Ethyl lactate

Ethyl lactate, also known as lactic acid ethyl ester, is the organic compound with the formula CH3CH(OH)CO2CH2CH3. It is the ethyl ester of lactic acid. A colorless liquid, it is a chiral ester. Being naturally derived, it is readily available as a single enantiomer. It is commonly used as a solvent.[2] 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.[3]

Ethyl lactate
Names
IUPAC name
Ethyl 2-hydroxypropanoate
Other names
Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.363
RTECS number
  • OD5075000
Properties
C5H10O3
Molar mass 118.132 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)
Miscible
Solubility in ethanol
and most alcohols		 Miscible
−11.3°
-72.6·10−6 cm3/mol
Structure
3.46 D [1]
Hazards
Main hazards Irritant (Xi)
Xi
R-phrases (outdated) R10 R37 R41
S-phrases (outdated) (S2) S24 S26 S39
NFPA 704 (fire diamond)
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 fuelHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 46 °C (115 °F; 319 K)
Related compounds
Related compounds
 Lactic acid, Methyl lactate
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

Production

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.

Applications

Because both enantiomers are found in nature, and because ethyl lactate is easily biodegradable, it is considered to be a "green solvent." Ethyl lactate and its aqueous solutions are used as sustainable media for organic synthesis.[4] Due to its relatively low toxicity, ethyl lactate is used commonly in pharmaceutical preparations, food additives,[5] and fragrances. Ethyl lactate is also used as solvent for nitrocellulose, cellulose acetate, and cellulose ethers.[6]

Further reading
  • Jacqueline S. Bennett; Kaitlyn L. Charles; Matthew R. Miner; Caitlin F. Heuberger; Elijah J. Spina; Michael F. Bartels; 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.

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. Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437.
  3. 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.
  4. Dolzhenko, Anton V. (2020). "Ethyl lactate and its aqueous solutions as sustainable media for organic synthesis". Sustainable Chemistry and Pharmacy. 18: 100322. doi:10.1016/j.scp.2020.100322.
  5. U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition Archived 7 January 2009 at the Wayback Machine
  6. "Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN 0-8155-1413-1, ISBN 978-0-8155-1413-8
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