Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.
Insect defenses
In nature, formic acid is found in most ants and in stingless bees of the genus Oxytrigona. Wood ants from the genus Formica can spray formic acid on their prey or to defend the nest. The puss moth caterpillar (Cerura vinula) will spray it as well when threatened by predators. It is also found in the trichomes of stinging nettle (Urtica dioica). Apart from that, this acid is incorporated in many fruits such as pineapple (0.21mg per 100g), apple (2mg per 100g) and kiwi (1mg per 100g), as well as in many vegetables, namely onion (45mg per 100g), eggplant (1.34 mg per 100g) and, in extremely low concentrations, cucumber (0.11mg per 100g). Formic acid is a naturally occurring component of the atmosphere primarily due to forest emissions.
As early as the 15th century, some alchemists and naturalists were aware that ant hills give off an acidic vapor. The first person to describe the isolation of this substance (by the distillation of large numbers of ants) was the English naturalist John Ray, in 1671. Ants secrete the formic acid for attack and defense purposes. Formic acid was first synthesized from hydrocyanic acid by the French chemist Joseph Gay-Lussac. In 1855, another French chemist, Marcellin Berthelot, developed a synthesis from carbon monoxide similar to the process used today.
Formic acid was long considered a chemical compound of only minor interest in the chemical industry. In the late 1960s, significant quantities became available as a byproduct of acetic acid production. It now finds increasing use as a preservative and antibacterial in livestock feed.
Formic acid is a colorless liquid having a pungent, penetrating odor at room temperature, comparable to the related acetic acid.
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