Butyric acid methyl ester

Structural formula
General
Surname	Butyric acid methyl ester
other names	Methyl butyrate; Butanoic acid methyl ester;
Molecular formula	C 5 H 10 O 2
Brief description	colorless liquid with a fruity odor
External identifiers / databases
EC number	210-792-1
ECHA InfoCard	100.009.812
PubChem	12180
Wikidata	Q420701
properties
Molar mass	102.13 g mol −1
Physical state	liquid
density	0.90 g cm −3 (20 ° C)
Melting point	−84 ° C
boiling point	103 ° C
Vapor pressure	32 h Pa (20 ° C); 55 hPa (30 ° C); 145 hPa (50 ° C);
solubility	1.6 g / 100 g water (21 ° C)
Refractive index	1.3878 (20 ° C)
safety instructions
H and P phrases	H: 225-315-319-335
	P: 210-240-280
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Butyric acid methyl ester ( methyl butyrate , methyl butanoate ), CH ₃ CH ₂ CH ₂ COOCH ₃ , is an ester with a fruit odor reminiscent of apple or pineapple . Butyric acid methyl ester is obtained through an acid-catalyzed reaction of methanol with butyric acid (butanoic acid).

Occurrence

Strawberries

In nature, methyl butyrate is found in bananas and strawberries, for example .

properties

Butyric acid methyl ester is a colorless liquid that boils at 102 ° C under normal pressure . The heat of vaporization under normal conditions is 39.3 kJ mol ⁻¹ , that at the boiling point is 33.79 kJ mol ⁻¹ . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) below the normal pressure boiling point with A = 4.58499, B = 1528.058 and C = −41.606 in the temperature range from 246 K to 375 K and above the normal pressure boiling point with A = 4.72086, B = 1758.314 and C = −2.421 in the temperature range from 375 K to 545 K.

The compound forms flammable vapor-air mixtures above the flash point. It has a flash point of 14 ° C. The lower explosion limit (LEL) is 1.6 vol% (67 g m ⁻³ ).

use

Butyric acid methyl ester is used in perfumes and as an odorant . The ester was used as a model substance for the study of biodiesel , but it turned out to be unsuitable.

Individual evidence

↑ ^a ^b ^c ^d ^e Data sheet methyl butyrate for synthesis (PDF) from Merck , accessed on April 28, 2017.
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on methyl butyrate in the GESTIS substance database of the IFA , accessed on April 11, 2018(JavaScript required) .
^ W. Riemenschneider, HM Bolt: Organic Esters. In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons, 2005.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-342.
↑ ^a ^b Entry on fruit esters. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
↑ S. Sunner, Ch Svensson, AS Zelepuga. Enthalpies of vaporization at 298.15 K for some 2-alkanones and methyl alkanoates. In: J. Chem. Thermodyn. . 11, 1979, pp. 491-495. doi: 10.1016 / 0021-9614 (79) 90127-7 .
^ V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985.
^ DR Stull: Vapor Pressure of Pure Substances - Organic Compounds. In: Ind. Eng. Chem. 39, 1947, pp. 517-540, doi: 10.1021 / ie50448a022 .
↑ E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ N. Milovanovic, R. Chen, R. Dowden, J. Turner: An investigation of using various diesel-type fuels in homogeneous charge compression ignition engines and their effects on operational and controlling issues. In: Intern. J. Eng. Res. 5, 2004, pp. 297-316, doi: 10.1243 / 146808704323224213 .

[Merck-1] Data sheet methyl butyrate for synthesis (PDF) from Merck , accessed on April 28, 2017.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on methyl butyrate in the GESTIS substance database of the IFA , accessed on April 11, 2018(JavaScript required) .

[3] W. Riemenschneider, HM Bolt: Organic Esters. In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons, 2005.

[CRC90_3_342-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-342.

[Römpp-5] Entry on fruit esters. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[6] S. Sunner, Ch Svensson, AS Zelepuga. Enthalpies of vaporization at 298.15 K for some 2-alkanones and methyl alkanoates. In: J. Chem. Thermodyn. . 11, 1979, pp. 491-495. doi: 10.1016 / 0021-9614 (79) 90127-7 .

[7] V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985.

[8] DR Stull: Vapor Pressure of Pure Substances - Organic Compounds. In: Ind. Eng. Chem. 39, 1947, pp. 517-540, doi: 10.1021 / ie50448a022 .

[Brandes-9] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[10] N. Milovanovic, R. Chen, R. Dowden, J. Turner: An investigation of using various diesel-type fuels in homogeneous charge compression ignition engines and their effects on operational and controlling issues. In: Intern. J. Eng. Res. 5, 2004, pp. 297-316, doi: 10.1243 / 146808704323224213 .