Ethyl formate Property

Melting point:

-80 °C (lit.)

Boiling point:

52-54 °C (lit.)

Density 

0.921 g/mL at 20 °C (lit.)

vapor density 

2.5 (vs air)

vapor pressure 

15.16 psi ( 55 °C)

refractive index 

n20/D 1.359(lit.)

FEMA 

2434 | ETHYL FORMATE

Flash point:

7 °F

storage temp. 

2-8°C

solubility 

Miscible with alcohol, benzene, and ether (Hawley, 1981)

form 

Liquid

color 

Clear

Odor

Characteristic; pleasant aromatic.

Odor Threshold

2.7ppm

explosive limit

16%

Water Solubility 

11 g/100 mL (18 ºC)

Sensitive 

Moisture Sensitive

Merck 

14,3807

JECFA Number

26

BRN 

906769

Henry's Law Constant

0.097(x 10^-3 atm?m³/mol) at 5.00 °C, 0.13 at 10.00 °C, 0.17 at 15.00 °C, 0.23 at 20.00 °C, 0.29 at 25.00 °C (column stripping-UV, Kutsuna et al., 2005)

Exposure limits

TLV-TWA 100 ppm (～300 mg/m³) (ACGIH, MSHA, and OSHA); IDLH 8000 ppm (NIOSH).

Stability:

Stable. Extremely flammable. May form explosive mixtures with air. Note low flash point and wide explosive limits. Incompatible with strong oxidizing agents, strong bases, strong acids, nitrates.

InChIKey

WBJINCZRORDGAQ-UHFFFAOYSA-N

CAS DataBase Reference

109-94-4(CAS DataBase Reference)

NIST Chemistry Reference

Formic acid, ethyl ester(109-94-4)

EPA Substance Registry System

Ethyl formate (109-94-4)

Safety

Hazard Codes 

F,Xn

Risk Statements 

11-20/22-36/37

Safety Statements 

9-16-24-26-33

RIDADR 

UN 1190 3/PG 2

WGK Germany 

1

RTECS 

LQ8400000

Autoignition Temperature

851 °F

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29151300

Hazardous Substances Data

109-94-4(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 4.29 g/kg (Smyth)

IDLA

1,500 ppm

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H302Harmful if swallowed

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P243Take precautionary measures against static discharge.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

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

P370+P378In case of fire: Use … for extinction.

P403Store in a well-ventilated place.

P403+P235Store in a well-ventilated place. Keep cool.

Ethyl formate Chemical Properties,Usage,Production

Description

Ethyl formate is an ester formed when ethanol (an alcohol) reacts with formic acid (a carboxylic acid). It is also known as ethyl methanoate because formic acid is also known as methanoic acid. Ethyl formate has the characteristic smell of rum and is also partially responsible for the flavor of raspberries.

Chemical Properties

Ethyl Formate occurs widely in fruits. It is a liquid with a slightly pungent, fruity, ethereal odor and is used in fruit flavors.

Chemical Properties

Ethyl formate has a characteristic, pungent odor similar to ethyl acetate and reminiscent of pineapple and a slightly bitter taste. It has been also reported to have a rum-like odor. The ester is slightly soluble in water (9 parts/100 at 18 °C) with gradual decomposition into formic acid and ethanol; it is miscible in ethanol, ether, and acetone (HSDB, 2013), as well as in benzene.

Physical properties

Colorless, clear liquid with a pleasant, fruity odor. An odor threshold concentration of 2.7 ppm_v was reported by Nagata and Takeuchi (1990).

History

Astronomers have identified ethyl formate in dust clouds in an area of the Milky Way galaxy called Sagittarius B2. The astronomers, from the Max Planck Institute for Radio Astronomy in Bonn, Germany, used the 30 meter IRAM radio telescope in Spain to analyze the spectra of radiation emitted from hot regions near a new star. It is among 50 molecules identified by the astronomers.

Occurrence

Reported in the oil of Boronia dentigeroides; it has been identified in Florida orange juice, several varieties of honey, apple and pear and in distilled liquors, such as rum. Also reported found in peach, raspberry, strawberry, pineapple, cabbage, vinegar, cheeses, butter, cream, milk powder, cooked beef, beer, coffee, tea, honey, corn oil, brandy and mussels.

Uses

As flavor for lemonades and essences; for manufacture of artificial rum and arrack; also as a solvent for nitrocellulose; as fungicide and larvicide for tobacco, cereals, dried fruits, etc.; in organic synthesis.

Uses

Plant volatiles such as ethyl formate have been shown to have insecticidal properties as fumigant. The efficacy of ethyl formate against insect pests of food commodities, bagged cereals, spices, pulses, dry fruits and oilcakes had been proved. The fumigant was known to provide a high mortality of mixed stage cultures of the key stored product pests, with limited efficacy against the pupal stage of few pests like S. oryzae. The advantages of ethyl formate include natural occurrence in food; rapid kill of insects (2-4 hours); fast breakdown of residues to natural products and low human toxicity. However the fumigant exhibits poor penetration characteristics and high doses (>120 g/t of grain) were required to control internal feeders, which was higher than the flammable limit of 85 g/t. Formulations of ethyl formate in liquid carbon dioxide were found to overcome the problems of flammability and poor penetration.

Uses

Ethyl Formate is a flavoring agent that occurs naturally in some plant oils, fruits, and juices but does not occur naturally in the ani- mal kingdom. it is used in food at a maximum level, as served, of 0.05% in baked goods; 0.04% in chewing gum, hard candy, and soft candy; 0.02% in frozen dairy desserts; 0.03% in gelatins, puddings, and fillings; and 0.01% in all other food categories. it is an ester of formic acid and is prepared by esterification of formic acid with ethyl alcohol or by distillation of ethyl acetate and formic acid in the presence of concentrated sulfuric acid.

Uses

Ethyl formate is used as a solvent; as aflavor for lemonades and essences; and as afungicide and larvicide for cereals, dry fruits,tobacco, and so on.

Definition

ChEBI: A formate ester resulting from the formal condensation of formic acid with ethanol.

Production Methods

Ethyl formate is manufactured via esterfication of formic acid and ethanol in the presence of sulfuric acid and alternatively by distillation of ethyl acetate and formic acid in the presence of sulfuric acid.

Aroma threshold values

Detection: 17 ppm

Taste threshold values

Taste characteristics at 60 ppm: sweet, chemical with clean, fresh, fruity lift.

General Description

A clear colorless liquid with a pleasant odor. Flash point -4°F. Less dense than water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Soluble in water. Slowly decomposed by water to formic acid, a corrosive material and ethyl alcohol, another flammable liquid.

Reactivity Profile

Ethyl formate 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. Ethyl formate is incompatible with the following: Nitrates; strong oxidizers, alkalis & acids [Note: Decomposes slowly in water to form ethyl alcohol and formic acid.] .

Hazard

Narcotic and irritant to skin and eyes; use in foods restricted to 0.0015%. Highly flammable, dangerous fire and explosion risk. Questionable carcinogen.

Health Hazard

The irritant action of ethyl formate inthe eyes, nose, and mucous membranes ismilder than that of methyl formate. How ever it is more narcotic than the methylester. Cats exposed to 10,000 ppm died after90 minutes, after deep narcosis. A 4-hourexposure to 8000 ppm was lethal to rats.Inhalation of 5000 ppm for a short periodproduces eye and nasal irritation and salivation in rats. The toxic effects from ingestion include somnolence, narcosis, gastritis,and dyspnea. The oral LD50 values in various test animals range between 1000 and2000 mg/kg.

Fire Hazard

Behavior in Fire: Vapor is heavier than air and may travel long distance to a source of ignition and flash back.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Agricultural Uses

Fumigant, Insecticide: Used as a fumigant, especially on dried fruit, Also used as a solvent for cellulose nitrate and acetate and in the production of synthetic flavors. Not currently registered for agricultural use in EU countries and the U.S. Used in Australia and there are 63 global suppliers.

Safety Profile

Moderately toxic by ingestion and subcutaneous routes. Mddly toxic by skin contact and inhalation. A powerful inhalation irritant in humans. A skin and eye irritant. Questionable carcinogen with experimental tumorigenic data. Highly flammable liquid. A very dangerous fire and explosion hazard when exposed to heat, flame, or oxilzers. To fight fire, use alcohol foam, spray, mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Safety

Ethyl methanoate is generally recognized as safe by the U.S. Food and Drug Administration.
According to the U.S Occupational Safety and Health Administration (OSHA), ethyl formate can irritate eyes, skin, mucous membranes, and the respiratory system of humans and other animals; it is also a central nervous system depressant.In industry, it is used as a solvent for cellulose nitrate, cellulose acetate, oils, and greases. It can be used as a substitute for acetone; workers may also be exposed to it under the following circumstances:
during spray, brush, or dip applications of lacquers
during the manufacture of safety glass
When fumigating tobacco, cereals, and dried fruits (as an alternative to methyl bromide under the U.S. Department of Agriculture quarantine system ).

Potential Exposure

This material is used as an emulsifier; food and feed additive; flavor, packaging material; as a solvent for cellulose nitrate and acetate; it is used as a fumigant and in the production of synthetic flavors. It is also a raw material in pharmaceutical manufacture

Environmental Fate

Photolytic. Reported rate constants for the reaction of ethyl formate and OH radicals in the atmosphere (296 K) and aqueous solution are 1.02 x 10^-11 and 6.5 x 10^-13 cm³/molecule?sec, respectively (Wallington et al., 1988b).
Chemical/Physical. Slowly hydrolyzes in water forming ethanol and formic acid (Windholz et al., 1983).

Shipping

UN1190 Ethyl formate, Hazard Class: 3; Labels: 3-Flammable liquid

Purification Methods

Free acid or alcohol is removed by standing the ester over anhydrous K2CO3, with occasional shaking, then decanting and distilling from P2O5. Alternatively, the ester can be kept over CaH2 for several days, then distilled from fresh CaH2. It cannot be dried with CaCl2 because it reacts rapidly with the ester to form a crystalline compound. [Beilstein 2 IV 23.]

Incompatibilities

May form explosive mixture with air. Reacts violently with nitrates, strong oxidizers, strong alkalis, and strong acids. Decomposes slowly in water, forming ethyl alcohol and formic acid. May accumulate static electrical charges, and may cause ignition of its vapors

Waste Disposal

Spray into a furnace in admixture with a flammable solvent