ETHYL CROTONATE Property

Melting point:

37.22°C (estimate)

Boiling point:

142-143 °C(lit.)

Density 

0.918 g/mL at 25 °C(lit.)

vapor density 

3.9 (vs air)

refractive index 

n20/D 1.424(lit.)

FEMA 

3486 | ETHYL TRANS-2-BUTENOATE

Flash point:

36 °F

storage temp. 

Flammables area

form 

Liquid

color 

Clear colorless

Odor

at 10.00 % in dipropylene glycol. pungent fruity acrid ester

Odor Type

fermented

JECFA Number

1806

LogP

1.806 (est)

EPA Substance Registry System

2-Butenoic acid, ethyl ester (10544-63-5)

Safety

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

16-26-36/37/39-45

RIDADR 

UN 1862 3/PG 2

WGK Germany 

2

RTECS 

GQ3500000

HS Code 

29161900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

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.

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

ETHYL CROTONATE Chemical Properties,Usage,Production

Chemical Properties

clear colorless liquid

Chemical Properties

Ethyl crotonate has a powerful, sour, caramellic-fruity odor.

Occurrence

Reported found in Fragaria vesca. Also reported found in guava fruit, guava peel, pineapple, white wine, yellow passion fruit, fresh mango, naranjilla fruit, mussel, loganberry, apple, papaya, concord grape, strawberry, rum, cocoa, plum, kiwifruit and other natural sources.

Uses

Crotonic Acid Ethyl Ester, is an intermediate for the preparation of various pharmaceutical compounds. It can be used for the synthesis of (+)-trans-Trikentrin A.

Definition

ChEBI: Ethyl crotonate is a fatty acid ester.

Preparation

By esterification of crotonic acid with ethyl alcohol in the presence of concentrated H2SO4.

Taste threshold values

Taste characteristics at 10 ppm: rum, cognac and pungent with caramellic and fruity nuances.

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 2716, 1990 DOI: 10.1021/ja00163a038
Synthetic Communications, 14, p. 701, 1984 DOI: 10.1080/00397918408059583

General Description

A clear colorless liquid with a pungent odor. Flash point 36°F. Less dense than water and insoluble in water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

ETHYL CROTONATE 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

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

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 Profile

Slightly toxic by ingestion. Corrosive. An eye irritant and lachrymator. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.