Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Acetone: Difference between pages

{{short description|Organic compound ((CH3)2CO); simplest ketone}}

{{distinguish|Acetoin}}

{{for|the musical instrument company|Ace Tone}}

| 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

|ImageFileL1_Ref = {{chemboximage|correct|??}}

|ImageSizeL1 = 136

|ImageNameL1 = Full structural formula of acetone with dimensions

|ImageFileR1 = Acetone-2D-skeletal.svg

|ImageFileR1_Ref = {{chemboximage|correct|??}}

|ImageSizeR1 = 130

|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<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|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>

* 2-Propanone<ref name=nist/>

* 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<ref name=smell/>

|Density = 0.7845 g/cm³ (25 °C)<ref name=h1/>

|MeltingPtC = −94.9

|MeltingPt_ref=<ref name=h1>[[#Haynes|Haynes]], p. 3.4</ref>

|MagSus = −33.8·10⁻⁶ cm³/mol<ref>[[#Haynes|Haynes]], p. 3.576</ref>

|BoilingPtC = 56.08

|BoilingPt_ref=<ref name=h1/>

|RefractIndex = 1.3588 (20 °C)<ref name=h1/>

|LogP = −0.24<ref>[[#Haynes|Haynes]], p. 5.173</ref>

|VaporPressure = {{Unbulleted list

| 9.39{{nbsp}}kPa (0&nbsp;°C)

| 30.6{{nbsp}}kPa (25&nbsp;°C)

| 374{{nbsp}}kPa (100&nbsp;°C)

| 2.8{{nbsp}}MPa (200&nbsp;°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}}</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 = 0.306{{nbsp}}mPa·s (25&nbsp;°C)<ref>[[#Haynes|Haynes]], p. 6.243</ref>

|ThermalConductivity = 0.161{{nbsp}}W/(m·K) (25&nbsp;°C)<ref>[[#Haynes|Haynes]], p. 6.254</ref>

}}

|Section3 = {{Chembox Structure

|Coordination = [[Trigonal planar]] at C2

|MolShape = Dihedral at C2

|Dipole = 2.88 D<ref>[[#Haynes|Haynes]], p. 9.60</ref>

}}

|Section4 = {{Chembox Thermochemistry

|Thermochemistry_ref=<ref>[[#Haynes|Haynes]], pp. 5.3, 5.67</ref>

|DeltaHf = −248.4{{nbsp}}kJ/mol

|DeltaHc = −1.79{{nbsp}}MJ/mol

|Entropy = 199.8{{nbsp}}J/(mol·K)

|HeatCapacity = 126.3{{nbsp}}J/(mol·K)

}}

|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|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|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&nbsp;h)<ref name=IDLH/>

|LCLo = 45,455{{nbsp}}ppm (mouse, 1&nbsp;h)<ref name=IDLH/>

|OtherCompounds = {{Unbulleted list

| [[Butanone]]

| [[Isopropyl alcohol]]

| [[Formaldehyde]]

| [[Urea]]

| [[Carbonic acid]]

}}

'''Acetone''' ('''2-propanone''' or '''dimethyl ketone''') is an [[organic compound]] with the [[chemical formula|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|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 the simplest and smallest [[ketone]] ({{chem2|>C\dO}}). It is a colorless, highly [[Volatile organic compound|volatile]] and [[flammable]] liquid with a characteristic pungent odor.

Acetone is [[miscibility|miscible]] with [[properties of water|water]] and serves as an important [[organic solvent]] in industry, home, and laboratory. About 6.7 million [[tonne]]s 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 [[plastic]]s.<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#Nail polish remover|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/|url-status=dead}}</ref>

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with [[diabetic ketoacidosis]] produce it in larger amounts. [[Ketogenic diet]]s that increase [[ketone bodies]] (acetone, [[β-hydroxybutyric acid]] and [[acetoacetic acid]]) in the blood are used to counter [[Epilepsy|epileptic attacks]] in children who suffer from [[refractory disease|refractory]] 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. Those names include 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 "acetone" name given by [[Antoine Bussy]], it was named "mesit" (from the Greek μεσίτης, meaning mediator) by [[Carl Reichenbach]] who also claimed 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.

Unlike many compounds with the ''acet-'' prefix having a 2-carbon chain, acetone has a 3-carbon chain which has caused confusion since there cannot be a [[ketone]] with 2 carbons. The prefix refers to acetone's relation to [[vinegar]] (''acetum'' in [[Latin]], also the source of the words "acid" and "acetic"), rather than its chemical structure.<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, 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 "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, 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,"] ''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 process for industrial production of acetone (Weizmann Process).<ref>[http://www.chemistryexplained.com/Va-Z/Weizmann-Chaim.html Chaim Weizmann] chemistryexplained.com</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|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 |url-status = dead}}</ref> followed by [[Taiwan]] and [[PRC|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] {{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>

===Current method===

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 [[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 (dehydrogenated) 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]].

:<chem>Ca(CH3COO)2 -> CaO_{(s)}{} + CO2_{(g)}{} + (CH3)2CO v</chem>

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|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/>

==Chemical properties==

The [[flame temperature]] of pure acetone is 1980&nbsp;°C.<ref>[[#Haynes|Haynes]], p. 15.49</ref>

Like most ketones, acetone exhibits the [[keto–enol tautomerism]] in which the nominal [[ketone|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>

:[[File:Acetone KetoEnol.svg|300px]]

In the presence of suitable [[catalyst]]s, two acetone molecules also combine to form the compound [[diacetone alcohol]] {{chem2|(CH3)C\dO(CH2)C(OH)(CH3)2}}, which on [[Dehydration reaction|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 [[iodine|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>

===Polymerisation===

One might expect acetone to also form [[polymer]]s and (possibly [[cyclic compound|cyclic]]) [[oligomer]]s of two types. In one type, units could be acetone molecules linked by [[ether]] bridges {{chem2|\sO\s}} derived from opening of the double bond, to give a [[polyketal]]-like (PKA) chain {{chem2|[\sO\sC(CH3)2\s]_{''n''} }}. The other type could be obtained through repeated aldol condensation, with one molecule of water removed at each step, yielding a [[poly(methylacetylene)]] (PMA) chain {{chem2|[\sCH\dC(CH3)\s]_{''n''} }}.<ref name=cata1996/>

The conversion of acetone to a polyketal (PKA) would be analogous to the formation of [[paraformaldehyde]] from [[formaldehyde]], and of [[trithioacetone]] from [[thioacetone]]. In 1960, Soviet chemists observed that the thermodynamics of this process is unfavourable for liquid acetone, so that it (unlike thioacetone and formol) is not expected to polymerise spontaneously, even with catalysts. However, they observed that the thermodynamics became favourable for crystalline solid acetone at the melting point (−96&nbsp;°C). They claimed to have obtained such a polymer (a white elastic solid, soluble in acetone, stable for several hours at room temperature) by depositing vapor of acetone, with some [[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> In 1962, [[Wasaburo Kawai]] reported the synthesis of a similar product, from liquid acetone cooled to −70 to −78&nbsp;°C, using [[N-Butyllithium|''n''-butyllithium]] or [[triethylaluminium]] as catalysts. He claimed that the [[infrared]] [[absorption spectrum]] showed the presence of {{chem2|\sO\s}} linkages but no {{chem2|C\dO}} groups.<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> However, conflicting results were obtained later by other investigators.<ref name=cata1996/>

[[File:Acetone-polymerisation.svg|thumb|Structure of possible acetone polymer]]

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

==Natural occurrence==

Humans exhale several milligrams of acetone per day. It arises from 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 |page=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>

===Metabolism===

Acetone 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 |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 |url-status=dead}}</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}}</ref>

==Uses==

===Industrial===

About a third of the world's acetone is used as a solvent, and a quarter is consumed as [[acetone cyanohydrin]], a precursor to [[methyl methacrylate]].<ref name=r1/>

====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 [[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 or [[soldering]], and to remove [[flux (metallurgy)#Rosin fluxes|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 [[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 litre of acetone can dissolve around 250 [[litre]]s 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 [[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| 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 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>{{Update inline|date=March 2024}}

====Chemical intermediate====

Acetone is used to [[organic synthesis|synthesize]] [[methyl methacrylate]]. It begins with the initial conversion of acetone to [[acetone cyanohydrin]] via reaction with [[hydrogen cyanide]] (HCN):

:<chem>(CH3)2CO + HCN -> (CH3)2C(OH)CN</chem>

In a subsequent step, the [[nitrile]] is [[hydrolysis|hydrolyzed]] to the unsaturated [[amide]], which is [[ester]]ified:

:<chem>(CH3)2C(OH)CN + CH3OH -> CH2=C(CH3)CO2CH3 + NH3</chem>

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]]:

:<chem>(CH3)2CO + 2 C6H5OH -> (CH3)2C(C6H4OH)2 + H2O</chem>

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/>

:<chem>2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3</chem>

Condensation with acetylene gives [[2-methylbut-3-yn-2-ol]], precursor to synthetic [[terpene]]s and [[terpenoid]]s.<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>

===Laboratory===

====Chemistry====

A variety of [[organic reaction]]s employ acetone as a [[chemical polarity|polar]], [[aprotic solvent]]. It is critical in 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 resides 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 [[desiccant|desiccatory]] use, acetone dries only via bulk displacement and dilution. It forms no [[azeotrope]]s 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 freezes well below −78&nbsp;°C. An acetone/dry ice mixture [[cooling bath|cools]] many a 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=9780935702767 |page=310}}</ref>

====Physics====

Under ultraviolet light, acetone fluoresces. Fluid flow experiments use its vapor as a [[tracer (fluids)|tracer]].<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>

====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>

Acetone also removes certain [[staining|stains]] from [[microscope slide]]s.<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>

===Medical===

Dermatologists use acetone with alcohol for acne treatments to [[chemical peel|chemically peel]] dry skin. Common agents used today 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. Acetone, [[hexachlorophene]], or a combination of these agents was used in this process.<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>

===Domestic and other niche uses===

[[Make-up artist]]s 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 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 ten minutes. This creates a vapor of acetone in the container. The acetone condenses evenly all over the part, causing the surface to soften and liquefy. Surface tension then smooths the semi-liquid plastic. When the part is removed from the chamber, the acetone component evaporates leaving a glassy-smooth part free of striation, patterning, and visible layer edges, common features in untreated 3D printed parts.<ref>[http://www.instructables.com/id/Quality-Finish-3D-Prints-with-Acetone/?ALLSTEPS "Quality Finish 3D Prints with Acetone"] instructables.com</ref>

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

==Safety==

Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a [[oxidizing flame|dull blue flame]]; in larger amounts, fuel evaporation causes incomplete combustion and a [[reducing flame|bright yellow flame]]. When hotter than 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 [[flashover|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 and accidental ignition is rare.<ref name=msds/> Acetone's [[auto-ignition temperature]] is the 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&nbsp;°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 acid|nitric]] and [[sulfuric acid]] mixtures.<ref>[[#Haynes|Haynes]], p. 16.3</ref> It may also explode when mixed with [[chloroform]] in the presence of a base.<ref>[[#Haynes|Haynes]], p. 16.5</ref>{{clarify|date=October 2023}} When oxidized without combustion, for example with [[hydrogen peroxide]], acetone may form [[acetone peroxide]], a highly [[Chemical stability|unstable]] [[primary explosive]]. Acetone peroxide may be formed accidentally, e.g. when waste [[hydrogen peroxide|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 | url-status = dead}}</ref> Acetone is not currently 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. Acetone has been rated as a [[generally recognized as safe]] (GRAS) substance when present in drinks, baked foods, desserts, and preserves at concentrations ranging from 5 to 8&nbsp;mg/L.<ref name= sids/>

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

===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.{{clarify|date=October 2023}} 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/>

===EPA classification===

In 1995, the [[United States Environmental Protection Agency]] (EPA) removed acetone from the list of [[volatile organic compound]]s. 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 (United States)|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>

==Extraterrestrial occurrence==

On 30 July 2015, scientists reported that upon the first touchdown of the ''[[Philae (spacecraft)|Philae]]'' lander on [[comet]] [[67P/Churyumov–Gerasimenko|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|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|url-status=dead|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 (journal)|Science]]|volume=349|issue=6247|page=493|doi=10.1126/science.aac5116|bibcode=2015Sci...349..493B|pmid=26228139|doi-access=free}}</ref>

==References==

{{reflist|30em}}

===Common sources===

*{{cite book|ref= Haynes| editor= Haynes, William M. | date = 2016| title = [[CRC Handbook of Chemistry and Physics]] | edition = 97th | publisher = [[CRC Press]] | isbn = 9781498754293}}

===Further reading===

{{Commons category|Acetone}}

* {{ICSC|0087|00}}

* [https://www.cdc.gov/niosh/npg/npgd0004.html NIOSH Pocket Guide to Chemical Hazards]

* [https://web.archive.org/web/20200318085127/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] {{Webarchive|url=https://web.archive.org/web/20181204125919/https://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?.%2Ftemp%2F~EQIVt8%3A1 |date=2018-12-04 }}

* {{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:Alkanones]]

[[Category:Ketone solvents]]

[[Category:Fuel additives]]

[[Category:Excipients]]

[[Category:Commodity chemicals]]

[[Category:GABAA receptor positive allosteric modulators]]

[[Category:Anticonvulsants]]