Formamide is an

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...

derived from

formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid. It has the chemical formula HCOOH and structure . This acid is an important intermediate in chemical synthesis and occurs naturally, most notably in some an ...

. It is a colorless liquid which is miscible with water and has an

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

-like odor. It is chemical feedstock for the manufacture of

sulfa drug Sulfonamide is a functional group (a part of a molecule) that is the basis of several groups of drugs, which are called sulphonamides, sulfa drugs or sulpha drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents th ...

s and other

pharmaceutical Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...

herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

s and

pesticides Pesticides are substances that are used to pest control, control pest (organism), pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for a ...

, and in the manufacture of

hydrocyanic acid Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the formula HCN and structural formula . It is a highly toxic and flammable liquid that boils slightly above room temperature, at . HCN is produced on an industrial s ...

. It has been used as a softener for paper and fiber. It is a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

for many

ionic compound In chemistry, a salt or ionic compound is a chemical compound consisting of an assembly of positively charged ions (Cation, cations) and negatively charged ions (Anion, anions), which results in a compound with no net electric charge (electrica ...

s. It has also been used as a solvent for

resins A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Comm ...

and

plasticizers A plasticizer (British English, UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity (physics), plasticity, to decrease its viscosity, and/or to decrease friction during its ...

. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life. Formamides are compounds of the type RR′NCHO. One important formamide is

dimethylformamide Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for 2,5-dimethylfuran, dimethylfuran, or dimethyl fumarate), this colourless liqui ...

, (CH₃)₂NCHO.

Production

Historical production

In the past, formamide was produced by treating

with

, which produces

ammonium formate Ammonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid. Reductive amination Acetone can be transformed into isopropylamine as follows: :CH3C(O)CH3 + 2 HCO2− +NH4 → (CH3)2CHNHCHO + 2 ...

, which in turn yields formamide upon heating: : HCOOH + NH₃ → : → HCONH₂ + H₂O Formamide is also generated by

aminolysis In chemistry, aminolysis (/am·i·nol·y·sis/) is any chemical reaction in which a molecule is Chemical decomposition, lysed (split into two parts) by reacting with ammonia () or an amine. The case where the reaction involves ammonia may be more ...

ethyl formate Ethyl formate is an ester formed when ethanol (an alcohol) reacts with formic acid (a carboxylic acid). Ethyl formate has the characteristic smell of rum and is partially responsible for the flavor of raspberries, occurring naturally in some plan ...

: :HCOOCH₂CH₃ + NH₃ → HCONH₂ + CH₃CH₂OH

Modern production

The current industrial process for the manufacture of formamide involves the

carbonylation In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...

of ammonia: : CO + NH₃ → HCONH₂ An alternative two-stage process involves the ammonolysis of

methyl formate Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colourless liquid with an ethereal odour, high vapor pressure, and low surface tension. The gas form is odourl ...

, which is formed from carbon monoxide and

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

: :CO + CH₃OH → HCOOCH₃ :HCO₂CH₃ + NH₃ → HCONH₂ + CH₃OH

Applications

Formamide is used in the industrial production of

hydrogen cyanide Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is ...

. It is also used as a solvent for processing various polymers such as

polyacrylonitrile Polyacrylonitrile (PAN) is a synthetic, semicrystalline organic polymer resin, with the linear formula (CH2CHCN)n. Almost all PAN resins are copolymers with acrylonitrile as the main monomer. PAN is used to produce large variety of products in ...

Reactions

Formamide decomposes into carbon monoxide and ammonia when heated above 100 °C. :HCONH₂ → CO + NH₃ The reaction is slow below 160 °C, but accelerates thereafter. At very high temperatures, the reaction products shift to

(HCN) and water instead: :HC(O)NH₂ → HCN + H₂O The same effect occurs in the presence of

solid acid Solid acids are acids that are insoluble in the reaction medium. They are often used as heterogeneous catalysts. Many solid acids are zeolites. A variety of techniques are used to quantify the strength of solid acids. Examples Examples of ino ...

catalysts.

Niche or laboratory applications

Formamide is a constituent of cryoprotectant

vitrification Vitrification (, via French ') is the full or partial transformation of a substance into a glass, that is to say, a non- crystalline or amorphous solid. Glasses differ from liquids structurally and glasses possess a higher degree of connectivity ...

mixtures used for cryopreservation of tissues and

organ Organ and organs may refer to: Biology * Organ (biology), a group of tissues organized to serve a common function * Organ system, a collection of organs that function together to carry out specific functions within the body. Musical instruments ...

s. Formamide is also used as an RNA stabiliser in

gel electrophoresis Gel electrophoresis is an electrophoresis method for separation and analysis of biomacromolecules (DNA, RNA, proteins, etc.) and their fragments, based on their size and charge through a gel. It is used in clinical chemistry to separate ...

by deionizing RNA. In capillary electrophoresis, it is used for stabilizing (single) strands of denatured DNA. Another use is to add it in sol-gel solutions in order to avoid cracking during

sintering Sintering or frittage is the process of compacting and forming a solid mass of material by pressure or heat without melting it to the point of liquefaction. Sintering happens as part of a manufacturing process used with metals, ceramics, plas ...

. Formamide, in its pure state, has been used as an alternative solvent for the electrostatic

self-assembly Self-assembly is a process in which a disordered system of pre-existing components forms an organized structure or pattern as a consequence of specific, local interactions among the components themselves, without external direction. When the ...

of polymer nanofilms. Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the

Leuckart reaction The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines. The reaction is an example of reductive amination. The reaction, named after Rudolf Leuckart (chemist), Rudolf Leuckart, uses either ammonium formate or ...

Biochemistry

Formamides are intermediates in the

methanogenesis Methanogenesis or biomethanation is the formation of methane coupled to energy conservation by microbes known as methanogens. It is the fourth and final stage of anaerobic digestion. Organisms capable of producing methane for energy conservation h ...

cycle.

Prebiotic chemistry

Formamide has been proposed as an alternative

to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. It forms by the hydrolysis of hydrogen cyanide. With a large dipole moment, its solvation properties are similar to those of water. Formamide has been shown to convert to traces of

guanine Guanine () (symbol G or Gua) is one of the four main nucleotide bases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine ( uracil in RNA). In DNA, guanine is paired with cytosine. The guanine nucleoside ...

upon heating in the presence of ultraviolet light. Several prebiotic chemical reactions producing amino acid derivatives have been shown to take place in formamide.

Safety

Contact with skin and eyes is not recommended. With an

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose requ ...

of grams per kg, formamide is of low acute toxicity. It also has low mutagenicity. Formamide is classified as toxic to reproductive health.

References

{{Authority control Amide solvents