Ethyl lactate
Names | |
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IUPAC name
Ethyl 2-hydroxypropanoate
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Other names
Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.002.363 |
EC Number |
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PubChem CID
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RTECS number
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UNII | |
UN number | 1192 |
CompTox Dashboard (EPA)
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Properties | |
C5H10O3 | |
Molar mass | 118.132 g·mol−1 |
Appearance | Colorless 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 |
Chiral rotation ([α]D)
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−11.3° |
-72.6·10−6 cm3/mol | |
Structure | |
3.46 D[1] | |
Hazards | |
GHS labelling: | |
Danger | |
H226, H318, H335 | |
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) | |
Flash point | 46 °C (115 °F; 319 K) |
Related compounds | |
Related compounds
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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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Ethyl lactate, also known as lactic acid ethyl
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.[6] Due to its relatively low toxicity, ethyl lactate is used commonly in pharmaceutical preparations, food additives,[7] and fragrances. Ethyl lactate is also used as solvent for nitrocellulose, cellulose acetate, and cellulose ethers.[8]
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
- doi:10.1039/b811909k.
- ^ "Ethyl lactate".
- ^ "ETHYL LACTATE | CAMEO Chemicals | NOAA".
- ISBN 978-3527306732.
- .
- S2CID 224957198.
- U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition Archived 7 January 2009 at the Wayback Machine
- ISBN 978-0-8155-1413-8