Octyl acetate

Octyl acetate

Octyl acetate
Skeletal formula of octyl acetate
Identifiers
CAS number  YesY
PubChem  YesY
ChemSpider  YesY
RTECS number AJ1400000
Jmol-3D images Image 1
Properties
Molecular formula C10H20O2
Molar mass 172.26 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; 476.2–484.5 K)[1][2]
112.55 °C (234.59 °F; 385.70 K)
at 30 mmHg[3][4]
Solubility in water 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]
Refractive index (nD) 1.415–1.422 (20 °C)[3]
Hazards
NFPA 704
[7]
2
1
0
Flash point 83–86 °C (181–187 °F; 356–359 K)[1][8][7]
Autoignition temperature 268–268.3 °C (514.4–514.9 °F; 541.2–541.5 K)[8][7]
Explosive limits 0.76–8.14%[8][7]
LD50 3000 mg/kg (oral, rat)[9]
5000 mg/kg (dermal, rabbit)[9]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

Octyl acetate, or octyl ethanoate, is 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 can be synthesized by a condensation 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 as a solvent for nitrocellulose, waxes, oils, and some resins.

References

  1. ^ a b c d Record in the GESTIS Substance Database from the IFA
  2. ^ a b c Yaws, Carl L. (2008). Thermophysical Properties of Chemicals and Hydrocarbons. http://www.williamandrew.com (New York: William Andrew, Inc.).  
  3. ^ a b c "Octyl acetate". http://chemdats.blogspot.com. 2014-11-04. Retrieved 2014-11-15. 
  4. ^ Acetic acid, octyl ester in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (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.  
  6. ^ Lide, David R., ed. (2009).  
  7. ^ a b c d "MSDS of Octyl acetate". http://www.fishersci.ca. Fisher Scientific. Retrieved 2014-09-15. 
  8. ^ a b c Sigma-Aldrich Co., Octyl acetate. Retrieved on 2014-11-15.
  9. ^ a b  
  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.  
  11. ^ Brechbill, Glen O. (2007). Classifying Aroma Chemicals. http://www.perfumerbook.com (New Jersey, USA: Fragrance Books, Inc.). p. 6.