Ethyl 2- acetate

Ethyl acetate (ETH-uhl ASS-uh-tate) is a clear, colorless, volatile, flammable liquid with a pleasant fruity odor. Its appealing odor and fruity taste (in dilute solutions) explains one of its primary uses as an additive in foods and drugs to improve their flavor. 

Ethyl acetate occurs naturally in fruits, where it is responsible for the pleasant odor and taste of the fruit. It is also found in yeasts and sugar cane. The compound is made synthetically by reacting acetic acid (CH3C00H) with ethanol (ethyl alcohol CH3CH20H) in the presence of a sulfuric acid catalyst. 

Ethyl acetate s primary use is as a solvent in a variety of commercial and industrial applications. About 65 percent 

Ethyl acetate. Red atoms are oxygen white atoms are hydrogen and black atoms are carbon. Gray sticks indicate double bonds, publishers 

Ethyl acetate is a byproduct of the fermentation of grapes in the wine-making process. The compound is also produced as wine ages in barrels and bottles. A moderate amount of ethyl 

Ethyl acetate (boiling point 77.1, density 0.9005, flash point -4°C) is manufactured from ethyl alcohol and acetic acid. 

A more recent process allows the manufacture of ethyl acetate from ethyl alcohol without the use of acetic acid or any other cofeedstocks. In the process (Fig. 1), ethyl alcohol is heated and passed through a catalytic dehydrogenation reactor where part of the ethyl alcohol is dehydrogenated to form ethyl acetate and hydrogen. 

BP Ethyl acetate PhEur Ethylis acetas USPNE Ethyl acetate 

Acetic acid ethyl ester acetic ester acetic ether acetoxyethane aethylis acetas aethylium aceticum ethyl ethanoate vinegar naphtha. 

In pharmaceutical preparations, ethyl acetate is primarily used as a solvent, although it has also been used as a flavoring agent. As a solvent, it is included in topical solutions and gels, and in edible printing inks used for tablets. 

Ethyl acetate has also been shown to increase the solubility of chlortalidone and to modify the polymorphic crystal forms obtained for piroxicam pivalate and mefenamic acid, and has been used in the formulation of microspheres.Its use as a chemical enhancer for the transdermal iontophoresis of insulin has been investigated. 

In food applications, ethyl acetate is mainly used as a flavoring agent. It is also used in artificial fruit essence and as an extraction solvent in food processing. 

The combustion of ethyl acetate in a flow system was studied by Fish and Waris [96]. Below 250 °C there was no oxidation under the conditions employed, (equimolar fuel and oxygen flows, residence time 

134 sec), while above 450 °C pyrolysis predominated. Between 320 and 360 °C the rate of reaction decreased with increasing temperature. Below 320 °C acetic acid and formaldehyde were the major products with smaller amounts of organic peroxides, peroxyacids and formic acid. Acetaldehyde was initially absent, but above 350 °C it was a major product. Anhydrides and very small amounts of hydrogen peroxide were also formed in the high temperature region, together with products which were also formed at low temperatures. No alcohols were detected under any conditions. 

The combustion of ethyl acetate has also been studied in a flow system by Salooja [47(a)] and in a static system by Hoare etal [45, 97]. Under the conditions employed, Salooja found that ethyl acetate was slightly more resistant to oxidation than methyl acetate, but that it ignited at a considerably lower temperature with explosive violence. 

The results using a static system [97] confirmed the existence of a region of negative temperature coefficient of the rate between 320 and 360 °C, and the limits for cool-flame formation for an equimolar mixture were determined. In contrast to the earlier work [96], methanol was found to be a major product at both 300 and 360 °C. Some iso-propanol and methane were detected, the yield of the latter being greater at the higher temperature. No carbon dioxide was observed, but carbon monoxide was a major product. 

LABORATORY CHEMICAL SAFETY SUMMARY ETHYL ACETATE  

Substance Ethyl acetate (Acetic acid ethyl ester, ethyl ethanoate, acetoxyethane) CAS 141-78-6 

Physical Properties CoIotIcss hquid hp 77 °C, mp -84 °C Moderately soluble in water (9 g/100 mL) 

Odor Pleasant fruity odor detectable at 7 to 50 ppm (mean =18 ppm) 

Flammability and Explosibility Ethyl acetate is a flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and flash hack. Ethyl acetate vapor forms explosive mixtures with air at concentrations of 2 to 11.5% (hy volume). Hazardous gases produced in ethyl acetate fires include carbon monoxide and carbon dioxide. Carbon dioxide or dry chemical extinguishers should be used for ethyl acetate fires. 

Doe JE Ethylene glycol monoethyl ether and ethylene glycol monoethyl ether acetate teratology studies. Environ Health Perspea 57 33-41, 1984 

World Elealth Organization Environmental Health Criteria 115, Methoxyethanol, 2-Ethoxyethanol, 2- and Their Acetates, pp 1-87. International Programme on Chemical Safety (IPCS), Geneva, 1990 

Lee NR, Sakai T, et ah Evaluation of exposure to ethylene glycol monoethyl ether acetates and their possible haematological effects on shipyard painters. Occup Environ Med 56(6) 378-382, 1999 

Sohnlein B, Letzel S, Welte D, et ah Occupational chronic exposure to organic solvents. Int Arch Occup Environ Health 64 479-484, 1993 

Synonyms Acetic ether ethyl acetic ester ethyl ethanoate 

The sensory perception of volatile acidity is not exclusively the result of acetic acid. Various acetate esters, most commonly ethyl acetate, contribute significantly to this defect. The ester is reported in wine at levels ranging from 30-60 mg/L (Riesen, 1992) to 150-200 mg/L (and more) in defective wines (Zoecklein et al., 1995). Sensorially perceived as as the odor of airplane glue or fingernail polish, its aroma detection level in wine is relatively low—12.3 mg/L (Riesen, 1992). 

Although high levels of ethyl acetate are often corollated with objectionable levels of acetic acid, the latter may represent a singular defect in the presence of low concentrations of the former. This is often the case with acetic acid produced by heterofermentative LAB (see Sec 1.4.1). 

Properties.—Colourless liquid, with an agreeable fruity smell b. p. 77° sp. gr. o 9o68 at 15° soluble in about 11 parts of water miscible in all pioportions with alcohol, ether, and acetic acid. 

Ijetween 115° and 120 . Wei d the distillate. This piocess furnishes an example oi Iiyifrohsix or saponijitation, 

You may object that by speaking of simplicity and beauty I am introducing aesthetic criteria of truth, and / frankly admit that / am strongly attracted by the simplicity and beauty of the mathematical schemes which nature presents us. You must have felt this too the almost frightening simplicity and wholeness of the relationship, which nature suddenly spreads out before 

500-mL round-bottomed flask with reflux condenser, stand with clamps, hotplate, glass jar, 250-mL Erlenmcyer flask, 50-mL measuring cyclinder, dropping pipette, wide-necked test tube, boiling chips, pipette, safety glasses, protective gloves. 

Acetic acid, ethanol, concentrated sulfuric acid, 0.5 mol/L NaOH, 1 % phe-nolphthalein solution, strips of polystyrene foam. 

One of the relevant examples in chemistry which can be treated in terms of the application of the rules of mathematics is the Law of Mass Action. This simple and beautiful mathematical treatment of equilibrium processes is of great scientific and economic importance (e.g. for the calculation of yields ). The synthesis of esters is a typical reversible process and occurs as shown in eqn. I  

We shall not refer here to the application of suitable mathematical examples to this equilibrium process, as these are dealt with in detail in textbooks of physical chemistry. The ester, which is present in the upper phase of the heterogeneous system formed, is hydrophobic and readily dissolves plastics, fats, resins and other high molecular mass organic substances. The process in which it is formed is reversed when it is treated with sodium hydroxide. 

Flammable liquid flash point (closed cup) -10°C (14°F) vapor pressure 173 torr at 20°C (68°F) vapor density 2.55 (air = 1) the vapor is heavier than air and can travel a considerable distance to a source of ignition and flash back autoignition temperature 454°C (850°F) flre-extinguishing agent dry chemical, CO2, or alcohol foam use water to flush and dilute any spill and to keep fire-exposed containers cool. 

Methyl acetate forms explosive mixtures with air within the range 3.1-16.0% by volume in air. Its reactions with strong oxidizers, alkalies, and acids are vigorous. 

EPA Designated Toxic Waste, RCRA Waste Number U112 DOT Label Flammable Liquid, UN 1173 

Synonyms ethyl ethanoate acetoxyethane acetic acid ethyl ester 

Ethyl acetate is used as a solvent for varnishes, lacquers, and nitrocellulose as an artificial fruit flavor in cleaning textiles and in the manufacture of artificial silk and leather, perfumes, and photographic Aims and plates (Merck 1996). 

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Bfi and 022- However, in the second binary, intermolecular forces between unlike molecules are much stronger than those between like molecules chloroform and ethyl acetate can strongly hydrogen bond with each other but only very weakly with them-... 

In the maximum-likelihood method used here, the "true" value of each measured variable is also found in the course of parameter estimation. The differences between these "true" values and the corresponding experimentally measured values are the residuals (also called deviations). When there are many data points, the residuals can be analyzed by standard statistical methods (Draper and Smith, 1966). If, however, there are only a few data points, examination of the residuals for trends, when plotted versus other system variables, may provide valuable information. Often these plots can indicate at a glance excessive experimental error, systematic error, or "lack of fit." Data points which are obviously bad can also be readily detected. If the model is suitable and if there are no systematic errors, such a plot shows the residuals randomly distributed with zero means. This behavior is shown in Figure 3 for the ethyl-acetate-n-propanol data of Murti and Van Winkle (1958), fitted with the van Laar equation. 

Figure 6-3. Residuals for the system ethyl acetate(1)-n-propanol(2) at eooc. Data of Murti and van Winkle, 1958.

Convergence is usually accomplished in 2 to 4 iterations. For example, an average of 2.6 iterations was required for 9 bubble-point-temperature calculations over the complete composition range for the azeotropic system ehtanol-ethyl acetate. Standard initial estimates were used. Figure 1 shows results for the incipient vapor-phase compositions together with the experimental data of Murti and van Winkle (1958). For this case, calculated bubble-point temperatures were never more than 0.4 K from observed values. 

ETHYL ACETATE 253-443 -1 2913E 02 -2 2599E 03 -9 6853E-02 2.8020E+01 4.332SE-05... 

A2 ETHYL ACETATE -A.A329EA02 -6 18S9EA02 2 0987E 02 9.62I0EA01... 

CARBON TETRACHLORIDE CARBON TETRACHLORIDE CARBON TETRACH.OR lOE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE CYCLOHEXANE 1 2-OlCHLOROETHANE I,2-DICHLORDETHANE 1 (2-DtCHLOROETHANE OI-ETHYL ETHER DI-ETHYL ETHER DI-ETHVL ETHER 01-ETHYL ETHER OI-ETHYL ETHER OI-ETHYL ETHER ETHYL ACETATE ETHYL ACETATE... 

Directly from the corresponding acid and alcohol, in the presence of a dehydrating agent. Thus when ethanol and acetic acid are mixed, ethyl acetate and water are formed, but in addition an equilibrium is established. 

CH3COOH + HOC2H5 - CH3GOOC2H3 + H2O If, however, concentrated sulphuric acid is present, the water is absorbed, the back reaction prevented, and a high yield of ethyl acetate is obtained. In practice the reaction is not so simple. It was formerly supposed that, since the sulphuric acid is usually added to the alcohol, ethyl hydrogen sulphate and water are formed, the latter being absorbed by the excess of sulphuric acid, A mixture of ethanol and acetic acid is then added to the ethyl hydrogen sulphate,... 

After about 20 minutes, when the liquid should be dry, filter it through a small fluted filter-paper into a 100 ml. distilling-flask attached to a water-condenser. Add some fragments of unglazed porcelain to the ethyl acetate, fit a 100° thermometer to the flask, and place the latter on a cold water-bath, which is then brought to the boil. Some ether is always formed as a by-product with the ethyl acetate, and by these means is carefully distilled off as a... 

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