Names | |
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Preferred IUPAC name Ethyl acetate | |
Systematic IUPAC name Ethyl ethanoate | |
Other names
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Identifiers | |
3D model (JSmol) | |
506104 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.005.001 |
E number | E1504 (additional chemicals) |
26306 | |
KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C4H8O2 | |
Molar mass | 88.106 g·mol−1 |
Appearance | Colorless liquid |
Odor | nail polish-like, fruity |
Density | 0.902 g/cm3 |
Melting point | −83.6 °C (−118.5 °F; 189.6 K) |
Boiling point | 77.1 °C (170.8 °F; 350.2 K) |
8.3 g/100 mL (at 20 °C) | |
Solubility in ethanol, acetone, diethyl ether , benzene | Miscible |
log P | 0.71 [1] |
Vapor pressure | 73 mmHg (9.7 kPa) at 20 °C [2] |
Acidity (pKa) | 25 |
−54.10×10−6 cm3/mol | |
Refractive index (nD) | 1.3720 |
Viscosity | 426 μPa·s (0.426 cP) at 25 °C |
Structure | |
1.78 D | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
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GHS labelling: | |
[3] | |
Danger | |
H225, H319, H336 [3] | |
P210, P233, P240, P305+P351+P338, P403+P235 [3] | |
NFPA 704 (fire diamond) | |
Flash point | −4 °C (25 °F; 269 K) |
Explosive limits | 2.0–11.5% [2] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 11.3 g/kg, rat |
LC50 (median concentration) | 16,000 ppm (rat, 6 h) 12,295 ppm (mouse, 2 h) 1600 ppm (rat, 8 h) [4] |
LCLo (lowest published) | 21 ppm (guinea pig, 1 h) 12,330 ppm (mouse, 3 h) [4] |
NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 400 ppm (1400 mg/m3) [2] |
REL (Recommended) | TWA 400 ppm (1400 mg/m3) [2] |
IDLH (Immediate danger) | 2000 ppm [2] |
Related compounds | |
Related carboxylate esters | |
Related compounds | |
Supplementary data page | |
Ethyl acetate (data page) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and in 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]
Ethyl acetate was first synthesized by the Count de Lauraguais in 1759 by distilling a mixture of ethanol and acetic acid. [6]
In 2004, an estimated 1.3 million tonnes were produced worldwide. [5] [7] The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tonnes. The global ethyl acetate market was valued at $3.3 billion in 2018. [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:
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:
Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene: [9]
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]
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.
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.
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:
In the Claisen condensation, anhydrous ethyl acetate and strong bases react to give ethyl acetoacetate: [14]
The LD50 for rats is 5620 mg/kg, [15] 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. [16] 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. [17] 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. [18]
Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.
Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.
Amyl acetate (pentyl acetate) is an organic compound and an ester with the chemical formula CH3COO[CH2]4CH3 and the molecular weight 130.19 g/mol. It is colorless and has a scent similar to bananas and apples. The compound is the condensation product of acetic acid and 1-pentanol. However, esters formed from other pentanol isomers (amyl alcohols), or mixtures of pentanols, are often referred to as amyl acetate. The symptoms of exposure to amyl acetate in humans are dermatitis, central nervous system depression, narcosis and irritation to the eyes and nose.
Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, ethene-vinyl acetate copolymers, polyvinyl alcohol, and other important industrial polymers.
Ethyl formate is an ester formed when ethanol reacts with formic acid. Ethyl formate has the characteristic smell of rum and is partially responsible for the flavor of raspberries, occuring naturally in some plant oils, fruits, and juices. Ethyl formate does not occur naturally in the animal kingdom.
Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.
Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.
n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol 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 chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate 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 lacquer and nitrocellulose. Like many esters it has a fruity or floral smell at low concentrations and occurs naturally in raspberries, pears and other plants. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache.
Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.
1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.
Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.
sec-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose. It is a clear flammable liquid with a sweet smell.
Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl alcohol and acetic acid, with the molecular formula . It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil or pear oil.
2-Ethoxyethanol, also known by the trademark Ethyl cellosolve, is a solvent used widely in commercial and industrial applications. It is a clear, colorless, nearly odorless liquid that is miscible with water, ethanol, diethyl ether, acetone, and ethyl acetate.
2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3H
8O
2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:
Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.
Tetramethyl orthosilicate (TMOS) is the chemical compound with the formula Si(OCH3)4. This molecule consists of four methoxy groups bonded to a silicon atom. The basic properties are similar to the more popular tetraethyl orthosilicate, which is usually preferred because the product of hydrolysis, ethanol, is less toxic than methanol.
Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.