Ethyl acetate

{{chembox

| Watchedfields = changed

| verifiedrevid = 477003783

| Name = Ethyl ethanoate

| ImageFile1 = Ethyl-acetate-2D-skeletal.svg

| ImageSize1 = 200px

| ImageName1 = Skeletal formula

| ImageFile2 = File:Ethyl-acetate-from-xtal-3D-bs-17.png

| ImageName2 = Ball-and-stick model

| PIN = Ethyl acetate

| ImageAlt3 = Ethyl acetate

| ImageFile3 = Ethyl acetate in a 50mL-beaker.jpg

|ImageSize3 = 150px

| SystematicName = Ethyl ethanoate

| OtherNames = {{ubl|Acetic ester|Acetic ether|Ethyl ester of acetic acid|Ethanoic ethyl ester}}

| Section1 = {{Chembox Identifiers

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 27750

| SMILES = O=C(OCC)C

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8525

| PubChem = 8857

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 76845O8NMZ

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02319

| InChI = 1/C3H8O2/c1-3-6-4(2)5/h3H2,1-2H3

| InChIKey = XEKOWRVHYACXOJ-UHFFFAOYAD

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 14152

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XEKOWRVHYACXOJ-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 141-78-6

| RTECS = AH5425000

| Beilstein = 506104

| Gmelin = 26306

}}

| Section2 = {{Chembox Properties

| C=4 | H=8 | O=2

| Appearance = Colorless liquid

| Odor = nail polish-like, fruity

| Density = 0.902 g/cm³

| Solubility = 8.3 g/100 mL (at 20 °C)

| Solvent = ethanol, acetone, {{nowrap|diethyl ether}}, benzene

| SolubleOther = Miscible

| MeltingPtC = −83.6

| BoilingPtC = 77.1

| Viscosity = 426 μPa·s (0.426 cP) at 25 °C

| RefractIndex = 1.3720

| pKa = 25

| LogP = 0.71{{Cite web|url=https://www.chemsrc.com/en/cas/141-78-6_1094578.html|title=ethyl acetate MSDS }}

| VaporPressure = {{convert|73|mmHg|kPa|abbr=on}} at 20 °C{{PGCH|0260}}

| MagSus = {{val|−54.10|e=-6|u=cm³/mol}}

}}

| Section3 = {{Chembox Structure

| Dipole = 1.78 D

}}

| Section4 =

| Section5 =

| Section6 =

| Section7 = {{Chembox Hazards

| ExternalSDS =

| MainHazards = {{ubl|Flammable (F),|Irritant (Xi)}}

| NFPA-H = 2

| NFPA-F = 3

| NFPA-R = 0

| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}{{GESTIS|ZVG=12040 |CAS=141-78-6 |Name=Ethyl acetate |Date=7 December 2020 }}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|225|319|336}}

| PPhrases = {{P-phrases|210|233|240|305+351+338|403+235}}

| FlashPtC = −4

| LD50 = 11.3 g/kg, rat

| PEL = TWA 400 ppm (1400 mg/m³)

| ExploLimits = 2.0–11.5%

| IDLH = 2000 ppm

| REL = TWA 400 ppm (1400 mg/m³)

| LC50 = 16,000 ppm (rat, 6 h)
12,295 ppm (mouse, 2 h)
1600 ppm (rat, 8 h){{IDLH|141786|Ethyl acetate}}

| LCLo = 21 ppm (guinea pig, 1 h)
12,330 ppm (mouse, 3 h)

}}

| Section8 = {{Chembox Related

| OtherFunction_label = carboxylate esters

| OtherFunction = {{ubl|Methyl acetate,|Propyl acetate,|Butyl acetate}}

| OtherCompounds = {{ubl|Acetic acid,|Ethanol,|Diethyl ether }}

}}

Ethyl acetate commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula {{chem2|CH3CO2CH2CH3}}, simplified to {{chem2|C4H8O2}}. This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.{{Ullmann|first1=Wilhelm|last1=Riemenschneider|first2=Hermann M.|last2=Bolt|title=Esters, Organic|doi=10.1002/14356007.a09_565.pub2}}

Production and synthesis

Ethyl acetate was first synthesized by the Count de Lauraguais in 1759 by distilling a mixture of ethanol and acetic acid.{{cite journal|last=Parker|first=Joseph|title=The Edinburgh Encyclopaedia|journal=The Edinburgh Encyclopaedia |volume=5|year=1832|url=https://books.google.com/books?id=8-JEAQAAMAAJ}}

In 2004, an estimated 1.3 million tonnes were produced worldwide.{{cite journal|last=Dutia|first=Pankaj|date=August 10, 2004|title=Ethyl Acetate: A Techno-Commercial Profile|journal=Chemical Weekly|pages=184|url=http://www.chemicalweekly.com/Profiles/Ethyl_Acetate.pdf#page=6|access-date=2009-03-21|format=PDF}} The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tonnes. The global ethyl acetate market was valued at $3.3 billion in 2018.{{Cite web|url=https://www.visiongain.com/global-ethyl-acetate-market-to-be-valued-at-3-3-billion-in-2018-reports-visiongain/|title="Global Ethyl Acetate Market to be valued at $3.3 billion in 2018" reports Visiongain|date=2019-09-05|website=Visiongain|language=en-US|access-date=2019-09-05}}

Ethyl acetate is produced 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:

:{{chem2|CH3CO2H + CH3CH2OH → CH3CO2CH2CH3 + H2O}}

The reaction can be accelerated by acid catalysts 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:

:{{chem2|2 CH3CHO → CH3CO2CH2CH3}}

Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene:{{cite journal | last1 = Misono | first1 = Makoto | year = 2009 | title = Recent progress in the practical applications of heteropolyacid and perovskite catalysts: Catalytic technology for the sustainable society | journal = Catalysis Today | volume = 144 | issue = 3–4| pages = 285–291 | doi = 10.1016/j.cattod.2008.10.054 }}

:{{chem2|C2H4 + CH3CO2H → CH3CO2C2H5}}

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 is also used). Coffee beans and tea leaves are decaffeinated with this solvent.[http://www.ico.org/decaffeination.asp ico.org] {{webarchive|url=https://web.archive.org/web/20070429084212/http://www.ico.org/decaffeination.asp |date=2007-04-29 }} It is also used in paints as an activator or hardener. Ethyl acetate is present in confectionery, perfumes, and fruits. In perfumes it evaporates quickly, leaving the scent of the perfume on the skin.

Ethyl acetate is an asphyxiant for use in insect collecting and study.{{Cite journal |last1=Littledyke |first1=M. |last2=Cherrett |first2=J. M. |date=June 1976 |title=Direct ingestion of plant sap from cut leaves by the leaf-cutting ants Atta cephalotes (L.) and acromyrmex octospinosus (reich) (Formicidae, Attini) |url=https://www.cambridge.org/core/journals/bulletin-of-entomological-research/article/abs/direct-ingestion-of-plant-sap-from-cut-leaves-by-the-leafcutting-ants-atta-cephalotes-l-and-acromyrmex-octospinosus-reich-formicidae-attini/AF32CE2FBBD06C93D5FC3DE8287B1777 |journal=Bulletin of Entomological Research |language=en |volume=66 |issue=2 |pages=205–217 |doi=10.1017/S0007485300006647 |issn=1475-2670|url-access=subscription }} In a killing jar charged with ethyl acetate, the vapors will kill the collected 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. However, ethyl acetate is regarded as potentially doing damage to insect DNA, making specimens processed this way less than ideal for subsequent DNA sequencing.{{cite journal|pmid=35804181 |date=2022 |last1=Cilia |first1=G. |last2=Flaminio |first2=S. |last3=Quaranta |first3=M. |title=A novel and non-invasive method for DNA extraction from dry bee specimens |journal=Scientific Reports |volume=12 |issue=1 |page=11679 |doi=10.1038/s41598-022-15595-8 |pmc=9270346 |bibcode=2022NatSR..1211679C }}

=Laboratory uses=

In the laboratory, mixtures containing ethyl acetate are commonly used in column chromatography and extractions.{{OrgSynth|prep=v95p0001

|title=Copper and Secondary Amine-Catalyzed Pyridine Synthesis from O-Acetyl Oximes and α,β-Unsaturated Aldehydes

|first=Wei Wen|last=Tan

|first2=Bin|last2=Wu

|first3=Ye|last3=Wei

|first4=Naohiko|last4=Yoshikai

|year=2018

|volume=95|pages=1–14

|doi=10.15227/orgsyn.095.0001|doi-broken-date=2020-03-22}} Ethyl acetate is rarely selected as a reaction solvent because it is prone to hydrolysis, transesterification, and condensations.

=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. Sensitivity varies, with most people having a perception threshold around 120 mg/L. Excessive amounts of ethyl acetate are considered a wine fault.

Reactions

Ethyl acetate is only weakly Lewis basic, like a typical carboxylic acid ester.

Ethyl acetate hydrolyses to give acetic acid and ethanol. Bases accelerate 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 a strong base, such as sodium hydroxide. This reaction gives ethanol and sodium acetate, which is unreactive toward ethanol:

:{{chem2|CH3CO2C2H5 + NaOH → C2H5OH + CH3CO2Na}}

In the Claisen condensation, anhydrous ethyl acetate and strong bases react to give ethyl acetoacetate:{{cite journal|journal=Org. Synth. | first1= J. K. H.|last1=Inglis|first2=K. C.|last2=Roberts | title = Ethyl Acetoacetate | volume = 6 | page= 36| doi= 10.15227/orgsyn.006.0036| year = 1926}}

:Image:Claisen ethyl acetate.png{{clear|left}}

Properties

= Physical properties =

File:Vapour pressure ethyl acetate.svg

File:Heat_of_evaporation_ethyl_acetate.svg

Its melting point is −83 °C, with a melting enthalpy of 10.48 kJ/mol. At atmospheric pressure, the compound boils at 77 °C. The vaporization enthalpy at the boiling point is 31.94 kJ/mol. The vapor pressure function follows the Antoine equation

: $\log_{10}(p) = A - \frac{B}{T + C},$

where

: $p$ is the vapor pressure in bars,

: $T$ is the absolute temperature in kelvins, and

: $A = 4.22809$ , $B = 1245.702$ , $C = -55.189$ are constants.

This function is valid within the temperature range of {{cvt|289|to(-)|349|K|C}}.

The enthalpy of vaporization in kJ/mol is calculated according to the empirical equation by Majer and SvobodaV. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985, ISBN 0-632-01529-2.

: $\Delta H_\text{vap} = A\exp(-\beta\,T_\text{r})\,(1 - T_\text{r})^\beta,$

where

: $T_\text{r} = T/T_\text{c}$ is the reduced temperature, and $T_\text{c}$ = 523.2 K is the critical temperature.

: $A$ = 54.26 kJ/mol and $\beta$ = 0.2982 are constants.

The following table summarizes the most important thermodynamic properties of ethyl acetate under various conditions.

Property	Type	Value	Remarks	References
class="wikitable" \|+ Compilation of key thermodynamic properties
Standard enthalpy of formation	$\Delta_f H^0_\text{liquid}$ $\Delta_f H^0_\text{gas}$	−480.57 kJ/mol −445.43 kJ/mol	as liquid as gas	K. B. Wiberg, L. S. Crocker, K. M. Morgan: Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups. In: J. Am. Chem. Soc. 113, 1991, pp. 3447–3450. doi:10.1021/ja00009a033.
Standard entropy	$S^0_\text{liquid}$ $S^0_\text{gas}$	259.4 J/(mol·K) 362.75 J/(mol·K)	as liquid as gas	G. S. Parks, H. M. Huffman, M. Barmore: Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. In: J. Am. Chem. Soc. 55, 1933, S. 2733–2740, doi:10.1021/ja01334a016.D. R. Stull, Jr.: The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969.
Combustion enthalpy	$\Delta_c H^0_\text{liquid}$	−2235.4 kJ/mol		M. E. Butwill, J. D. Rockenfeller: Heats of combustion and formation of ethyl acetate and isopropyl acetate. In: Thermochim. Acta. 1, 1970, pp. 289–295. doi:10.1016/0040-6031(70)80033-8.
Heat capacity (25 °C)	$c_p$	168.94 J/(mol·K) 1.92 J/(g·K) 113.64 J/(mol·K) 1.29 J/(g·K)	as liquid as gas	{{cite journal \|first1=M. \|last1=Pintos \|first2=R. \|last2=Bravo \|first3=M. C. \|last3=Baluja \|first4=M. I. \|last4=Paz Andrade \|first5=G. \|last5=Roux-Desgranges \|first6=J.-P. E. \|last6=Grolier \|title=Thermodynamics of alkanoate + alkane binary mixtures. Concentration dependence of excess heat capacities and volumes \|journal=Can. J. Chem. \|year=1988 \|volume=66 \|issue=5 \|pages=1179–1186 \|doi=10.1139/v88-193 }}
Critical temperature	$T_\text{c}$	523.2 K
Critical pressure	$p_\text{c}$	38.82 bar		D. Ambrose, J. H. Ellender, H. A. Gundry, D. A. Lee, R. Townsend: Thermodynamic properties of organic oxygen compounds. LI. The vapour pressures of some esters and fatty acids. In: J. Chem. Thermodyn. 13, 1981, S. 795–802. doi:10.1016/0021-9614(81)90069-0.
Critical density	$\rho_\text{c}$	3.497 mol/L		S. Young, G. L. Thomas: The vapour pressures, molecular volumes, and critical constants of ten of the lower esters. In: J. Chem. Soc. 63, 1893, S. 1191.
Acentric factor	$\omega_c$	0.36641		J. Schmidt: Auslegung von Sicherheitsventilen für Mehrzweckanlagen nach ISO 4126-10 {{in lang\|de}}. In: Chem. Ing. Techn. 83, 2011, pp. 796–812. doi:10.1002/cite.201000202.

Safety

The {{LD50}} for rats is 5620 mg/kg,Hazard Ethyl Acetate MSDS {{cite web|url=http://hazard.com/msds/mf/baker/baker/files/e2850.htm|title=Ethyl Acetate MSDS Number: E2850}} indicating low acute toxicity. Given that the chemical is naturally present in many organisms, there is little risk of toxicity.

World Health Organization(WHO) has assessed the Acceptable Daily Intake(ADI) of Ethyl Acetate at 25mg per kg of body weight.WHO Evaluations {{Cite web|url=https://apps.who.int/food-additives-contaminants-jecfa-database/Home/Chemical/3075|title=Ethyl Acetate ADI}} This is similar to the ADI of other artifcial sweeteners that are friendly and have been commonly used for a long time.FDA Information {{Cite web|url=https://www.fda.gov/food/food-additives-petitions/aspartame-and-other-sweeteners-food|archive-url=https://web.archive.org/web/20230601065858/https://www.fda.gov/food/food-additives-petitions/aspartame-and-other-sweeteners-food|url-status=dead|archive-date=June 1, 2023|title=Aspartame and Other Sweeteners in Food}}{{Cite journal|title=Re-evaluation of glutamic acid (E 620), sodium glutamate (E 621), potassium glutamate (E 622), calcium glutamate (E 623), ammonium glutamate (E 624) and magnesium glutamate (E 625) as food additives|journal=EFSA Journal|year=2017|doi=10.2903/j.efsa.2017.4910}} According to European Food Safety Authority(EFSA), Ethyl Acetate taken orally is rapidly metabolized and broken down. The half-life in blood after ingestion exposure is known to be appproximately 35 seconds.{{Cite journal|author=Williams ES, Ryder VE|title=Spaceflight Maximum Allowable Concentrations for Ethyl Acetate|journal=Aerosp Med Hum Perform|year=2023|doi=10.3357/AMHP.6057.2023}}

Overexposure to ethyl acetate may cause irritation of the eyes, nose, and throat. Severe overexposure may cause weakness, drowsiness, and unconsciousness.{{cite book|editor-last=Mackison|editor-first=F. W.|editor2-first=R. S.|editor2-last=Stricoff|editor3-first=L. J. Jr. |editor3-last=Partridge|title=NIOSH/OSHA – Occupational Health Guidelines for Chemical Hazards|series=DHHS (NIOSH) Publication No. 81–123|location=Washington, DC|publisher=U.S. Government Printing Office|date=January 1981}} Humans exposed to a concentration of 400 ppm in 1.4 mg/L ethyl acetate for a short time were affected by nose and throat irritation.{{cite book|editor-last=Clayton|editor-first=G.D.|editor2-first=F.E.|editor2-last=Clayton|title=Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology|edition=4th|location=New York, NY|publisher=John Wiley & Sons|date=1993–1994|page=2981}} Ethyl acetate is an irritant of the conjunctiva and mucous membrane of the respiratory tract. Animal experiments have shown that, at very high concentrations, the ester has central nervous system depressant and lethal effects; at concentrations of 20,000 to 43,000 ppm (2.0–4.3%), there may be pulmonary edema with hemorrhages, symptoms of central nervous system depression, secondary anemia and liver damage. In humans, concentrations of 400 ppm cause irritation of the nose and pharynx; cases have also been known of irritation of the conjunctiva with temporary opacity of the cornea. In rare cases exposure may cause sensitization of the mucous membrane and eruptions of the skin. The irritant effect of ethyl acetate is weaker than that of propyl acetate or butyl acetate.{{citation|title=Encyclopedia of Occupational Health and Safety|location=Geneva, Switzerland|publisher=International Labour Office|date=1983|page=782}}

References

External links

https://pubchem.ncbi.nlm.nih.gov/compound/ethyl_acetate#section=Toxicity
[https://www.cdc.gov/niosh/npg/npgd0260.html NIOSH Pocket Guide to Chemical Hazards]
[https://www.cdc.gov/niosh/ipcsneng/neng0367.html International Chemical Safety Cards]
[http://hazard.com/msds/mf/baker/baker/files/e2850.htm Material safety data (MSDS)] for ethyl acetate
[https://web.archive.org/web/20060112033533/http://www.npi.gov.au/database/substance-info/profiles/38.html National Pollutant Inventory – Ethyl acetate fact sheet]
[http://www.chm.bris.ac.uk/motm/ethylacetate/ethylh.htm Ethyl Acetate: Molecule of the Month]
[https://web.archive.org/web/20070528143740/http://hsc.csu.edu.au/chemistry/core/acidic/chem935/chem935net.html#net4 Purpose of Using Concentrated Sulfuric Acid in Esterification for Catalysis]
Basic facts and contact SEKAB [https://www.sekab.com/en/products-services/product/ethyl-acetate/] SEKAB ethyl acetate
[http://www.chemicalweekly.com/Profiles/Ethyl_Acetate.pdf A Techno Commercial Profile of Ethyl Acetate in India]
Calculation of [http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Ethyl%20acetate vapor pressure], [http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Ethyl%20acetate liquid density], [http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Ethyl%20acetate dynamic liquid viscosity], [http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Ethyl%20acetate surface tension] of ethyl acetate

Category:Acetate esters

Category:Ethyl esters

Category:Flavors

Category:Ester solvents

Category:Commodity chemicals

Category:Sweet-smelling chemicals