Ethyl lactate

Ethyl (−)-L-lactate
Names
IUPAC name
Ethyl (S)-2-hydroxypropanoate
Other names
Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
Identifiers
687-47-8 (L-isomer) Yes
97-64-3 (racemate)
7699-00-5 (D-isomer)
ChemSpider 13837423 Yes
Jmol-3D images Image
PubChem 7344
RTECS number OD5075000
Properties
Molecular formula
 C5H10O3
Molar mass 118.13 g·mol−1
Appearance Clear to slightly yellow liquid
Density 1.03 g/cm3
Melting point −26 °C (−15 °F; 247 K)
Boiling point 151 °C (304 °F; 424 K)
Miscible
Solubility in ethanol
and most alcohols		 Miscible
−11.3°
Structure
Dipole moment 3.46 D [1]
Hazards
Main hazards Irritant (Xi)
EU classification Xi
R-phrases R10 R37 R41
S-phrases (S2) S24 S26 S39
NFPA 704
Flammability code 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 fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
2
3
0
Flash point 46 °C (115 °F; 319 K)
Related compounds
Related compounds
 Lactic acid
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 Yes verify (what is: Yes/?)
Infobox references

Ethyl lactate, also known as lactic acid ethyl ester, is a monobasic ester formed from lactic acid and ethanol, commonly used as a solvent. This compound is considered biodegradable and can be used as a water-rinsible degreaser. Ethyl lactate is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. The odor of ethyl lactate when dilute is mild, buttery, creamy, with hints of fruit and coconut.

Ethyl lactate is produced from biological sources, and can be either the levo (S) form or dextro (R) form, depending on the organism that is the source of the lactic acid. Most biologically sourced ethyl lactate is ethyl (−)-L-lactate (ethyl (S)-lactate). Ethyl lactate is also produced industrially from petrochemical stocks, and this ethyl lactate consists of the racemic mixture of levo and dextro forms. In some jurisdictions, the natural product is exempt from many restrictions placed upon use and disposal of solvents. Because both enantiomers are found in nature, and because ethyl lactate is easily biodegradable, it is considered to be a green solvent.

Due to its relatively low toxicity, ethyl lactate is used commonly in pharmaceutical preparations, food additives,[2] and fragrances. Ethyl lactate is also used as solvent for nitrocellulose, cellulose acetate, and cellulose ethers.[3]

Ethyl lactate hydrolyzes in the presence of water and acids or bases into lactic acid and ethanol.

Ethyl lactate can be used as a cosolvent to produce suitable conditions for the formation of aryl aldimines.[4]

References

  1. ↑ Aparicio, Santiago; Alcalde, Rafael (2009). "The green solvent ethyl lactate: an experimental and theoretical characterization". Green Chemistry 11 (1): 65–78. doi:10.1039/b811909k.
  2. ↑ U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition
  3. ↑ "Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN 0-8155-1413-1, ISBN 978-0-8155-1413-8
  4. ↑ Jacqueline S. Bennett, Kaitlyn L. Charles, Matthew R. Miner, Caitlin F. Heuberger, Elijah J. Spina, Michael F. Bartels and Taylor Foreman (2009). "Ethyl lactate as a tunable solvent for the synthesis of aryl aldimines". Green Chem. 11 (2): 166–168. doi:10.1039/b817379f.

Further reading