Methyl propionate

Methyl propionate

Names
Preferred IUPAC name Methyl propanoate
Other names Methyl propionate Propanoic acid, methyl ester Propionic acid, methyl ester
Identifiers
CAS Number	554-12-1^Y
3D model (JSmol)	Interactive image
ChemSpider	10653
ECHA InfoCard	100.008.238
PubChem CID	11124
UNII	NB21C0D33W^Y
CompTox Dashboard (EPA)	DTXSID101036506, DTXSID201064449 DTXSID7027201, DTXSID101036506, DTXSID201064449
InChI InChI=1S/C4H8O2/c1-3-4(5)6-2/h3H2,1-2H3 Key: RJUFJBKOKNCXHH-UHFFFAOYSA-N InChI=1/C4H8O2/c1-3-4(5)6-2/h3H2,1-2H3 Key: RJUFJBKOKNCXHH-UHFFFAOYAS
SMILES O=C(OC)CC
Properties
Chemical formula	C4H8O2
Molar mass	88.106 g·mol^−1
Appearance	Colorless liquid[1]
Density	0.915 g/L[1]
Melting point	−88 °C (−126 °F; 185 K)[1]
Boiling point	80 °C (176 °F; 353 K)[1]
Solubility in water	72 g/L (20 °C)[1]
Magnetic susceptibility (χ)	-55.0·10^−6 cm^3/mol
Hazards
Flash point	−2 °C (28 °F; 271 K)[1]
Autoignition temperature	465 °C (869 °F; 738 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methyl propionate, also known as methyl propanoate, is an organic compound with the molecular formula CH₃CH₂CO₂CH₃. It is a colorless liquid with a fruity, rum-like odor.^[2]

Preparation

Methyl propionate can be prepared by esterification of propionic acid with methanol. Industrially, it is prepared by carboalkoxylation, i.e., the reaction of ethylene with carbon monoxide and methanol in the presence of a catalyst:

C₂H₄ + CO + MeOH → MeO₂CCH₂CH₃

The reaction is catalyzed by nickel carbonyl and palladium(0) complexes.^[3][4]

Uses

Condensation of Methyl propionate with formaldehyde followed by dehydration yields methyl methacrylate:^[4]

MeO₂CCH₂CH₃ + CH₂O → MeO₂CCH(CH₂OH)CH₃

MeO₂CCH(CH₂OH)CH₃ → MeO₂CC(=CH₂)CH₃

Methyl propionate is used as a solvent for cellulose nitrate and lacquers, and as a raw material for the production of paints, varnishes and other chemicals such as methyl methacrylate.^[2][3]

Due to its fruity smell and taste, it is also used in fragrances and flavoring.^[2][5]

References

1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
2. "Methyl Propionate Hazardous Substance Fact Sheet" (PDF). New Jersey Department of Health and Senior Services.
3. Ulf-Rainer Samel; Walter Kohler; Armin Otto Gamer; Ullrich Keuser (2000). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a22_223.pub2. ISBN 9783527306732.(mayth and yafs)
4. Scott D. Barnicki "Synthetic Organic Chemicals" in Handbook of Industrial Chemistry and Biotechnology edited by James A. Kent, New York : Springer, 2012. 12th ed. ISBN 978-1-4614-4259-2.
5. "Methyl propionate". thegoodscentscompany.com.