Ethyl Acetate

Base Information

• Chemical Name: Ethyl Acetate
• CAS No.: 141-78-6
• Molecular Formula: C4H8O2
• Molecular Weight: 88.1063
• Hs Code.: 2915.39
• European Community (EC) Number: 205-500-4
• ICSC Number: 0367
• NSC Number: 70930
• UN Number: 1173
• UNII: 76845O8NMZ
• DSSTox Substance ID: DTXSID1022001
• Nikkaji Number: J2.952A,J3.639.860D
• Wikipedia: Ethyl acetate,Ethyl_acetate
• Wikidata: Q407153
• NCI Thesaurus Code: C76707
• RXCUI: 1314355
• Metabolomics Workbench ID: 44758
• ChEMBL ID: CHEMBL14152
• Mol file: 141-78-6.mol

Synonyms:ethyl acetate

Chemical Property of Ethyl Acetate

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 73 mm Hg ( 20 °C)
• Melting Point: -83.6 °C, 190 K, -118 °F
• Refractive Index: n20/D 1.3720(lit.)
• Boiling Point: 77.1 °C, 350 K, 171 °F
• PKA: 16-18(at 25℃)
• Flash Point: -4 °C
• PSA: 26.30000
• Density: 0.898 g/cm³
• LogP: 0.56940
• Storage Temp.: 2-8°C
• Solubility.: Miscible with ethanol, acetone, diethyl ether and benzene.
• Water Solubility.: 80 g/L (20 ºC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 49.5
• Transport DOT Label: Flammable Liquid

Purity/Quality:

Ethyl acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi,Xn,T
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Esters (
• Canonical SMILES: CCOC(=O)C
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and respiratory tract. The substance may cause effects on the central nervous system. Exposure far above the OEL could cause lowering of consciousness.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking.
• 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 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). Ethyl Acetate is generally used as a solvent in organic reactions. Environmental contaminants; Food contaminants. 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.3 – 1 - Laboratory uses In the laboratory, mixtures containing ethyl acetate are commonly used in column chromatography and extractions. Ethyl acetate is rarely selected as a reaction solvent because it is prone to hydrolysis and trans esterification. 3 – 2 - Occurrence in wines 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. 3 – 3 - Entomological killing agent In the field of entomology, ethyl acetate is an effective asphyxiant for use in insect collecting and study. In a killing jar charged with ethyl acetate, the vapors will kill the collected (usually adult) 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. 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.
• 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.
• 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.

Technology Process of Ethyl Acetate

There total 1007 articles about Ethyl Acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 39.0%

(PPh3)3CoH(N2) (21373-88-6,16920-54-0) → methane (34557-54-5,27936-85-2) + cobalt acetate (55881-15-7) + nitrogen (7727-37-9) + hydrogen (1333-74-0) + ethyl acetate (141-78-6)

Guidance literature:

With acetic acid anhydride; In toluene; Ac2O added to toluene soln. of CoH(N2)(PPh3)3, evacuated, stirred at room temp. for 1 day; hexane added, recrystd. from pyridine;

DOI:10.1021/ja00263a007

Reference yield:

ethanol (64-17-5) + trimethylsilanyl-acetic acid ethyl ester (4071-88-9) → ethyl trimethylsilyl ether (1825-62-3) + ethyl acetate (141-78-6)

Guidance literature:

DOI:10.1021/ja01189a011

Reference yield:

ethyl bromoacetate (105-36-2) → hydrogen bromide (10035-10-6,12258-64-9) + acetaldehyde (75-07-0,9002-91-9) + ethyl acetate (141-78-6)

Guidance literature:

at 250 - 300 ℃;

upstream raw materials:

pyridine

N-chloro-succinimide

ethanol

benzene

Downstream raw materials:

1-ethylpyrrolidine

2-(1-cyclohexenyl)cyclohexanone

1-piperidinylcarbonnitrile

2-cyclopentylidenecyclopentan-1-one

Refernces

• 1、 Hou, Xiaoxiong,Zhao, Jinxian,Liu, Junjie,Han, Yahong,Pei, Yongli,Ren, Jun. "Activated carbon aerogel supported copper catalysts for the hydrogenation of methyl acetate to ethanol: Effect of KOH activation". . p. 9430 - 9438. Retrieved 2019.
• 2、 Rakhimov, A. I.,Chapurkin, V. V.,Val'dman, A. I.,Val'dman, D. I.,Saloutin, V. I.,et al.. "THERMAL DECOMPOSITION OF PEROXIDE DERIVATIVES OF POLYFLUORINATED β-KETOESTERS". . . Retrieved 1990.
• 3、 Akhrem, I. S.,Vartanyan, R. S.,Afanas'eva, L. V.,Vol'pin, M. E.. "SPLITTING OF C-C BONDS IN β-DICARBONYL COMPOUNDS CATALYZED BY TRANSITION METAL COMPLEXES". . p. 1217 - 1220. Retrieved 1983.
• 4、 Khatuntsev, I. I.,Pastushenko, E. V.,Terent'ev, A. B.. "RADICAL REACTION OF ETHYL ORTHOACETATE WITH 3,3,3-TRIFLUOROPROPENE". . p. 1435 - 1438. Retrieved 1986.
• 5、 Men'Shchikov,Gol'Dshtein,Semenov. "Kinetics of ethanol dehydrogenation into ethyl acetate". . p. 12 - 17. Retrieved 2014.
• 6、 Rachmady,Vannice. "Acetic acid hydrogenation over supported platinum catalysts". . p. 322 - 334. Retrieved 2000.
• 7、 Ro, Insoo,Liu, Yifei,Ball, Madelyn R.,Jackson, David H. K.,Chada, Joseph Paul,Sener, Canan,Kuech, Thomas F.,Madon, Rostam J.,Huber, George W.,Dumesic, James A.. "Role of the Cu-ZrO2 Interfacial Sites for Conversion of Ethanol to Ethyl Acetate and Synthesis of Methanol from CO2 and H2". . p. 7040 - 7050. Retrieved 2016.
• 8、 Hawes,Kabel. "-". . p. 606,609. Retrieved 1968.
• 9、 Church,Joshi. "-". . p. 1804. Retrieved 1951.
• 10、 Silbaugh, Trent L.,Devlaminck, Pierre,Sofranko, John A.,Barteau, Mark A.. "Selective oxidation of ethanol over Ag, Cu and Au nanoparticles supported on Li2O/Γ-Al2O3". . p. 40 - 47. Retrieved 2018.