Fulminic acid

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Fulminic acid


Fulminic acid is an organic compound with the formula HCNO. It is a nitrile oxide and is related to the better known compound cyanic acid (HOCN). Fulminic acid is one of the simplest compounds containing both a carbon-nitrogen triple bond and a nitrogen-oxygen double bond. Due to the presence of these functional groups, fulminic acid is a highly reactive species and is considered a chemical intermediate in the synthesis of some more complex molecules.

The history of fulminic acid dates back to the early 19th century when it was first synthesized by Justus von Liebig and Friedrich Wöhler in an attempt to understand the composition of the explosive silver fulminate. Despite its instability, fulminic acid has been of interest in both organic chemistry and inorganic chemistry for its role in the formation of metal fulminates, which are used in detonators and primers for explosives.

Fulminic acid is typically prepared in a laboratory setting through the reaction of ethanol with sodium hypochlorite in the presence of sodium cyanide. This process yields fulminic acid as a highly unstable intermediate, which can then be reacted with metals to form metal fulminates.

Due to its instability and explosive nature, fulminic acid is not commonly encountered outside of a laboratory or industrial setting. It is primarily of interest for its role in the synthesis of other chemicals, particularly those involved in the production of explosives.

The structure of fulminic acid has been a subject of study, and it has been determined to have a linear configuration with a triple bond between the carbon and nitrogen atoms and a double bond between the nitrogen and oxygen atoms. This structure contributes to its reactivity and instability.

In terms of safety, handling fulminic acid requires extreme caution due to its explosive potential. It is sensitive to heat, shock, and friction, making it dangerous to work with outside of controlled environments.

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Contributors: Prab R. Tumpati, MD