Octyl acetate

Octyl acetate, or octyl ethanoate, is an organic compound with the formula CH3(CH2)7O2CCH3. It is classified as an ester that is formed from 1-octanol (octyl alcohol) and acetic acid. It is found in oranges, grapefruits, and other citrus products.[10]

Octyl acetate
Skeletal formula of octyl acetate
Ball-and-stick model of the octyl acetate molecule
Space-filling model of the octyl acetate molecule
Names
Preferred IUPAC name
Octyl acetate
Other names
n-Octyl acetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.581
RTECS number
  • AJ1400000
UNII
  • InChI=1S/C10H20O2/c1-3-4-5-6-7-8-9-12-10(2)11/h3-9H2,1-2H3 checkY
    Key: YLYBTZIQSIBWLI-UHFFFAOYSA-N checkY
  • InChI=1/C10H20O2/c1-3-4-5-6-7-8-9-12-10(2)11/h3-9H2,1-2H3
    Key: YLYBTZIQSIBWLI-UHFFFAOYAX
  • O=C(OCCCCCCCC)C
Properties
C10H20O2
Molar mass 172.268 g·mol−1
Appearance Colorless liquid
Odor Fruity, slightly waxy floral odor
Density 0.863–0.87 g/cm3[1][2]
Melting point −38.5 – −38 °C (−37.3 – −36.4 °F; 234.7–235.2 K)[1][2]
Boiling point 203–211.3 °C (397.4–412.3 °F; 476.1–484.4 K)[1][2]
112.55 °C (234.59 °F; 385.70 K)
at 30 mmHg[3][4]
0.021 g/100 g (0 °C)
0.018 g/100 g (29.7 °C)
0.018 g/100 g (40 °C)
0.012 g/100 g (92.1 °C)[5]
Solubility Soluble in EtOH, ether
Vapor pressure 0.01 kPa (−3 °C)
0.0072–0.0073 (14.75 °C)
0.02–0.1 kPa (27 °C)[3]
1 kPa (66.3 °C)
10 kPa (120 °C)[6]
1.415–1.422 (20 °C)[3]
Thermochemistry
331–343.74 J/mol·K[4]
Hazards
NFPA 704 (fire diamond)
Flash point 83–86 °C (181–187 °F; 356–359 K)[1][7][8]
268–268.3 °C (514.4–514.9 °F; 541.1–541.5 K)[7][8]
Explosive limits 0.76–8.14%[7][8]
Lethal dose or concentration (LD, LC):
3000 mg/kg (oral, rat)[9]
5000 mg/kg (dermal, rabbit)[9]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Octyl acetate can be synthesized by the Fischer esterification of 1-octanol and acetic acid:

CH3(CH2)7OH + CH3CO2H → CH3(CH2)7O2CCH3 + H2O

Uses

Because of its fruity odor,[11] octyl acetate is used as the basis for artificial flavors and in perfumery. It is also a solvent for nitrocellulose, waxes, oils, and some resins.

References

  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. Yaws, Carl L. (2008). Thermophysical Properties of Chemicals and Hydrocarbons. New York: William Andrew, Inc. ISBN 978-0-8155-1596-8. LCCN 2008020146. Archived from the original on 2009-03-02. Retrieved 2020-04-23.
  3. "Octyl acetate". chemdats.blogspot.com. 2014-11-04. Archived from the original on 2014-12-25. Retrieved 2014-11-15.
  4. Acetic acid, octyl ester in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-11-22)
  5. Stephenson, Richard M. (1992). "Mutual Solubilities: Water-Ketones, Water-Ethers, and Water-Gasoline-Alcohols". Journal of Chemical & Engineering Data. 37 (1): 80–95. doi:10.1021/je00005a024.
  6. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  7. "MSDS of Octyl acetate". fishersci.ca. Fisher Scientific. Retrieved 2014-09-15.
  8. Sigma-Aldrich Co., Octyl acetate. Retrieved on 2014-11-15.
  9. "Fragrance raw materials monographs". Food and Cosmetics Toxicology. 12 (7–8): 815–816. 1974. doi:10.1016/0015-6264(74)90132-1.
  10. Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.
  11. Brechbill, Glen O. (2007). Classifying Aroma Chemicals. New Jersey, USA: Fragrance Books, Inc. p. 6.
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