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Octyl acetate

From Wikipedia, the free encyclopedia

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 Edit this at Wikidata
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[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]
1.415–1.422 (20 °C)[4]
Thermochemistry
331–343.74 J/mol·K[6]
Hazards
NFPA 704 (fire diamond)
[7]
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
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 ?)

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

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Transcription

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. ^ a b c d Record  in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ 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.
  3. ^ 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.
  4. ^ a b c "Octyl acetate". chemdats.blogspot.com. 2014-11-04. Archived from the original on 2014-12-25. Retrieved 2014-11-15.
  5. ^ Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  6. ^ 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)
  7. ^ a b c d "MSDS of Octyl acetate". 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 "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.
This page was last edited on 18 March 2024, at 10:47
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