Метиламин: свойства, производство и применение

Organic chemical compound
Chembox
| pronounce = ,/m//ɛ//θ//ə//l//ə/'/m//iː//n///(METHələMEEN), ,/m//ɛ//θ//ə/'/l//æ//m//ə//n///(METHəLAmən), /m//ə/'/θ//ɪ//l//ə/,/m//iː//n///(məTHILəmeen)
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 415838275
| ImageFile = MeNH2. svg
| ImageFile Ref =
| ImageSize = 200
| ImageName = Skeletal formula of methylamine with all explicit hydrogens added
| ImageFileL1 = Methylamine 3D balls. png
| ImageFileL1 Ref =
| ImageNameL1 = Ball and stick model of methylamine
| ImageFileR1 = Methylamine 3D vdW. png
| ImageFileR1 Ref =
| ImageNameR1 = Spacefill model of methylamine
| PIN = Methanamine
| OtherNames =
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| Section4 = Chembox Hazards
| ExternalSDS = emdchemicals. com
| GHSPictograms =
| GHSSignalWord = DANGER
| HPhrases =
| PPhrases =
| NFPA H = 3
| NFPA F = 4
| NFPA R = 0
| FlashPtF = 14
| FlashPt notes = (liquid, gas is extremely flammable)
| IDLH = 100 ppm
|CH3OH + NH3 → CH3NH2 + H2O
In this way, an estimated 115,000 tons were produced in 2005. An example of this process includes the use of the Hofmann rearrangement, to yield methylamine from acetamide and bromine. In the laboratory, methylamine hydrochloride is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride. |[NH4]Cl + CH2O → [CH2\dNH2]Cl + H2O
|[CH2\dNH2]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.

Methylamine is a good nucleophile as it is an unhindered amine. As an amine it is considered a weak base. Its 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 methylamine 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. Additionally, methylamine is produced during PADI4 dependent arginine demethylation.

The LD50 (mouse, s. c.) is 2.5 g/kg. The Occupational Safety and Health Administration (OSHA) and National Institute for Occupational Safety and Health (NIOSH) have set occupational exposure limits at 10 ppm or 12 mg/m3 over an eight hour time weighted average.

In the United States, methylamine is controlled as a List 1 precursor chemical by the Drug Enforcement Administration due to its use in the illicit production of methamphetamine.

Fictional characters Walter White and Jesse Pinkman use methylamine as part of a process to synthesize methamphetamine in the AMC series Breaking Bad.