Chemistry:Ethyl lactate

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	687-47-8 (L-isomer) Y 97-64-3 (racemate) Y 7699-00-5 (D-isomer) Y
3D model (JSmol)	Interactive image
ChemSpider	13837423 Y
EC Number	202-598-0
PubChem CID	7344
RTECS number	OD5075000
UNII	F3P750VW8I Y
UN number	1192
InChI InChI=1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3 Y Key: LZCLXQDLBQLTDK-UHFFFAOYSA-N Y InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3 Key: LZCLXQDLBQLTDK-UHFFFAOYAV
SMILES CCOC(=O)C(C)O
Properties
Chemical formula	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)
Solubility in water	Miscible
Solubility in ethanol and most alcohols	Miscible
Chiral rotation ([α]D)	−11.3°
Magnetic susceptibility (χ)	-72.6·10−6 cm3/mol
Structure
Dipole moment	3.46 D
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H318, H335
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+361+353, P304+340, P305+351+338, P310, P312, P370+378, P403+233, P403+235, P405, P501
NFPA 704 (fire diamond)	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

Tracking categories (test):

• SizeSet

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.