Ethyl levulinate Property

Melting point:

<25 °C

Boiling point:

93-94 °C/18 mmHg (lit.)

Density 

1.016 g/mL at 25 °C (lit.)

vapor pressure 

11Pa at 25℃

refractive index 

n20/D 1.422(lit.)

FEMA 

2442 | ETHYL LEVULINATE

Flash point:

195 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

H2O: freely soluble

form 

Liquid

color 

Clear yellow

Specific Gravity

1.01

Odor

at 100.00 %. sweet fruity floral berry green pineapple rhubarb

Odor Type

fruity

Water Solubility 

Soluble in water.

JECFA Number

607

Merck 

14,3819

BRN 

507641

Dielectric constant

12.0（21℃）

InChIKey

GMEONFUTDYJSNV-UHFFFAOYSA-N

LogP

0.324 at 20℃

CAS DataBase Reference

539-88-8(CAS DataBase Reference)

NIST Chemistry Reference

Pentanoic acid, 4-oxo-, ethyl ester(539-88-8)

EPA Substance Registry System

Pentanoic acid, 4-oxo-, ethyl ester (539-88-8)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

2

RTECS 

OI1700000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29183000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

Ethyl levulinate Chemical Properties,Usage,Production

Chemical Properties

clear yellowish liquid

Chemical Properties

Ethyl levulinate has an ethereal, fruity, green, sweet, pineapple, apple, rhubarb odor.

Occurrence

Reported found in white bread, roasted onion, wheat bread, cognac, malt whiskey, grape wines, cocoa, bilberry wine, Bourbon vanilla and cherimoya (Annona cheremolia Mill.).

Uses

Solvent for cellulose acetate and starch ethers, flavoring.

Uses

Ethyl levulinate is used to develop a preparative HPLC method to preserve wine aromas and isolates fruity characteristics of red wine aroma extracts

Uses

Ethyl levulinate was used to develop a preparative HPLC method to preserve wine aromas and isolates fruity characteristics of red wine aroma extracts.

Definition

ChEBI: Ethyl levulinate is an oxo carboxylic acid.

Preparation

Usually obtained by direct esterification of levulinic acid with ethanol and H2SO4 in benzene or in toluene; also in the presence of HCI in ethanol; other methods starting from glucose, fructose and others are of less importance.

Taste threshold values

Taste characteristics at 40 ppm: fruity, green, waxy and melon.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 486, 1994 DOI: 10.1021/jo00081a034
Synthetic Communications, 8, p. 279, 1978 DOI: 10.1080/00397917808065622

General Description

Ethyl levulinate is diluent for biodiesel fuels with high saturated fatty acid content.

Flammability and Explosibility

Not classified

Safety Profile

A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes

Purification Methods

Stir the ester with Na2CO3 and charcoal, filter and distil. It is freely soluble in H2O and EtOH [IR, NMR: Sterk Monatsh Chem 99 1770 1968, Thomas & Schuette J Am Chem Soc 53 2328 1931, Cox & Dodds J Am Chem Soc 55 3392 1933]. [Beilstein 3 IV 1562.]