Methyl butyrate

Not to be confused with 2-methylbutyrate or 3-methylbutyrate.
Methyl butyrate[1]
Methyl butanoate
Ball-and-stick model
Names
Preferred IUPAC name
Methyl butanoate
Other names
Butanoic acid methyl ester
Methyl butyrate
Butyric acid methyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.812 Edit this at Wikidata
EC Number
  • 210-792-1
MeSH C043811
RTECS number
  • ET5500000
UNII
  • InChI=1S/C5H10O2/c1-3-4-5(6)7-2/h3-4H2,1-2H3 ☒N
    Key: UUIQMZJEGPQKFD-UHFFFAOYSA-N ☒N
  • InChI=1/C5H10O2/c1-3-4-5(6)7-2/h3-4H2,1-2H3
    Key: UUIQMZJEGPQKFD-UHFFFAOYAW
  • CCCC(=O)OC
Properties
C5H10O2
Molar mass 102.133 g·mol−1
Appearance Colorless liquid
Density 0.898 g/cm3
Melting point −95 °C (−139 °F; 178 K)
Boiling point 102 °C (216 °F; 375 K)
1.5 g/100 mL (22 °C)
−66.4×10−6 cm3/mol
1.386
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability (yellow): no hazard codeSpecial hazards (white): no code
1
3
Flash point 12 °C (54 °F; 285 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Methyl butyrate, also known under the systematic name methyl butanoate, is the methyl ester of butyric acid. Like most esters, it has a fruity odor, in this case resembling apples or pineapples.[2] At room temperature, it is a colorless liquid with low solubility in water, upon which it floats to form an oily layer. Although it is flammable, it has a relatively low vapor pressure (40 mmHg at 30 °C (86 °F)), so it can be safely handled at room temperature without special safety precautions.[3]

Methyl butyrate is present in small amounts in several plant products, especially pineapple oil.[4] It can be produced by distillation from essential oils of vegetable origin, but is also manufactured on a small scale for use in perfumes[5] and as a food flavoring.

Methyl butyrate has been used in combustion studies as a surrogate fuel for the larger fatty acid methyl esters found in biodiesel.[6] However, studies have shown that, due to its short-chain length, methyl butyrate does not reproduce well the negative temperature coefficient (NTC) behaviour and early CO2 formation characteristics of real biodiesel fuels. Therefore, methyl butyrate is not a suitable surrogate fuel for biodiesel combustion studies.[7]

  1. ^ Merck Index, 13th Edition
  2. ^ Methyl butyrate, thegoodscentscompany.com
  3. ^ Aldrich Chemicals Handbook, Sigma-Aldrich Company, Milwaukee, (2007)
  4. ^ Flath, Robert A.; Forrey, R. R. (1970). "Volatile components of Smooth Cayenne pineapple". Journal of Agricultural and Food Chemistry. 18 (2): 306–309. doi:10.1021/jf60168a018.
  5. ^ Use of methyl butyrate as an additive in perfume Archived 2008-05-31 at the Wayback Machine
  6. ^ Methyl butyrate as a component of biodiesel Archived March 6, 2006, at the Wayback Machine
  7. ^ Gaïl, S.; Thomson, M.J.; Sarathy, S.M.; Syed, S.A.; Dagaut, P.; Diévart, P.; Marchese, A.J.; Dryer, F.L. (2007). "A wide-ranging kinetic modeling study of methyl butanoate combustion". Proceedings of the Combustion Institute. 31: 305–311. doi:10.1016/j.proci.2006.08.051.