Ethyl acetate

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Ethyl acetate

Ethyl acetate (systematically

IUPAC nomenclature of organic chemistry

The IUPAC nomenclature of organic chemistry is a systematic name method of naming Organic compounds as recommended by the International Union of Pure and Applied Chemistry ....
, ethyl ethanoate, commonly abbreviated EtOAc or EA) is the organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
with the formula CH₃COOCH₂CH₃. This colorless liquid has a characteristic sweet smell (similar to pear drops) like certain glue

Glue

This is a list of various types of adhesive. Historically, the term "glue" only referred to protein colloids prepared from animal flesh. The meaning has been extended to refer to any fluid adhesive....
s or nail polish removers, in which it is used. Ethyl acetate is the ester

Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
from ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
and acetic acid

Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
; it is manufactured on a large scale for use as a solvent. In 1985, about 400k tons were produced yearly in Japan, North America, and Europe (combined).

l acetate is synthesized industrially mainly via the classic Fischer esterification

Fischer esterification

Fischer esterification or Fischer-Speier esterification is a special type of esterification and the process of forming an ester by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst....
reaction of ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
and acetic acid

Acetic acid

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Production

Ethyl acetate is synthesized industrially mainly via the classic Fischer esterification

Fischer esterification

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
and acetic acid

Acetic acid

CH₃CH₂OH + CH₃COOH CH₃COOCH₂CH₃ + H₂O

Water (molecule)

File:Blue-water-pool.jpgWater is the most abundant molecule on Earth's surface, constituting about 70% of the Earth's surface in liquid, solid, and gaseous states....

The reaction can be accelerated with the acid catalysts and the equilibrium can be shifted to the right by removal of water. It is also prepared industrially using the Tishchenko reaction

Tishchenko reaction

The Tishchenko reaction is a chemical reaction that involves disproportionation of an aldehyde lacking a hydrogen atom in the alpha position in the presence of an alkoxide....
, by combining two equivalents of acetaldehyde

Acetaldehyde

Acetaldehyde is an organic compound with the chemical formula CarbonHydrogen3CHOxygen or MeCHO. It is a flammable liquid with a fruity smell....
in the presence of an alkoxide

Alkoxide

An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO–, where R is the organic substituent....
catalyst:

2 CH₃CHO ? CH₃COOCH₂CH₃

By dehydrogenation of ethanol

A specialized industrial route entails the catalytic dehydrogenation

Dehydrogenation

Dehydrogenation is a chemical reaction that involves the elimination of hydrogen . It is the reverse process of hydrogenation. Dehydrogenation reactions may be either large scale industrial processes or smaller scale laboratory procedures....
of ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
. This method is less cost effective than the esterification but is applied with surplus ethanol in a chemical plant. Typically dehydrogenation is conducted with copper at an elevated temperature but below 250 °C. The copper may have its surface area increased by depositing it on zinc, promoting the growth of snowflake, fractal like structures (dendrites

Dendrite (metal)

A dendrite in metallurgy is a characteristic tree-like structure of crystals growing as molten metal freezes, the shape produced by faster growth along energetically favourable crystallography directions....
). Surface area can be again increased by deposition onto a zeolite

Zeolite

Zeolites are Microporous material, aluminosilicate minerals commonly used as commercial absorbents. The term zeolite was originally coined in 1756 by Sweden mineralogist Axel Fredrik Cronstedt, who observed that upon rapidly heating the material stilbite, it produced large amounts of steam from water that had been absorbed by the material....
, typically ZSM-5

ZSM-5

ZSM-5 is an aluminosilicate zeolite mineral belonging to the pentasil family of zeolites. Its chemical formula is NanAlnSi96-nO192?16H2O ....
. Traces of rare earth

Rare earth

Rare earth may refer to:* Rare earth element* Rare Earth hypothesis* Rare Earth * Rare Earth Records* Rare-earth magnet...
and alkali metal

Alkali metal

The alkali metals are a chemical series of chemical elements comprising Periodic table group of the periodic table: lithium , sodium , potassium , rubidium , caesium , and francium ....
s are beneficial to the process. Byproducts of the dehydrogenation include diethyl ether

Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
, which is thought to primarily arise due to aluminum sites in the catalyst, acetaldehyde and its aldol products, higher esters, and ketones. Separations of the byproducts is complicated by the fact that ethanol forms an azeotrope

Azeotrope

An azeotrope is a mixture of two or more liquids in such a ratio that its composition cannot be changed by simple distillation. This occurs because, when an azeotrope is boiled, the resulting vapor has the same ratio of constituents as the original mixture....
with water, as does ethyl acetate with ethanol and water, and methyl ethyl ketone (MEK, which forms from 2-butanol) with both ethanol and ethyl acetate. These azeotropes are "broken" by pressure swing distillation or membrane distillation.

Uses

Ethyl acetate is primarily used as a solvent

Solvent

A solvent is a liquid or gas that dissolves a solid, liquid, or gaseous solute, resulting in a solution.The most common solvent in everyday life is water....
and diluent, being favored because of its low cost, low toxicity, and agreeable odor. For example, it is commonly used to clean circuit boards and some nail varnish remover (acetone

Acetone

Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
and acetonitrile

Acetonitrile

Acetonitrile is the chemical compound with chemical formula CH3CN. This colourless liquid is the simplest organic nitrile and is widely used as a solvent....
are also used). Coffee beans and tea leaves are decaffeinated with this solvent. It is also used in paints as an activator or hardener. Ethyl acetate is present in confectionery, perfumes, and fruits. In perfumes, it evaporates quickly, leaving but the scent of the perfume on the skin.

Laboratory uses

In the laboratory, mixtures containing ethyl acetate are commonly used in column chromatography

Column chromatography

Column chromatography in chemistry is a method used to purify individual chemical compounds from mixtures of compounds. It is often used for preparative applications on scales from micrograms up to kilograms....
and extractions

Liquid-liquid extraction

Liquid-liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds based on their relative solubility in two different miscible liquids, usually Water and an solvent....
. Ethyl acetate is rarely selected as a reaction solvent because it is prone to hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
and transesterification

Transesterification

In organic chemistry, transesterification is the process of exchanging the alcohol group of an ester compound with another alcohol. These reactions are often catalyst by the addition of an acid or base ....
.

Occurrence in wines

Ethyl acetate is the most common ester

Ester

Wine

Wine is an alcoholic beverage often made of fermentation grape juice. The natural chemical balance of grapes is such that they can ferment without the addition of sugars, acids, enzymes or other nutrients....
, being the product of the most common volatile organic acid

Organic acid

An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids whose acidity is associated with their carboxyl group -COOH....
— acetic acid

Acetic acid

Fermentation (wine)

The process of Fermentation in wine is the catalyst function that turns grape juice into an alcoholic beverage. During fermentation yeast interact with sugars in the juice to create ethanol, commonly known as ethyl alcohol, and carbon dioxide ....
. The aroma of ethyl acetate is most vivid in younger wines and contributes towards the general perception of "fruitiness" in the wine. Sensitivity varies with most people having a perception threshold around 120 mg/L. Excessive amounts of ethyl acetate is considered a wine fault

Wine fault

A wine fault or defect is an unpleasant characteristic of a wine often resulting from poor winemaking practices or storage conditions, and leading to wine spoilage....
. Exposure to oxygen

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
can exacerbate the fault due to the oxidation of ethanol to acetaldehyde

Acetaldehyde

Acetaldehyde is an organic compound with the chemical formula CarbonHydrogen3CHOxygen or MeCHO. It is a flammable liquid with a fruity smell....
, which leaves the wine with a sharp vinegar

Vinegar

Vinegar is an acidic liquid processed from the fermentation of ethanol in a process that yields its key ingredient, acetic acid . It also may come in a diluted form....
-like taste.

Other uses

In the field of entomology

Entomology

Entomology is the science study of insects. At some 1.3 million described species, insects account for more than two-thirds of all known organisms,date back some 400 million years, and have many kinds of interactions with humans and other forms of life on earth....
, ethyl acetate is an effective asphyxiant for use in insect collecting

Insect collecting

Insect collecting is historically a widespread, essential predecessor of scientific entomology and at the same time the formerly popular educational hobby of collecting insects, that has left traces in European cultural history, literature and songs ....
and study. In a killing jar

Killing jar

A killing jar is a device used by entomologists to kill captured insects quickly, humanely and with minimum damage.The jar, typically glass, must be Hermetic seal and usually has a 0.5-1.5 inch layer of hardened plaster of paris on the bottom to absorb the killing agent....
charged with ethyl acetate, the vapors will kill the collected (usually adult) insect quickly without destroying it. Because it is not hygroscopic, ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection.

Reactions

Ethyl acetate can be hydrolyzed in acidic or basic conditions to regain acetic acid and ethanol. The use of an acid catalyst accelerates the hydrolysis, which is subject to the Fischer equilibrium mentioned above. In the laboratory, and usually for illustrative purposes only, ethyl esters are typically hydrolyzed in a two step process starting with a stoichiometric amount of strong base, such as sodium hydroxide

Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
. This reaction gives ethanol and sodium acetate

Sodium acetate

Sodium acetate, is the sodium Salt of acetic acid. It is an inexpensive chemical produced in industrial quantities for a wide range of uses....
, which is unreactive toward ethanol:

CH₃CO₂C₂H₅ + NaOH ? C₂H₅OH + CH₃CO₂Na

Safety

The LD₅₀

LD50

In toxicology, the median lethal dose, LD50 , or LCt50 of a toxic substance or radiation is the Dose required to kill half the members of a tested population....
for rats is 11.3 g/kg, indicating low toxicity.

External links

for ethyl acetate
Calculation of , , , of ethyl acetate