Ethyl lactate Property

Melting point:

-26°C

Boiling point:

154 °C (lit.)

alpha 

D14 -10°

Density 

1.031 g/mL at 25 °C (lit.)

vapor pressure 

81hPa at 20℃

refractive index 

1.4124

FEMA 

2440 | ETHYL LACTATE

Flash point:

54.6±6.4 °C

solubility 

Miscible with water (with partial decomposition), ethanol (95%), ether, chloroform, ketones, esters, and hydrocarbons.

form 

clear liquid

pka

13.21±0.20(Predicted)

color 

Colorless

Odor

Mild characteristic.

optical activity

[α]20/D 10.5°, neat

Odor Type

fruity

Water Solubility 

100g/L at 20℃

JECFA Number

931

Merck 

14,3817

Dielectric constant

13.1（25℃）

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

LZCLXQDLBQLTDK-UHFFFAOYSA-N

LogP

0.7 at 25℃

CAS DataBase Reference

97-64-3(CAS DataBase Reference)

NIST Chemistry Reference

Propanoic acid, 2-hydroxy-, ethyl ester(97-64-3)

EPA Substance Registry System

Ethyl lactate (97-64-3)

Safety

Hazard Codes 

Xi

Risk Statements 

10-37-41

Safety Statements 

24-26-39

RIDADR 

1192

WGK Germany 

1

RTECS 

OD5075000

HazardClass 

3.2

PackingGroup 

III

HS Code 

29181100

Hazardous Substances Data

97-64-3(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethyl lactate Chemical Properties,Usage,Production

Description

Ethyl lactate, an ester of lactic acid, is a "green" solvent derived from processing corn. Lactate esters solvents are commonly used solvents in the paints and coatings industry and have numerous attractive advantages including being 100% biodegradable, easy to recycle, noncorrosive, noncarcinogenic, and nonozone depleting.
Ethyl lactate is an important organic ester, which is biodegradable and can be used as food additive, in perfumery, as flavour chemicals and solvent, which can dissolve acetic acid cellulose and many resins (Tanaka et al., 2002). It is a particularly attractive solvent for the coatings industry as a result of its high solvency power, high boiling point, low vapour pressure and low surface tension. Ethyl lactate is a desirable coating for wood, polystyrene and metals and also acts as a very effective paint stripper and graffiti remover. It has replaced solvents including N-methyl Pyrrolidone (NMP) (Reisch, 2008), toluene, acetone and xylene, which has resulted in the workplace being made a great deal safer.

ethyl lactate structure

Chemical properties

Ethyl lactate appears as colorless to light yellow transparent liquid with rum, fruit and cream aroma. The freezing point:-25°C; the boiling point: 154°C, specific rotation [a] 14d:-10°. It is easily soluble in ethanol, acetone, ether, esters and other organic solvents; there is some degree of hydrolysis upon being miscible with water. Mouse oral LD50: 2.5g/kg, ADI is subject to no special provisions (FAO/WHO, 1994).

Ethyl lactate is a common solvent in pharmaceutical, cosmetic, detergent, coatings, food and fragrance production. It is considered biodegradable in its natural form and it is exempt from many restrictions imposed in accordance with the disposal of chemicals. For this reason it is a highly desirable product in a “green”, environmentally conscious industry. In the presence of water, acids and bases the chemical will hydrolyse into ethanol and lactic acid.

Uses

Ethyl Lactate is a solvent manufactured from l (+) lactic acid which is miscible in water and most organic solvents and is cleared for use as a flavoring agent. it is a naturally occurring constituent of california and spanish sherries. it is a clear, colorless, nontoxic liquid of low volatility, having a ph of 7–7.5. it is used as a food and beverage flavoring agent.Ethyl lactate is used in the electronics industry to remove salts and fat from circuit boards; it is also a component in paint strippers.

Production method

Ethyl lactate is usually produced by the esterification of lactic acid with ethanol using sulfuric acid catalyst.

Usage limit

FEMA (mg/mL): Soften drink: 5.4; Cold drinks: 17; Candies 28; baked goods 71; pudding class 8.3; gums 580 to 3100; alcohol 1000; syrup 35.
Take moderate as limit (FDA § 172.515, 2000).

Toxicity

ADI is not subject to specific special provisions (FAO/WHO, 1994).
GRAS (FEMA).
LD50 2500 mg/kg (mouse, oral).

Chemical Properties

Ethyl Lactate is a colorless liquid with a light ethereal, buttery odor. It miscible in water, alcohols, ketones , esters, hydrocarbons, ether and oil. The odor threshold is reported to be 0.89 mg/m3 and the odor nuisance threshold to be 65 mg/m3.

Occurrence

Ethyl lactate is reported to be found in apple, citrus fruits, pineapple, peas, sauerkraut, vinegar, bread, beer, grape brandy, rum, whisky, cider, sherry, wine, cocoa, banty beer, plum brandy and pear brandy. It has been approved by the US FDA for food use.

Uses

Ethyl lactate is used as a solvent for nitrocellulose, cellulose acetate, and many cellulose ethers and resins. It is also used in lacquers, paints, enamels, varnishes, stencil sheets, safety glass and flavoring. Ethyl lactate is furthermore used in some cosmetic formulations in soaps, detergents, creams and lotions with a maximum concentration of 0.2 %. In recent years it has been used as degreaser as a substitute for trichloroethylene.

Preparation

Ethyl lactate is produced by the esterification of lactic acid with ethanol in the presence of a little mineral oil, or by combination of acetaldehyde with hydrocyanic acid to form acetaldehyde cyanhydrin. This is followed by treatment with ethanol (95%) and hydrochloric or sulfuric acid. Purification is achieved using fractional distillation. The commercial product is a racemic mixture.

Definition

ChEBI: Ethyl 2-hydroxypropanoate is the ethyl ester obtained of 2-hydroxypropanoic acid. It has a role as a metabolite. It is a secondary alcohol, a lactate ester and an ethyl ester. It is functionally related to a 2-hydroxypropanoic acid.

Synthesis Reference(s)

Synthetic Communications, 19, p. 1335, 1989 DOI: 10.1080/00397918908054542

General Description

A clear colorless liquid with a mild odor. Flash point 115°F. Denser than water and soluble in water. Vapors heavier than air.

Air & Water Reactions

Flammable. Soluble in water.

Reactivity Profile

Ethyl lactate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

Inhalation of concentrated vapor may cause drowsiness. Contact with liquid causes mild irritation of eyes and (on prolonged contact) skin. Ingestion may cause narcosis.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety

Ethyl lactate is used as a flavoring agent in pharmaceutical preparations, and is found in food products. The estimated acceptable daily intake for lactic acid is 12.5 mg/kg body-weight.
In general, lactate esters have an oral LD50 > 2000 mg/kg; and the inhalation LC50 is generally above 5000 mg/m3. They have the potential of causing eye and skin irritation (on prolonged contact), but not sensitization. Ethyl lactate is moderately toxic by intraperitoneal, subcutaneous, and intravenous routes. There is low oral and skin contact toxicity; although ingestion may cause nausea, stomach and throat pain, and narcosis. Inhalation of concentrated vapor of ethyl lactate may cause irritation of the mucous membranes, drowsiness, and narcosis.
LD50 (rat, oral): >5.0 g/kg
LD50 (mouse, oral): 2.5 g/kg
LD50 (mouse, SC): 2.5 g/kg
LD50 (mouse, IV): 0.6 g/kg
LD50 (rabbit, skin): >5.0 g/kg

Veterinary Drugs and Treatments

Ethyl lactate shampoo can be used when an antibacterial shampoo (bacteriostatic and bactericidal) is needed particularly in animals with surface and superficial pyodermas that cannot tolerate benzoyl peroxide. It also has keratoplastic effect, which provides anti-seborrheic activity.
A lipid soluble compound, ethyl lactate penetrates hair follicles and sebaceous glands where bacterial lipases convert it into lactic acid and ethanol, which are responsible for its antibacterial action. It is not as active as benzoyl peroxide against staphylococcal organisms, but is less irritating and drying.

storage

Stable at normal temperature and pressure. Ethyl lactate is a flammable liquid and vapor. Store in a cool, dry, and well-ventilated location away from any fire hazard area, in a tightly closed container.

Incompatibilities

Incompatible with bases or strong alkalis and may cause fire or explosion with strong oxidizing agents.

Regulatory Status

GRAS listed. Reported in the EPA TSCA Inventory.