Octyl acetate

Octyl acetate
Names
	IUPAC name Octyl ethanoate
	Other names Octyl acetate; n-Octyl acetate
Identifiers
CAS Number	112-14-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:87495 ;
ChemSpider	7872 ;
ECHA InfoCard	100.003.581
PubChem CID	8164;
RTECS number	AJ1400000;
UNII	X0FN2J413S ;
CompTox Dashboard (EPA)	DTXSID8044202 ;
	InChI InChI=1S/C10H20O2/c1-3-4-5-6-7-8-9-12-10(2)11/h3-9H2,1-2H3 Key: YLYBTZIQSIBWLI-UHFFFAOYSA-N ; InChI=1/C10H20O2/c1-3-4-5-6-7-8-9-12-10(2)11/h3-9H2,1-2H3 Key: YLYBTZIQSIBWLI-UHFFFAOYAX;
	SMILES O=C(OCCCCCCCC)C;
Properties
Chemical formula	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]
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]
Thermochemistry
Heat capacity (C)	331–343.74 J/mol·K[4]
Hazards
NFPA 704 (fire diamond)	[7] 2 1 0
Flash point	83–86 °C (181–187 °F; 356–359 K)[1][7][8]
Autoignition; temperature	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).
	verify (what is ?)
	Infobox references

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

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

Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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.
"Octyl acetate". http://chemdats.blogspot.com. 2014-11-04. Archived from the original on 2014-12-25. Retrieved 2014-11-15. External link in |website= (help)
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), http://webbook.nist.gov (retrieved 2014-11-22)
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.
Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
"MSDS of Octyl acetate". http://www.fishersci.ca. Fisher Scientific. Retrieved 2014-09-15. External link in |website= (help)
Sigma-Aldrich Co., Octyl acetate. Retrieved on 2014-11-15.
"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.

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[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[tpocah-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.

[chemdats-3] "Octyl acetate". http://chemdats.blogspot.com. 2014-11-04. Archived from the original on 2014-12-25. Retrieved 2014-11-15. External link in |website= (help)

[nist-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), 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. doi:10.1021/je00005a024.

[crc-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.

[fca-7] "MSDS of Octyl acetate". http://www.fishersci.ca. Fisher Scientific. Retrieved 2014-09-15. External link in |website= (help)

[sigma-8] Sigma-Aldrich Co., Octyl acetate. Retrieved on 2014-11-15.

[FCT-9] "Fragrance raw materials monographs". Food and Cosmetics Toxicology. 12 (7–8): 815–816. 1974. doi:10.1016/0015-6264(74)90132-1.

[Ullmann-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.