Methyl butyrate

Not to be confused with 2-methylbutyrate or 3-methylbutyrate.

Methyl butyrate[1]

Names
Preferred IUPAC name

Methyl butanoate

Other names

Butanoic acid methyl ester
Methyl butyrate
Butyric acid methyl ester

Identifiers

CAS Number

* 623-42-7 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 11680 N

EC Number |

* 210-792-1

MeSH | C043811

PubChem CID

* 12180

RTECS number |

* ET5500000

UNII |

* CGX598508O Y

InChI

* 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

SMILES

* CCCC(=O)OC

Properties

Chemical formula

| 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)

Solubility in water

| 1.5 g/100 mL (22 °C)

Magnetic susceptibility (χ)

| −66.4×10−6 cm3/mol

Refractive index (nD)

| 1.386
Hazards
NFPA 704 (fire diamond)  |

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 YN ?)
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 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]

## References

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
6. ↑ Methyl butyrate as a component of biodiesel
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.

* v
* t
* e

Esters

Methyl Esters|

* Methyl formate
* Methyl acetate
* Methyl propionate
* Methyl butyrate
* Methyl pentanoate

Ethyl Esters|

* Ethyl formate
* Ethyl acetate
* Ethyl propionate
* Ethyl butyrate
* Ethyl pentanoate
* Ethyl hexanoate
* Ethyl heptanoate
* Ethyl octanoate
* Ethyl decanoate

Propyl Esters|

* Propyl acetate
* Propyl propanoate
* Isopropyl acetate
* Isopropyl palmitate

Butyl Esters|

* Butyl acetate
* Butyl butyrate

Amyl Esters|

* Amyl acetate
* Isoamyl acetate
* Sec-Amyl acetate
* Pentyl propanoate
* Pentyl butyrate
* Pentyl pentanoate
* Pentyl hexanoate

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