3-Pentanone

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title: "3-Pentanone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["ketone-solvents", "pentanones"] topic_path: "general/ketone-solvents" source: "https://en.wikipedia.org/wiki/3-Pentanone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477220092 | Name = 3-Pentanone | ImageFile = 3-Pentanone structure.svg | ImageSize = 140px | ImageName = Skeletal formula of 3-pentanone | ImageFile1 = 3-Pentanone-3D-balls.png | ImageSize1 = 160px | ImageName1 = Ball-and-stick model of 3-pentanone | PIN = Pentan-3-one | OtherNames = Diethyl ketone, diethylketone, 3-pentanone, dimethyl acetone, propione, DEK, metacetone, methacetone, ethyl ketone fraction |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 7016 | InChI = 1/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 | InChIKey = FDPIMTJIUBPUKL-UHFFFAOYAJ | ChEMBL_Ref = | ChEBI_Ref = | ChEBI = 87755 | PubChem = 7288 | EC_number = 202-490-3 | ChEMBL = 45315 | RTECS = SA8050000 | UNNumber = 1156 | StdInChI_Ref = | StdInChI = 1S/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 | StdInChIKey_Ref = | StdInChIKey = FDPIMTJIUBPUKL-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 96-22-0 | UNII_Ref = | UNII = 9SLZ98M9NK | SMILES = O=C(CC)CC |Section2={{Chembox Properties | C=5 | H=10 | O=1 | Density = 0.81 g/cm3 at 20 °C | MeltingPtC = -39 | MeltingPt_ref = | BoilingPtC = 102 | BoilingPt_ref = | Solubility = 35 g/L | Appearance = Colorless liquid | Odor = Acetone-like | VaporPressure = 35 mmHg | MagSus = −58.14·10−6 cm3/mol |Section7={{Chembox Hazards | AutoignitionPtC = 425 | FlashPtC = 12.78 | PEL = none | ExploLimits = 1.6–6.4% | IDLH = N.D. | REL = TWA 200 ppm (705 mg/m3) | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases =

3-Pentanone (also known as diethyl ketone) is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.

Uses

3-Pentanone is primarily used as starting material in chemical synthesis. A major application is in the industrial synthesis of vitamin E. It has also been used in the synthesis of Oseltamivir (Tamiflu).

3-Pentanone itself finds some use as a specialty solvent in paint, although it is less common than butanone.

Syntheses

Ketonic decarboxylation route

3-Pentanone is produced by ketonic decarboxylation of propanoic acid using metal oxide catalysts: :2 CH3CH2CO2H → (CH3CH2)2CO + CO2 + H2O

in the laboratory, the reaction can be conducted in a tube furnace.

Carbonylation route

It can also be prepared by combining ethylene, CO, and H2. When the reaction is catalyzed by dicobalt octacarbonyl, water can be used as a source of hydrogen. A proposed intermediate is the ethylene-propionyl species [CH3C(O)Co(CO)3(ethylene)] which undergoes a migratory insertion to form [CH3COCH2CH2Co(CO)3]. The required hydrogen arises from the water shift reaction. For details, see | 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 H2O | journal=Bulletin of the Chemical Society of Japan | year= 1981 | volume = 54 | issue = 7| pages= 2089–2092 | doi =10.1246/bcsj.54.2089 | doi-access = free If the water shift reaction is not operative, the reaction affords a polymer containing alternating carbon monoxide and ethylene units. Such aliphatic polyketones are more conventionally prepared using palladium catalysts.

Safety

The TLV value for 3-pentanone is 200 ppm (705 mg/m3).

References

References

  1. {{GESTIS
  2. {{PGCH. 0212
  3. (6 December 2022). "100 Years of Vitamin E: From Discovery to Commercialization". European Journal of Organic Chemistry.
  4. 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
  5. Furniss, Brian. (1996). "Vogel's Textbook of Practical Organic Chemistry". Longman Science & Technical.
  6. J. Liu. (2004). "The Complete Delineation of the Initiation, Propagation, and Termination Steps of the Carbomethoxy Cycle for the Carboalkoxylation of Ethene by Pd–Diphosphane Catalysts". [[Angew. Chem. Int. Ed.]].
  7. link. (2010-01-02 , ScienceLab.com, updated 11/06/2008)

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ketone-solventspentanones