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Formic acid
2007 Schools Wikipedia Selection. Related subjects: Chemical compounds Formic acid
Formic acid (systematically called methanoic acid) is the simplest
carboxylic acid. Its formula is CH2O2 or HCOOH.

In nature, it is found in the stings and bites of many insects of the

order Hymenoptera, including bees and ants. It is also a significant
combustion product resulting from alternative fueled vehicles
burning methanol (and ethanol, if contaminated with water) when
mixed with gasoline. Its name comes from the Latin word for ant,
formica, referring to its early isolation by the distillation of ant
bodies. A chemical compound such as a salt from the neutralization General
of formic acid with a base, or an ester derived from formic acid, is Systematic name methanoic acid
referred to as formate (or methanoate). The formate ion has the
formic acid
formula HCOO−. Other names hydrogen carboxylic acid
aminic acid
Properties CH2O2
Molecular formula
HCOOH
Formic acid is miscible with water and most polar organic solvents,
SMILES O=CO
and somewhat soluble in hydrocarbons. In hydrocarbons and in the
vapor phase, it actually consists of hydrogen-bonded dimers rather Molar mass 46.0254 g/mol
than individual molecules. In the gas phase, this hydrogen-bonding Appearance colourless, fuming liquid
results in severe deviations from the ideal gas law. Liquid and solid
formic acid consists of an effectively infinite network of hydrogen- CAS number [64-18-6]
bonded formic acid molecules. Properties
Density and phase 1.22 g/cm³, liquid
Formic acid shares most of the chemical properties of other
carboxylic acids, although under normal conditions it will not form Solubility in water miscible
either an acyl chloride or an acid anhydride. Until very recently, all Melting point 8.4°C (281.5 K)
attempts to form either of these derivatives have resulted in carbon
Boiling point 100.8°C (373.9 K)
monoxide instead. It has now been shown that the anhydride may be
produced by reaction of formyl fluoride with sodium formate at Acidity (pKa) 3.75
−78°C, and the chloride by passing HCl into a solution of
Viscosity 1.57 c P at 26°C
1-formimidazole in monochloromethane at −60°C. Heat can also
cause formic acid to decompose to carbon monoxide and water. Structure
Formic acid shares some of the reducing properties of aldehydes. Molecular shape Planar
Formic acid is unique among the carboxylic acids in its ability to Dipole moment 1.41 D(gas)
participate in addition reactions with alkenes. Formic acids and Hazards
alkenes readily react to form formate esters. In the presence of MSDS External MSDS
certain acids, including sulfuric and hydrofluoric acids, however, a
variant of the Koch reaction takes place instead, and formic acid Main hazards Corrosive
adds to the alkene to produce a larger carboxylic acid.

Most simple formate salts are water- soluble. NFPA 704

History
Flash point 69°C
As early as the 15th century, some alchemists and naturalists were R-phrases R10, R35

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aware that ant hills gave off an acidic vapor. The first person to S-phrases S1/2, S23, S26, S45
describe the isolation of this substance (by the distillation of large
RTECS number LQ4900000
numbers of dead ants) was the English naturalist John Ray, in 1671.
Ants secrete the formic acid for attack and defense purposes. Formic Supplementary data page
acid was first synthesized from hydrocyanic acid by the French Structure & properties n, εr, etc.
chemist Joseph Gay-Lussac. In 1855, another French chemist,
Marcellin Berthelot, developed a synthesis from carbon monoxide Phase behaviour
Thermodynamic data
that is similar to that used today. Solid, liquid, gas
Spectral data UV, IR, NMR, MS
In the chemical industry, formic acid was long considered a chemical
compound of only minor industrial interest. In the late-1960s, Related compounds
however, significant quantities of it became available as a byproduct acetic acid
Related carboxylic acids
of acetic acid production. It now finds increasing use as a propionic acid
preservative and antibacterial in livestock feed. formaldehyde
Related compounds
methanol
Production Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references
A significant amount of formic acid is produced as a byproduct in
the manufacture of other chemicals, especially acetic acid. This production is insufficient to meet the present demand for
formic acid, and some formic acid must be produced for its own sake.

When methanol and carbon monoxide are combined in the presence of a strong base, the formic acid derivative methyl
formate results, according to the chemical equation

CH3OH + CO → HCOOCH3

In industry, this reaction is performed in the liquid phase at elevated pressure. Typical reaction conditions are 80°C and 40
atm. The most widely-used base is sodium methoxide. Hydrolysis of the methyl formate produces formic acid:

HCOOCH3 + H2O → HCOOH + CH3OH

Direct hydrolysis of methanol requires a large excess of water to proceed efficiently, and some producers perform it by an
indirect route by first reacting the methyl formate with ammonia to produce formamide, and then hydrolyzing the
formamide with sulfuric acid to produce formic acid:

HCOOCH3 + NH3 → HCONH2 + CH3OH

HCONH2 + H2O + ½H2SO4 → HCOOH + ½ (NH4)2SO4

This technique has problems of its own, particularly disposing of the ammonium sulfate byproduct, so some
manufacturers have recently developed energy efficient means of separating formic acid from the large excess amount of
water used in direct hydrolysis. In one of these processes (used by BASF) the formic acid is removed from the water via
liquid extraction with an organic base.

In the laboratory formic acid can be obtained by heating oxalic acid in anhydrous glycerol and extraction by steam
distillation. Another preparation (which must be performed under a fume hood) is the acid hydrolysis of ethyl isonitrile
using HCl solution.

C2H5NC + 2H2O → C2H5NH2 + HCOOH

The isonitrile being obtained by reacting ethyl amine with chloroform (note that the fume hood is required because of the
overpoweringly objectionable odour of the isonitrile).

Uses

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The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay
or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer, and so it is widely
used to preserve winter feed for cattle. In the poultry industry, it is sometimes added to feed to kill salmonella bacteria.
Other uses:

It is used to process organic latex (sap) into raw rubber.

Beekeepers use formic acid as a miticide against the Varroa mite.
It is of minor importance in the textile industry and for the tanning of leather.
Some formate esters are artificial flavorings or perfumes.
It is the active ingredient in some brands of household limescale remover.

In synthetic organic chemistry, formic acid is often used as a source of hydride ion. The Eschweiler-Clarke reaction and
the Leuckart-Wallach reaction are examples of this application. It is also used as a source of hydrogen in transfer
hydrogenation.

In the laboratory formic acid is also used as source for carbon monoxide, which is set free by the addition of sulfuric acid.
Formic acid is also a source for a formyl group for example in the formylation of metylaniline to N-methylformanilide in
toluene.

Fuel cells that use modified formic acid are promising.

Safety
The principal danger from formic acid is from skin or eye contact with liquid formic acid or with the concentrated vapors.
Any of these exposure routes can cause severe chemical burns, and eye exposure can result in permanent eye damage.
Inhaled vapors may similarly cause irritation or burns in the respiratory tract. Since carbon monoxide may be also be
present in formic acid vapors, care should be taken wherever large quantities of formic acid fumes are present. The US
OSHA Permissible Exposure Level ( PEL) of formic acid vapor in the work environment is 5 parts per million parts of air
( ppm).

Formic acid is readily metabolized and eliminated by the body. Nonetheless, some chronic effects have been documented.
Some animal experiments have demonstrated it to be a mutagen, and chronic exposure may cause liver or kidney damage.
Another possibility with chronic exposure is development of a skin allergy that manifests upon re-exposure to the
chemical.

The hazards of solutions of formic acid depend on the concentration. The following table lists the EU classification of
formic acid solutions:

Concentration
Classification R-Phrases
by weight
2%–10% Irritant (Xi) R36/38
10%–90% Corrosive (C) R34
>90% Corrosive (C) R35
Safety symbol
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