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Revision as of 19:53, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475924415 of page Acetone for the Chem/Drugbox validation project (updated: '').  Latest revision as of 21:04, 23 December 2024 edit Pthalomidnight (talk | contribs)2 edits →Polymerisation: fixed typo: changed "polymers" to "polymerize" 
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{{short description|Organic compound ((CH3)2CO); simplest ketone}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{distinguish|Acetoin}}
{{for|the musical instrument company|Ace Tone}}
{{ou}}
{{Chembox {{Chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 427486157 | verifiedrevid = 477239274
| IUPACName = Acetone<ref>] lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.</ref>
| Reference = <ref>''Merck Index'', 11th Edition, '''58'''</ref>
| Reference = <ref>'']'', '''15th Ed.''' (2013), p. 13, '''65''', O'Neil: ].{{subscription required}}</ref>
| ImageFileL1 = Acetone-CRC-MW-ED-dimensions-2D.png
|ImageFileL1 = Acetone-CRC-MW-ED-dimensions-2D-Vector.svg
| ImageFileL1_Ref = {{chemboximage|correct|??}}
|ImageClassL1 = skin-invert
| ImageSizeL1 = 136
|ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Full structural formula of acetone with dimensions
|ImageSizeL1 = 136
| ImageFileR1 = Acetone-2D-skeletal.svg
|ImageNameL1 = Full structural formula of acetone with dimensions
| ImageFileR1_Ref = {{chemboximage|correct|??}}
|ImageFileR1 = Acetone-2D-skeletal.svg
| ImageSizeR1 = 101
|ImageClassR1 = skin-invert
| ImageNameR1 = Skeletal formula of acetone
|ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageFileL2 = Acetone-3D-balls.png
|ImageSizeR1 = 130
| ImageFileL2_Ref = {{chemboximage|correct|??}}
|ImageNameR1 = Skeletal formula of acetone
| ImageSizeL2 = 131
|ImageFileL2 = Acetone-3D-balls.png
| ImageNameL2 = Ball-and-stick model of acetone
|ImageFileL2_Ref = {{chemboximage|correct|??}}
| ImageFileR2 = Acetone-3D-vdW.png
|ImageSizeL2 = 131
| ImageFileR2_Ref = {{chemboximage|correct|??}}
|ImageNameL2 = Ball-and-stick model of acetone
| ImageSizeR2 = 106
|ImageFileR2 = Acetone-3D-vdW.png
| ImageNameR2 = Space-filling model of acetone
|ImageFileR2_Ref = {{chemboximage|correct|??}}
| SystematicName = Propan-2-one<ref>{{Cite web|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=180|title = Acetone – PubChem Public Chemical Database|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref>
|ImageSizeR2 = 106
| OtherNames = Dimethyl ketone<ref name = "Acetone">{{Cite web|url = http://webbook.nist.gov/cgi/cbook.cgi?ID=67-64-1|title = Acetone|work = NIST Chemistry WebBook|location = USA|publisher = National Institute of Standards and Technology}}</ref><br />
|ImageNameR2 = Space-filling model of acetone
β-Ketopropane<ref name = "Acetone" /><br />
|ImageFile3 = Sample of Acetone.jpg
Propanone<ref>{{Cite book
|ImageName3 = Sample of acetone
| isbn = 0444519947, 9780444519948
|PIN = Propan-2-one<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 723 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| pages = 92–94
|SystematicName = 2-Propanone
| last = Klamt
|OtherNames = {{plainlist|
| first = Andreas
* Acetonum ({{IPA|la|aˈkeːtonum}})
| title = COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design
* Dimethyl ketone<ref name=nist>{{nist|name=Acetone|id=C67641|access-date=2014-05-11|mask=FFFF|units=SI}}</ref>
| year = 2005
* Dimethyl ]
| publisher = Elsevier
* Ketone propane<ref name=NIOSH />
}}</ref><br />
2-Propanone<ref name = "Acetone" /><br /> * 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>
Dimethyl formaldehyde<ref>{{Cite book
* 2-Propanone<ref name=nist />
| title = Handbook of preservatives
* 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 = |url = https://archive.org/details/100mostimportant0000myer/page/4}}</ref>
| last1 = Ash
* Spirit of Saturn (archaic)<ref name=gorman1962 />
| first1 = Michael
| last2 = Ash
| first2 = Irene
| page = 369
| year = 2004
| publisher = Synapse Information Resources, Inc.
| isbn = 1890595667}}</ref>
| Section1 = {{Chembox Identifiers
| Abbreviations = DMK
| CASNo = 67-64-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 180
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
| 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(C)=O
| 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 |Section1 = {{Chembox Identifiers
| C = 3 |CASNo = 67-64-1
|CASNo_Ref = {{cascite|correct|CAS}}
| H = 6
| O = 1 |PubChem = 180
|ChemSpiderID = 175
| ExactMass = 58.041864814 g mol<sup>−1</sup>
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| Appearance = Colorless liquid
|UNII = 1364PS73AF
| Odor = Pungent, irritating, floral
|UNII_Ref = {{fdacite|correct|FDA}}
| Density = 0.791 g cm<sup>−3</sup><ref>{{Cite web|title = Acetone CHROMASOLV® Plus, for HPLC, ≥99.9%|url = http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=650501{{!}}SIAL&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC|publisher = Sigma-Aldrich|accessdate = 15 September 2011}}</ref>
|EINECS = 200-662-2
| MeltingPtKL = 178
|UNNumber = 1090
| MeltingPtKH = 180
|KEGG = D02311
| BoilingPtKL = 329
|KEGG_Ref = {{keggcite|correct|kegg}}
| BoilingPtKH = 330
| LogP = -0.042 |MeSHName = Acetone
|ChEBI = 15347
| VaporPressure = 24.46-24.60 kPa (at 20 °C)
|ChEBI_Ref = {{ebicite|correct|EBI}}
| pKa = 24.2
| pKb = -10.2 |ChEMBL = 14253
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| RefractIndex = 1.35900
|RTECS = AL3150000
| Viscosity = 0.3075 cP
|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
}} }}
| Section3 = {{Chembox Structure |Section2 = {{Chembox Properties
|C=3 | H=6 | O=1
| Coordination = Triagonal planar at C2
|Appearance = Colourless liquid
| MolShape = Dihedral at C2
|Odour = Pungent, fruity<ref name=smell />
| Dipole = 2.91 D
|Density = 0.7845 g/cm<sup>3</sup> (25 °C)<ref name=h1 />
|MeltingPtC = −94.9
|MeltingPt_ref=<ref name=h1>], p. 3.4</ref>
|MagSus = −33.8·10<sup>−6</sup> cm<sup>3</sup>/mol<ref>], p. 3.576</ref>
|BoilingPtC = 56.08
|BoilingPt_ref=<ref name=h1 />
|RefractIndex = 1.3588 (20 °C)<ref name=h1 />
|LogP = −0.24<ref>], 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
| Section4 = {{Chembox Thermochemistry
|19.16 (H<sub>2</sub>O)<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>
| DeltaHf = -250.03-(-248.77) kJ mol<sup>−1</sup>
|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>
| DeltaHc = -1.772 MJ mol<sup>−1</sup>
| Entropy = 200.4 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 125.45 J K<sup>−1</sup> mol<sup>−1</sup>
}} }}
|Solubility = Miscible<ref name=h1 />
| Section5 = {{Chembox Hazards
|SolubleOther = Miscible in ], ], ], ], ]<ref name=h1 />
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
|Viscosity = 0.306{{nbsp}}mPa·s (25&nbsp;°C)<ref>], p. 6.243</ref>
| GHSSignalWord = '''DANGER'''
|ThermalConductivity = 0.161{{nbsp}}W/(m·K) (25&nbsp;°C)<ref>], p. 6.254</ref>
| HPhrases = {{H-phrases|225|319|336}}
}}
| PPhrases = {{P-phrases|210|261|305+351+338}}
|Section3 = {{Chembox Structure
| EUIndex = 606-001-00-8
|Coordination = ] at C2
| EUClass = {{Hazchem F}} {{Hazchem Xi}}
|MolShape = Dihedral at C2
| RPhrases = {{R11}}, {{R36}}, {{R66}}, {{R67}}
|Dipole = 2.88 D<ref>], p. 9.60</ref>
| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S26}}
}}
| NFPA-F = 3
|Section4 = {{Chembox Thermochemistry
| NFPA-H = 1
|Thermochemistry_ref=<ref>], pp. 5.3, 5.67</ref>
| NFPA-R = 0
|DeltaHf = −248.4{{nbsp}}kJ/mol
| FlashPt = −17 °C
|DeltaHc = −1.79{{nbsp}}MJ/mol
| Autoignition = 465 °C
|Entropy = 199.8{{nbsp}}J/(mol·K)
| ExploLimits = 13.2–57.0%
|HeatCapacity = 126.3{{nbsp}}J/(mol·K)
| TLV-TWA = 500 ppm
}}
| TLV-STEL = 750 ppm
|Section5 = {{Chembox Hazards
| LD50 = >2000 mg/kg, oral (rat)
|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>], p. 15.13</ref>
|ExploLimits = 2.5–12.8%<ref name=ig />
|PEL = 1000{{nbsp}}ppm (2400{{nbsp}}mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0004}}</ref>
|REL = TWA 250{{nbsp}}ppm (590{{nbsp}}mg/m<sup>3</sup>)<ref name=NIOSH />
|IDLH = 2500{{nbsp}}ppm<ref name=NIOSH />
|TLV-C = 500 ppm<ref name=da />
|TLV-STEL = 250 ppm<ref name=da>], 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 />
}} }}
| Section6 = {{Chembox Related | Section6 = {{Chembox Related
|OtherCompounds = {{Unbulleted list
| OtherCpds = ]<br />
] | ]
| ]
| ]
| ]
| ]
}}
}} }}
}} }}

'''Acetone''' ('''2-propanone''' or '''dimethyl ketone''') is an ] with the ] {{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 ] ({{chem2|>C\dO}}). It is a colorless, highly ], and ] liquid with a characteristic pungent odour, very reminiscent of the smell of ]s.

Acetone is ] with ] and serves as an important ] in industry, home, and laboratory. About 6.7 million ]s were produced worldwide in 2010, mainly for use as a solvent and for production of ] and ], which are precursors to widely used ]s.<ref name=r1>, 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 ]. It serves as a solvent in household products such as ] and ]. It has ] (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 ] produce it in larger amounts. ]s that increase ] (acetone, ] and ]) in the blood are used to counter ] in children who suffer from ] 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 ], acetone was given many different names. They included "spirit of Saturn", which was given when it was thought to be a compound of ] and, later, "pyro-acetic spirit" and "pyro-acetic ester".<ref name=gorman1962>Mel Gorman, History of acetone (1600–1850), 1962</ref>

Prior to the name "acetone" being coined by ] chemists (see ]), it was named "mesit" (from the Greek μεσίτης, meaning mediator) by ], who also claimed that ] consisted of mesit and ].<ref>C. Reichenbach (1834) (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 ] and ] which were first synthesised from acetone.

Unlike many compounds with the ''acet-'' prefix which have a 2-carbon chain, acetone has a 3-carbon chain. That has caused confusion because there cannot be a ] with 2 carbons. The prefix refers to acetone's relation to ] (''acetum'' in ], also the source of the words "acid" and "acetic"), rather than its chemical structure.<ref name=chemtymology />

== History ==
Acetone was first produced by ] in 1606 by distillation of ].<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 ] and German chemist ] determined the ] for acetone.<ref>Dumas, J. (1832) (On pyro-acetic spirit), ''Annales de Chimie et de Physique'', 2nd series, '''49''' : 208–210.</ref><ref>Liebig, Justus (1832) (On compounds produced by the action of ethylene and acetic spirit), ''Annales de Chimie et de Physique'', 2nd series, '''49''' : 146–204 ().</ref> In 1833, French chemists ] and ] decided to name acetone by adding the suffix ''-one'' to the stem of the corresponding acid (viz, ]) just as a similarly prepared product of what was then confused with ] was named margarone.<ref>Bussy, Antoine (1833) (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 .</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 ] realized that acetone was methyl ];<ref>Williamson, A. W. (1852) ''Journal of the Chemical Society'', '''4''' : 229–239; ().</ref> the following year, the French chemist ] concurred.<ref>Gerhardt, Charles (1853) (Research on anhydrous organic acids), ''Annales de Chimie et de Physique'', 3rd series, '''37''' : 285–342; </ref> In 1865, the German chemist ] published the modern structural formula for acetone.<ref>Kekulé, Auguste (1865) ''Bulletin de la Société chimique de Paris'', '''1''' : 98–110; ().</ref><ref>Kekulé, Auguste (1866) (Investigations into aromatic compounds), ''Annalen der Chemie und Pharmacie'', '''137''' : 129–196; ().</ref> Johann Josef Loschmidt had presented the structure of acetone in 1861,<ref>Loschmidt, J. (1861) Vienna, Austria-Hungary: Carl Gerold's Sohn.</ref> but his privately published booklet received little attention. During ], ] developed the process for industrial production of acetone (Weizmann Process).<ref> 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 ] 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 ] and ]. The largest producer of acetone is ], owning 17% of the world's capacity, with also significant capacity (7–8%) by ], ] and ] in 2010.<ref name=CEH /> INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in ] (Belgium). ] of acetone in summer 2011 was 1100–1250 USD/tonne in the United States.<ref name=icispricing_132> {{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 ]. Approximately 83% of acetone is produced via the ];<ref name=Ullmann /> as a result, acetone production is tied to phenol production. In the cumene process, ] is ] with propylene to produce ], which is ] by air to produce ] and acetone:
:]
Other processes involve the direct oxidation of propylene (]), or the ] of propylene to give ], which is oxidized (dehydrogenated) to acetone.<ref name = Ullmann />

=== Older methods ===
Previously, acetone was produced by the ] of ]s, for example ] in ].
:<chem>Ca(CH3COO)2 -> CaO_{(s)}{} + CO2_{(g)}{} + (CH3)2CO v</chem>
After that time, during ], acetone was produced using ] with '']'' ], which was developed by ] (later the first president of ]) 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=9780313337581 |page=5}}</ref> in the preparation of ].<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 ==
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<sup>−3</sup>&nbsp;M<sup>−1</sup>

Like most ketones, acetone exhibits the ] in which the nominal ] structure {{chem2|(CH3)2C\dO}} of acetone itself is in equilibrium with the ] 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>
:]

In the presence of suitable ]s, two acetone molecules also combine to form the compound ] {{chem2|(CH3)C\dO(CH2)C(OH)(CH3)2}}, which on ] gives ] {{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 ] 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 ] and hard acids like ]. 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 = ]|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 ] of pure acetone is 1980&nbsp;°C.<ref>], p. 15.49</ref>
=== Polymerisation ===
At its melting point (−96&nbsp;°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 ] 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>

== Natural occurrence ==
Humans exhale several milligrams of acetone per day. It arises from decarboxylation of ].<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 ] of ]. Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ], in which acetone is formed in body tissue. Certain health conditions, such as alcoholism and diabetes, can produce ], uncontrollable ketosis that leads to a sharp, and potentially fatal, increase in the acidity of the blood. Since it is a byproduct of fermentation, acetone is a byproduct of the distillery industry.<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 ] via ] to ] and ], and ultimately ]/energy, or by a different pathway via ] to ], ], ] (usable for energy) and ].<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|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 ], a precursor to ].<ref name=r1 />
===Chemical intermediate ===
Acetone is used to ] ]. It begins with the initial conversion of acetone to ] via reaction with ] (HCN):
:<chem>(CH3)2CO + HCN -> (CH3)2C(OH)CN</chem>
In a subsequent step, the ] is ] to the unsaturated ], which is ]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 is a component of many polymers such as ]s, ]s, and ]s. The synthesis involves the ] of acetone with ]:
:<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 ] and ]. These products arise via an initial ] to give ].<ref name=Ullmann />
:<chem>2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3</chem>
Condensation with acetylene gives ], precursor to synthetic ]s and ]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>
=== Solvent ===
Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning ], cleaning tools used with it, and dissolving two-part ] and ] before they harden. It is used as one of the volatile components of some ]s and ]es. As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting or ], and to remove ] 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 ], acetone is used extensively as a solvent for the safe transportation and storage of ], which cannot be safely ] as a pure compound. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One litre of acetone can dissolve around 250 ]s of acetylene at a pressure of {{convert|10|bar|MPa}}.<ref> {{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> {{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 ] and as a ] in ].<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 ] in some ]s.<ref>, FDA/Center for Drug Evaluation and Research</ref>{{Update inline|date=March 2024}}
==== Lab and domestic solvent ====
A variety of ]s employ acetone as a ], ], e.g. the ].

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 ] 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 ] use, acetone dries only via bulk displacement and dilution. It forms no ]s with water (see ]).<ref>. Solvent—recycling.com. Retrieved on 2012-11-26.</ref> Acetone also removes certain ] from ]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>

Acetone freezes well below −78&nbsp;°C. An acetone/dry ice mixture ] 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>
]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 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 ====
] 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 ], acetone helps find ] in fatty tissues (such as the ]) for ].<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 ]s to ] dry skin. Common agents used today for chemical peeling are ], ], ], 30% ] in ], and ] (TCA). Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting. Acetone, ], or a combination of these agents was used in this process.<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 ] effects in animal models of ], 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=]|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 ] 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>

== Safety ==
Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a ]; in larger amounts, fuel evaporation causes incomplete combustion and a ]. When hotter than acetone's ] of {{convert|-20|C|F}}, air mixtures of 2.5{{nbh}}12.8% acetone (by volume) may explode or cause a ]. Vapors can flow along surfaces to distant ignition sources and flash back.

] 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 ] 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 ] and ] mixtures.<ref>], p. 16.3</ref> It may also explode when mixed with ] in the presence of a base.<ref>], p. 16.5</ref>{{clarify|date=October 2023}} When oxidized without combustion, for example with ], acetone may form ], a highly ] ]. Acetone peroxide may be formed accidentally, e.g. when waste ] 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>. 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 ], a ], or a concern for chronic ] 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 ] (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 ] 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 (LD<sub>50</sub>) is 3&nbsp;g/kg, and by inhalation (LC<sub>50</sub>) is 44&nbsp;g/m<sup>3</sup> over 4 hours.<ref> {{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">, 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 ] (primarily into ] and ].<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 ] (EPA) removed acetone from the list of ]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 ].<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>. 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 '']'' lander on ] ]{{'s}} surface, measurements by the COSAC and Ptolemy instruments revealed sixteen ]s, four of which were seen for the first time on a comet, including ], acetone, ], and ].<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=]|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 = ] | edition = 97th | publisher = ] | isbn = 978-1-4987-5429-3}}

=== Further reading ===
{{Commons category|Acetone}}
* {{ICSC|0087|00}}
*
*
* {{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 , , , of acetone

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

{{Authority control}}

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