Ethyl nitrate

Description

Ethyl nitrate has formula C₂H₅NO₃. It is used in organic synthesis and as an intermediate in the preparation of some drugs, dyes, and perfumes.
Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. Originally thought to be a pollutant, formed mainly by the combustion of fossil fuels, recent analysis of ocean water samples reveal that in places where cool water rises from the deep, the water is saturated with alkyl nitrates, likely formed by natural processes.

Chemical Properties

Ethyl nitrate is capable of explosive decomposition when exposed to heat.

Uses

Organic synthesis, drugs, perfumes, dyes, rocket propellant.

Preparation

Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at ?10 °C . The reaction was subsequently studied in detail.

Production Methods

The alkyl nitrates are produced from the corresponding alcohols by esterification with nitric acid in the presence of urea or urea nitrate.

General Description

A clear colorless liquid with a pleasant odor. Flash point 50°F. Prolonged exposure to fire or heat may cause vigorous decomposition and rupturing of the container. Denser than water and insoluble in water. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Organonitrates, such as Ethyl nitrate, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive.

Hazard

Flammable, dangerous, fire and explosion risk.

Health Hazard

In humans ethyl nitrate can cause headache, narcosis and vomiting, but no cases of industrial intoxication have been reported .

Industrial uses

Ethyl nitrate is used in the synthesis of certain drugs, perfumes and dyes. It has also found some use as a rocket fuel.

Safety Profile

A poison by intraperitoneal route. Mutation data reported. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxibzing materials. A moderate explosion hazard when exposed to heat (explodes @ 185'F). To fight fire, use foam, CO2, dry chemical, water to blanket fire. Incompatible with Lewis acids. When heated to decomposition it emits toxic fumes of NOx. See also NITRATES and ESTERS.

Metabolism

There is no information concerning the in vivo metabolism of ethyl nitrate, but it seems likely that one route for biotransformation is hydrolysis to yield an alcohol and nitrate. Such a pathway is common to other alkyl nitrates such as nitroglycerin and amyl nitrate.

Raw materials

Preparation Products