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Formic Acid, Or Anthranilic Acid, How Was It Made?

Feb. 16, 2022


Formic Acid, Or Anthranilic Acid, How Was It Made?cid=3


More than 600 years ago, scientists discovered that ant mounds emitted acidic vapors. In 1671, the English naturalist John Ray described the isolation of the active ingredient. To do this, he collected and distilled large quantities of dead ants, and the acid he later discovered became known as formic acid, from the Latin word for ant, formica. Its correct name is now formic acid.


The first synthesis of formic acid was made by a French chemist using hydrocyanic acid as a starting material. in 1855, another French chemist developed a method of synthesis from carbon monoxide, similar to the one used today.


Urtic acid is also present in its natural state in stinging nettles and is associated with a burning sensation upon contact with them. It is also present in the bites and stings of many insects, including bees and ants, which use it as a chemical defense mechanism. When an ant constricts its venomous gland, the formic acid stored in this gland is sprayed by stinging and in the form of a jet (up to a meter in some species!) sprayed at the ant's attacker. Since formic acid has a pH of about 2-3, the attacker will usually escape or be killed.


Formic Acid, Or Anthranilic Acid, How Was It Made?cid=3



Structure and properties

Formic acid has the chemical formula HCOOH and is a planar molecule.

Formic acid dimer formic acid is a colorless fuming liquid that is miscible with water. In the gas phase, it consists of hydrogen-bonded dimers rather than individual molecules. In the gas phase, significant deviations from the ideal gas law occur due to this hydrogen bonding. In the liquid and solid state, formic acid can be considered as an effectively infinite network of hydrogen-bonded molecules.

As the first of a family of carboxylic acids, formic acid has most of the same chemical properties, so it reacts with bases to form water-soluble formates. However, formic acid is unique among carboxylic acids in that it reacts with olefins to form formate esters.


Production

Formic acid is a by-product of the acetic acid production process. However, the industrial demand for formic acid is higher than what can be produced by this route, so specialized production routes have been developed. One method combines methanol and carbon monoxide in the presence of a strong base (such as sodium methanol) to produce methyl formate according to the chemical equation.

CH3OH + CO ----> HCOOCH3

Hydrolysis produces formic acid.

HCOOCH3 + H2O ----> HCOOH + CH3OH


Formic Acid, Or Anthranilic Acid, How Was It Made?cid=3



Applications

In Europe, formic acid is mainly used in livestock feed as a preservative and antimicrobial agent. It can be sprayed on fresh hay or other silage to stop or delay certain spoilage processes. As a result, it allows the feed to survive longer, so it is widely used to preserve winter feed for cattle. In the poultry industry, it is sometimes added to feed to kill Salmonella. Some beekeepers also use formic acid as a fumigant to kill mites that attack bees. Formic acid is used in textile dyeing, leather tanning, nickel plating baths, electroplating, coagulating rubber latex, regenerating old rubber, debarking and plumping raw hides, and some commercial paint strippers. It is used in the manufacture of metal salts, including nickel, cadmium and potassium formate. Used as a solvent for perfumes, as well as for the manufacture of paints, glass, vinyl resin plasticizers and formate for flavor and fragrance. Used in the synthesis of artificial sweeteners, aspartame.



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Formic Acid, Or Anthranilic Acid, How Was It Made?cid=3