Methyl lactate

Methyl lactate, also known as lactic acid methyl ester, is the organic compound with the formula CH3CH(OH)CO2CH3. It is the methyl ester of lactic acid. A colorless liquid, it is the simplest chiral ester. Being naturally derived, it is readily available as a single enantiomer.

Methyl DL-Lactate
Methyl L-lactate
Names
IUPAC name
Methyl 2-hydroxypropanoate
Other names
2-Hydroxy- Methyl Ester Propanoic Acid; 2-Hydroxypropanoic Acid, Methyl Ester; Lactic Acid, Methyl Ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.119
RTECS number
  • OD5670000
UNII
  • InChI=1S/C4H8O3/c1-3(5)4(6)7-2/h3,5H,1-2H3
    Key: LPEKGGXMPWTOCB-UHFFFAOYSA-N
  • CC(C(=O)OC)O
Properties
C4H8O3
Molar mass 104.105 g·mol−1
Appearance colourless clear liquid
Density 1.093 g/cm3
Melting point −66 °C (−87 °F; 207 K)
Boiling point 144 to 145 °C (291 to 293 °F; 417 to 418 K)
Miscible
Solubility in ethanol
and most alcohols		 Miscible
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant (Xi)
GHS labelling:[1]
GHS02: Flammable GHS07: Exclamation mark
Warning
H226, H319, H335
P210, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
2
0
Flash point 49 °C (120 °F; 322 K)
Safety data sheet (SDS) MSDS
Related compounds
Related compounds
 Lactic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

It is a solvent for nitrocellulose, cellulose acetate, cellulose acetobutyrate and cellulose acetopropionate. It is used in the manufacture of lacquers and dopes where it contributes high tolerance for diluents, good flaw and blush resistance.[2]

The synthesis of 1,2-propanediol from methyl lactate has been commercialized using a MACHO catalyst.[3]

See also

References
  1. GHS: Record of Methyl lactate in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. "Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN 0-8155-1413-1, ISBN 978-0-8155-1413-8
  3. Dub, Pavel A.; Gordon, John C. (2018). "The role of the metal-bound N–H functionality in Noyori-type molecular catalysts". Nature Reviews Chemistry. 2 (12): 396–408. doi:10.1038/s41570-018-0049-z. S2CID 106394152.
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