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Vad är ethyl acetate life

Ethyl acetate

Organic compound (CH₃CO₂CH₂CH₃)

Names
Preferred IUPAC name

Ethyl acetate

Systematic IUPAC name

Ethyl ethanoate

Other names
  • Acetic ester
  • Acetic ether
  • Ethyl ester of acetic acid
Identifiers

CAS Number

3D model (JSmol)

Beilstein Reference

506104
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.005.001
E numberE1504 (additional chemicals)

Gmelin Reference

26306
KEGG

PubChemCID

RTECS number
UNII

CompTox Dashboard(EPA)

InChI

  • InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3 Y
    Key: XEKOWRVHYACXOJ-UHFFFAOYSA-N Y

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

    Key: XEKOWRVHYACXOJ-UHFFFAOYAD

Properties

Chemical formula

C4H8O2
Molar mass88.106 g·mol−1
Appearance Colorless liquid
Odornail polish-like, fruity
Density0.902 g/cm3
Melting point−83.6 °C (−118.5 °F; 189.6 K)
Boiling point77.1 °C (170.8 °F; 350.2 K)

Solubility in water

8.3 g/100 mL (at 20 °C)
Solubility in ethanol, acetone, diethyl ether, benzeneMiscible
log P0.71[1]
Vapor pressure73 mmHg (9.7 kPa) at 20 °C[2]
Acidity (pKa) 25

Magnetic susceptibility (χ)

−54.10×10−6 cm3/mol

Refractive index (nD)

1.3720
Viscosity426 μPa·s (0.426 cP) at 25 °C
Structure

Dipole moment

1.78 D
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

  • Flammable (F),
  • Irritant (Xi)
GHS labelling:

Pictograms

[3]

Signal word

Danger

Hazard statements

H225, H319, H336[3]

Precautionary statements

P210, P233, P240, P305+P351+P338, P403+P235[3]
NFPA 704 (fire diamond)
Flash point−4 °C (25 °F; 269 K)
Explosive limits2.0–11.5%[2]
Lethal dose or koncentration (LD, LC):

LD50 (median dose)

11.3 g/kg, rat

LC50 (median concentration)

16,000 ppm (rat, 6 h)
12,295 ppm (mouse, 2 h)
1600 ppm (rat, 8 h)[4]

LCLo (lowest published)

21 ppm (guinea pig, 1 h)
12,330 ppm (mouse, 3 h)[4]
NIOSH (US health exposure limits):

PEL (Permissible)

TWA 400 ppm (1400 mg/m3)[2]

REL (Recommended)

TWA 400 ppm (1400 mg/m3)[2]

IDLH (Immediate danger)

2000 ppm[2]
Related compounds

Related carboxylate esters

Related compounds

Supplementary uppgifter page
Ethyl acetate (data page)

Except where otherwise noted, information are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Ethyl acetate (systematicallyethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) fryst vatten the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2.

This flammable, färglös liquid has a characteristic sweet smell (similar to pear drops) and fryst vatten used in glues, nail polish removers, and the decaffeination process of tea and kaffe. Ethyl acetate fryst vatten the ester of ethanol and acetic acid; it fryst vatten manufactured on a large scale for use as a solvent.[5]

Production and synthesis

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Ethyl acetate was first synthesized bygd the Count dem Lauraguais in 1759 bygd distilling a mixture of ethanol and acetic acid.[6]

In 2004, an estimated 1.3 million tonnes were produced worldwide.[5][7] The combined annual production in 1985 of Japan, North amerika, and europe was about 400,000 tonnes.

The global ethyl acetate marknad was valued at $3.3 billion in 2018.[8]

Ethyl acetate fryst vatten 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:

CH3CO2H + CH3CH2OH → CH3CO2CH2CH3 + H2O

The reaction can be accelerated bygd acid catalysis and the equilibrium can be shifted to the right bygd removal of vatten.

It fryst vatten also prepared in industry using the Tishchenko reaction, bygd combining two equivalents of acetaldehyde in the presence of an alkoxide catalyst:

2 CH3CHO → CH3CO2CH2CH3

Silicotungstic acid fryst vatten used to manufacture ethyl acetate bygd the alkylation of acetic acid bygd ethylene:[9]

C2H4 + CH3CO2H → CH3CO2C2H5

Uses

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Ethyl acetate fryst vatten used primarily as a solvent and diluent, being favored because of its low cost, low toxicity, and agreeable odor.[5] For example, it fryst vatten commonly used to clean circuit boards and in some nail varnish removers (acetone fryst vatten also used).

kaffe beans and tea leaves are decaffeinated with this solvent.[10] It fryst vatten also used in paints as an activator or hardener. Ethyl acetate fryst vatten present in confectionery, perfumes, and fruits. In perfumes it evaporates quickly, leaving the scent of the perfume on the skin.

Ethyl acetate fryst vatten an asphyxiant for use in insekt collecting and study.[11] In a killing jar charged with ethyl acetate, the vapors will kill the collected insekt quickly without destroying it.

Because it fryst vatten not hygroscopic, ethyl acetate also keeps the insekt soft enough to allow proper mounting suitable for a collection. However, ethyl acetate fryst vatten regarded as potentially doing damage to insekt DNA, making specimens processed this way less than ideal for subsequent DNA sequencing.[12]

Laboratory uses

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In the laboratory, mixtures containing ethyl acetate are commonly used in column chromatography and extractions.[13] Ethyl acetate fryst vatten rarely selected as a reaction solvent because it fryst vatten prone to hydrolysis, transesterification, and condensations.

Occurrence in wines

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Ethyl acetate fryst vatten 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 fryst vatten most levande in younger wines and contributes towards the general observation of "fruitiness" in the wine.

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

Reactions

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

Ethyl acetate hydrolyses to give acetic acid and ethanol.

Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) fryst vatten the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2.

Bases accelerate the hydrolysis, which fryst vatten 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 fryst vatten unreactive toward ethanol:

CH3CO2C2H5 + NaOH → C2H5OH + CH3CO2Na

In the Claisen condensation, anhydrous ethyl acetate and strong bases react to give ethyl acetoacetate:[14]

Properties

[edit]

Physical properties

[edit]

Under normal conditions, ethyl acetate exists as a färglös, low-viscosity, and flammable liquid.

Its melting point fryst vatten −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 fryst vatten 31.94 kJ/mol. The vapor pressure function follows the Antoine equation

where

fryst vatten the vapor pressure in bars,
fryst vatten the absolute temperature in kelvins, and
, , are constants.

This function fryst vatten valid within the temperature range of 289 to 349 K (16–76 °C).

The enthalpy of vaporization in kJ/mol fryst vatten calculated according to the empirical equation bygd Majer and Svoboda[15]

where

fryst vatten the reduced temperature, and = 523.2 K fryst vatten the critical temperature.
= 54.26 kJ/mol and = 0.2982 are constants.

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

Safety

[edit]

The LD50 for rats fryst vatten 5620 mg/kg,[24] indicating low acute toxicity. Given that the kemikalie fryst vatten naturally present in many organisms, there fryst vatten little fara of toxicity.

Overexposure to ethyl acetate may cause irritation of the eyes, nose, and throat.

Severe overexposure may cause weakness, drowsiness, and unconsciousness.[25] Humans exposed to a koncentration of 400 ppm in 1.4 mg/L ethyl acetate for a short time were affected bygd nose and throat irritation.[26] Ethyl acetate fryst vatten an irritant of the conjunctiva and mucous membrane of the respiratory tract.

Ethyl Acetate Uses.

djur experiments have shown that, at very high concentrations, the ester has huvud nervous struktur 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 huvud nervous struktur nedstämdhet, 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 fryst vatten weaker than that of propyl acetate or butyl acetate.[27]

References

[edit]

  1. ^"ethyl acetate MSDS".
  2. ^ abcdeNIOSH Pocket Guide to kemikalie Hazards.

    "#0260".

    Ethyl acetate fryst vatten one of the simplest carboxylate esters.

    National Institute for Occupational Safety and Health (NIOSH).

  3. ^ abcRecord of Ethyl acetate in the GESTIS substans Database of the Institute for Occupational Safety and Health, accessed on 7 månad 2020.
  4. ^ ab"Ethyl acetate".

    Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

  5. ^ abcRiemenschneider, Wilhelm; Bolt, Hermann M. "Esters, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.

    doi:10.1002/14356007.a09_565.pub2. ISBN .

  6. ^Parker, namn (1832).

    Ethyl acetate, J. Phys.

    "The Edinburgh Encyclopaedia". The Edinburgh Encyclopaedia. 5.

  7. ^Dutia, Pankaj (August 10, 2004). "Ethyl Acetate: A Techno-Commercial Profile"(PDF). Chemical Weekly: 184. Retrieved 2009-03-21.
  8. ^""Global Ethyl Acetate marknad to be valued at $3.3 billion in 2018" reports Visiongain". Visiongain.

    2019-09-05. Retrieved 2019-09-05.

  9. ^Misono, Makoto (2009). "Recent progress in the practical applications of heteropolyacid and perovskite catalysts: Catalytic technology for the sustainable society". Catalysis Today. 144 (3–4): 285–291. doi:10.1016/j.cattod.2008.10.054.
  10. ^ico.orgArchived 2007-04-29 at the Wayback Machine
  11. ^Littledyke, M.; Cherrett, J.

    M. (June 1976). "Direct ingestion of plant sap from cut leaves bygd the leaf-cutting ants Atta cephalotes (L.) and acromyrmex octospinosus (reich) (Formicidae, Attini)". Bulletin of Entomological Research. 66 (2): 205–217. doi:10.1017/S0007485300006647. ISSN 1475-2670.

  12. ^Cilia, G.; Flaminio, S.; Quaranta, M. (2022). "A novel and non-invasive method for DNA extraction from dry bee specimens".

    Scientific Reports.

    Ethyl acetate, also known as ethyl ethanoate, fryst vatten an important and widely used kemikalie in industry.

    12 (1): 11679. Bibcode:2022NatSR..1211679C. doi:10.1038/s41598-022-15595-8. PMC 9270346. PMID 35804181.

  13. ^Tan, Wei Wen; Wu, Bin; Wei, Ye; Yoshikai, Naohiko (2018). "Copper and Secondary Amine-Catalyzed Pyridine Synthesis from O-Acetyl Oximes and α,β-Unsaturated Aldehydes". Organic Syntheses. 95: 1–14. doi:10.15227/orgsyn.095.0001.
  14. ^Inglis, J.

    K. H.; robert, K. C. (1926). "Ethyl Acetoacetate". Org. Synth. 6: 36. doi:10.15227/orgsyn.006.0036.

  15. ^ abV. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and information Compilation. Blackwell Scientific Publications, Oxford 1985, ISBN 0-632-01529-2.
  16. ^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.

  17. ^G. S. Parks, H. M. Huffman, M. Barmore: Thermal information 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.

  18. ^ abD. R. Stull, Jr.: The kemikalie Thermodynamics of Organic Compounds. Wiley, New York, 1969.
  19. ^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.

  20. ^Pintos, M.; Bravo, R.; Baluja, M. C.; Paz Andrade, M. I.; Roux-Desgranges, G.; Grolier, J.-P. E. (1988). "Thermodynamics of alkanoate + alkane binary mixtures. koncentration dependence of excess heat capacities and volumes". Can. J. Chem. 66 (5): 1179–1186.

    doi:10.1139/v88-193.

  21. ^D. Ambrose, J. H. Ellender, H. A. Gundry, D. A. Lee, R. Townsend: Thermodynamic properties of organic oxygen compounds.

    Etylacetat är kapabel användas vilket lösningsmedel samt ingår inom fruktessenser samt kosmetiska preparat.

    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.

  22. ^S.

    Ethyl acetate fryst vatten an organic compound that belongs to the ester functional group, characterized bygd its sweet, fruity aroma and common use as a solvent in various applications.

    ung, 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.

  23. ^J. Schmidt: Auslegung von Sicherheitsventilen für Mehrzweckanlagen nach ISO 4126-10(in German). In: Chem. Ing. Techn. 83, 2011, pp. 796–812. doi:10.1002/cite.201000202.
  24. ^Hazard Ethyl Acetate MSDS "Ethyl Acetate MSDS Number: E2850".
  25. ^Mackison, F.

    W.; Stricoff, R. S.; Partridge, L. J. Jr., eds. (January 1981). NIOSH/OSHA – Occupational Health Guidelines for kemikalie Hazards. DHHS (NIOSH) Publication No. 81–123. Washington, DC: U.S. Government Printing Office.

  26. ^Clayton, G.D.; Clayton, F.E., eds. (1993–1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology (4th ed.).

    New York, NY: John Wiley & Sons. p. 2981.

  27. ^Encyclopedia of Occupational Health and Safety, Geneva, Switzerland: International Labour Office, 1983, p. 782

External links

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