Ethyl lactate

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Ethyl (-)-L-lactate
Ethyl L-lactate
Identifiers
CAS number 687-47-8 (L-isomer) YesY, 97-64-3 (racemate), 7699-00-5 (D-isomer)
PubChem 7344
ChemSpider 13837423 YesY
RTECS number OD5075000
Jmol-3D images Image 1
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 to 155 °C (304 to 311 °F; 424 to 428 K)
Solubility in water Miscible
Solubility in ethanol
and most alcohols
Miscible
Chiral rotation [α]D −11.3°
Structure
Dipole moment 3.46 D [1]
Hazards
EU classification Irritant Xi
R-phrases R10 R37 R41
S-phrases (S2) S24 S26 S39
Main hazards Irritant (Xi)
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
Flash point 46 °C (115 °F; 319 K)
Related compounds
Related compounds Lactic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[edit]

  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. ^ [1][dead link] 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[edit]

  • Pereira, Carla S. M.; Silva, Viviana M. T. M.; Rodrigues, Alírio E. (2011). "Ethyl lactate as a solvent: Properties, applications and production processes – a review". Green Chemistry 13 (10): 2658. doi:10.1039/C1GC15523G.