Methyl butyrate

Methyl butyrate[1]
IUPAC name Methyl butanoate
Identifiers
CAS number	623-42-7 Y
RTECS number	ET5500000
Jmol-3D images	Image 1
SMILES CCCC(=O)OC
Properties
Molecular formula	C5H10O2
Molar mass	102.13 g/mol
Appearance	Colourless liquid
Density	898 kg/m³
Melting point	-95 °C (178K)
Boiling point	102 °C (375K)
Solubility in water	1.5 g/100 mL (22 °C)
Refractive index (nD)	1.386
Hazards
NFPA 704	3 1 0
Flash point	12 °C
Y butyrate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

It is present in small amounts in several plant products, especially pineapple oil.^[3] It can be produced by distillation from essential oils of vegetable origin, but is also manufactured on a small scale for use in perfumes^[4] and as a food flavouring.

Methyl butanoate has been used in combustion studies as a surrogate fuel for the larger fatty acid methyl esters found in biodiesel.^[5] However, studies have shown that, due to its short-chain length, methyl butanoate does not reproduce well the negative temperature coefficient (NTC) behaviour and early CO₂ formation characteristics of real biodiesel fuels. Therefore, methyl butanoate is not a suitable surrogate fuel for biodiesel combustion studies.^[6]

References

1. ^ Merck Index, 13th Edition
2. ^ Aldrich Chemicals Handbook, Sigma-Aldrich Company, Milwaukee, (2007)
3. ^ 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. 
4. ^ Use of methyl butyrate as an additive in perfume
5. ^ Methyl butyrate as a component of biodiesel
6. ^ A wide-ranging kinetic modeling study of methyl butanoate combustion