|Molecular formula||C 4 H 8 O 2|
colorless liquid with a fruity odor
|External identifiers / databases|
|Molar mass||88.11 g mol −1|
0.894 g cm −3 (25 ° C)
−83 ° C
77 ° C
moderate in water (85.3 g l −1 at 20 ° C)
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C|
Ethyl acetate , also called ethyl acetate or often referred to as ethyl acetate for short , is a chemical compound from the group of carboxylic acid esters . It is the ester formed from acetic acid and ethanol . The colorless liquid is a characteristic fruity-smelling solvent that is often used in the chemical industry and laboratories.
Extraction and presentation
According to Le Chatelier's principle ( law of mass action ), this equilibrium reaction is shifted to the side of the products through continuous separation of the water produced or continuous removal of the ester.
The Tishchenko reaction is another way of producing ethyl acetate . Then acetaldehyde is reacted at temperatures of 0-5 ° C. in the presence of aluminum triethanolate solution in a stirred tank cascade.
At 95% conversion , the selectivity of ethyl acetate reaches about 96% (based on acetaldehyde). The main by-product is acetaldol , which is produced by the aldol addition of acetaldehyde. The product mixture is separated in a continuous distillation column and the ethyl acetate is distilled off.
Under normal conditions, ethyl acetate is a colorless, low-viscosity and flammable liquid. The melting point is −83 ° C, with a melting enthalpy of 10.48 kJ · mol −1 . At normal pressure , the compound boils at 77 ° C. The heat of vaporization at the boiling point is 31.94 kJ mol −1 . According to Antoine, the vapor pressure function results from log 10 (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.22809, B = 1245.702 and C = −55.189 in the temperature range from 289 K to 349 K. The temperature dependence of the enthalpy of vaporization can be calculated according to the equation Δ V H 0 = Aexp (−βT r ) (1 − T r ) β (Δ V H 0 in kJ / mol, T r = ( Describe T / T c ) reduced temperature) with A = 54.26 kJ / mol, β = 0.2982 and T c = 523.2 K in the temperature range between 298 K and 363 K.
|Standard enthalpy of formation||Δ f H 0 liquid
Δ f H 0 gas
|−480.57 kJ mol −1
−445.43 kJ mol −1
|as a liquid
as a gas
|Standard entropy||S 0 liquid
S 0 gas
|259.4 J mol −1 K −1
362.75 J mol −1 K −1
|as a liquid
as a gas
|Enthalpy of combustion||Δ c H 0 liquid||−2235.4 kJ mol −1|
|Heat capacity||c p||168.94 J mol −1 K −1 (25 ° C)
1.92 J g −1 K −1 (25 ° C)
113.64 J mol −1 K −1 (25 ° C )
1.29 J g −1 K −1 (25 ° C)
|as a liquid
as a gas
|Critical temperature||T c||523.2 K|
|Critical pressure||p c||38.82 bar|
|Critical density||ρ c||3.497 mol·l −1|
|Acentric factor||ω c||0.36641|
Vapor pressure function of ethyl acetate
Approx. 8 ml of ethyl acetate dissolve in 100 ml of water at 20 ° C. The compound forms azeotropic mixtures with water and many organic solvents. The azeotrope with water contains 8.43% water at normal pressure and boils at 70.38 ° C. The azeotrope composition and the azeotrope boiling point are pressure dependent. With decreasing pressure, the water content in the azeotropic mixture and its boiling point decrease.
|p in Torr||25th||50||75||100||200||300||400||500||600||700||760||800||900||1000||1100||1200||1300||1400||1500|
|p in mbar||33||67||100||133||267||400||533||667||800||933||1013||1067||1200||1333||1467||1600||1733||1866||2000|
|x (H 2 O) in%||3.60||4.00||4.36||4.70||5.79||6.56||7.11||7.54||7.92||8.25||8.43||8.54||8.80||9.04||9.26||9.47||9.67||9.86||10.04|
|T b in ° C||−1.89||10.0||17.4||23.0||37.6||46.8||53.8||59.4||64.1||68.2||70.4||71.8||75.1||78.2||81.0||83.5||85.9||88.2||90.3|
The azeotropic compositions and boiling points with other organic solvents can be found in the following table. No azeotropes are formed with toluene , benzene , n- propanol , n- butanol , iso- butanol , sec- butanol , acetone , 1,4-dioxane , methyl acetate and isopropyl acetate .
|Content of ethyl acetate||in%||38||54||56||69||75|
|boiling point||in ° C||65||72||62||72||76|
|solvent||chloroform||Carbon tetrachloride||Butanone||Carbon disulfide||Acetonitrile|
|Content of ethyl acetate||in%||72||43||82||3||77|
|boiling point||in ° C||78||75||77||46||75|
Ethyl acetate forms highly flammable vapor-air mixtures. The compound has a flash point of −4 ° C. The explosion range is between 2% by volume (73 g / m 3 ) as the lower explosion limit (LEL) and 12.8% by volume (470 g / m 3 ) as the upper explosion limit (UEL). A correlation of the explosion limits with the vapor pressure function results in a lower explosion point of −6 ° C and an upper explosion point of 25 ° C. The explosion limits are pressure dependent. A decrease in pressure leads to a reduction in the explosion area. The lower explosion limit changes only slightly up to a pressure of 100 mbar and only increases at pressures below 100 mbar. The upper explosion limit decreases analogously with falling pressure.
|Lower explosion limit (LEL)||in% by volume||1.7||1.8||1.8||1.8||1.9||1.9||2.0||2.1||2.2||2.8||3.5|
|in g m −3||62||63||64||65||67||69||71||74||79||102||126|
|Upper explosion limit (UEL)||in% by volume||12.8||12.6||12.2||11.8||11.6||11.6||11.6||11.4||11.4||9.9||8.1|
|in g m −3||468||461||448||433||426||419||419||426||426||364||295|
The limit oxygen concentration at 20 ° C is 9.8% by volume, at 100 ° C it is 9.4% by volume. The maximum explosion pressure is 9.5 bar. The maximum explosion pressure decreases as the outlet pressure decreases.
|Maximum explosion pressure (in bar)||at 20 ° C||9.2||7.1||5.4||2.6||1.8||1.4||1.1|
The limit gap width was determined to be 0.95 mm (50 ° C). This results in an assignment to explosion group IIA. With a minimum ignition energy of 0.46 mJ, vapor-air mixtures are extremely ignitable. The ignition temperature is 470 ° C. The substance therefore falls into temperature class T1. The ignition temperature drops significantly with increasing pressure. The electrical conductivity of <1 · 10 −7 S · m −1 is in the middle range for liquid substances.
|Ignition temperature||in ° C||470||350||300||240||220|
According to the dangerous goods regulations , ethyl acetate is assigned to class 3 (flammable liquids) with packaging group II (medium level of danger) (label: 3).
Ethyl acetate is a versatile solvent. Ethyl acetate is used as an extractant , e.g. B. for the decaffeination of coffee beans or for the extraction of natural flavorings for the flavoring of lemonades , sweets and medicines . It is naturally present in small amounts in rum and some other spirits . It also occurs in small quantities in wine , especially if the grapes have been damaged by hail or rot ; it then causes a solvent tone in the wine.
In electricity storage technology, ethyl acetate is used as an electrolyte. The advantage of organic liquids over aqueous electrolytes is their good functionality at low temperatures. The disadvantage is the significantly lower energy density.
Due to its strong dissolving power, ethyl acetate is also used as an ingredient in nail polish removers and thinners.
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