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3-Heptanone

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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
3D model (JSmol)
Beilstein Reference 506161
ChEBI
ChemSpider
ECHA InfoCard 100.003.081 Edit this at Wikidata
EC Number
  • 203-388-1
MeSH 3-Heptanone
PubChem CID
RTECS number
  • MJ5250000
UNII
UN number 1224
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H14O/c1-3-5-6-7(8)4-2/h3-6H2,1-2H3Key: NGAZZOYFWWSOGK-UHFFFAOYSA-N
SMILES
  • CCC(=O)CCCC
Properties
Chemical formula C7H14O
Molar mass 114.188 g·mol
Appearance Colorless liquid
Odor powerful, fruity
Density 0.812 g cm
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 1% (20 °C)
Vapor pressure 4 mmHg (20 °C)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
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)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 50 ppm (230 mg/m)
REL (Recommended) TWA 50 ppm (230 mg/m)
IDLH (Immediate danger) 1000 ppm
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound


3-Heptanone (butyl ethyl ketone), is a seven carbon ketone. It is a colorless liquid with a "green odor," also described to have a fruity scent. 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.

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. http://www.chemicalbook.com/ProductMSDSDetailCB0852672_EN.htm External MSDS
  3. "Ethyl butyl ketone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  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.
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