Formamide
Encyclopedia
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 used primarily for manufacturing sulfa drugs and synthesizing vitamins and as a softener
for paper and fiber. In its pure form, it dissolves many ionic compound
s that are insoluble in water, so it is also used as a solvent
.
Formamide will begin to partially decompose into carbon monoxide and ammonia at 180°C. When heated strongly, formamide decomposes to hydrogen cyanide (HCN) and water vapor.
was reacted with ammonia
to produce ammonium formate
, which was turned into formamide by heating:
Today's industrial method is based on aminolysis
of methyl formate
:
with the possibility of the resulting methanol being recycled into more methyl formate, by reaction with formic acid.
While ultimately, the two inputs to this system are identical (formic acid and ammonia), benefit is obtained by virtue of the fact that they can be conducted in separate locations.
s.
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
.
and ammonia
to be reacted to form copies of itself. If heated slightly and in the presence of these chemicals, the formamide will slowly grow in quantity.
to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth.
at 130 degrees C in the presence of ultra violet light.
on contact with skin or eyes and may be deadly if ingested. Inhalation of large amounts of formamide vapor may require medical attention. It is also a teratogen. Formamide should never be handled without proper safety attire including gloves and goggles. There is a small risk of decompostion into hydrogen cyanide and water.
Amide
In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...
derived from formic acid
Formic acid
Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...
. It is a clear liquid which is miscible with water and has an ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
-like odor. It is used primarily for manufacturing sulfa drugs and synthesizing vitamins and as a softener
Softener
Softener may refer to:* Water softener* Fabric softener* Stool softener* Food softener* Plastic softener, generically known as a Plasticizer...
for paper and fiber. In its pure form, it dissolves many ionic compound
Ionic compound
In chemistry, an ionic compound is a chemical compound in which ions are held together in a lattice structure by ionic bonds. Usually, the positively charged portion consists of metal cations and the negatively charged portion is an anion or polyatomic ion. Ions in ionic compounds are held together...
s that are insoluble in water, so it is also used as a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
.
Formamide will begin to partially decompose into carbon monoxide and ammonia at 180°C. When heated strongly, formamide decomposes to hydrogen cyanide (HCN) and water vapor.
Production
In the past, formic acidFormic acid
Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...
was reacted with ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
to produce ammonium formate
Ammonium formate
Ammonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.-Uses:Pure ammonium formate decomposes into formamide and water when heated, and this is its primary use in industry...
, which was turned into formamide by heating:
- HCOOHFormic acidFormic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...
+ NH3AmmoniaAmmonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
→ HCOONH4Ammonium formateAmmonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.-Uses:Pure ammonium formate decomposes into formamide and water when heated, and this is its primary use in industry... - HCOONH4 → HCONH2 + H2O
Today's industrial method is based on aminolysis
Aminolysis
Aminolysis is any chemical reaction in which a molecule is split into two parts by reacting with a molecule of ammonia or an amine.An example of an aminolysis reaction is the replacement of a halogen in an alkyl group by an amine and the elimination of hydrogen halide .Another common example is...
of methyl formate
Methyl formate
Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of an ester, it is a clear liquid with an ethereal odor, high vapor pressure, and low surface tension.-Production:...
:
- HCOOCH3 + NH3AmmoniaAmmonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
→ HCONH2 + CH3OHMethanolMethanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
with the possibility of the resulting methanol being recycled into more methyl formate, by reaction with formic acid.
- HCOOHFormic acidFormic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...
+ CH3OHMethanolMethanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
→ HCOOCH3 + H2OWaterWater is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...
While ultimately, the two inputs to this system are identical (formic acid and ammonia), benefit is obtained by virtue of the fact that they can be conducted in separate locations.
Applications
Formamide is also a constituent of cryoprotectant vitrification mixtures used for cryopreservation of tissues and organOrgan (anatomy)
In biology, an organ is a collection of tissues joined in structural unit to serve a common function. Usually there is a main tissue and sporadic tissues . The main tissue is the one that is unique for the specific organ. For example, main tissue in the heart is the myocardium, while sporadic are...
s.
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
Sintering
Sintering is a method used to create objects from powders. It is based on atomic diffusion. Diffusion occurs in any material above absolute zero, but it occurs much faster at higher temperatures. In most sintering processes, the powdered material is held in a mold and then heated to a temperature...
.
Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly
Self-assembly
Self-assembly is a term used to describe processes 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...
of polymer nanofilms.
Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction
Leuckart reaction
The Leuckart reaction is the chemical reaction of ammonium salts of formic acid with aldehydes to form amines by reductive amination. The reaction is named after Rudolf Leuckart....
.
Self-replication
Formamide is self-complementary and so can cause dissolved carbon monoxideCarbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
and ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
to be reacted to form copies of itself. If heated slightly and in the presence of these chemicals, the formamide will slowly grow in quantity.
Hypothetical Biochemistry
Formamide has also been put forward as an alternative solventSolvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth.
RNA base creation
Formamide has been shown to create guanineGuanine
Guanine is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine . In DNA, guanine is paired with cytosine. With the formula C5H5N5O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with...
at 130 degrees C in the presence of ultra violet light.
Safety
Formamide is highly corrosiveCorrosive
A corrosive substance is one that will destroy or irreversibly damage another surface or substance with which it comes into contact. The main hazards to people include damage to the eyes, the skin, and the tissue under the skin; inhalation or ingestion of a corrosive substance can damage the...
on contact with skin or eyes and may be deadly if ingested. Inhalation of large amounts of formamide vapor may require medical attention. It is also a teratogen. Formamide should never be handled without proper safety attire including gloves and goggles. There is a small risk of decompostion into hydrogen cyanide and water.