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141-78-6

Basic Information
CAS No.: 141-78-6
Name: Ethyl acetate
Article Data: 1071
Molecular Structure:
Molecular Structure of 141-78-6 (Ethyl acetate)
Formula: C4H8O2
Molecular Weight: 88.1063
Synonyms: Ethyl ethanoate;Ethyl ester;Acetic ester;Ester of ethanol;AI3-00404;Acetate d'ethyle;Acetic acid, ethyl ester;Acetidin;Acetoxyethane;Aethylacetat;
EINECS: 205-500-4
Density: 0.898 g/cm3
Melting Point: -83.6 °C, 190 K, -118 °F
Boiling Point: 77.1 °C, 350 K, 171 °F
Flash Point: -4 °C
Solubility: 8.3 g/100 mL (20 °C) in water, miscible with ethanol, acetone, diethyl ether, benzene
Appearance: colorless liquid
Hazard Symbols: FlammableF,IrritantXi
Risk Codes: 11-36-66-67
Safety: 16-26-33
Transport Information: UN 1173 3/PG 2
PSA: 26.30000
LogP: 0.56940
Synthetic route
64-17-5

ethanol

4232-27-3

2,4-dinitrophenyl acetate

141-78-6

ethyl acetate

Conditions
ConditionsYield
With [{lμ2-3-1κO-((carboxylatomethyl)amino)-4-chlorobenzoato}(N,N,N-κ3-2,3,5,6-tetrakis(2-pyridyl)pyrazine)zinc(II)]n(dimethylformamide)(water) In dimethyl sulfoxide at 80℃; for 5h; Time;85%
64-17-5

ethanol

64-19-7

acetic acid

141-78-6

ethyl acetate

Conditions
ConditionsYield
niobium(V) oxide at 200℃; for 1h; Product distribution; examination of niobic acid as an efficient catalyst; var. catalysts, temps;;100%
With sulfuric acid at 70℃; for 5h; Reagent/catalyst;96%
With 1-butyl-2-methylbenzimidazolium tetrafluoroborate at 80℃; for 2h;95%
64-17-5

ethanol

A

75-07-0

acetaldehyde

B

64-19-7

acetic acid

C

141-78-6

ethyl acetate

Conditions
ConditionsYield
With oxygen; Pd on Zeolite Y at 90 - 110℃; under 760.051 - 1520.1 Torr; Product distribution / selectivity;A 0.5%
B 7.5%
C 49.6%
With oxygen; Pd on Zeolite Y In water at 70 - 150℃; under 22801.5 Torr; Conversion of starting material;A 0.1%
B 3.6%
C 22.5%
With oxygen; Pt on Zeolite ZSM-5 at 110℃; under 1520.1 Torr; Product distribution / selectivity;A 7.4%
B 3.9%
C 10.2%
64-17-5

ethanol

A

75-07-0

acetaldehyde

B

141-78-6

ethyl acetate

Conditions
ConditionsYield
With copper supported on ZnAl2O4 at 399.84℃; Temperature; Flow reactor;A 90%
B n/a
With oxygen; Sb2O4-MoO3 (Sb4Mo10O31) at 200 - 350℃; in a flow system;A n/a
B 30%
With oxygen; Sb2O4-MoO3 (Sb4Mo10O31) at 200 - 350℃; Product distribution; selectivity and activity of the Sb-Mo-O catalyst in the oxidation of ethanol;A n/a
B 30%
64-67-5

diethyl sulfate

107-21-1

ethylene glycol

141-78-6

ethyl acetate

Conditions
ConditionsYield
With lithium hydroxide at 35℃; under 50 Torr; Temperature; Pressure; Reagent/catalyst;62%
75-07-0

acetaldehyde

141-78-6

ethyl acetate

Conditions
ConditionsYield
With [{(PhN)MeC(Nt-Bu)}AlMe(μ-OMe)]2 at 20℃; for 16h; Tishchenko-Claisen Dismutation; Inert atmosphere; Schlenk technique; Green chemistry;95%
With Rh(PhBP3)(H)2(NCMe); hydrogen In toluene at 20℃; under 760.051 Torr; for 0.166667h; Tishchenko reaction;68%
With magnesium oxide; copper at 400℃;
74-85-1

ethene

64-19-7

acetic acid

A

60-29-7

diethyl ether

B

64-17-5

ethanol

C

141-78-6

ethyl acetate

Conditions
ConditionsYield
Stage #1: acetic acid With water at 92.4℃;
Stage #2: ethene; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 92.4 - 194.4℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;
A 3.2%
B 3.6%
C 92.7%
With water; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 92.4 - 165℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;A 3%
B 3.4%
C 91.5%
With water; lithium nitrate; silica; tungstophosphoric acid; water; mixture of, heated at 150 C at 102.2 - 165℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;A 2.2%
B 5%
C 90.1%
With water; lithium nitrate; silica; tungstosilicic acid; water; mixture of, heated at 150 C at 102.2 - 165℃; under 6750.68 Torr; Conversion of starting material; Gas phase;A 4.7%
B 7.6%
C 87.7%
943406-22-2

4-(3-(3,4-dimethylcyclopenta-1,3-dienone)-4-(cyclohexylamino)benzyl)-2-(3,4-dimethylcyclopenta-1,3-dienone)-N-cyclohexylbenzeneamine

A

4-(3-(2,3,5-trimethylcyclopenta-1,3-diene)-4-(cyclohexylamino)benzyl)-2-(2,3,5,-trimethylcyclopenta-1,3-diene)-N-cyclohexylbenzeneamine

B

141-78-6

ethyl acetate

Conditions
ConditionsYield
With methyllithium; CeCl3 In tetrahydrofuran; diethyl etherA 46%
B n/a
64-17-5

ethanol

108-24-7

acetic anhydride

141-78-6

ethyl acetate

Conditions
ConditionsYield
With silver trifluoromethanesulfonate at 60℃; for 0.0666667h; neat (no solvent);97%
With tetrakis(triphenylphosphineoxide)dioxouranium(VI) perchlorate In dichloromethane-d2 at 22℃; for 2h; Mechanism; Reagent/catalyst; Solvent;97%
With vanadyl sulfate trihydrate at 20℃; for 8h;93%
64-17-5

ethanol

141-78-6

ethyl acetate

Conditions
ConditionsYield
With water; potassium iodide at 20℃; for 3h; Electrochemical reaction; Green chemistry;95.2%
With HCl(CO)Ru(Phen-(tBu)PNN); potassium tert-butylate In neat (no solvent) for 14h; Schlenk technique; Inert atmosphere;59%
With iodine; hexachloroplatinate(II) In water47%
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    Name Ethyl acetate Synonyms Acetic acid ethyl ester Molecular Structure Molecular Formula

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Specification

Ethyl acetate, with the CAS registry number 141-78-6, is a clear colorless liquid with a fruity odor. Its EINECS registry number is 205-500-4. This chemical is soluble in water which is an organic compound with the formula CH3COOCH2CH3. Ethyl acetate is stable under normal temperature conditions and recommended use. In addition, it is a flammable liquid with a flash point lower than 37.8°C (100°F). The substance may be toxic to blood, kidneys, liver, central nervous system (CNS). Ethyl acetate should be stored in a segregated and approved area, and should keep its container in a cool, well-ventilated area, which should be tightly closed and sealed until ready for use.

Physical properties about Ethyl acetate are:
(1)ACD/LogP: 0.785; (2)ACD/LogD (pH 5.5): 0.79; (3)ACD/LogD (pH 7.4): 0.79; (4)ACD/BCF (pH 5.5): 2.33; (5)ACD/BCF (pH 7.4): 2.33; (6)ACD/KOC (pH 5.5): 63.70; (7)ACD/KOC (pH 7.4): 63.70; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.373; (11)Molar Refractivity: 22.355 cm3; (12)Molar Volume: 98.045 cm3; (13)Polarizability: 8.862 10-24cm3; (14)Surface Tension: 23.568000793457 dyne/cm; (15)Density: 0.899 g/cm3; (16)Flash Point: -3.333 °C; (17)Enthalpy of Vaporization: 31.94 kJ/mol; (18)Boiling Point: 73.935 °C at 760 mmHg; (19)Vapour Pressure: 111.716003417969 mmHg at 25°C

Production of Ethyl acetate:
In industry, Ethyl acetate is synthesized mainly by ethanol and acetic acid via the classic Fischer esterification reaction. This reaction occurs at room temperature with the yield about 65%, that will more quickly by acid catalysis.
CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O
Additionally, Ethyl acetate is also prepared industrially by combining two equivalents of acetaldehyde in the presence of an alkoxide catalyst using the Tishchenko reaction. The yield is about 95%-96%. This method is less cost than others.
2 CH3CHO [Al(OR)3] → CH3COOCH2CH3
What's more, it can also be produced by ethylic acid and ethene via the esterification reaction. The reaction equation is as the following:
CH3COOH + C2H4 → CH3COOC2H5

Uses of Ethyl acetate:
 Ethyl acetate is the ester of ethanol and acetic acid. Because of its low cost, low toxicity, and agreeable odor, it is used as a solvent and diluent. Ethyl acetate is also used in glues or nail polish removers. Since it is prone to hydrolysis and transesterification, Ethyl acetate is rarely selected as a reaction solvent. In the laboratory, mixtures that contains ethyl acetate are used in column chromatography and extractions.Ethyl acetate is the most common ester in wine. The aroma of ethyl acetate is most vivid in younger wines and contributes towards the general perception of "fruitiness" in the wine. Ethyl acetate is an effective asphyxiant for use in insect collecting and study. Because it is not hygroscopic, Ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection. It is also used in paints as an activator or hardener.

Safety information of Ethyl acetate:
When you are using Ethyl acetate, you should be very cautious. This chemical is irritating to eyes which is also highly flammable. Repeated exposure may cause skin dryness or cracking. Its vapour may cause drowsiness and dizziness. It should be kept away from sources of ignition - no smoking. In case of contact with eyes, you need rinse immediately with plenty of water and seek medical advice. Whenever you need, you can take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCOC(=O)C
(2)InChI: InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
(3)InChIKey: XEKOWRVHYACXOJ-UHFFFAOYSA-N

The toxicity data of Ethyl acetate is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LCLo inhalation 61gm/m3 (61000mg/m3)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 336, 1955.
cat LD50 subcutaneous 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: OTHER CHANGES
Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
guinea pig LD50 oral 5500mg/kg (5500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: COMA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(4), Pg. 66, 1983.
guinea pig LD50 subcutaneous 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
human TCLo inhalation 400ppm (400ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.
mouse LC50 inhalation 45gm/m3/2H (45000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 65, 1982.
mouse LD50 intraperitoneal 709mg/kg (709mg/kg)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 5, 1961.
mouse LD50 oral 4100mg/kg (4100mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: COMA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(4), Pg. 66, 1983.
rabbit LD50 oral 4935mg/kg (4935mg/kg)   Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972.
rabbit LD50 skin > 20mL/kg (20mL/kg)   Union Carbide Data Sheet. Vol. 10/4/1968,
rat LC50 inhalation 200gm/m3 (200000mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
rat LD50 oral 5620mg/kg (5620mg/kg)   Yakkyoku. Pharmacy. Vol. 32, Pg. 1241, 1981.
rat LDLo subcutaneous 5gm/kg (5000mg/kg)   Bolletino della Societe Italiana di Biologia Sperimentale. Vol. 18, Pg. 45, 1943.