Ethyl formate

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Ethyl formate
Names
Preferred IUPAC name
Ethyl formate
Systematic IUPAC name
Ethyl methanoate
Other names
Areginal
Ethyl formiate
Formic acid ethyl ester
Properties
C3H6O2
Molar mass 74.08 g/mol
Appearance Colorless liquid
Odor Fruity, rum or raspberry-like
Density 0.917 g/cm3
Melting point −80 °C (−112 °F; 193 K)
Boiling point 54 °C (129 °F; 327 K)
10.5 g/100 ml (at 20°C)[1]
Solubility Miscible with acetone, benzene, ethanol, diethyl ether
Vapor pressure 200 mmHg (20°C)
Thermochemistry
Hazards
Safety data sheet Mathesongas
Flash point -20 °C
Lethal dose or concentration (LD, LC):
1850 mg/kg (rat, oral)
1110 mg/kg (guinea pig, oral)
2075 mg/kg (rabbit, oral)
10,000 ppm (cat, 1.5 hr)
8000 ppm (rat, 4 hr)
Related compounds
Related compounds
Methyl formate
Methyl acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethyl formate or ethyl methanoate is a volatile ester obtained from ethanol and formic acid, with a pleasant fruity smell, reminiscent of rum or raspberry. It has the formula HCOOCH2CH3 or C3H6O2.

Properties

Chemical

Ammonia reacts with ethyl formate to give formamide:

HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH

Physical

Ethyl formate is a colorless volatile liquid, with a fruity rum-like odor, poorly soluble in water but miscible with many organic solvents.

Availability

Ethyl formate can be purchased from chemical suppliers and online.

Preparation

Ethyl formate is best synthesized by the Fischer esterification between conc. formic acid and anh. ethanol, in the presence of a desiccant, such as anhydrous calcium chloride, under reflux. The resulting impure ethyl formate can be purified by adding it in cold water and then extracted using a separatory funnel and dried with anhydrous calcium chloride or sodium sulfate.

Another route involves treating sodium formate (which can be obtained from the haloform reaction of ethanol or isopropanol) with anhydrous ethanol and concentrated sulfuric acid.[3]

The industrial route involves the reaction of ethanol with carbon dioxide in an autoclave at 100-125 °C and 200 for 10-20 hours, in inert conditions, in the presence of gold supported on titanium dioxide catalyst.[4] However this route is not feasible for the amateur chemist.

Projects

  • Organic extractions
  • Make formamide

Handling

Safety

Ethyl formate is irritant if inhaled. It is also very flammable.

Storage

In closed bottles, away from ignition sources

Disposal

Ethyl formate can be safely disposed of by burning it outside or in an incinerator.

References

  1. http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=0623
  2. Tabuchi; Journal of Chemical Physics; vol. 28; (1958); p. 1014,1018
  3. https://www.researchgate.net/file.PostFileLoader.html?id=56e532e0dc332d21e773a9ca&assetKey=AS%3A339109211066368%401457861344459.
  4. http://www.google.com/patents/US20130102807

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