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Encyclopedia > Ethyl acetate
Ethyl acetate
Other names ethyl ester,
ethyl acetate,
acetic ester,
ester of ethanol
Identifiers
CAS number 141-78-6
RTECS number AH5425000
SMILES CCOC(C)=O
Properties
Molecular formula C4H8O2
Molar mass 88.105 g/mol
Appearance colorless liquid
Density 0.897 g/cm³, liquid
Melting point

−83.6 °C (189.55 K) Image File history File links Download high-resolution version (1100x663, 26 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Ethyl acetate ... Image File history File links Size of this preview: 800 × 426 pixelsFull resolution (1100 × 586 pixel, file size: 99 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...

Boiling point

77.1 °C (350.25 K) Italic text This article is about the boiling point of liquids. ...

Solubility in water 8.3 g/100 mL (20 °C)
Solubility in ethanol,
acetone, diethyl ether,
benzene
Miscible
Refractive index (nD) 1.3720
Viscosity 0.426 cP at 25 °C
Structure
Dipole moment 1.78 D
Hazards
MSDS External MSDS
Main hazards Flammable (F),
Irritant (Xi)
NFPA 704

Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... “Grain alcohol” redirects here. ... The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... This article is about the chemical compound. ... For benzine, see petroleum ether. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... For other uses, see Viscosity (disambiguation). ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... This page provides supplementary chemical data on ethyl acetate. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ...

3
1
0
 
R-phrases R11, R36, R66, R67
S-phrases S16, S26, S33
Flash point −4 °C
Related Compounds
Related carboxylate esters Methyl acetate,
Butyl acetate
Related compounds Acetic acid,
ethanol
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Ethyl acetate is the organic compound with the formula CH3CH2OC(O)CH3. This colorless liquid has a characteristic, not unpleasant smell (similar to pear drops) like certain glues or nail polish removers, in which it is used. As the ester derived from ethanol and acetic acid, thus commonly abbreviated EtOAc, it is manufactured on a large scale for use as a solvent. R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... The term carboxylate ester refers to an ester, where the parent acid is a carboxylic acid. ... Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. ... The chemical compound n-butyl acetate, also known as 1-butyl ethanoate, is commonly used as a solvent in the production of lacquers and other products. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound with the formula CH3COOH best recognized for giving vinegar its sour taste and pungent smell. ... “Grain alcohol” redirects here. ... This page provides supplementary chemical data on ethyl acetate. ... This page provides supplementary chemical data on ethyl acetate. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... This page provides supplementary chemical data on ethyl acetate. ... This page provides supplementary chemical data on ethyl acetate. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... Nuclear magnetic resonance spectroscopy most commonly known as NMR spectroscopy is the name given to the technique which exploits the magnetic properties of certain nuclei. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or informally, mass-spec and MS) is an analytical technique used to measure the mass-to-charge ratio of ions. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... Look up glue in Wiktionary, the free dictionary. ... Anatomy In anatomy, a nail is a horn-like piece at the end of a humans or an animals finger or toe. ... A carboxylic acid ester. ... “Grain alcohol” redirects here. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound with the formula CH3COOH best recognized for giving vinegar its sour taste and pungent smell. ...

Contents

Properties

Ethyl acetate is a moderately polar solvent that has the advantages of being volatile, relatively non-toxic, and non-hygroscopic. It is a weak hydrogen bond acceptor, and is not a donor due to the lack of an acidic proton (one directly bonded to an electronegative atom such as fluorine, oxygen, or nitrogen). Ethyl acetate can dissolve up to 3% water and has a solubility of 8% in water at room temperature. At elevated temperature its solubility in water is higher. It is unstable in the presence of strong aqueous bases and acids. The ability of a liquid to evaporate quickly and at relatively low temperatures. ... A hygroscopic substance is a substance that absorbs water readily from its surroundings. ... An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ... For alternative meanings see acid (disambiguation). ... It has been suggested that this article or section be merged with electronegativity. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Acids and bases: Acid-base reaction pH Self-ionization of water Buffer solutions Systematic naming Acid-base extraction Acidity function Proton affinity Acids: Strong acids Weak acids Superacids Lewis acids Mineral acids Organic acids Bases: Strong bases Weak bases Superbases Lewis bases Organic bases edit In chemistry, a base is... For other uses, see Acid (disambiguation). ...


Uses and occurrence

Ethyl acetate is widely employed as a solvent for nail varnishes and nail varnish removers. Industrially it is used to decaffeinate coffee beans and tea leaves.[citation needed] In chemistry, it is often mixed with a non-polar solvent such as hexanes as a chromatography solvent. It is also used as a solvent for extractions. It is rarely used as a reaction mixture due to the weakness of the ester linkage — it hydrolyzes in the presence of strong acids and bases to give acetic acid and ethanol. Decaffeination is the act of removing caffeine from coffee beans, mate, cocoa, tea leaves and other caffeine containing materials. ... the 3rd ingredient in big mac ... In chemistry, liquid-liquid extraction (or more briefly, solvent extraction) is a useful method to separate components (compounds) of a mixture. ... A carboxylic acid ester. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound with the formula CH3COOH best recognized for giving vinegar its sour taste and pungent smell. ... “Grain alcohol” redirects here. ...


Ethyl acetate is also present in confectionery, perfumes, and fruits. It is used in perfumes because it evaporates at a fast rate, leaving but the scent of the perfume on the skin. It also confers a fruity smell, as do most esters. It is also used in paints as an activator or hardener.


Occurrence in wines

Ethyl acetate is present in wines. It may be considered a contaminant at too high concentrations, as typically occurs when wine is exposed to air for a prolonged period. When present at too high concentration in wine, it is regarded as an off-flavour. For other uses, see Wine (disambiguation). ...


Other uses

In the field of entomology, ethyl acetate is an effective poison for use in insect collecting and study. In a killing jar 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. Not to be confused with Etymology, the study of the origin of words. ... Beetle collection at the Melbourne Museum, Australia Insect collecting is historically a widespread, essential predecessor of scientific entomology and at the same time the formerly popular (until the mid-20th century) educational hobby of collecting insects, that has left traces in European cultural history, literature and songs (e. ... A killing jar is a device used by entomologists to kill captured insects quickly, humanely and with minimal damage. ... A hygroscopic substance is a substance that absorbs water readily from its surroundings. ...


Synthesis

Ethyl acetate is synthesized via the Fischer esterification reaction from acetic acid and ethanol, typically in the presence of an acid catalyst such as sulfuric acid. Fischer esterification is the process of forming an ester by refluxing a carboxylic acid and an alcohol in the presence of an acid (catalyst). ... Acetic acid, also known as ethanoic acid, is an organic chemical compound with the formula CH3COOH best recognized for giving vinegar its sour taste and pungent smell. ... “Grain alcohol” redirects here. ... R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, εr, etc. ...

CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O

H2O and HOH redirect here. ...

Industrial synthesis

Industrially, ethyl acetate can be produced by the catalytic oxidization of ethanol. For cost reasons, this method is primarily applied to conversion of surplus ethanol feedstock as opposed to predetermined generation on an industrial scale. In addition, it is commonly accepted as far less practical and less cost effective.


Catalysts for hydrogenation include copper, operating at an elevated temperature but below 250 °C. The copper may have its surface area increased by depositing it on zinc, promoting the the growth of snowflake, fractal like, structures. This surface area can be again increased by deposition onto a zeolite, typically ZSM-5. Traces of rare earth metals or alkalies, such as that of sodium and potassium, have also been found to be beneficial to the process. Byproducts of hydrogenation include diethyl ether (thought to primarily arise due to aluminum sites in the catalyst), acetaldehyde, acetaldehyde aldol products, higher esters and ketones. Acetaldehyde and MEK complicate conversion and purification as ethanol forms an azeotrope with water, as does ethyl acetate with ethanol and water and MEK with both ethanol and the acetate. To obtain a high purity product, these azeotropes must be "broken", and this can be achieved by making use of pressure swing distillation. Zeolite The micro-porous molecular structure of a zeolite, ZSM-5 Zeolites (Greek, zein, to boil; lithos, a stone) are minerals that have a micro-porous structure. ... R-phrases , , S-phrases , , , Flash point −39 °C Autoignition temperature 185 °C RTECS number AB1925000 Supplementary data page Structure and properties n, εr, etc. ... Mek is a three issue comic book miniseries published in 2003 by WildStorm, written by Warren Ellis, pencilled by Steve Rolston and inked by Al Gordon. ...


The composition of the distillate removed from the conversion products is biased towards acetate at atmospheric pressure and ethanol at increased pressure. First, the raw product is fed into a high pressure column where the bulk of the contaminating ethanol is removed. By then feeding the ethanol depleted distillate into a low pressure column, the acetate can be removed from the remaining ethanol azeotrope.


MEK forms during the conversion process from 2-butanol. The latter fails to form an azeotrope with the acetate and so MEK can be removed by hydrogenation of the contaminated product over nickel and further distillation to strip away 2-butanol. This provides the simultaneous benefit of removing the acetylaldehyde contaminant by returning it to an ethanol form and is easily accomplished as hydrogen is a byproduct of the initial dehydrogenation process.


It may also be possible to break the azeotropes with the use of membrane distillation, molecular sieves, an entrainer or absorption medium.


The distilled ethanol and rehydrogenated contaminants can then be recycled into the raw feedstock.


Reactions

Ethyl acetate can be hydrolyzed in acid or basic conditions to regain acetic acid and ethanol. The use of an acid catalyst such as sulfuric acid gives poor yields due to it being an equilibrium — the reverse reaction of the Fischer esterification. Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ... R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, εr, etc. ...


To obtain high yields, it is preferable to use a stoichiometric amount of strong base, such as sodium hydroxide. This reaction gives ethanol and sodium acetate, which is not able to react with ethanol any longer: Sodium hydroxide (NaOH), also known as lye, caustic soda and sodium hydrate, is a caustic metallic base. ... Sodium acetate, (also rarely, sodium ethanoate) is the sodium salt of acetic acid. ...

CH3CO2C2H5 + NaOH → C2H5OH + CH3CO2Na

See also

For other uses, see Solvent (disambiguation). ...

External links

  • Material safety data (MSDS) for ethyl acetate
  • National Pollutant Inventory - Ethyl acetate fact sheet
  • Ethyl Acetate: Molecule of the Month
  • Purpose of Using Concentrated Sulfuric Acid in Esterification for Catalysis

References

  • Chembytes e-zine - Team effort: Steve Colley describes work to develop a new route to make ethyl acetate starting from low grade renewable feedstocks (2001)[1]
  • Ingenia Online - Renewable Processing: The Green Alternative; Using Bio-Ethanol To Manufacture An Industrial Solvent by Mike Ashley (Issue 29, 2006)[2]

  Results from FactBites:
 
Ethyl Acetate (3857 words)
Ethyl acetate is a clear, colorless, flammable liquid with a pleasant, fruity odor.
The oral LD(50) for acute exposure to ethyl acetate is 4,935 mg/kg for rabbits and 5,620 mg/kg for rats; and the 8-hour rat inhalation LC(50) is 1600 ppm [Sax and Lewis 1989].
Containers of ethyl acetate should be protected from physical damage and ignition sources, and should be stored separately from nitrates, strong oxidizers, strong alkalies, or strong acids, chlorosulfonic acid, lithium aluminum hydride, 2-chloromethyl furan, oleum, and potassium t-butoxide.
Ethyl Acetate (Natural) Decaffeination (401 words)
Ethyl Acetate (for the extraction of the caffeine which is a natural component of the coffee)
It is at this point that the bean experiences an ethyl acetate wash. The ethyl acetate employed in this process is of natural origin, obtained from the fermentation of sugar cane and not from chemical synthesis.
The beans are subjected to the ethyl acetate while in the extractor.
  More results at FactBites »

 
 

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