Chemical Properties
Colorless liquid; pungent odor. Highly flammable. Slightly soluble in water; soluble in alcohol,
ether; decomposes in water.
Uses
Triethyl orthoformate is used in Bodroux-Chichibabin aldehyde synthesis to prepare an aldehyde with one carbon higher by reacting with Grignard reagent. It is also used in the electrophilic formylation of activated aromatic species such as phenol.
Application
Sweet, somewhat camphoraceous-herbaceous odor with a Fimecdle-like note.
Triethyl orthoformate has been suggested for use in industrial
fragrances for masking, etc. and may find
some application in that field. It tends to lift
the odor of the conventional components of a
pine fragrance and increase the radiation, an
effect often desirable for masking purposes.
General Description
Triethyl orthoformate is a clear, colorless liquid with a pungent odor. Less dense than water. Flash point 86°F. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.
Reactivity Profile
Triethyl orthoformate 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
Triethyl orthoformate 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: Triethyl orthoformate 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.
Flammability and Explosibility
Flammable
Safety Profile
Moderately toxic by
ingestion. Mddly toxic by inhalation, skin
contact, and subcutaneous routes. A skin
and eye irritant. A very dangerous fire
hazard when exposed to heat or flame; can
react vigorously with oxidzing materials. To
fight fire, use foam, CO2, dry chemical.
When heated to decomposition it emits
acrid smoke and irritating fumes. See also
ESTERS.
Purification Methods
Fractionate triethyl orthoformate first at atmospheric pressure, then in a vacuum. If impure, then shake it with aqueous 2% NaOH, dry it with solid KOH and distil it from sodium through a 20cm Vigreux column (p 11). Alternatively, wash it with H2O, dry it over anhydrous K2CO3, filter and fractionate it through a Widmer column. [Sah & Ma J Am Chem Soc 54 2964 1932, Ohme & Schmitz Justus Liebigs Ann Chem 716 207 1968, Beilstein 2 IV 25.] IRRITANT and FLAMMABLE.
