3-Pentanone:Uses, Synthesis and Hazards

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.

Synthesis

Carbonylation route

3-Pentanone 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.¹

Incompatibilities

Strong oxidizers, alkalis, mineral acids, (hydrogen peroxide + nitric acid).

Hazards

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

Reference

1.Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002 by Wiley-VCH, Wienheim.

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