''n''-Butyl acetate is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula . A colorless, flammable liquid, it is the ester derived from n-
butanol
Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4 H9 O H, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a bu ...
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
The other three isomers (four, including
stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
s) of butyl acetate are
isobutyl acetate
The chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate (IUPAC name) 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 lacque ...
,
''tert''-butyl acetate, and
''sec''-butyl acetate (two
enantiomers).
Production and use
Butyl acetate is commonly manufactured by the
Fischer esterification of
butanol
Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4 H9 O H, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a bu ...
(or its isomer to make an isomer of butyl acetate) and
acetic acid with the presence of
sulfuric acid:
[
:]
Butyl acetate is mainly used as a solvent for coatings and inks.[ It is a component of fingernail polish.]
Occurrence in nature
Apples, especially of the 'Red Delicious
Red Delicious is a type of apple with a red exterior and sweet taste that was first recognized in Madison County, Iowa, in 1872. Today, the name ''Red Delicious'' comprises more than 50 cultivars. From 1968 to 2018, it was the most produced cu ...
' variety, are flavored in part by this chemical. The alarm pheromone
A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavi ...
s emitted by the Koschevnikov gland The Koschevnikov gland is a gland of the honeybee located near the sting shaft. The gland produces an alarm pheromone that is released when a bee stings. The pheromone contains more than 40 different compounds, including pentylacetate, butyl ...
of honey bee
A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the current cosm ...
s contain butyl acetate.
References
External links
Ethylene and other chemicals in fruit
{{Esters
Ester solvents
Flavors
Acetate esters
Commodity chemicals
Sweet-smelling chemicals