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.
UsesEdit
3-Pentanone is primarily used as starting material in chemical synthesis. A major application is in the industrial synthesis of vitamin E.<ref>Template:Cite journal</ref><ref name=Ullmann>Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002 by Wiley-VCH, Wienheim. {{#invoke:doi|main}}</ref> 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.
SynthesesEdit
Ketonic decarboxylation routeEdit
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.<ref>Template:Cite book</ref>
Carbonylation routeEdit
It can also be prepared by combining ethylene, CO, and H2.<ref name=Ullmann/> 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<ref> Template:Cite journal </ref> 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.<ref>Template:Cite journal</ref>
SafetyEdit
The TLV value for 3-pentanone is 200 ppm (705 mg/m3).<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>Chemicals & Laboratory Equipment, Material Safety Data Sheet for 3-pentanone Template:Webarchive, ScienceLab.com, updated 11/06/2008</ref>