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Ethyl lactate

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Ethyl lactate
Names
IUPAC name Ethyl 2-hydroxypropanoate
Other names Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.363 Edit this at Wikidata
EC Number
  • 202-598-0
PubChem CID
RTECS number
  • OD5075000
UNII
UN number 1192
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3Key: LZCLXQDLBQLTDK-UHFFFAOYSA-N
  • InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3Key: LZCLXQDLBQLTDK-UHFFFAOYAV
SMILES
  • CCOC(=O)C(C)O
Properties
Chemical formula C5H10O3
Molar mass 118.132 g·mol
Appearance Colorless liquid
Density 1.03 g/cm
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 (D) −11.3°
Magnetic susceptibility (χ) -72.6·10 cm/mol
Structure
Dipole moment 3.46 D
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H226, H318, H335
Precautionary statements P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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
3 2 0
Flash point 58 °C (136 °F; 331 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. 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.

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

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. "Ethyl lactate".
  3. "ETHYL LACTATE | CAMEO Chemicals | NOAA".
  4. Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437. ISBN 3527306730.
  5. 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.
  6. 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. S2CID 224957198.
  7. U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition Archived 7 January 2009 at the Wayback Machine
  8. "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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