Appearance Colorless, oily liquid Boiling point 210 °C Molar mass 45.04 g/mol | Formula CH3NO Density 1.13 g/cm³ | |
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Formamide
Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.
Contents
- Formamide
- Historical production
- Modern production
- Applications
- Niche or laboratory applications
- Hypothetical biochemistry
- RNA base creation
- Safety
- References
Formamide will begin to partially decompose into carbon monoxide and ammonia at 180 °C together with traces of hydrogen cyanide (HCN) and water. In the presence of solid acid catalysts, formamide yields HCN in high yield:
low temperature: HC(O)NH2 → CO + NH3 high temperature, acid-catalyzed: HC(O)NH2 → HCN + H2OHistorical production
In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yield formamide upon heating:
HCOOH + NH3 → HCOONH4 HCOONH4 → HCONH2 + H2OFormamide is also generated by aminolysis of ethyl formate:
HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OHModern production
The current industrial process for the manufacture of formamide involves either the carbonylation of ammonia:
CO + NH3 → HCONH2An alternative two-stage process involves the aminolysis of methyl formate, which is formed from carbon monoxide and methanol:
CO + CH3OH → HCOOCH3 HCO2CH3 + NH3 → HC(O)NH2 + CH3OHApplications
Formamide is used in the industrial production of hydrogen cyanide. It is also used as a solvent for processing various polymers such as polyacrylonitrile.
Niche or laboratory applications
Formamide is a constituent of cryoprotectant vitrification mixtures used for cryopreservation of tissues and organs.
Formamide is also used as an RNA stabiliser in gel electrophoresis 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.
Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms.
Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.
Hypothetical biochemistry
Formamide has also been proposed as an alternative solvent to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. It can be formed by the reaction of hydrogen cyanide and water, has a large dipole moment, and dissolves almost everything that will dissolve in water.
RNA base creation
Formamide has been shown to create guanine at 130 °C in the presence of ultra violet light.
Safety
Formamide is moderately irritating to the eyes, skin and mucous membranes. Inhalation of large amounts of formamide vapor may require medical attention. It is also a teratogen. Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption. Formamide should never be handled without proper safety attire including gloves and goggles.