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 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10653
ECHA InfoCard 100.008.238 Edit this at Wikidata
PubChem CID
  • 11124
UNII
  • NB21C0D33W checkY
CompTox Dashboard (EPA)
  • DTXSID101036506, DTXSID201064449 DTXSID7027201, DTXSID101036506, DTXSID201064449 Edit this at Wikidata
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
  • 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 cm3/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
Chemical compound

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. ^ a b c d e f g Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b c "Methyl Propionate Hazardous Substance Fact Sheet" (PDF). New Jersey Department of Health and Senior Services.
  3. ^ a b 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. ^ a b 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.