3-Pentanone

3-Pentanone
IUPAC name Pentan-3-one
Other names diethyl ketone, diethylketone, 3-pentanone, dimethyl acetone, propione, DEK, metacetone, methacetone
Identifiers
CAS number	96-22-0 Y
ChemSpider	7016 Y
UNII	9SLZ98M9NK Y
ChEMBL	CHEMBL45315 Y
Jmol-3D images	Image 1
SMILES O=C(CC)CC
InChI InChI=1S/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 Y Key: FDPIMTJIUBPUKL-UHFFFAOYSA-N Y InChI=1/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3 Key: FDPIMTJIUBPUKL-UHFFFAOYAJ
Properties
Molecular formula	C5H10O
Molar mass	86.13 g mol−1
Appearance	Colorless liquid[1]
Odor	Acetone-like
Density	0.815 g/cm³
Melting point	−39 °C; −38 °F; 234 K
Boiling point	100–102 °C
Solubility in other solvents	water: 50 g/L (20 °C)
Hazards
Flash point	12.78 °C; 55.00 °F; 285.93 K
Autoignition temperature	425 °C; 797 °F; 698 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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. It is mainly used as a solvent in paint and a precursor to vitamin E.^[2] It is easily soluble in diethyl ether and partially soluble in acetone, methanol, and water.^[3] Two related and more important ketones are 2-pentanone and methyl isopropyl ketone.

3-Pentanone is produced industrially from propionic acid using metal oxide catalysts:

2 CH₃CH₂CO₂H → (CH₃CH₂)₂CO + CO₂ + H₂O

It can also be prepared from ethylene, CO, and H₂^[2] or by ketonic decarboxylation of propanoic acid over a manganese(II) oxide catalyst in a tube furnace.^[4]

Safety

The TLV value for 3-pentanone is 200 ppm (705 mg/m³).^[2] 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.^[3]

References