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Monomethylamine, also known as methanamine, is an organic compound with a formula of CH3NH2.
This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group.
Monomethylamine is the simplest primary amine.
CAS Number: 74-89-5
Monomethylamine is sold as a solution in methanol, ethanol, tetrahydrofuran, or water, or as the anhydrous gas in pressurized metal containers.
Industrially, Monomethylamine is transported in its anhydrous form in pressurized railcars and tank trailers.
Monomethylamine has a strong odor similar to rotten fish.
Monomethylamine is used as a building block for the synthesis of numerous other commercially available compounds.
Monomethylamine is a basic alkylamine and is a primary amine in its simplest form.
Monomethylamine is a colorless gas co-produced with dimethylamine (DMA) and trimethylamine (TMA).
Monomethylamine has a strong fishy odor.
Monomethylamine is used as a building block for the synthesis of many other commercial compounds.
Monomethylamine is used to produce a variety of chemical derivatives such as N-methyl-2-pyrrolidone (NMP), Monomethylethanolamine (MMEA), Methyldiethanolamine (MDEA), Metam sodium, Triazines, etc.
Monomethylamine is usually sold as an anhydrous gas in pressurized containers or as solution in water.
Monomethylamine is available as anhydrous (liquified gas under pressure) & 40%, 45% & 50% solution.
Clear, colorless liquid with strong ammoniacal odor.
Monomethylamine is used as an intermediate for example in the production of pesticides, solvents (i.e. N-Methylpyrrolidone), pharmaceuticals and refining applications.
Monomethylamine is an organic compound with a formula of CH₃NH₂.
This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group.
Monomethylamine is the simplest primary amine.
Industrial production
Monomethylamine has been produced industrially since the 1920s (originally by Commercial Solvents Corporation for dehairing of animal skins).
This was made possible by Kazimierz Smoleński [pl] and his wife Eugenia who discovered amination of alcohols, including methanol, on alumina or kaolin catalyst after WWI, filed two patent applications in 1919 and published an article in 1921.
Monomethylamine is now prepared commercially by the reaction of ammonia with methanol in the presence of an aluminosilicate catalyst.
Dimethylamine and trimethylamine are co-produced; the reaction kinetics and reactant ratios determine the ratio of the three products.
Monomethylamine most favored by the reaction kinetics is trimethylamine.
CH3OH + NH3 → CH3NH2 + H2O
In this way, an estimated 115,000 tons were produced in 2005.
Laboratory methods
Monomethylamine was first prepared in 1849 by Charles-Adolphe Wurtz via the hydrolysis of methyl isocyanate and related compounds.
An example of this process includes the use of the Hofmann rearrangement, to yield Monomethylamine from acetamide and bromine.
In the laboratory, Monomethylamine is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride.
[NH4]Cl + CH2O → [CH2=NH2]Cl + H2O
[CH2=NH2]Cl + CH2O + H2O → [CH3NH3]Cl + HCOOH
The colorless hydrochloride salt can be converted to an amine by the addition of a strong base, such as sodium hydroxide (NaOH):
[CH3NH3]Cl + NaOH → CH3NH2 + NaCl + H2O
Another method entails reducing nitromethane with zinc and hydrochloric acid.
Another method of methylamine production is spontaneous decarboxylation of glycine with a strong base in water.
Reactivity and applications
Monomethylamine is a good nucleophile as it is an unhindered amine.
As an amine Monomethylamine is considered a weak base.
Monomethylamine's use in organic chemistry is pervasive.
Some reactions involving simple reagents include: with phosgene to methyl isocyanate, with carbon disulfide and sodium hydroxide to the sodium methyldithiocarbamate, with chloroform and base to methyl isocyanide and with ethylene oxide to methylethanolamines.
Liquid Monomethylamine has solvent properties analogous to those of liquid ammonia.
Representative commercially significant chemicals produced from methylamine include the pharmaceuticals ephedrine and theophylline, the pesticides carbofuran, carbaryl, and metham sodium, and the solvents N-methylformamide and N-methylpyrrolidone.
The preparation of some surfactants and photographic developers require methylamine as a building block.
Biological chemistry
Monomethylamine arises as a result of putrefaction and is a substrate for methanogenesis.
Additionally, Monomethylamine is produced during PADI4-dependent arginine demethylation.
