3-Heptanone

3-Heptanone

Skeletal formula of 3-Heptanone
Names
Preferred IUPAC name Heptan-3-one
Other names Ethyl butyl ketone 3-Oxoheptane Butyl ethyl ketone
Identifiers
CAS Number	106-35-4  Y
3D model (JSmol)	Interactive image
Beilstein Reference	506161
ChEBI	CHEBI:50139
ChemSpider	7514  Y
ECHA InfoCard	100.003.081
EC Number	203-388-1
MeSH	3-Heptanone
PubChem CID	7802
RTECS number	MJ5250000
UNII	10GA6SR3AT  Y
UN number	1224
CompTox Dashboard (EPA)	DTXSID2047438
InChI InChI=1S/C7H14O/c1-3-5-6-7(8)4-2/h3-6H2,1-2H3 Key: NGAZZOYFWWSOGK-UHFFFAOYSA-N
SMILES CCC(=O)CCCC
Properties
Chemical formula	C7H14O
Molar mass	114.188 g·mol−1
Appearance	Colorless liquid
Odor	powerful, fruity [1]
Density	0.812 g cm−3
Melting point	−39 °C (−38 °F; 234 K)
Boiling point	146 to 149 °C (295 to 300 °F; 419 to 422 K)
Solubility in water	4.3 mg/mL (%1) (20 °C) [1]
Vapor pressure	4 mmHg (20 °C) [1]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H319, H332
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P235, P501
Flash point	41 °C (106 °F; 314 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	2760 mg/kg (rat, oral) [2]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 50 ppm (230 mg/m3) [1]
REL (Recommended)	TWA 50 ppm (230 mg/m3) [1]
IDLH (Immediate danger)	1000 ppm [1]
Safety data sheet (SDS)	[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Heptanone (butyl ethyl ketone), is a seven carbon ketone. It is a colourless liquid with a "green odour," also described as having a fruity scent and a melon-banana flavour. It is often used as a perfume/fragrance, as a solvent for cellulose, nitrocellulose, or vinyl resins, and as a synthetic building block in the preparation of other organic molecules. ^[4]

Preparation

3-Heptanone is produced industrially through reductive condensation of propionaldehyde (propanal) with butanone (methyl ethyl ketone). This reaction yields hept-4-en-3-one, which is subsequently hydrogenated to 3-heptanone.

CH
_³CH
_²CHO   +   CH
_³C(O)CH
_²CH
_³   →  CH
_³CH
_²C(O)CHCHCH
_²CH
_³  +   H
_²O

CH
_³CH
_²C(O)CHCHCH
_²CH
_³  +   H
_²   →  CH
_³CH
_²C(O)CH
_²CH
_²CH
_²CH
_³

References

1. NIOSH Pocket Guide to Chemical Hazards. "#0266". National Institute for Occupational Safety and Health (NIOSH).
2. "Ethyl butyl ketone". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
3. http://www.chemicalbook.com/ProductMSDSDetailCB0852672_EN.htm External MSDS
4. Siegel, Hardo; Eggersdorfer, Manfred (2012). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry . Vol. 20. p. 195. doi:10.1002/14356007.a15_077. ISBN   9783527306732.