Octyl acetate

Last updated
Octyl acetate
Octyl acetate.svg
Octyl-acetate-Mercury-3D-bs.png
Octyl-acetate-Mercury-3D-sf.png
Names
Preferred IUPAC name
Octyl acetate
Other names
n-Octyl acetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.581 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
RTECS number
  • AJ1400000
UNII
  • InChI=1S/C10H20O2/c1-3-4-5-6-7-8-9-12-10(2)11/h3-9H2,1-2H3 Yes check.svgY
    Key: YLYBTZIQSIBWLI-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColorless 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)
[7]
NFPA 704.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

Lactones are cyclic carboxylic esters are intramolecular esters derived from hydroxy carboxylic acids. They can be saturated or unsaturated. Some contain heteroatoms replacing one or more carbon atoms of the ring.

1-Pentanol,, is an organic compound with the formula CH3CH2CH2CH2CH2OH and is classified as a primary alcohol. It is a colourless liquid with a distinctive aroma. It is one of 8 isomeric alcohols with the formula C5H11OH. It is used as a solvent, a biological drying agent and in the synthesis of some fragrance compounds. It is also a common component of fusel alcohols, the undesirable byproducts of alcoholic fermentation.

<span class="mw-page-title-main">Vinyl alcohol</span> Chemical compound

Vinyl alcohol, also called ethenol or ethylenol, is the simplest enol. With the formula CH2CHOH, it is a labile compound that converts to acetaldehyde immediately upon isolation near room temperature. It is not a practical precursor to any compound.

<span class="mw-page-title-main">Sodium acetate</span> Chemical compound

Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

<span class="mw-page-title-main">Acetyl chloride</span> Organic compound (CH₃COCl)

Acetyl chloride is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.

Myristic acid is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. Its salts and esters are commonly referred to as myristates or tetradecanoates. The name of the acyl group derived from myristic acid is myristoyl or tetradecanoyl. The acid is named after the binomial name for nutmeg, from which it was first isolated in 1841 by Lyon Playfair.

<span class="mw-page-title-main">Acetone</span> Organic compound ((CH3)2CO); simplest ketone

Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.

<span class="mw-page-title-main">Butyl acetate</span> Chemical compound

n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.

<span class="mw-page-title-main">Isoamyl acetate</span> Chemical compound with banana odor

Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl alcohol and acetic acid, with the molecular formula . It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil or pear oil.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

<span class="mw-page-title-main">Allyl acetate</span> Chemical compound

Allyl acetate is an organic compound with formula C3H5OC(O)CH3. This colourless liquid is a precursor to especially allyl alcohol, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.

Tridecylic acid, or tridecanoic acid, is the organic compound with the formula CH3(CH2)11CO2H. It is a 13-carbon saturated fatty acid. It is a white solid.

<span class="mw-page-title-main">1-Octanol</span> Chemical compound

1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils. It is used to evaluate the lipophilicity of pharmaceutical products.

<span class="mw-page-title-main">4-Methylcyclohexanemethanol</span> Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

<span class="mw-page-title-main">2-Octanol</span> Chemical compound

2-Octanol is an organic compound with the chemical formula CH3CH(OH)(CH2)5CH3. It is a colorless oily liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol is classified fatty alcohol. A secondary alcohol, it is chiral.

Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.

In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols

References

  1. 1 2 3 4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 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. 1 2 3 "Octyl acetate". chemdats.blogspot.com. 2014-11-04. Archived from the original on 2014-12-25. Retrieved 2014-11-15.
  4. 1 2 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. 1 2 3 4 "MSDS of Octyl acetate". fishersci.ca. Fisher Scientific. Retrieved 2014-09-15.
  8. 1 2 3 Sigma-Aldrich Co., Octyl acetate. Retrieved on 2014-11-15.
  9. 1 2 "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 is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.