Product Name: |
Ethyl acetate |
Synonyms: |
Ethyl Acetate Biosynthesis;(Benzoylthio);Ethyl acetate Manufacturer;Ethyl acetate( 99.8%, HyDry, Water≤50 ppm (by K.F.));Ethyl acetate( 99.8%, HyDry, with molecular sieves, Water≤50 ppm (by K.F.));Dichloro 2-;ALCOHOL, REAGENT, DENATURED;ALCOHOL |
CAS: |
141-78-6 |
MF: |
C4H8O2 |
MW: |
88.11 |
EINECS: |
205-500-4 |
Product Categories: |
Intermediates;Organics;Alcohol;Analytical Chemistry;LC-MS SolventsProteomics;Solvents and Solutions for Mass Spectrometry;CHROMASOLV LC-MSCHROMASOLV Solvents (HPLC, LC-MS);LC-MS Plus and Gradient;Mass Spectrometry;Mass Spectrometry (MS)&LC-MS;Chromatography/CE Reagents;CHROMASOLV PlusCHROMASOLV Solvents (HPLC, LC-MS);CHROMASOLV(R) PlusSolvents;Amber Glass Bottles;Pesticide Residue Analysis (PRA) SolventsSolvent Bottles;PRA;ACS Grade Solvents;E-H, Puriss p.a.Solvents;Ethyl AcetateChromatography/CE Reagents;Pestanal/Residue Analysis;Puriss p.a.;Solvents - GC/SH;Anhydrous Grade SolventsSolvents;AnhydrousSolvents;Returnable Container Solvents;Ethyl Acetate;Certified Natural ProductsFlavors and Fragrances;E-FSolvents;Ethyl AcetateFlavors and Fragrances;Prepackaged SamplesFlavors and Fragrances;Redi-Pack Bulk;Alphabetical Listings;Flavors and Fragrances;Hematology and Histology;Routine Histology Stains;PVC Coated Bottles;ReagentPlus(R) Solvent Grade ProductsSolvents;ReagentPlus(R)Solvents;Solvent Bottles;Sure/Seal? Bottles;Alpha Sort;E;E-LAlphabetic;EQ - EZ;Volatiles/ Semivolatiles;HPLC Plus Grade Solvents (CHROMASOLV);HPLC/UHPLC Solvents (CHROMASOLV);UHPLC Solvents (CHROMASOLV);ACS and Reagent Grade Solvents;Carbon Steel Flex-Spout Cans;ReagentPlus;ReagentPlus Solvent Grade Products;Semi-Bulk Solvents;Analytical Reagents for General Use;Puriss p.a.;PVC Coated Bottles;Sure/Seal Bottles;Anhydrous;Anhydrous Solvents;Products;Returnable Containers;GC Solvents;Pesticide Residue Analysis (PRA) Solvents;Solvents for GC applications;Solvents for Organic Residue Analysis;Trace Analysis Reagents &;Biotech Solvents;CHROMASOLV for HPLC;Composite Drums;Drums Product Line;HPLC Grade Solvents (CHROMASOLV);NOWPak Products;ACS Grade;ACS Grade Solvents;NULL;Solvents for HPLC & Spectrophotometry;Solvents for Spectrophotometry;Aluminum Bottles;ReagentPlus(R)Semi-Bulk Solvents;Ethyl AcetateSolvent Bottles;Spectrophotometric Grade Solvents;Spectrophotometric GradeSolvents;Protein Sequencing;Protein Structural Analysis;Reagents for Protein Sequencing;Chemical Class;EQ - EZAnalytical Standards;EstersAnalytical Standards;Ethyl AcetateSolvents;Biotech SolventsSolvents;CHROMASOLV Solvents (HPLC, LC-MS);CHROMASOLV(R) HPLC Grade SolventsSolvents;Solvents;CHROMASOLV for HPLCSemi-Bulk Solvents;CHROMASOLV(R) for HPLCSolvents;Composite Drums;Drums Product Line;NOWPak(R) Products;ACS Grade SolventsSolvents;ACS GradeSolvents;Analytical Reagents for General Use;E-L, Puriss p.a. ACS;Puriss p.a. ACS;ACS GradeDrums Product Line;Closed Head Drums;Ethyl AcetateSaturated fatty acids and derivatives;Ethyl EsterMore...Close...;ACS GradeSemi-Bulk Solvents;Carbon Steel Flex-Spout Cans;Esters;Capillary GC SolventsSolvent Bottles;GC Capillary;CHROMASOLV(R) LC-MSSolvents;Ethyl AcetateSpectroscopy;LEDA HPLC;Ethyl Acetate;Carthamus tinctorius (Safflower oil);Ephedra sinica;Nutrition Research;Panax ginseng;Phytochemicals by Plant (Food/Spice/Herb);Solvent by Type;Zingiber officinale (Ginger);Pharmacopoeia;Pharmacopoeia A-Z;Alphabetical Listings;Certified Food Grade Products;Certified Natural Products;Flavors and Fragrances;Kosher Certified Products;E-F;E-H;Residue Analysis (Japan only);Solvent by Application;Solvents by Special Grades (Japan Customers Only);Aluminum Bottles;Solvent Bottles;Solvent Packaging Options;Amber Glass Bottles;Analytical Reagents;Analytical/Chromatography;CHROMASOLV Plus;Chromatography Reagents &;HPLC &;Solvent |
Mol File: |
141-78-6.mol |
|
Melting point |
−84 °C(lit.) |
Boiling point |
76.5-77.5 °C(lit.) |
density |
0.902 g/mL at 25 °C(lit.) |
vapor density |
3 (20 °C, vs air) |
vapor pressure |
73 mm Hg ( 20 °C) |
refractive index |
n20/D 1.3720(lit.) |
FEMA |
2414 | ETHYL ACETATE |
Fp |
26 °F |
storage temp. |
2-8°C |
solubility |
Miscible with ethanol, acetone, diethyl ether and benzene. |
pka |
16-18(at 25℃) |
form |
Liquid |
color |
APHA: ≤10 |
Specific Gravity |
0.902 (20/20℃) |
Relative polarity |
0.228 |
Odor |
Pleasant fruity odor detectable at 7 to 50 ppm (mean = 18 ppm) |
Odor Threshold |
0.87ppm |
explosive limit |
2.2-11.5%, 38°F |
Water Solubility |
80 g/L (20 ºC) |
λmax |
λ: 256 nm Amax:
≤1.00 |
Merck |
14,3757 |
JECFA Number |
27 |
BRN |
506104 |
Henry's Law Constant |
0.39 at 5.00 °C, 0.58 at 10.00 °C, 0.85 at 15.00 °C, 1.17 at 20.00 °C, 1.58 at 25.00 °C (column stripping-UV, Kutsuna et al., 2005) |
Exposure limits |
TLV-TWA 400 ppm (~1400 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 10,000 ppm (NIOSH). |
Stability: |
Stable. Incompatible with various plastics, strong oxidizing agents. Highly flammable. Vapour/air mixtures explosive. May be moisture sensitive. |
InChIKey |
XEKOWRVHYACXOJ-UHFFFAOYSA-N |
CAS DataBase Reference |
141-78-6(CAS DataBase Reference) |
NIST Chemistry Reference |
Ethyl acetate(141-78-6) |
EPA Substance Registry System |
Ethyl acetate (141-78-6) |
Hazard Codes |
F,Xi,Xn,T |
Risk Statements |
11-36-66-67-20/21/22-10-39/23/24/25-23/24/25-68/20/21/22 |
Safety Statements |
16-26-33-36/37-45-7-25 |
RIDADR |
UN 1173 3/PG 2 |
WGK Germany |
1 |
RTECS |
AH5425000 |
F |
1 |
Autoignition Temperature |
427 °C |
TSCA |
Yes |
HS Code |
2915 31 00 |
HazardClass |
3 |
PackingGroup |
II |
Hazardous Substances Data |
141-78-6(Hazardous Substances Data) |
Toxicity |
LD50 orally in rats: 11.3 ml/kg (Smyth) |
organic ester compound |
Ethyl Acetate is an
organic ester compound with a molecular formula of C4H8O2 (commonly
abbreviated as EtOAc or EA), appears as a colorless liquid. It is highly
miscible with all common organic solvents (alcohols, ketones, glycols,
esters), which make it a common solvent for cleaning, paint removal and
coatings. |
Purification and water removal methods |
Ethyl acetate generally has a content of 95% to 98% containing a small amount of water, ethanol and acetic acid. It can be further purified as following: add 100mL of acetic anhydride into 1000mL of ethyl acetate; add 10 drops of concentrated sulfuric acid, heat and reflux for 4h to remove impurities such as ethanol and water, and then further subject to distillation. Distillate is oscillated by 20~30g of anhydrous potassium carbonate and further subject to re-distillation. The product has a boiling point of 77 °C and purity being over 99%. |
Uses |
Industry Applications Role/Benefit Flavor and essence Food flavor Used largely to prepare bananas, pears, peaches, pineapple and grape scent food flavors, etc Alcoholic essence Used slightly as fragrance volatile Perfume essence Used slightly as fragrance volatile Chemical manufacture Production of acetamide, acetyl acetate, methyl heptanone, etc Organic chemical raw materials Production of organic acid Extracting agent Laboratory Dilution and extraction Supply excellent dissolving capacity Chromatographic analysis Standard material Column chromatography and extractions Main component of mobile phase Reaction solvent Be prone to hydrolysis and transesterification Chemical analysis Thermometer calibration for sugar separation Standard material Determination of bismuth, boron, gold, molybdenum, platinum and thallium Solvent Entomology Insect collecting and study Used as effective asphyxiant to kill the collected insect quickly without destroying it Textile industry Cleaning agent Supply excellent dissolving capacity Printing Flexographic and rotogravure printing Dissolve the resin, control the viscosity and modify the drying rate Electronics industry Viscosity reducer Reduce the viscosity of resins used in photoresist formulations Paint manufacture Solvent Dissolve and dilute the paints Health & personal care products The formulation of nail polish, nail polish removers and other manicuring products Supply excellent dissolving capacity Pharmaceutical Medicine manufacturing Extraction agent; intermediate Cosmetics Aroma enhancer In perfume to enhance aroma Others Tanning extracts Used for desulfurization of tanning, cigarette materials, oil field drilling, metal flotation, descaling, etc Production of adhesive Solvent Extract many compounds (phosphorus, cobalt, tungsten, arsenic) from aqueous solution Extracting agent |
Production |
Industrial
production of ethyl acetate is mainly classified into three processes. |
Extinguishing agent |
dry powder, dry sand, carbon dioxide, foam, and 1211 fire extinguishing agent |
Professional standards |
TWA 1400 mg/m³; STEL 2000 mg/m³ |
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. |
Chemical Properties |
Ethyl acetate has a pleasant ethereal fruity, brandy-like odor, reminiscent of pineapple, somewhat nauseating in high concentration. It has fruity sweet taste when freshly diluted in water. Ethyl acetate is probably one of the most used of all flavor chemicals by volume. Ethyl acetate is slowly decomposed by moisture and then acquires an acid status due to the acetic acid formed. |
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. |
Uses |
Ethyl acetate is
used primarily as a solvent and diluent, being favored because of its low
cost, low toxicity, and agreeable odor. For example, it is commonly used to
clean circuit boards and in some nail varnish removers (acetone and
acetonitrile are also used). Coffee beans and tea leaves are decaffeinated with
this solvent.It is also used in paints as an activator or hardener.[citation
needed] Ethyl acetate is present in confectionery, perfumes, and
fruits. In perfumes, it evaporates quickly, leaving only the scent of the
perfume on the skin. |
Uses |
Ethyl acetate is used as a solvent for varnishes, lacquers, and nitrocellulose; as anartificial fruit flavor; in cleaning textiles;and in the manufacture of artificial silk andleather, perfumes, and photographic filmsand plates (Merck 1996). |
Uses |
Pharmaceutic aid (flavor); artificial fruit essences; solvent for nitrocellulose, varnishes, lacquers, and aeroplane dopes; manufacture of smokeless powder, artificial leather, photographic films and plates, artificial silk, perfumes; cleaning textiles, etc. |
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: |
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. |
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: |
Aroma threshold values |
Detection: 5 ppb to 5 ppm |
Air & Water Reactions |
Highly flammable. Slightly soluble in water. Ethyl acetate is slowly hydrolyzed by moisture. |
Reactivity Profile |
Ethyl acetate is also sensitive to heat. On prolonged storage, materials containing similar functional groups have formed explosive peroxides. Ethyl acetate may ignite or explode with lithium aluminum hydride. Ethyl acetate may also ignite with potassium tert-butoxide. Ethyl acetate is incompatible with nitrates, strong alkalis and strong acids. Ethyl acetate will attack some forms of plastics, rubber and coatings. Ethyl acetate 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, 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.). |
Health Hazard |
The acute toxicity of ethyl acetate is low. Ethyl acetate vapor causes eye, skin, and respiratory tract irritation at concentrations above 400 ppm. Exposure to high concentrations may lead to headache, nausea, blurred vision, central nervous system depression, dizziness, drowsiness, and fatigue. Ingestion of ethyl acetate may cause gastrointestinal irritation and, with larger amounts, central nervous system depression. Eye contact with the liquid can produce temporary irritation and lacrimation. Skin contact produces irritation. Ethyl acetate is regarded as a substance with good warning properties. No chronic systemic effects have been reported in humans, and ethyl acetate has not been shown to be a human carcinogen, reproductive, or developmental toxin |
Fire Hazard |
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 |
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. |
Safety Profile |
Potentially poisonous by ingestion. Toxicity depends upon alcohols in question, generally ethanol with methanol as a denaturant. A flammable liquid and dangerous fire hazard; can react vigorously with oxidzing materials. Moderate explosion hazard. See ETHANOL, METHYL ALCOHOL, and n-PROPYL ALCOHOL. |
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. |
Chemical 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. |
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 |
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. |
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. |
Shipping |
UN1173 Ethyl acetate, Hazard Class: 3; Labels: 3-Flammable liquid. |
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.] |
Incompatibilities |
Ethyl acetate can react vigorously with strong oxidizers, strong alkalis, strong acids, and nitrates to cause fires or explosions. It also reacts vigorously with chlorosulfonic acid, lithium aluminum hydride, 2-chloromethylfuran, and potassium tert-butoxide. |
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. |
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. |
Raw materials |
Etanol-->Sulfuric acid-->Acetic acid glacial-->Potassium carbonate-->1-Butanol-->Calcium oxide-->Potassium Acetate-->ketene |
Preparation Products |
N-ETHYL 3-NITROBENZENESULFONAMIDE-->Methyl 4-bromo-3-nitrobenzoate-->ETHYL ISONICOTINOYLACETATE-->Sodium 1-heptanesulfonate-->D-glucose pentakis[3,4-dihydroxy-5-[(trihydroxy-3,4,5-benzoyl)oxy]benzoate]-->Ampicillin sodium-->Diphenyl N-cyanocarbonimidate-->4(1H)-Pyrimidinone, 2-methyl- (8CI,9CI)-->4-FLUOROBENZYL ISOCYANATE-->2-(2-FORMYL-PHENOXY)-PROPIONIC ACID-->N-METHOXYCARBONYLMALEIMIDE-->2-Amino-6-bromopyridine-->3-METHYL-4-PYRIDINECARBOXYLIC ACID-->N-BENZYL-6-CHLORO-N-METHYLPYRIDAZIN-3-AMINE-->polyurethane adhesive for dry laminating-->2-ISOCYANATO-4,6-DIMETHOXYPYRIMIDINE-->Methyl 3-bromo-4-methylbenzoate-->N-Acetylethylenediamine-->3-Hydroxypiperidine-->ETHYL PICOLINOYLACETATE-->N-Hexadecyltrimethylammonium chloride-->Boc-O-benzyl-L-tyrosine-->2-Acetylthiazole-->ALUMINUM DI(ISOPROPOXIDE)ACETOACETIC ESTER CHELATE-->Tea polyphenol-->2-(4-Ethoxyphenyl)-2-methylpropanol-->BOC-Glycine-->dry laminating adhesive AD-->adhesive No.1 for shrink packaging-->Triphenylsilanol-->granular adhesive PUA-->special adhesive JA-501 for laminating packaging materials-->special adhesive JA-502 for aluminum-plastics laminating tape-->Enoximone-->coating adhesive tiemao 102-->adhesive M-861 for polyolefin plastics-->self curing adhesive SL-B404-->wealant XY-2-->Water-proof adhesive-->adhesive JX-18-1 |