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Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and 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.[5]
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Ethyl acetate was first synthesized by the Count de Lauraguais in by distilling a mixture of ethanol and acetic acid.[6]
In , an estimated 1.3 million tonnes were produced worldwide.[5][7] The combined annual production in of Japan, North America, and Europe was about 400,000 tonnes. The global ethyl acetate market was valued at $3.3 billion in .[8]
Ethyl acetate is synthesized in industry mainly via the classic Fischer esterification reaction of ethanol and acetic acid. This mixture converts to the ester in about 65% yield at room temperature:
CH3CO2H + CH3CH2OH ' CH3CO2CH2CH3 + H2O
The reaction can be accelerated by acid catalysis and the equilibrium can be shifted to the right by removal of water.
It is also prepared in industry using the Tishchenko reaction, by combining two equivalents of acetaldehyde in the presence of an alkoxide catalyst:
2 CH3CHO ' CH3CO2CH2CH3
Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene:[9]
C2H4 + CH3CO2H ' CH3CO2C2H5
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Ethyl acetate is used primarily as a solvent and diluent, being favored because of its low cost, low toxicity, and agreeable odor.[5] For example, it is commonly used to clean circuit boards and in some nail varnish removers (acetone is also used). Coffee beans and tea leaves are decaffeinated with this solvent.[10] 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 the scent of the perfume on the skin.
Ethyl acetate is an asphyxiant for use in insect collecting and study.[11] In a killing jar charged with ethyl acetate, the vapors will kill the collected 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. However, ethyl acetate is regarded as potentially doing damage to insect DNA, making specimens processed this way less than ideal for subsequent DNA sequencing.[12]
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In the laboratory, mixtures containing ethyl acetate are commonly used in column chromatography and extractions.[13] Ethyl acetate is rarely selected as a reaction solvent because it is prone to hydrolysis, transesterification, and condensations.
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Ethyl acetate is the most common ester in wine, being the product of the most common volatile organic acid ' acetic acid, and the ethyl alcohol generated during the fermentation. 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 are considered a wine fault.
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Ethyl acetate is only weakly Lewis basic, like a typical carboxylic acid ester.
Ethyl acetate hydrolyses to give acetic acid and ethanol. Bases accelerate 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 a strong base, such as sodium hydroxide. This reaction gives ethanol and sodium acetate, which is unreactive toward ethanol:
CH3CO2C2H5 + NaOH ' C2H5OH + CH3CO2Na
In the Claisen condensation, anhydrous ethyl acetate and strong bases react to give ethyl acetoacetate:[14]
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Vapor pressure of ethyl acetate Heat of evaporation of ethyl acetateUnder normal conditions, ethyl acetate exists as a colorless, low-viscosity, and flammable liquid. Its melting point is '83 °C, with a melting enthalpy of 10.48 kJ/mol. At atmospheric pressure, the compound boils at 77 °C. The vaporization enthalpy at the boiling point is 31.94 kJ/mol. The vapor pressure function follows the Antoine equation
log 10 ' ( p ) = A ' B T + C , {\displaystyle \log _{10}(p)=A-{\frac {B}{T+C}},}
where
p {\displaystyle p}
bars,T {\displaystyle T}
absolute temperature in kelvins, andA = 4. {\displaystyle A=4.}
B = .702 {\displaystyle B=.702}
C = ' 55.189 {\displaystyle C=-55.189}
This function is valid within the temperature range of 289 to 349 K (16'76 °C).
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The enthalpy of vaporization in kJ/mol is calculated according to the empirical equation by Majer and Svoboda[15]
Δ H vap = A exp ' ( ' β T r ) ( 1 ' T r ) β , {\displaystyle \Delta H_{\text{vap}}=A\exp(-\beta \,T_{\text{r}})\,(1-T_{\text{r}})^{\beta },}
where
T r = T / T c {\displaystyle T_{\text{r}}=T/T_{\text{c}}}
reduced temperature, andT c {\displaystyle T_{\text{c}}}
critical temperature.A {\displaystyle A}
β {\displaystyle \beta }
The following table summarizes the most important thermodynamic properties of ethyl acetate under various conditions.
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The LD50 for rats is mg/kg,[24] indicating low acute toxicity. Given that the chemical is naturally present in many organisms, there is little risk of toxicity.
Overexposure to ethyl acetate may cause irritation of the eyes, nose, and throat. Severe overexposure may cause weakness, drowsiness, and unconsciousness.[25] Humans exposed to a concentration of 400 ppm in 1.4 mg/L ethyl acetate for a short time were affected by nose and throat irritation.[26] Ethyl acetate is an irritant of the conjunctiva and mucous membrane of the respiratory tract. Animal experiments have shown that, at very high concentrations, the ester has central nervous system depressant and lethal effects; at concentrations of 20,000 to 43,000 ppm (2.0'4.3%), there may be pulmonary edema with hemorrhages, symptoms of central nervous system depression, secondary anemia and liver damage. In humans, concentrations of 400 ppm cause irritation of the nose and pharynx; cases have also been known of irritation of the conjunctiva with temporary opacity of the cornea. In rare cases exposure may cause sensitization of the mucous membrane and eruptions of the skin. The irritant effect of ethyl acetate is weaker than that of propyl acetate or butyl acetate.[27]
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Ethyl acetate (also known as ethyl ethanoate, acetic acid ethyl ester, acetoxyethane, 1-acetoxyethane, EtOAC, ETAC, EA) is an organic ester compound with a molecular formula of C 4 H 8 O 2 . It is a colourless liquid with a fruity characteristic odour that is commonly recognised in glues and nail polish remover. Ethyl acetate is extremely flammable with a flashpoint of -4° C and a flammability rating of 3 and is also highly miscible with all common organic solvents (alcohols, ketones, glycols, esters) but only slightly miscibility in water. This product is commonly used as a solvent for cleaning, paint removal and coatings.
Chemical and physical properties of ethyl acetate:
Molecular Formula: C4H8O2 / CH3'COO'CH2'CH3 / CH3COOC2H5
Synonyms: ethyl ethanoate, acetic acid ethyl ester, acetoxyethane, 1-acetoxyethane, EtOAC, ETAC, EA
Cas Number: 141-78-6
Molecular Mass: 88. g/mol
Exact Mass: 88. g/mol
Flashpoint: 24°F / -4°C
Boiling Point: 171°F / 77.1 °C at 760 mm Hg
Melting Point: '83.6 °C / '118.5 °F
Vapour Pressure: 93.2 mm Hg at 25 °C
Water Solubility: 64 g/L (at 25 °C)
Density: 0.902 g/cm3
Log P: 0.71
There are various methods for manufacturing ethyl acetate. Originally, it was synthesised by distilling ethanol and acetic acid in the presence of sulfuric acid. It is now primarily produced commercially via the Tishchenko method of condensing two equivalents of acetaldehyde using an alkoxide catalyst.
2 CH3CHO ' CH3CO2CH2CH3
Another primary method is using Fischer esterification which involves reacting acetic acid with ethanol, a process accelerated by acid catalysis.
CH3CO2H + CH3CH2OH ' CH3CO2CH2CH3 + H2O
Other methods include as a by-product of the oxidation of butane with acetic acid, the ethanolysis of polyvinyl acetate, and the alkylation of acetic acid.
Ethyl ethanoate has an NFPA health rating of 1 and can cause significant irritation. Overexposure to the eyes, nose and skin can cause irritation, drowsiness, and unconsciousness. If inhaled, ethyl ethanoate can irritate the throat and respiratory passages and cause headaches and nausea.
An NFPA fire rating of 3 indicates that it can be ignited under almost all ambient temperature conditions. Heat, sparks, or flames can ignite this solvent and create vapours that will travel to the source of the ignition. These vapours are heavier than air and will, therefore, spread into surrounding areas.
An instability rating of 0 indicates that it is normally stable, even under fire conditions.
Personal protective equipment should be worn at all times when handling ethyl ethanoate. Eye protection must be worn even when contact lenses are being used. If contaminated, hands should be washed immediately, and clothing should be removed and replaced.
In the case of spillage, isolation of leak area of 50 metres in all directions is recommended. All ignition or flame sources should be removed and entryways into water systems and sewers should be prohibited. Soak up and absorb the spillage using combustible materials. Only attempt to eliminate the leak if it is safe to do so.
Responses for firefighting include using dry chemical, CO2, water spray or alcohol-resistant foam extinguishers for smaller fires. Larger fires require fog or alcohol-resistant foam.
A chemical stockist would have a bulk petrochemical storage facility to regulate this product. Storage is normally in a cool, dry and well ventilated facility away from oxidising agents. Ethyl acetate should be kept out of direct sunlight, heat and open flames. Ethyl acetate should be stored in drummed containers such as iso tanks made of stainless steel, aluminium or carbon steel.
A bulk solvent exporter would normally distribute this solvent in bulk vessels or tank trucks. For transportation purposes, ethyl acetate is classed as a flammable liquid with a fire hazard rating of 2. A full bulk chemical distributor would export the solvent throughout regions such as the UK, Europe, Africa and America. This product is a packing group 2.
Ethyl acetate has many uses in the industrial and commercial industries as both a solvent and a diluent.
Ethyl acetate is used in various industrial applications such as in paints as a hardener, adhesives, paint and coating additives, degreasing solvents, active agents, processing aids and plasticisers. At a lower purity, it can be used in printing and pharmaceuticals. It is also used in coating formulations for wood furniture, agricultural, construction equipment, mining equipment and marine uses.
Laboratory uses include in mixtures used in column chromatography and extractions.
The most common use of ethyl acetate is as an ester in wine as it is naturally produced during the fermentation process. It contributes to wine's fruity flavours. It also contributes to the decaffeination of coffee beans and tea leaves.
Commercial products containing this solvent include automotive products, cleaning and furnishing care products, paints, coatings, inks and plastics. It is also used in air care products and perfumes, as it evaporates quickly leaving only the scent to remain.
As a high purity solvent, it is used in cleaning electric circuit boards and as a nail polish remover. At a lower purity, it can be used as in perfumes, food, decaffeination of tea/coffee and a carrier solvent for herbicides.
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