| Revision as of 18:01, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465357996 of page 3-Pentanone for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 11:55, 22 July 2024 edit Project Osprey (talk | contribs)Extended confirmed users9,963 edits ref |
| Line 1: |
Line 1: |
|
|
{{Chembox |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
|
| Verifiedfields = changed |
|
{{chembox |
|
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 443349552 |
|
| verifiedrevid = 477220092 |
|
| Name = 3-Pentanone |
|
| Name = 3-Pentanone |
|
| ImageFile = 3-Pentanone.png |
|
| ImageFile = 3-Pentanone structure.svg |
|
| ImageSize = 140px |
|
| ImageSize = 140px |
|
| ImageName = Skeletal formula of 3-pentanone |
|
| ImageName = Skeletal formula of 3-pentanone |
|
| ImageFile1 = 3-Pentanone-3D-balls.png |
|
| ImageFile1 = 3-Pentanone-3D-balls.png |
|
| ImageSize1 = 160px |
|
| ImageSize1 = 160px |
|
| ImageName1 = Ball-and-stick model of 3-pentanone |
|
| ImageName1 = Ball-and-stick model of 3-pentanone |
|
|
| PIN = Pentan-3-one <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
|
| ImageName = 3-Pentanone |
|
|
⚫ |
| OtherNames = Diethyl ketone, diethylketone, 3-pentanone, dimethyl acetone, propione, DEK, metacetone, methacetone, ethyl ketone fraction |
|
| IUPACName = Pentan-3-one |
|
|
⚫ |
|Section1={{Chembox Identifiers |
| ⚫ |
| OtherNames = diethyl ketone, diethylketone, 3-pentanone, dimethyl acetone, propione, DEK, metacetone, methacetone |
|
|
⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
| ⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
| ChemSpiderID = 7016 |
|
| ChemSpiderID = 7016 |
|
| InChI = 1/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 |
|
| InChI = 1/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 |
|
| InChIKey = FDPIMTJIUBPUKL-UHFFFAOYAJ |
|
| InChIKey = FDPIMTJIUBPUKL-UHFFFAOYAJ |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEBI = 87755 |
|
|
| PubChem = 7288 |
|
|
| EC_number = 202-490-3 |
|
| ChEMBL = 45315 |
|
| ChEMBL = 45315 |
|
|
| RTECS = SA8050000 |
|
|
| UNNumber = 1156 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 |
|
| StdInChI = 1S/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 |
| Line 26: |
Line 31: |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 96-22-0 |
|
| CASNo = 96-22-0 |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = 9SLZ98M9NK |
|
| UNII = 9SLZ98M9NK |
|
| SMILES = O=C(CC)CC |
|
| SMILES = O=C(CC)CC |
|
⚫ |
}} |
|
⚫ |
|Section2={{Chembox Properties |
|
⚫ |
| C=5 | H=10 | O=1 |
|
|
| Density = 0.81 g/cm<sup>3</sup> at 20 °C<ref name=GESTIS/> |
|
⚫ |
| MeltingPtC = -39 |
|
|
| MeltingPt_ref = <ref name=GESTIS/> |
|
|
| BoilingPtC = 102 |
|
|
| BoilingPt_ref = <ref name=GESTIS/> |
|
|
| Solubility = 35 g/L<ref name=GESTIS>{{GESTIS|ZVG=13610}}</ref> |
|
|
| Appearance = Colorless liquid<ref name=PGCH/> |
|
⚫ |
| Odor = Acetone-like<ref name=GESTIS/> |
|
|
| VaporPressure = 35 mmHg<ref name=PGCH/> |
|
|
| MagSus = -58.14·10<sup>−6</sup> cm<sup>3</sup>/mol |
|
⚫ |
}} |
|
⚫ |
|Section7={{Chembox Hazards |
|
|
| AutoignitionPtC = 425 |
|
|
| FlashPtC = 12.78 |
|
|
| PEL = none<ref name=PGCH>{{PGCH|0212}}</ref> |
|
|
| ExploLimits = 1.6%-6.4%<ref name=PGCH/> |
|
|
| IDLH = N.D.<ref name=PGCH/> |
|
|
| REL = TWA 200 ppm (705 mg/m<sup>3</sup>)<ref name=PGCH/> |
|
|
| GHSPictograms = {{GHS02}}{{GHS07}} |
|
|
| GHSSignalWord = Danger |
|
|
| HPhrases = {{H-phrases|225|335|336}} |
|
|
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|271|280|303+361+353|304+340|312|370+378|403+233|403+235|405|501}} |
|
|
}} |
|
}} |
|
}} |
| ⚫ |
| Section2 = {{Chembox Properties |
|
| ⚫ |
| C=5|H=10|O=1 |
|
|
| Density = 0.815 g/cm³ |
|
| ⚫ |
| MeltingPtC = -39 |
|
|
| BoilingPt = 100–102 °C |
|
|
| Solvent = other solvents |
|
|
| SolubleOther = water: 50 g/L (20 °C) |
|
| ⚫ |
| Odor = Acetone-like |
|
|
|
|
|
|
|
'''3-Pentanone''' (also known as '''diethyl ketone''') is a simple, symmetrical dialkyl ketone. It is a colorless liquid ] with an odor like that of ]. It is soluble in about 25 parts water, but miscible with organic solvents. |
| ⚫ |
}} |
|
|
|
|
| ⚫ |
| Section7 = {{Chembox Hazards |
|
|
|
==Uses== |
|
| Autoignition = 425 °C |
|
|
|
3-Pentanone is primarily used as starting material in chemical synthesis. A major application is in the industrial synthesis of ].<ref>{{cite journal |last1=Müller |first1=Marc-André |last2=Schäfer |first2=Christian |last3=Litta |first3=Gilberto |last4=Klünter |first4=Anna-Maria |last5=Traber |first5=Maret G. |last6=Wyss |first6=Adrian |last7=Ralla |first7=Theo |last8=Eggersdorfer |first8=Manfred |last9=Bonrath |first9=Werner |title=100 Years of Vitamin E: From Discovery to Commercialization |journal=European Journal of Organic Chemistry |date=6 December 2022 |volume=2022 |issue=45 |doi=10.1002/ejoc.202201190|url=https://pure.rug.nl/ws/files/373357775/100_Years_of_Vitamin_E.pdf }}</ref><ref name=Ullmann>Hardo Siegel, Manfred Eggersdorfer "Ketones" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, 2002 by Wiley-VCH, Wienheim. {{doi|10.1002/14356007.a15_077}}</ref> It has also been used in the ] (Tamiflu). |
| ⚫ |
}} |
|
|
|
|
|
|
3-Pentanone itself finds some use as a specialty solvent in paint, although it is less common than ]. |
|
|
|
|
|
==Syntheses== |
|
|
|
|
|
===Ketonic decarboxylation route=== |
|
|
3-Pentanone is produced by ] of ] using metal oxide catalysts: |
|
|
:2 CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>H → (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>CO + CO<sub>2</sub> + H<sub>2</sub>O |
|
|
|
|
|
in the laboratory, the reaction can be conducted in a ].<ref>{{cite book|author=Furniss, Brian|author2=Hannaford, Antony|author3=Smith, Peter|author4= Tatchell, Austin|name-list-style=amp|title=Vogel's Textbook of Practical Organic Chemistry|edition=5th|year=1996|publisher=Longman Science & Technical|location=London|isbn=9780582462366|page=|url=https://archive.org/details/TextbookOfPracticalOrganicChemistry5thEd}}</ref> |
|
|
|
|
|
===Carbonylation route=== |
|
|
It can also be prepared by combining ], CO, and H<sub>2</sub>.<ref name=Ullmann/> When the reaction is catalyzed by ], water can be used as a source of hydrogen. A proposed intermediate is the ethylene-propionyl species which undergoes a ] to form . The required hydrogen arises from the ]. For details, see<ref> |
|
|
{{cite journal |
|
|
| author = Murata K. |
|
|
| author2 = Matsuda A. |
|
|
| title = Application of Homogeneous Water-Gas Shift Reaction III Further Study of the Hydrocarbonylation – A highly Selective Formation of Diethyl Keton from Ethene, CO and H<sub>2</sub>O |
|
|
| journal=] |
|
|
| year= 1981 |
|
|
| volume = 54 |
|
|
| issue = 7| pages= 2089–2092 |
|
|
| doi =10.1246/bcsj.54.2089 | doi-access = free |
|
}} |
|
}} |
|
|
</ref> |
|
|
If the water shift reaction is not operative, the reaction affords a polymer containing alternating carbon monoxide and ethylene units. Such aliphatic ]s are more conventionally prepared using ] catalysts.<ref>{{cite journal | author = J. Liu | author2 = B.T. Heaton | author3 = J.A. Iggo | author4 = R. Whyman | name-list-style = amp | journal = ] | year = 2004 | volume = 43 | pages = 90–94 | doi = 10.1002/anie.200352369 | title = The Complete Delineation of the Initiation, Propagation, and Termination Steps of the Carbomethoxy Cycle for the Carboalkoxylation of Ethene by Pd–Diphosphane Catalysts| issue = 1 | pmid = 14694480 }}</ref> |
|
|
|
|
|
==Safety== |
|
|
The ] value for 3-pentanone is 200 ppm (705 mg/m<sup>3</sup>).<ref name=Ullmann/> 3-pentanone can be hazardous if it comes in contact with the skin or eyes, and can cause irritation of the skin and redness, watering, and itching of the eyes. This chemical can also cause nervous system or organ damage if ingested. Although considered stable, 3-pentanone is extremely flammable if exposed to flame, sparks, or another source of heat. For safety, it should be stored in a flammable materials cabinet away from heat or sources of ignition, preferably in a cool, well-ventilated area.<ref name=MSDS> {{Webarchive|url=https://web.archive.org/web/20100102190642/http://sciencelab.com/xMSDS-3_Pentanone-9926426 |date=2010-01-02 }}, ScienceLab.com, updated 11/06/2008</ref> |
|
|
|
|
|
==See also== |
|
|
* ] |
|
|
* ] |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
|
|
|
|
{{DEFAULTSORT:Pentanone, 3-}} |
|
|
] |
|
|
] |