General Description
A clear colorless liquid with a fruity odor. Flash point 24°F. Less dense than water. Vapors heavier than air.
Reactivity Profile
ETHYL ACETATE(141-78-6) is also sensitive to heat. On prolonged storage, materials containing similar functional groups have formed explosive peroxides. This chemical may ignite or explode with lithium aluminum hydride. ETHYL ACETATE(141-78-6) may also ignite with potassium tert-butoxide. ETHYL ACETATE(141-78-6) is incompatible with nitrates, strong alkalis and strong acids. ETHYL ACETATE(141-78-6) will attack some forms of plastics, rubber and coatings. ETHYL ACETATE(141-78-6) is incompatible with oxidizers such as hydrogen peroxide, nitric acid, perchloric acid and chromium trioxide. Violent reactions occur with chlorosulfonic acid. . SOCl2 reacts with esters, such as ETHYL ACETATE(141-78-6), forming toxic SO2 gas and water soluble/toxic acyl chlorides, catalyzed by Fe or Zn (Spagnuolo, C.J. et al. 1992. Chemical and Engineering News 70(22):2.).
Air & Water Reactions
Highly flammable. Slightly soluble in water. This chemical is slowly hydrolyzed by moisture.
Hazard
Toxic by inhalation and skin absorption;
irritant to eyes and skin. Flammable, dangerous fire
and explosion risk, flammable limits in air 2.2–9%.
Questionable carcinogen.
Health Hazard
Headache, irritation of respiratory passages and eyes, dizziness and nausea, weakness, loss of consciousness.
Potential Exposure
This material is used as a solvent for
nitrocellulose and lacquer. It is also used in making dyes,flavoring and perfumery, and in smokeless powder
manufacture
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Shipping
UN1173 Ethyl acetate, Hazard Class: 3; Labels:
3-Flammable liquid.
Incompatibilities
May form explosive mixture with air.
Heating may cause violent combustion or explosion.
Incompatible with strong acids; strong alkalies; nitrates,
strong oxidizers; chlorosulfonic acid; lithium aluminum
hydride; oleum will hydrolyze on standing forming acetic
acid and ethyl alcohol. This reaction is greatly accelerated
by alkalies. Decomposes under influence of UV light,
bases, and acids. Attacks aluminum and plastics.
Description
Ethyl acetate (systematically, ethyl ethanoate, commonly abbreviated EtOAc or EA) is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, decaffeinating tea and coffee, and cigarettes (see list of additives in cigarettes). Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tons. In 2004, an estimated 1.3M tons were produced worldwide.
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Generators of waste containing this contaminant (≧100 kg/
mo) must conform with EPA regulations governing storage,
transportation, treatment, and waste disposal.
Physical properties
Clear, colorless, mobile liquid with a pleasant, sweet fruity odor. Experimentally determined
detection and recognition odor threshold concentrations were 23 mg/m3 (6.4 ppmv) and 48 mg/m3
(13.3 ppmv), respectively (Hellman and Small, 1974). Cometto-Mu?iz and Cain (1991) reported
an average nasal pungency threshold concentration of 67,300 ppmv.
Occurrence
Although it has been reported present in some natural fruital aromas and in some distillates (rum, rum ether),
it has not been reported yet as a constituent of essential oils; it has been identified also in the petals of Magnolia fuscata. Reported
found in many foods including fresh and cooked apple, apricot, banana (169 ppm), sweet and sour cherry, citrus peel oils and juices,
blueberry, cranberry, black currants, raspberry, blackberry, guava, passion fruit, melon, peaches, papaya, pineapple, cabbage, onion,
leek, potato, tomato (3 to 6 ppm), clove, ginger, vinegar, breads, cheeses (0.2 to 0.8 ppm), butter (2 ppm), yogurt, milk, meats, cognac,
beer (4 to 64 ppm), whiskies, cider, sherry, grape wines, rum, cocoa, coffee, tea, filberts, peanuts, popcorn, oats, honey, soybeans,
coconut, olive oil (0.02 ppm) and olive.
Definition
ChEBI: Ethyl acetate is the acetate ester formed between acetic acid and ethanol. It has a role as a polar aprotic solvent, an EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor, a metabolite and a Saccharomyces cerevisiae metabolite. It is an acetate ester, an ethyl ester and a volatile organic compound.
Preparation
Ethyl acetate is made by esterification of acetic acid with ethanol, from acetaldehyde, or by the direct addition of ethylene to acetic acid. BP started a 220,000 tonne/year plant in 2001 to operate the last of these processes, known as AVADA. Ethylene and acetic acid react in the presence of a heteropolyacid catalyst to give ethyl acetate at a claimed high selectivity and 99.97% purity. This is the world’s largest ethyl acetate plant and is motivated by its increasing use as a more “acceptable” solvent than hydrocarbons.
In some countries, where ethanol is expensive or there is surplus acetaldehyde capacity, ethyl acetate is made by a Tishchenko reaction. Sasol in South Africa was said to be investigating such a process in the early 2000s. Ethanol is a solvent for surface coatings, cleaning preparations, and cosmetics. Industrial ethanol is aerobically fermented to white vinegar (dilute acetic acid) of the type used for pickling. Gourmet vinegars—wine vinegar, cider vinegar, and so on, made by fermentation of alcoholic beverages—are also available. Ten percent of industrial ethanol production was used for vinegar in the United States in 2001.
Production Methods
Ethyl acetate can be manufactured by the slow distillation of a
mixture of ethanol and acetic acid in the presence of concentrated
sulfuric acid. It has also been prepared from ethylene using an
aluminum alkoxide catalyst.
Production Methods
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:
CH3CH2OH + CH3COOH ? CH3COOCH2CH3 + 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 → CH3COOCH2CH3.
Reactions
Ethyl acetate can be hydrolyzed in acidic or basic conditions to regain acetic acid and ethanol. The use of an acid catalyst accelerates 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 strong base, such as sodium hydroxide. This reaction gives ethanol and sodium acetate, which is unreactive toward ethanol:
CH3CO2C2H5 + Na OH → C2H5OH + CH3CO2Na
The rate constant is 0.111 dm3 / mol.sec at 25 °C.
Aroma threshold values
Detection: 5 ppb to 5 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 back." Ethyl acetate vapor forms explosive mixtures with air at concentrations of 2 to 11.5% (by 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.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Pharmaceutical Applications
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, mefenamic acid, and fluconazole,and has been used in the formulation of microspheres. Ethyl acetate has been used as a solvent in the preparation of a
liposomal amphotericin B dry powder inhaler formulation.(9) 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.
Safety
Ethyl acetate is used in foods, and oral and topical pharmaceutical
formulations. It is generally regarded as a relatively nontoxic and
nonirritant material when used as an excipient.
However, ethyl acetate may be irritant to mucous membranes,
and high concentrations may cause central nervous system
depression. Potential symptoms of overexposure include irritation
of the eyes, nose, and throat, narcosis, and dermatitis.
Ethyl acetate has not been shown to be a human carcinogen or a
reproductive or developmental toxin.
The WHO has set an estimated acceptable daily intake of ethyl
acetate at up to 25 mg/kg body-weight.
In the UK, it has been recommended that ethyl acetate be
temporarily permitted for use as a solvent in food and that the
maximum concentration consumed in food should be set at
1000 ppm.
LD50 (cat, SC): 3.00 g/kg
LD50 (guinea-pig, oral): 5.50 g/kg
LD50 (guinea-pig, SC): 3.00 g/kg
LD50 (mouse, IP): 0.709 g/kg
LD50 (mouse, oral): 4.10 g/kg
LD50 (rabbit, oral): 4.935 g/kg
LD50 (rat, oral): 5.62 g/kg
Synthesis
By reacting acetic acid and ethanol in the presence of sulfuric acid; by distillation of sodium potassium, or lead acetate
with ethanol in the presence of sulfuric acid; by polymerizatin of acetaldehyde in the presence of aluminum ethylate or aluminum
acetate as catalysts.
Carcinogenicity
Ethyl acetate was not mutagenic in bacterial
assays; it was not genotoxic in a number
of in vivo assays but did cause chromosomal
damage in hamster cells in vitro.
Ethyl acetate has a fruity odor detectable
at 10ppm.
The 2003 ACGIH threshold limit valuetime-
weighted average (TLV-TWA) for ethyl
acetate is 400pm (1440mg/m3).
Source
Identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var.
reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method
(Beaulieu and Grimm, 2001).
Environmental Fate
Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 1.00 g/g which is 54.9%
of the ThOD value of 1.82 g/g.
Photolytic. Reported rate constants for the reaction of ethyl acetate and OH radicals in the
atmosphere (296 K) and aqueous solution are 1.51 x 10-12 and 6.60 x 10-13 cm3/molecule?sec,
respectively (Wallington et al., 1988b).
Chemical/Physical. Hydrolyzes in water forming ethanol and acetic acid (Kollig, 1993). The
estimated hydrolysis half-life at 25 °C and pH 7 is 2.0 yr (Mabey and Mill, 1978).
Metabolism
Ethyl acetate is hydrolysed to ethyl alcohol, which is then partly excreted in the expired air and urine. The rest is metabolized, the acetate fraction becoming incor porated in the body pool (Fassett, 1963).
storage
Ethyl acetate should be stored in an airtight container, protected
from light and at a temperature not exceeding 30°C. Ethyl acetate is
slowly decomposed by moisture and becomes acidic; the material
can absorb up to 3.3% w/w water.
Ethyl acetate decomposes on heating to produce ethanol and
acetic acid, and will emit acrid smoke and irritating fumes. It is
flammable and its vapor may travel a considerable distance to an
ignition source and cause a ‘flashback’.
The alkaline hydrolysis of ethyl acetate has been shown to be
inhibited by polyethylene glycol and by mixed micelle systems.
Purification Methods
The most common impurities in EtOAc are water, EtOH and acetic acid. These can be removed by washing with aqueous 5% Na2CO3, then with saturated aqueous CaCl2 or NaCl, and drying with K2CO3, CaSO4 or MgSO4. More efficient drying is achieved if the solvent is further dried with P2O5, CaH2 or molecular sieves before distillation. CaO has also been used. Alternatively, ethanol can be converted to ethyl acetate by refluxing with acetic anhydride (ca 1mL per 10mL of ester), the liquid is then fractionally distilled, dried with K2CO3 and redistilled. [Beilstein 2 III 127.]
Toxicity evaluation
Ethyl acetate is rapidly hydrolyzed to ethanol and acetic acid.
When ethyl acetate was injected intraperitoneal at 1.6 g kg-1,
hydrolysis to acetic acid and ethanol occurred rapidly. The
biological half-life value of the conversion of ethyl acetate to
ethanol was found to be between 5 and 10 min. At doses higher
than 1.6 g kg-1 in rats the rate of hydrolysis exceeded the
ethanol oxidation leading to the ethanol accumulation in the
vascular system.
Regulatory Status
Included in the FDA Inactive Ingredients Database (oral tablets and
sustained-action tablets; topical and transdermal preparations).
Included in nonparenteral medicines licensed in the UK (tablets,
topical solutions, and gels). Ethyl acetate is also accepted for use in
food applications in a number of countries including the UK.
Included in the Canadian List of Acceptable Non-medicinal
Ingredients.
