Propyl acetate

Last updated
Propyl acetate
Propyl-acetate-2D-skeletal.svg
Propyl acetate 3D ball.png
Names
Preferred IUPAC name
Propyl acetate
Systematic IUPAC name
Propyl ethanoate
Other names
Acetic acid propyl ester
n-Propyl ethanoate
n-Propyl acetate
n-Propyl ester of acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.352 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-686-1
PubChem CID
RTECS number
  • AJ3675000
UNII
UN number 1276
  • InChI=1S/C5H10O2/c1-3-4-7-5(2)6/h3-4H2,1-2H3 Yes check.svgY
    Key: YKYONYBAUNKHLG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H10O2/c1-3-4-7-5(2)6/h3-4H2,1-2H3
    Key: YKYONYBAUNKHLG-UHFFFAOYAC
  • O=C(OCCC)C
Properties
C5H10O2
Molar mass 102.133 g·mol−1
AppearanceColorless liquid
Odor Mild, fruity [1]
Density 0.89 g/cm3 [2]
Melting point −95 °C (−139 °F; 178 K) [2]
Boiling point 102 °C (216 °F; 375 K) [2]
18.9 g/L [2]
Vapor pressure 25 mmHg (20 °C) [1]
−65.91·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H319, H336
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
2
3
2
Flash point 10 °C (50 °F; 283 K) [2]
450 °C (842 °F; 723 K)
Explosive limits 1.7–8% [1]
Lethal dose or concentration (LD, LC):
9370 mg/kg (oral, rat)
8300 mg/kg (oral, mouse)
6640 mg/kg (oral, rabbit)
8700 mg/kg (oral, rat) [3]
17800 mg/kg (dermal, rabbit) [4]
8941 ppm (cat, 5 hr) [5]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 200 ppm (840 mg/m3) [1]
REL (Recommended)
TWA 200 ppm (840 mg/m3) ST 250 ppm (1050 mg/m3) [1]
IDLH (Immediate danger)
1700 ppm [1]
Related compounds
Related esters
Ethyl acetate
Isopropyl acetate
n-butyl acetate
Isobutyl acetate
Related compounds
Propan-1-ol
Acetic acid
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 ?)

Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct. [6]

Related Research Articles

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2,4,6-Trinitrophenylmethylnitramine or tetryl (C7H5N5O8) is an explosive compound used to make detonators and explosive booster charges.

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

Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to nylon.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

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

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

<span class="mw-page-title-main">Ethyl formate</span> Chemical compound

Ethyl formate is an ester formed when ethanol reacts with formic acid. Ethyl formate has the characteristic smell of rum and is also partially responsible for the flavor of raspberries. It occurs naturally in the body of ants and in the stingers of bees.

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

Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.

<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">Isobutyl acetate</span> Chemical compound

The chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate or β-methylpropyl acetate, is a common solvent. It is produced from the esterification of isobutanol with acetic acid. It is used as a solvent for lacquer and nitrocellulose. Like many esters it has a fruity or floral smell at low concentrations and occurs naturally in raspberries, pears and other plants. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache.

<span class="mw-page-title-main">Propan-1-ol</span> Primary alcohol compound

Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

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

Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.

<i>sec</i>-Butyl acetate Chemical compound

sec-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose. It is a clear flammable liquid with a sweet smell.

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

Isoamyl acetate, also known as isopentyl acetate, is an organic compound that is the 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">2-Ethoxyethanol</span> Chemical compound

2-Ethoxyethanol, also known by the trademark Cellosolve or ethyl cellosolve, is a solvent used widely in commercial and industrial applications. It is a clear, colorless, nearly odorless liquid that is miscible with water, ethanol, diethyl ether, acetone, and ethyl acetate.

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

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3
H
8
O
2
that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

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

Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.

<span class="mw-page-title-main">Ethenone</span> Organic compound with the formula H2C=C=O

In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.

<span class="mw-page-title-main">1,2-Dichloropropane</span> Chemical compound

1,2-Dichloropropane is an organic compound classified as a chlorocarbon. It is a colorless, flammable liquid with a sweet odor. it is obtained as a byproduct of the production of epichlorohydrin, which is produced on a large scale.

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

Thallous acetate or thallium(I) acetate is a salt of thallium and acetate with the chemical formula TlCH3COO. It is used in microbiology as a selective growth medium. It is poisonous.

<i>sec</i>-Amyl acetate Chemical compound

sec-Amyl acetate is an organic compound and an ester. It is formed in an esterification reaction of sec-amyl alcohol (2-pentanol) and acetic acid. It is a colorless liquid.

References

  1. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0532". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. "n-Propyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. Union Carbide Data Sheet. Vol. 1/25/1965
  5. "n-Propyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. Papa, Anthony J. (2011-10-15), "Propanols", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, doi:10.1002/14356007.a22_173.pub2 , retrieved 2022-03-29