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| | Methylamine Chemical Properties |
| Melting point | -93 °C(lit.) | | Boiling point | -6.3 °C(lit.) | | density | 0.785 g/mL at 25 °C | | vapor density | 1.08 (20 °C, vs air) | | vapor pressure | 27 psi ( 20 °C) | | refractive index | n20/D 1.371 | | Fp | 61 °F | | storage temp. | Store below +30°C. | | solubility | highly soluble in water (108g/100g) at 25°C; soluble in alcohol and
miscible with ether; HCl salt is soluble in water and absolute alcohol; compound
is insoluble in chloroform, acetone, ether, and ethyl acetate | | pka | 10.63(at 25℃) | | form | Gas | | Specific Gravity | 0.901 (20℃/4℃) (40% Soln.) | | PH | 14 (H2O, 20°C) | | Odor Threshold | 0.035ppm | | explosive limit | 4.9-20.8% | | Water Solubility | Miscible with water, ethanol, benzene, acetone and ether. | | Merck | 14,6014 | | BRN | 741851 | | Henry's Law Constant | (x 10-5 atm?m3/mol):
1.11 at 25 °C (Christie and Crisp, 1967) | | Exposure limits | TLV-TWA 10 ppm (～12.3 mg/m3)(ACGIH,
MSHA, and OSHA); IDLH 100 ppm
(NIOSH). | | Stability: | Stable. Highly flammable. Note wide explosion limits. Incompatible with oxidizing agents, acids, alkalies, alkaline earth metals, copper and its alloys, zinc and its alloys. | | LogP | -0.570 | | CAS DataBase Reference | 74-89-5(CAS DataBase Reference) | | EPA Substance Registry System | Methylamine (74-89-5) |
| | Methylamine Usage And Synthesis |
| Organic Chemicals | Methylamine, also known as amino methane, is an important kind of organic chemical raw materials and intermediates and is a flammable colorless gas at normal temperature and pressure. Upon being liquefied or compressed at high concentrations, it has a strong odor of ammonia. It has fishy odor at very low concentrations. It is easily soluble in water and soluble in alcohol and ether. It is flammable and can form explosive mixtures with air with the explosive limit being 4.3% to 21%. It has weak alkalinity with the alkaline being stronger than ammonia. It can interact with inorganic acid to form water-soluble salts. It is obtained through the reaction between methanol and ammonia at high pressure and high temperature in the action of catalyst. Alternatively, it can be obtained through the reaction between formaldehyde and ammonium chloride upon being heated to 300 ℃ in the presence of zinc chloride. Methylamine can be used to make pesticides, pharmaceuticals, rubber vulcanization accelerator, dyes, explosives, leather, petroleum, surfactants, and ion exchange resin, paint strippers, and coatings as well as additives. It is an important raw material for the manufacturing of pesticide dimethoate, carbaryl, and chlordimeform. The inhalation toxicity of methylamine belongs to low toxicity category. The maximum allowable air concentration is 5mg/m3 (0.4ppm). It is corrosive and can cause irritation of the eyes, skin and mucous membranes. In case of fire, high heating temperature, it can cause risk of fire with cylinders and accessories damage being capable of causing an explosion.
| | Poisoning | Methylamine belongs to moderate-poisoning drug with a strong irritant and corrosive property. During the process of production and in transit, when there is leakage occurring due to accident, it can cause acute poisoning of contacted people.
This product can be subject to inhalation in its gaseous state from the respiratory tract. Its solution can be absorbed through the skin. Its salt can cause poisoning upon mistakenly oral administration. This product has a strong stimulating effect on eye; upper respiratory tract, skin and mucous membranes. Inhalation of it at high concentrations can cause damage to the lungs with people in severe cases getting pulmonary edema and respiratory distress syndrome, finally leading to death. However, it has been no yet reported of cases of systemic poisoning around the world. Liquid methylamine has strong irritation and corrosion effect and can cause eye and skin chemical burning. In case of 40% aqueous methylamine being splashed into the eyes, the victims can get burning eyes, photophobia, lacrimation, conjunctival hyperemia, eyelid irritation, corneal edema and superficial ulcers with those symptoms being able to last 1 to 2 weeks. Long-term exposure to low concentrations of methylamine can cause dryness and discomfort of the eyes, nose, and throat.
[first-aid]
Upon skin contact, the victim should immediately remove the contaminated clothing, wash it thoroughly with a large amount of flowing water. For first-aid, the victim can apply 1 to 2% acetic acid, 0.5% citric acid to wash the skin, mucous membranes and mouth.
When the eyes are contaminated, they should raise the eyelid and wash the eyes with flowing clean water and saline for at least 15 minutes, followed by fluorescein staining. If there is corneal injury occurring, the victims should be invited to an ophthalmologist for treatment.
For patients inhaling nitric methylamine gas and getting poisoned, they should be rapidly transferred from the scene of fresh air and keep the airway open. For patients with breathing difficulties, they should be given oxygen. Patients of respiratory and cardiac arrest should be immediately subject to artificial respiration and sent to hospital immediately after treatment in a timely manner.
This information is edited by Xiongfeng Dai from Chemicalbook. | | Uses | Methylamine is an important kind of fatty amines organic chemicals and is used in a variety of industries such as manufacture of dyestuffs, treatment of cellulose, acetate rayon, as fuel additive, rocket propellant, and leather tanning processes. It can be used in the synthesis of the N-methyl-chloroacetamide that is the intermediate of the organic phosphorus insecticide dimethoate and omethoate; synthesis of the intermediate of the monocrotophos, α-chloro acetoacetyl methylamine; synthesis of the intermediates of carbamate pesticide, carbamoyl chloride and methyl isocyanate; as well as the synthesis of other pesticides varieties such as formamidine, amitraz, and tribenuron, etc. In addition, it can also be used in medicine, rubber, dyes, leather industry and photosensitive materials.
| | Production method | There are a lot of ways for manufacturing of methylamine. But in industry, people mainly apply methanol amination.
CH3OH + NH3 → CH3NH2 + H2O
2CH3OH + NH3 → (CH3) 2NH + 2H2O
3CH3OH + NH3 → (CH3) 3N + 3H2O
It is obtained through the following process: methanol and ammonia is at a ratio of 1.5 to 4 and subject to continuous vapor phase catalytic amination at high temperature and high pressure with activated alumina as a catalyst to generate the mixture crude product of mono-, di-, trimethylamine. The crude mixture further goes through a series of distillation column for continuous pressure and distillation separation, have cooling for deamination, dehydration can yield respectively mono-, di-, trimethylamine products.
| | Chemical Properties | Methylamine is a colorless, fi sh-like smelling gas at room temperature. It is used in a variety of industries, such as the manufacture of dyestuffs, treatment of cellulose, acetate rayon, as a fuel additive, rocket propellant, and in leather tanning processes. | | Chemical Properties | colourless gas (or solution in water or methanol) | | Chemical Properties | Methylamine is a derivative of ammonia in which a methyl group is substituted for
a hydrogen (Schweizer et al 1978). Its reactivity is governed primarily by the
unshared pair of electrons on the nitrogen, therefore methylamine is a strongly
alkaline base whose most characteristic reaction is the formation of salts with
acids. It will react with acid halides and acid anhydrides to form N-substituted
amines. Methylamine reacts with nitrous acid to form methanol with liberation of
nitrogen. It is capable of reacting with aldehydes to form aldimines or Schiffs
bases (Astle 1961). | | Chemical Properties | Methylamine is a colorless gas with a fish- or
ammonia-like odor; at low concentrations a fishy odor.
Shipped as a liquefied compressed gas. The odor threshold
is 3.2 ppm. | | Physical properties | Colorless, flammable gas with a strong ammonia-like odor. An experimentally determined
recognition odor threshold concentration of 21 ppbv was reported by Leonardos et al. (1969). Odor
threshold concentrations of 4.7 ppmv and 35 ppbv were experimentally determined by Nishida et
al. (1979) and Nagata and Takeuchi (1990), respectively. | | Uses | Methylamine is used in dyeing and tanning;in photographic developer, as a fuel additive,and as a rocket propellant. It is also usedin organic synthesis and as a polymerizationinhibitor. It occurs in certain plants, such asMentha aquatica. | | Uses | Tanning and dyeing industries; fuel
additive; chemical intermediate in the production
of pharmaceuticals, insecticides, and
surfactants | | Uses | Intermediate for accelerators, dyes, pharmaceuticals, insecticides, fungicides, surface active
agents, tanning, dyeing of acetate textiles, fuel additive, polymerization inhibitor, component of paint
removers, solvent, photographic developer, rocket
propellent. | | Definition | methylamine: A colourless flammablegas, CH3NH2; m.p. –93.5°C; b.p.–6.3°C. It can be made by a catalyticreaction between methanol and ammoniaand is used in the manufactureof other organic chemicals. | | Definition | A colorless flammable gas that
smells like ammonia. It is the simplest primary
amine, used for making herbicides
and other organic chemicals. | | Production Methods | Several methods are currently used for synthesis of methylamine. Virtually all
produce a mixture of primary, secondary, and tertiary amines which can be
continuously separated by distillation and extraction. The most commonly used
synthesis involves heating ammonium chloride and methyl alcohol (ratio varies
from 2:1 to 6:1, depending on desired ratio of amines) to about 300°C in the
presence of a catalyst such as zinc chloride. Alternatively, methylamine can be
synthesized by heating ammonium chloride and formaldehyde in the presence of
H2 and a hydrogenation catalyst such as nickel or platinum. Methylamine is
generally marketed as a liquid or a 33% aqueous solution (HSDB 1988). | | Definition | ChEBI: The simplest of the methylamines, consisting of ammonia bearing a single methyl substituent. | | General Description | A colorless gas or a liquid. Pungent fishy odor resembling odor of ammonia. The liquid boils at 20.3°F hence vaporizes rapidly when unconfined. Vapors are heavier than air and may collect in low-lying areas. Easily ignited under most conditions. Under prolonged exposure to intense heat the containers may rupture violently and rocket. Used for making pharmaceuticals, insecticides, paint removers, surfactants, rubber chemicals. | | Air & Water Reactions | Highly flammable. Very soluble in water; the solutions are strongly basic and therefore corrosive. Liquid fumes in air. | | Reactivity Profile | METHYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. | | Hazard | (Gas and liquid) Dangerous fire risk. Explosive limits in air 5–21%. Strong irritant to tissue.
Eye, skin and upper respiratory tract irritant. | | Health Hazard | VAPOR: Irritating to eyes, nose and throat. If inhaled will cause coughing or difficult breathing. LIQUID: Will burn skin and eyes. | | Health Hazard | Exposures to methylamine are known to cause adverse health effects among occupational workers. The workers demonstrate symptoms of toxicity that include, but are not limited to, irritation to the eyes, nose, and throat. Studies have indicated that the compound causes injury to the eyes through corneal opacities and edema hemorrhages in the conjunctiva, and injury to the liver. Studies of Guest and Varma indicated no signifi cant deleterious effects on the internal organs or skeletal deformities in experimental mice | | Health Hazard | Most of the studies on the toxicity of methylamine suggest it acts locally as an
irritant and a sensitizer. Vapors result in eye irritation with tearing and inflammation
with repeated exposure capable of inducing corneal damage. Exposure by
inhalation irritates the mucous membranes of the nose, throat and lung, leading to
coughing and respiratory distress. Skin contact with methylamine can lead to
burns and dermatitis (Beard and Noe 1981). First aid for skin exposure requires
immediate flushing with water.
Persons exposed to methylamine can detect a faint fishlike odor at less than 10
p.p.m. Little irritation occurs however, above 20 p.p.m. Methylamine can induce
temporary irritation of the eyes, nose, and throat. The permissible exposure level
(PEL) has been set at 10 p.p.m. (OSHA 1977) and the level immediately dangerous
to life or health (IDLH) is 100 p.p.m. (Standards Completion Program,
OSHA and NIOSH 1978). | | Health Hazard | 250 ppm produced damage to respiratorymucosa of the nasal turbinates. Exposureto 750 ppm produced severe body weightlosses, liver damage, and nasal degenerativechanges.
Any adverse health effects in humans dueto methylamine, other than its irritant action,is unknown.
LC50 value, inhalation (mice): 2400 mg/kg/2 h. | | Fire Hazard | FLAMMABLE. POISONOUS GASES MAY BE PRODUCED IN FIRE. Containers may explode in fire. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Toxic nitrogen oxides may be formed. Vapors are heavier than air and may travel considerable distance to a source of ignition and flash back. | | Industrial uses | Methylamine and its hydrochloride salt are widely used in organic synthesis for
introducing the methylamino group. In 1976, industrial consumption was 32,000
tons/year. One of its most important uses is in the preparation of amide-type
surfactants. It is also used in the preparation of drugs such as adrenaline and
synthetic caffeine. It serves as the base for more than twenty commercial products,
among those included are photographic developers, insecticides, and antihistamine
drugs (Beard and Noe 1981). It is also widely used in tanning and has been
used in the separation of aromatics from aliphatic hydrocarbons (Sittig 1981). | | Safety Profile | Poison by
subcutaneous route. Moderately toxic by
inhalation. A severe skin irritant. Mutation
data reported. A strong base. Flammable gas
at ordinary temperature and pressure. Very
dangerous fire hazard when exposed to heat,
flame, or sparks. Explosive when exposed to
heat or flame. To fight fire, stop flow of gas.
Forms an explosive mixture with
nitromethane. When heated to decomposition it emits toxic fumes of NOx.
See also AMINES. | | Potential Exposure | Methylamine is used in organic
synthesis; a starting material for N-oleyltaurine, a surfactant; and p-N-methylaminophenol sulfate, a photographic
developer. It has possible uses in solvent extraction systems
in separation of aromatics from aliphatic hydrocarbons.
It is also used in the synthesis of many different pharmaceuticals; pesticides and rubber chemicals. | | Carcinogenicity | Methylamine was positive in the
mouse lymphoma assay and negative in the Ames assay. | | Source | Methylamine was detected in cauliflower (65 ppm), carrots (3,970 ppm), tea leaves (50
ppm), red and white cabbage (3.4 to 22.7 ppm), corn (27 ppm), kale leaves (16.6 ppm), barley
seeds (4.5 ppm), epidermis of apples (4.5 ppm), celery (6.4 ppm), sweetflag, celandine, and
tobacco leaves (Duke, 1992). | | Environmental fate | Photolytic. The rate constant for the reaction of methylamine and OH radicals in the atmosphere
at 300 K is 1.3 x 10-13 cm3/molecule?sec (Hendry and Kenley, 1979).
Low et al. (1991) reported that the photooxidation of aqueous primary amine solutions by UV
light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions.
Chemical/Physical. In an aqueous solution, chloramine reacted with methylamine to form Nchloromethylamine
(Isaac and Morris, 1983).
Reacts with acids forming water-soluble salts. | | Metabolism | Methylamine is a normal body constituent in several species and is known to be
generated endogenously from epinephrine (Schayer et al 1952) and creatine
(Davis and DeRopp 1961). It has also recently been detected in the urine of male
CBA/cA mice treated with N-methylformamide (Kestell et al 1985). Mammalian
metabolism of methylamine is rapid yet the enzymes involved are not yet known.
Simehnhoff (1975) suggested that methylamine is methylated to dimethylamine as
it appeared not to be oxidized by amine oxidases yet was rapidly absorbed and not
excreted in the urine. Dar et al (1985) conducted studies using methyl-[14C]-
labeled methylamine injected i.p. into rats to assess the role of monoamine oxidase
in the metabolism of methylamine in the rats. Methylamine underwent rapid
oxidation as more than 30% of the 14C was recovered as 14CO2 in the first 2-6 h
following exposure and 52% was expired in the first 24 h. Pretreatment of the rats
with long acting monoamine oxidase inhibitors significantly inhibited methylamine
metabolism, however short term inhibitors were without effect. Combinations
of the drugs suggested that monoamine oxidase was not responsible for
metabolism of methylamine and that a closely related enzyme such as methylamine
oxidase, previously proposed by Werner and Seiber (1963), may be
involved.
It has also been reported that intestinal microflora may degrade methylamine
(Iyer and Kailio 1958). Dar et al (1985) found that pretreatment of rats with
neomycin to reduce bacterial microorganisms resulted in only a slight inhibition of
14C expiration during the initial 6 h following methylamine administration. These
results indicate that, at least in the rat, bacterial oxidation of methylamine in the
intestine is negligible. | | storage | Methylamine is stored in a cool, well-ventilated noncombustible area separatedfrom possible sources of ignition andoxidizing substances and mercury. Itssolutions are stored in a flammable liquidstorage room or cabinet. The gas is shippedin steel cylinders or tank cars; the liquid isshipped in steel drums or tank cars. | | Shipping | UN1061 Methylamine, anhydrous, Hazard Class:
2.1; Labels: 2.1-Flammable gas. UN1235 Methylamine,
aqueous solution, Hazard Class: 3; Labels: 3-Flammable
liquid, 8-Corrosive material. Cylinders must be transported
in a secure upright position, in a well-ventilated truck.
Protect cylinder and labels from physical damage. The
owner of the compressed gas cylinder is the only entity
allowed by federal law (49CFR) to transport and refill
them. It is a violation of transportation regulations to refill
compressed gas cylinders without the express written permission of the owner. | | Purification Methods | Dry the amine with sodium or BaO. It is commercially available in metal cylinders. [Beilstein 4 IV 118.] | | Toxicity evaluation | The corrosive nature of methylamine produces irritation effects at
all points of contact which is largely responsible for its toxic actions.
Using radiotracer techniques, labeled macromolecules were fragmented
and the formaldehyde generated interacts with proteins in
vivo suggesting a risk factor for initiation of endothelial injury and
subsequent atherosclerosis. Increased semicarbazide-sensitive
amine oxidase catalyzes the conversion of methylamine to formaldehyde
and increased activity has been found in patients with
diabetes mellitus, chronic heart failure, and cerebral infarct and is
associated with obesity. The deamination of methylamine may
contribute to protein deposition, the formation of plaques, and
inflammation and be may be involved in the pathophysiology of
chronic vascular and neurologic disorders such as diabetes,
atherosclerosis, and Alzheimer’s disease. | | Incompatibilities | A medium-strong base. Reacts violently
with strong acids; mercury, strong oxidizers; nitromethane.
Corrosive to copper, zinc alloys; aluminum, and galvanized
surfaces. | | Waste Disposal | Return refillable compressed
gas cylinders to supplier. Controlled incineration (incinerator
equipped with a scrubber or thermal unit to reduce nitrogen
oxides emissions). |
| | Methylamine Preparation Products And Raw materials |
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