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Methyl lactate

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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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.119 Edit this at Wikidata
PubChem CID
RTECS number
  • OD5670000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H8O3/c1-3(5)4(6)7-2/h3,5H,1-2H3Key: LPEKGGXMPWTOCB-UHFFFAOYSA-N
SMILES
  • CC(C(=O)OC)O
Properties
Chemical formula C4H8O3
Molar mass 104.105 g·mol
Appearance colourless clear liquid
Density 1.093 g/cm
Melting point −66 °C (−87 °F; 207 K)
Boiling point 144 to 145 °C (291 to 293 °F; 417 to 418 K)
Solubility in water Miscible
Solubility in ethanol
and most alcohols 		Miscible
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Irritant (Xi)
GHS labelling:
Pictograms GHS02: Flammable GHS07: Exclamation mark
Signal word Warning
Hazard statements H226, H319, H335
Precautionary statements P210, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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.

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

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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