Octyl acetate
From Wikipedia the free encyclopedia
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| Names | |
|---|---|
| Preferred IUPAC name Octyl acetate | |
| Other names n-Octyl acetate | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.581 |
PubChem CID | |
| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) | |
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| 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[4][6] |
| 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)[3] | |
| 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)[4] 1 kPa (66.3 °C) 10 kPa (120 °C)[5] |
Refractive index (nD) | 1.415–1.422 (20 °C)[4] |
| Thermochemistry | |
Heat capacity (C) | 331–343.74 J/mol·K[6] |
| 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): | |
LD50 (median dose) | 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). | |
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 can be synthesized by the Fischer esterification of 1-octanol and acetic acid:
- CH3(CH2)7OH + CH3CO2H → CH3(CH2)7O2CCH3 + H2O
Uses[edit]
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[edit]
- ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b c 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.
- ^ 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.
- ^ a b c "Octyl acetate". chemdats.blogspot.com. 2014-11-04. Archived from the original on 2014-12-25. Retrieved 2014-11-15.
- ^ Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
- ^ a b 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)
- ^ a b c d "MSDS of Octyl acetate". fishersci.ca. Fisher Scientific. Retrieved 2014-09-15.
- ^ a b c Sigma-Aldrich Co., Octyl acetate. Retrieved on 2014-11-15.
- ^ a b "Fragrance raw materials monographs". Food and Cosmetics Toxicology. 12 (7–8): 815–816. 1974. doi:10.1016/0015-6264(74)90132-1.
- ^ 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.
- ^ Brechbill, Glen O. (2007). Classifying Aroma Chemicals. New Jersey, USA: Fragrance Books, Inc. p. 6.