Formic acid

[5] Formic acid is found naturally in insects, weeds, fruits and vegetables, and forest emissions.

[6][7] Wood ants from the genus Formica can spray formic acid on their prey or to defend the nest.

[8] Formic acid is a naturally occurring component of the atmosphere primarily due to forest emissions.

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.

In 1855, another French chemist, Marcellin Berthelot, developed a synthesis from carbon monoxide similar to the process used today.

[13][14] Owing to its tendency to hydrogen-bond, gaseous formic acid does not obey the ideal gas law.

[13] As of 2009[update], the largest producers are BASF, Eastman Chemical Company, LC Industrial, and Feicheng Acid Chemicals, with the largest production facilities in Ludwigshafen (200 thousand tonnes or 440 million pounds per year, BASF, Germany), Oulu (105 thousand tonnes or 230 million pounds, Eastman, Finland), Nakhon Pathom (n/a, LC Industrial), and Feicheng (100 thousand tonnes or 220 million pounds, Feicheng, China).

[24] When methanol and carbon monoxide are combined in the presence of a strong base, the result is methyl formate, according to the chemical equation:[13] In industry, this reaction is performed in the liquid phase at elevated pressure.

Some routes proceed indirectly by first treating the methyl formate with ammonia to give formamide, which is then hydrolyzed with sulfuric acid: A disadvantage of this approach is the need to dispose of the ammonium sulfate byproduct.

This problem has led some manufacturers to develop energy-efficient methods of separating formic acid from the excess water used in direct hydrolysis.

In one of these processes, used by BASF, the formic acid is removed from the water by liquid-liquid extraction with an organic base.

[citation needed] A significant amount of formic acid is produced as a byproduct in the manufacture of other chemicals.

Formic acid can also be obtained by aqueous catalytic partial oxidation of wet biomass by the OxFA process.

[28][29] A Keggin-type polyoxometalate (H5PV2Mo10O40) is used as the homogeneous catalyst to convert sugars, wood, waste paper, or cyanobacteria to formic acid and CO2 as the sole byproduct.

[31] Formate is formed by the electrochemical reduction of CO2 (in the form of bicarbonate) at a lead cathode at pH 8.6:[32] or If the feed is CO2 and oxygen is evolved at the anode, the total reaction is: Formic acid is named after ants which have high concentrations of the compound in their venom, derived from serine through a 5,10-methenyltetrahydrofolate intermediate.

It arrests certain decay processes and causes the feed to retain its nutritive value longer, In Europe, it is applied on silage, including fresh hay, to promote the fermentation of lactic acid and to suppress the formation of butyric acid; it also allows fermentation to occur quickly, and at a lower temperature, reducing the loss of nutritional value.

[39][40] Electrolytic conversion of electrical energy to chemical fuel has been proposed as a large-scale source of formate by various groups.

[citation needed] Formic acid is used as a volatile pH modifier in HPLC and capillary electrophoresis.

Concentrated formic acid slowly decomposes to carbon monoxide and water, leading to pressure buildup in the containing vessel.

The U.S. OSHA Permissible Exposure Level (PEL) of formic acid vapor in the work environment is 5 parts per million (ppm) of air.

Skeletal structure of formic acid
Skeletal structure of formic acid
3D model of formic acid
3D model of formic acid
NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code
Cyclic dimer of formic acid; dashed green lines represent hydrogen bonds
The Eschweiler–Clark reaction
The Eschweiler–Clark reaction