acetylene gives 2-methylbut-3-yn-2-ol, precursor to synthetic terpenes and terpenoids.<ref>{{cite book | last1=Wittcoff | first1=Harold | last2=Reuben | first2=B. G. | last3=Plotkin | first3=Jeffrey S. | title=Industrial organic chemicals. | publisher=Wiley-Interscience | publication-place=Hoboken, N.J. | date=2004 | isbn=0-471-44385-9 | oclc=53307689 | page=259}}</ref>

=== Solvent === Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning polyester resin, cleaning tools used with it, and dissolving two-part epoxies and superglue before they harden. It is used as one of the volatile components of some paints and varnishes.<ref name="Myers" /> As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting or soldering, 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.<ref name=attack>{{cite book | last1=Ivanov | first1=Vitalii | last2=Trojanowska | first2=Justyna | last3=Machado | first3=Jose | last4=Liaposhchenko | first4=Oleksandr | last5=Zajac | first5=Jozef | last6=Pavlenko | first6=Ivan | last7=Edl | first7=Milan | last8=Perakovic | first8=Dragan | title=Advances in design, simulation and manufacturing II: proceedings of the 2nd International Conference on Design, Simulation, Manufacturing: The Innovation Exchange, DSMIE-2019, June 11–14, 2019, Lutsk, Ukraine | publication-place=Cham | date=2019 | isbn=978-3-030-22365-6 | oclc=1104227601 | pages=430–435}}</ref>

Although itself flammable, acetone is used extensively as a solvent for the safe transportation and storage of acetylene, which cannot be safely pressurized 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 litres of acetylene at a pressure of {{convert|10|bar|MPa}}.<ref>[http://www.msha.gov/alerts/hazardsofacetylene.htm Mine Safety and Health Administration (MSHA) – Safety Hazard Information – Special Hazards of Acetylene] {{Webarchive|url=https://web.archive.org/web/20160122062046/http://www.msha.gov/alerts/hazardsofacetylene.htm |date=2016-01-22 }}. 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] {{Webarchive|url=https://web.archive.org/web/20150915040643/http://www.aga.com/web/web2000/com/WPPcom.nsf/pages/History_Acetylene_1 |date=2015-09-15}}. Aga.com, Retrieved on 2012-11-26</ref> Acetone is used as a solvent by the pharmaceutical industry and as a 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| publisher = Taylor & Francis| url-access = registration| url = https://archive.org/details/excipienttoxicit103wein/page/32}}</ref> Acetone is also present as an excipient in some pharmaceutical drugs.<ref>[http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm Inactive Ingredient Search for Approved Drug Products]{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}, FDA/Center for Drug Evaluation and Research</ref>{{Update inline|date=March 2024}}

==== Lab and domestic solvent ==== A variety of organic reactions employ acetone as a polar, aprotic solvent, e.g. the Jones oxidation. 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.<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> Despite common desiccatory use, acetone dries only via bulk displacement and dilution. It forms no azeotropes with water (see azeotrope tables).<ref>[http://www.solvent--recycling.com/azeotrope_1.html What is an Azeotrope?]. Solvent—recycling.com. Retrieved on 2012-11-26.</ref> Acetone also removes certain stains from microscope slides.<ref>{{cite journal |last1=Engbaek |first1=K |last2=Johansen |first2=KS |last3=Jensen |first3=ME |title=A new technique for Gram staining paraffin-embedded tissue. |journal=Journal of Clinical Pathology |date=February 1979 |volume=32 |issue=2 |pages=187–90 |doi=10.1136/jcp.32.2.187 |pmid=86548 |pmc=1145607}}</ref>

Acetone freezes well below −78 °C. An acetone/dry ice mixture cools many low-temperature reactions.<ref name="AA">{{cite book |last1=Addison |first1=Ault |title=Studyguide for Techniques and Experiments for Organic Chemistry |date=1998 |location=Sausalito, CA |isbn=978-0-935702-76-7 |page=310}}</ref> Make-up artists 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.<ref>{{cite book | last1=Davis | first1=Gretchen | last2=Hall | first2=Mindy | title=The makeup artist handbook: techniques for film, television, photography, and theatre | publisher=Focal Press | publication-place=Waltham, MA | date=2012 | isbn=978-0-240-81894-8 | oclc=776632427 | page=3}}</ref> Acetone is a main ingredient in many nail polish removers because it breaks down nail polish.<ref>{{Cite web |title=Acetone |url=https://www.chemicalsafetyfacts.org/chemicals/acetone/ |access-date=2024-05-27 |website=Chemical Safety Facts |language=en-US}}</ref> It is used for all types of nail polish removal, like gel nail polish, dip powder and acrylic nails.<ref>{{Cite web |title=How to Take Off Gel & Acrylic Nails {{!}} Just Ask Sally |url=https://www.sallybeauty.com/just-ask-sally/articles/how-to-take-off-gel-and-acrylic-nails/#:~:text=Give%20it%20enough%20time,%20then,pliable%20and%20comes%20off%20easily. |access-date=2024-05-27 |website=www.sallybeauty.com}}</ref>

==== Biology ==== Proteins precipitate in acetone.<ref name=Simpson2009 /> The chemical modifies peptides, both at α- or ε-amino groups, and in a poorly understood but rapid modification of certain glycine residues.<ref name="Simpson2009">{{cite journal | last1=Simpson | first1=Deborah M. | last2=Beynon | first2=Robert J. | title=Acetone Precipitation of Proteins and the Modification of Peptides | journal=Journal of Proteome Research | publisher=American Chemical Society (ACS) | volume=9 | issue=1 | date=2009-12-14 | issn=1535-3893 | doi=10.1021/pr900806x | pages=444–450| pmid=20000691 }}</ref> In pathology, acetone helps find lymph nodes in fatty tissues (such as the mesentery) for tumor staging.<ref name="acetone-patho-springer">{{cite journal |last1=Basten |first1=O. |last2=Bandorski |first2=D. |last3=Bismarck |first3=C. |last4=Neumann |first4=K. |last5=Fisseler-Eckhoff |first5=A. |title=Acetonkompression |journal=Der Pathologe |date=2009 |volume=31 |issue=3 |pages=218–224 |doi=10.1007/s00292-009-1256-7 |pmid=20012620 |s2cid=195684316 |language=de}}</ref> The liquid dissolves the fat and hardens the nodes, making them easier to find.<ref name="acetone-patho-wiley">{{cite journal |last1=Leung |first1=C. A. W. |last2=Fazzi |first2=G. E. |last3=Melenhorst |first3=J. |last4=Rennspiess |first4=D. |last5=Grabsch |first5=H. I. |title=Acetone clearance of mesocolic or mesorectal fat increases lymph node yield and may improve detection of high-risk Stage II colorectal cancer patients |journal=Colorectal Disease |date=November 2018 |volume=20 |issue=11 |pages=1014–1019 |doi=10.1111/codi.14335 |pmid=29989291 |s2cid=205030844 |url=http://eprints.whiterose.ac.uk/133347/13/Leung_et_al-2018-Colorectal_Disease.pdf |doi-access=free}}</ref>

=== Medical === Dermatologists use acetone with alcohol for acne treatments to chemically peel dry skin. Common agents used for chemical peeling are salicylic acid, glycolic acid, azelaic 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, using acetone, hexachlorophene, or a combination of these agents.<ref>{{cite book | last=MacFarlane | first=Deborah F. | title=Skin cancer management: a practical approach | publisher=Springer | publication-place=New York | date=2010 | isbn=978-0-387-88495-0 | oclc=663098001 | page=35}}</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 |author1=Likhodii SS |author2=Serbanescu I |author3=Cortez MA |author4=Murphy P |author5=Snead OC |author6=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|s2cid=3213318 }}</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" /> 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.<ref name=acc>{{cite web |url=https://www.tera.org/Peer/VCCEP/Acetone/acevccep.pdf |author=American Chemistry Council Acetone Panel |title=Acetone (CAS No. 67-64-1) VCCEP Submission |date=September 10, 2003 |pages=6, 9 |access-date=2018-04-14}}</ref>

== Atmospheric chemistry == Acetone has a relatively long lifetime in the atmosphere of about 2 weeks.<ref name=":2">{{Cite journal |last=Fischer |first=E. V. |last2=Jacob |first2=D. J. |last3=Millet |first3=D. B. |last4=Yantosca |first4=R. M. |last5=Mao |first5=J. |date=2012 |title=The role of the ocean in the global atmospheric budget of acetone |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2011GL050086 |journal=Geophysical Research Letters |language=en |volume=39 |issue=1 |doi=10.1029/2011GL050086 |issn=1944-8007 |pmc=7983863 |pmid=33758438}}</ref> Because of its long lifetime, it can be transported by atmospheric winds to the upper troposphere and lower stratosphere<ref name=":4">{{Cite journal |last=Wang |first=Siyuan |last2=Apel |first2=Eric C. |last3=Schwantes |first3=Rebecca H. |last4=Bates |first4=Kelvin H. |last5=Jacob |first5=Daniel J. |last6=Fischer |first6=Emily V. |last7=Hornbrook |first7=Rebecca S. |last8=Hills |first8=Alan J. |last9=Emmons |first9=Louisa K. |last10=Pan |first10=Laura L. |last11=Honomichl |first11=Shawn |last12=Tilmes |first12=Simone |last13=Lamarque |first13=Jean-François |last14=Yang |first14=Mingxi |last15=Marandino |first15=Christa A. |date=2020 |title=Global Atmospheric Budget of Acetone: Air-Sea Exchange and the Contribution to Hydroxyl Radicals |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2020JD032553 |journal=Journal of Geophysical Research: Atmospheres |language=en |volume=125 |issue=15 |article-number=e2020JD032553 |doi=10.1029/2020JD032553 |issn=2169-8996}}</ref> where it can influence hydrogen radical (HOx) production and ozone (O3) levels<ref name=":4" />. These two peroxy radicals can then undergo a series of reactions to produce hydrogen oxide radicals (HOx)<ref name=":3" /> and can therefore have a significant impact on atmospheric chemistry<ref name=":0">{{Cite journal |last=Franco |first=B. |last2=Clarisse |first2=L. |last3=Stavrakou |first3=T. |last4=Müller |first4=J.-F. |last5=Pozzer |first5=A. |last6=Hadji-Lazaro |first6=J. |last7=Hurtmans |first7=D. |last8=Clerbaux |first8=C. |last9=Coheur |first9=P.-F. |date=2019 |title=Acetone Atmospheric Distribution Retrieved From Space |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2019GL082052 |journal=Geophysical Research Letters |language=en |volume=46 |issue=5 |pages=2884–2893 |doi=10.1029/2019GL082052 |issn=1944-8007}}</ref> including concentration of ozone (O3) in the upper troposphere.<ref name=":0" /> Photolysis is just one possible processes that removes acetone from the atmosphere.<ref name=":1">{{Cite journal |last=Jacob |first=Daniel J. |last2=Field |first2=Brendan D. |last3=Jin |first3=Emily M. |last4=Bey |first4=Isabelle |last5=Li |first5=Qinbin |last6=Logan |first6=Jennifer A. |last7=Yantosca |first7=Robert M. |last8=Singh |first8=Hanwant B. |date=2002 |title=Atmospheric budget of acetone |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2001JD000694 |journal=Journal of Geophysical Research: Atmospheres |language=en |volume=107 |issue=D10 |pages=ACH 5–1–ACH 5-17 |doi=10.1029/2001JD000694 |issn=2156-2202}}</ref><ref name=":23">{{Cite journal |last=Fischer |first=E. V. |last2=Jacob |first2=D. J. |last3=Millet |first3=D. B. |last4=Yantosca |first4=R. M. |last5=Mao |first5=J. |date=2012 |title=The role of the ocean in the global atmospheric budget of acetone |url=https://onlinelibrary.wiley.com/doi/abs/10.1029/2011GL050086 |journal=Geophysical Research Letters |language=en |volume=39 |issue=1 |doi=10.1029/2011GL050086 |issn=1944-8007 |pmc=7983863 |pmid=33758438}}</ref> Acetone can also be removed by ocean processes and by deposition to dry land surfaces.<ref name=":1" /><ref name=":23" /> The contributions of each sink to the removal of acetone from the atmosphere is still not fully understood.<ref name=":23" />

== Safety == Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a dull blue flame; in larger amounts, fuel evaporation causes incomplete combustion and a bright yellow flame. When above acetone's flash point of {{convert|-20|C|F}}, air mixtures of 2.5{{nbh}}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 discharge may ignite acetone vapors, though acetone has a very high ignition initiation energy and accidental ignition is rare.<ref name="msds" /> Acetone's auto-ignition temperature is relatively high {{convert|465|C|F}};<ref name="ig" /> moreover, auto-ignition temperature depends upon experimental conditions, such as exposure time, and has been quoted as high as 535 °C.<ref>{{cite book | last=Hauptmanns | first=Ulrich | title=Process and plant safety | publication-place=Berlin | date=2014 | isbn=978-3-642-40954-7 | oclc=888160502 | page=20}}</ref> 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.<ref name="msds">{{cite web |url=http://hazard.com/msds/mf/baker/baker/files/a0446.htm |title=Acetone MSDS |website=hazard.com |date=1998-04-21 |access-date=2012-11-26 |url-status=usurped |archive-url=https://archive.today/20120709035156/http://hazard.com/msds/mf/baker/baker/files/a0446.htm |archive-date=2012-07-09}}</ref>

Acetone should be stored away from strong oxidizers, such as concentrated nitric and sulfuric acid mixtures.<ref>Haynes, p. 16.3</ref> It may explode when stored with chloroform in the presence of a base.<ref>Haynes, p. 16.5</ref><ref>{{cite web |title=Acetone |url=https://cameochemicals.noaa.gov/chemical/8 |website=CAMEO Chemicals |publisher=NOAA |access-date=14 April 2026|archive-url=https://web.archive.org/web/20260307065126/https://cameochemicals.noaa.gov/chemical/8|archive-date=7 March 2026|url-status=live}}</ref> 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.<ref>{{cite book | last1=Bingham | first1=Eula | last2=Cohrssen | first2=Barbara | last3=Patty | first3=F. A. | title=Patty's toxicology | publication-place=Hoboken, New Jersey | date=2012 | isbn=978-1-62198-026-1 | oclc=810064538 | page=736}}</ref>

=== 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.<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> It is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled.<ref name= sids>{{cite web| title = SIDS Initial Assessment Report: Acetone | publisher = Environmental Protection Agency | url = http://www.inchem.org/documents/sids/sids/67641.pdf | access-date = 2014-09-11 | archive-url = https://web.archive.org/web/20140309040008/http://www.inchem.org/documents/sids/sids/67641.pdf | archive-date = 2014-03-09 }}</ref> Acetone is not regarded as a carcinogen, a mutagen, or a concern for chronic neurotoxicity effects.<ref name="msds" /> 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.<ref name="sids" />

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.<ref>{{cite web |title=What are the potential health effects of acetone? |url=http://ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/health_ace.html |access-date=2008-10-21 |url-status = live|archive-url= https://web.archive.org/web/20081017104151/http://www.ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/health_ace.html |archive-date=2008-10-17 |publisher=Canadian Centre for Occupational Health and Safety}}</ref> Acute toxicity for mice by ingestion (LD50) is 3 g/kg, and by inhalation (LC50) is 44 g/m3 over 4 hours.<ref>[http://www.sciencelab.com/msds.php?msdsId=9927062 Safety (MSDS) data for propanone] {{Webarchive|url=https://web.archive.org/web/20180316170132/http://www.sciencelab.com/msds.php?msdsId=9927062 |date=2018-03-16}} sciencelab.com/msds Retrieved on 2018-03-19</ref>

=== 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.<ref>{{cite journal|url=https://www.govinfo.gov/content/pkg/FR-1995-06-16/pdf/95-14804.pdf |title=Air Quality: Revision to Definition of Volatile Organic Compounds—Exclusion of Acetone|journal=Federal Register|volume=60|issue=116|date=June 16, 1995 |pages=31634–31637|author= U.S. Environmental Protection Agency}}</ref> 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".<ref name=smell>[https://www.atsdr.cdc.gov/toxprofiles/tp21.pdf Toxicological Profile for Acetone]. U.S. Environmental Protection Agency June 2022 p. 7</ref>

==Abiotic sources== On 30 July 2015, scientists reported that upon the first touchdown of the ''Philae'' lander on comet 67P{{'s}} surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, 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|archive-url=https://web.archive.org/web/20181223235109/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|archive-date=23 December 2018|title=Philae probe finds evidence that comets can be cosmic labs|newspaper=The Washington Post|agency=Associated Press|first=Frank|last=Jordans|date=30 July 2015|access-date=30 July 2015}}</ref><ref name="esa20150730">{{cite web|url=https://www.esa.int/Science_Exploration/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|access-date=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 |date=31 July 2015|journal=Science|volume=349|issue=6247|page=493|doi=10.1126/science.aac5116|bibcode=2015Sci...349..493B|pmid=26228139|doi-access=free}}</ref>

== References ==

== Notes ==

{{refbegin}} * {{cite book|ref= Haynes| editor= Haynes, William M. | date = 2016| title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 978-1-4987-5429-3}} {{refend}}

== Further reading == {{Commons category}} {{EB1911 poster|Acetone}} * [https://web.archive.org/web/20200318085127/http://sdsdata.org/244731 Acetone Safety Data Sheet (SDS)] * 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 * [https://www.nlm.nih.gov/toxnet/index.html Hazardous substances databank entry at the national library of medicine] * {{ICSC|0087|00}} * [https://www.cdc.gov/niosh/npg/npgd0004.html NIOSH Pocket Guide to Chemical Hazards] * {{SIDS|name=Acetone|id=67641}}

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