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2-Octanone

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2-Octanone Basic information

Product Name:
2-Octanone
Synonyms:
  • femanumber2802
  • n-C6H13COCH3
  • octan-2-
  • Octan-2-one
  • 2-OCTANONE 98+% FCC
  • 2-OCTANONE OEKANAL
  • 2-OCTANONE REAGENT GRADE 98%
  • 2-OCTANONE, STANDARD FOR GC
CAS:
111-13-7
MF:
C8H16O
MW:
128.21
EINECS:
203-837-1
Mol File:
111-13-7.mol
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2-Octanone Chemical Properties

Melting point:
-16 °C
Boiling point:
173 °C(lit.)
Density 
0.819 g/mL at 25 °C(lit.)
vapor pressure 
1.8-2.614hPa at 20-25℃
FEMA 
2802 | 2-OCTANONE
refractive index 
n20/D 1.416(lit.)
Flash point:
133 °F
storage temp. 
Sealed in dry,2-8°C
solubility 
0.9g/l
form 
Liquid
color 
Clear colorless to very slightly yellow
Odor
at 10.00 % in dipropylene glycol. earthy weedy natural woody herbal
Odor Type
earthy
Water Solubility 
0.9 g/L
Merck 
14,4711
JECFA Number
288
BRN 
635843
Dielectric constant
7.4(100℃)
Stability:
Stable. Incompatible with strong oxidizing agents. Flammable.
LogP
1.95-2.37 at 25℃
CAS DataBase Reference
111-13-7(CAS DataBase Reference)
NIST Chemistry Reference
2-Octanone(111-13-7)
EPA Substance Registry System
2-Octanone (111-13-7)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
21-10
Safety Statements 
36/37-16
RIDADR 
UN 1224 3/PG 3
WGK Germany 
1
RTECS 
RH1484000
TSCA 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29141990
Hazardous Substances Data
111-13-7(Hazardous Substances Data)
Toxicity
Both the acute oral LD50 in rats and the acute dermal LD50 in rabbits exceeded 5 g/kg (Moreno, 1973).

MSDS

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2-Octanone Usage And Synthesis

Synthesis

1-Octyne (7.5 g) and formic acid (100 mL) were heated in an oil bath at 100 ºC until all starting material was consumed. The progress of the reaction was monitored by GC analysis of the reaction solution. Quantitative GC analysis at the end of the reaction (6 h) indicated 92% yield of 2-octanone. The cooled reaction mixture was taken up with CH2Cl2 (170 mL), and the solution was washed with water, sodium carbonate solution, and water, dried over MgSO4, and evaporated in vacuo. The residue was distilled (bp 171–173 ºC) to give 2-octanone (7.42 g, 85%).

Reference: Menashe, N.; Reshef, D.; Shvo, Y. J. Org. Chem. 1991, 56, 2912–2914.

References

[1]Bangs, William E., and G. A. Reineccius. "Influence of Dryer In feed Matrices on the Retention of Volatile Flavor Compounds During Spray Drying." Journal of Food Science 47.1(1982):254-259. Kida, T, et al. "New cleavable surfactants derived from glucono-1,5-lactone. " Journal of the American Oil Chemists’ Society 71.7(1994):705-710.
[2]Tan, Guan Huat, and Lukman Bola Abdulra'uf. "Recent developments and applications of microextraction techniques for the analysis of pesticide residues in fruits and vegetables." Pesticides-Recent Trends in Pesticide Residue Assay. InTech, 2012.

Description

2-Octanone has a floral and bitter, green, fruity (unripe apple) odor with a bitter camphoraceous taste. May be synthesized by the oxidation of methyl hexyl carbinol with K2Cr2O7 and sulfuric acid; also by oxidation of 2-octanol over zinc oxide at 330 - 340°C.

Chemical Properties

2-Octanone has a floral and bitter, green, fruity (unripe apple) odor and bitter, camphoraceous taste. Insoluble in water; solublein alcohol, hydrocarbons, ether, esters, etc. Com-bustible.

Occurrence

Reported found in apple, apricot, banana, cranberry, grape, raisin, papaya, peach, raspberry, strawberry, leek, peas, clove, wheat bread, many cheeses, butter, milk, cooked egg, yogurt, caviar, fatty fish, meats, beer, hop oil beer, cognac, rum, grape wines, cocoa, coffee, tea, roasted filberts and peanuts, pecans, potato chips, oats, soybean, olive, beans, walnut, trassi, mushroom, fig, rice, buckwheat, quince, sweet corn, corn oil, malt, wort, krill, Bourbon vanilla, mountain papaya, shrimp, crab, crayfish, clam, truffle, maté and mastic gum oil.

Uses

2-Octanone may be used as an analytical reference standard for the quantification of the analyte in sugar-cane spirits and rum samples and whey protein concentrate using chromatography based techniques.

Uses

2-Octanone is used in perfumes, high-boiling solvent, especially for epoxy resin coatings and in leather finishes. It is used in flavoring, odorant. It can act as antiblushing agent for nitrocellulose lacquers.

Production Methods

2-Octanone can be produced by oxidation of methyl hexyl carbinol, 2-octanol, or 1-octene or by reductive condensation of acetone with pentanol. Commercial samples can have a purity of 98%.

Preparation

By oxidation of methyl hexyl carbinol with K2Cr2O7 and sulfuric acid; also by oxidation of 2-octanol over zinc oxide at 330 to 340°C.

Definition

ChEBI: A methyl ketone that is octane substituted by an oxo group at position 2.

Aroma threshold values

Detection: 41 to 62 ppb

Taste threshold values

Taste characteristics at 10 ppm: dairy, waxy, cheese, woody, mushroom and yeast.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 5924, 1991 DOI: 10.1021/jo00020a040
Tetrahedron Letters, 26, p. 2107, 1985 DOI: 10.1016/S0040-4039(00)94791-9

General Description

2-Octanone is a volatile flavor compound reported to be found in blue cheese, acerola fruit, blue crab and cray fish.

Industrial uses

Methyl n-hexyl ketone is used as solvent for vinyl compounds and dyes and is suitable for dispersing dyes in light-weight petroleum oils for newsprint inks.

Safety Profile

Poison by ingestion. Moderately toxic by intraperitoned route. A sktn irritant. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use foam, alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHER and KETONES.

2-Octanone Preparation Products And Raw materials

Raw materials

2-OctanoneSupplier

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