Ethyl Butyrate - Wikipedia

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  • 1 Uses
  • 2 Production
  • 3 Table of physical properties
  • 4 See also
  • 5 References
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Appearance move to sidebar hide From Wikipedia, the free encyclopedia Ethyl butyrate
Names
Preferred IUPAC name Ethyl butanoate
Other names Butanoic acid ethyl esterEthyl butyrateButyric acid ethyl esterEthyl n-butanoateEthyl n-butyrateButyric etherUN 1180
Identifiers
CAS Number
  • 105-54-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:88764 checkY
ChEMBL
  • ChEMBL44800 checkY
ChemSpider
  • 7475 checkY
ECHA InfoCard 100.003.007 Edit this at Wikidata
EC Number
  • 203-306-4
PubChem CID
  • 7762
UNII
  • UFD2LZ005D checkY
CompTox Dashboard (EPA)
  • DTXSID6040111 Edit this at Wikidata
InChI
  • InChI=1S/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3 checkYKey: OBNCKNCVKJNDBV-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3Key: OBNCKNCVKJNDBV-UHFFFAOYAO
SMILES
  • CCCC(=O)OCC
Properties[1]
Chemical formula C6H12O2
Molar mass 116.160 g·mol−1
Appearance Colorless liquid with fruity odor (typically pineapple)
Density 0.879 g/cm3
Melting point −93 °C (−135 °F; 180 K)
Boiling point 120–121 °C (248–250 °F; 393–394 K)
Solubility in water Soluble in 150 parts
Vapor pressure 1510 Pa (11.3 mmHg)
Magnetic susceptibility (χ) −77.7×10−6 cm3/mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable
Signal word Warning
Hazard statements H226
Precautionary statements P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1 2 0
Flash point 26 °C; 78 °F; 299 K c.c.
Autoignitiontemperature 463 °C (865 °F; 736 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1350 mg/kg (oral, rat)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references
Chemical compound

Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an ester with the chemical formula CH3CH2CH2COOCH2CH3. It is soluble in propylene glycol, paraffin oil, and kerosene. It has a fruity odor, similar to pineapple, and is a key ingredient used as a flavor enhancer in processed orange juices.[1] It also occurs naturally in many fruits, albeit at lower concentrations.[2]

Uses

[edit]

It is commonly used as artificial flavoring resembling orange juice[3] and is hence used in nearly all orange juices sold in the US, including those sold as "fresh" or “concentrated".[4] It is also used in alcoholic beverages (e.g. martinis, daiquiris etc.), as a solvent in perfumery products, and as a plasticizer for cellulose.

Ethyl butyrate is one of the most common chemicals used in flavors and fragrances. It can be used in a variety of flavors: orange (most common), cherry, pineapple, mango, guava, bubblegum, peach, apricot, fig, and plum. Ethyl butyrate is synthesised in Jamaican rum upon the estrification of butyric acid from muck and ethanol during the distillation process. This gives Jamaican rum its pleasant flavour. In industrial use, it is also one of the cheapest chemicals, which only adds to its popularity.

Production

[edit]

It can be synthesized by reacting ethanol and butyric acid. This is a condensation reaction, meaning water is produced in the reaction as a byproduct. Ethyl butyrate from natural sources can be distinguished from synthetic ethyl butyrate by Stable Isotope Ratio Analysis (SIRA).[5]

Table of physical properties

[edit]
iconThis section needs additional citations for verification. Please help improve this article by adding citations to reliable sources in this section. Unsourced material may be challenged and removed. (January 2017) (Learn how and when to remove this message)
Property Value
Critical temperature (Tc) 296 °C (569 K)
Critical pressure (pc) 3.10 MPa (30.64 bar)
Critical density (ρc) 2.38 mol.l−1
Refractive index (n) at 20 °C 1.390 - 1.394

See also

[edit]
  • Butyric acid
  • Butyrates
  • Methyl butyrate

References

[edit]
  1. ^ a b c Merck Index, 12th Edition, 3822
  2. ^ Schieberle, H.-D. Belitz, W. Grosch, P. (2009). Food chemistry (4th rev. and extended ed.). Berlin: Springer. ISBN 9783540699330.{{cite book}}: CS1 maint: multiple names: authors list (link)
  3. ^ Andrea Walker (12 May 2009). "Ask an Academic: Orange Juice". The New Yorker.
  4. ^ Hamilton, Alissa. Squeezed. Yale University.
  5. ^ Ashurst, P.R.; Dennis, M.J. (1998). Analytical methods of food authentication (1st ed.). London: Blackie Academic & Professional. ISBN 9780751404265. Retrieved 27 January 2016.
[edit]
  • MSDS sheet
  • Sorption of ethyl butyrate and octanal constituents of orange essence by polymeric adsorbents Archived 2009-05-01 at the Wayback Machine
  • Biosynthesis of ethyl butyrate using immobilized lipase: a statistical approach Archived 2009-05-01 at the Wayback Machine
  • v
  • t
  • e
Esters
Methyl esters
  • Methyl formate
  • Methyl acetate
  • Methyl propionate
  • Methyl butyrate
  • Methyl pentanoate
  • Methyl hexanoate
  • Methyl heptanoate
  • Methyl benzoate
Ethyl esters
  • Ethyl formate
  • Ethyl acetate
  • Ethyl propionate
  • Ethyl butyrate
  • Ethyl pentanoate
  • Ethyl hexanoate
  • Ethyl heptanoate
  • Ethyl octanoate
  • Ethyl decanoate
  • Ethyl palmitate
  • Ethyl benzoate
Propyl esters
  • Propyl acetate
  • Propyl propanoate
  • Propyl benzoate
  • Isopropyl acetate
  • Isopropyl palmitate
Butyl esters
  • Butyl acetate
  • Butyl butyrate
  • Isobutyl acetate
  • sec-Butyl acetate
  • tert-Butyl acetate
Amyl esters
  • Amyl acetate
  • Pentyl propanoate
  • Pentyl butyrate
  • Pentyl pentanoate
  • Pentyl hexanoate
  • Isoamyl formate
  • Isoamyl acetate
  • Sec-Amyl acetate
Hexyl esters
  • Hexyl acetate
Phenyl esters
  • Phenyl acetate
Heptyl esters
  • Heptyl acetate
  • Heptyl butyrate
Benzyl esters
  • Benzyl acetate
  • Benzyl benzoate
Authority control databases Edit this at Wikidata
  • GND
Retrieved from "https://en.wikipedia.org/w/index.php?title=Ethyl_butyrate&oldid=1305953709" Categories:
  • Ethyl esters
  • Butyrate esters
  • Ester solvents
  • Flavors
  • Plasticizers
  • Sweet-smelling chemicals
Hidden categories:
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  • Articles without KEGG source
  • ECHA InfoCard ID from Wikidata
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