Ethyl butyrate

Ethyl butyrate
Names
Preferred IUPAC name
Ethyl butanoate
Other names
Butanoic acid ethyl ester
Ethyl butyrate
Butyric acid ethyl ester
Ethyl n-butanoate
Ethyl n-butyrate
Butyric ether
UN 1180
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.007 Edit this at Wikidata
EC Number
  • 203-306-4
UNII
  • InChI=1S/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3 checkY
    Key: OBNCKNCVKJNDBV-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3
    Key: OBNCKNCVKJNDBV-UHFFFAOYAO
  • CCCC(=O)OCC
Properties[1]
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)
Soluble in 150 parts
Vapor pressure 1510 Pa (11.3 mmHg)
−77.7×10−6 cm3/mol
Hazards
GHS labelling:
GHS02: Flammable
Warning
H226
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 26 °C; 78 °F; 299 K c.c.
463 °C (865 °F; 736 K)
Lethal dose or concentration (LD, LC):
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 ?)

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

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

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

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

References

  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.