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| | Ethylamine Chemical Properties |
| Melting point | -81 °C(lit.) | | Boiling point | 17 °C | | density | 0.81 g/mL at 20 °C | | vapor density | 1.56 (15 °C, vs air) | | vapor pressure | 874 mm Hg ( 20 °C) | | refractive index | n20/D 1.384 | | FEMA | 4236 | ETHYLAMINE | | Fp | 48 °F | | storage temp. | 2-8°C | | solubility | soluble in water in all proportions; soluble in ethanol, methanol,
paraffin hydrocarbons, aromatic and aliphatic hydrocarbons, ethyl ether, ethyl
acetate, acetone, and mineral oil. | | pka | 10.7(at 25℃) | | form | Liquid | | color | Colorless to Light yellow to Light orange | | Odor | Pungent; strong ammoniacal. | | explosive limit | 14% | | Odor Type | ammoniacal | | Odor Threshold | 0.046ppm | | Water Solubility | miscible | | Merck | 14,3762 | | JECFA Number | 1579 | | BRN | 505933 | | Henry's Law Constant | 1.23(x 10-5 atm?m3/mol at 25 °C) (Christie and Crisp, 1967) | | Exposure limits | TLV-TWA 10 ppm (～18 mg/m3) (ACGIH,
MSHA, and OSHA): IDLH 4000 ppm
(NIOSH). | | Stability: | Stable. Highly flammable. Incompatible with oxidizing agents, alkali metals, alkaline earth metals, acids, many reactive organic and inorganic compounds. Reacts with or disssolves most types of paint, plastic and rubber. | | LogP | -0.13 | | CAS DataBase Reference | 75-04-7(CAS DataBase Reference) | | NIST Chemistry Reference | Ethylamine(75-04-7) | | EPA Substance Registry System | Ethylamine (75-04-7) |
| | Ethylamine Usage And Synthesis |
| Product characteristics | Ethylamine, also known as aminoethane or ethylamine, is colorless transparent liquid and highly volatile. It has ammonia flavor and is flammable. Its relative molecular mass is 45.09; relative density 0.6829; melting point-80.6 ℃; boiling point 16.6℃; flash point-17℃(closed). It will spontaneously combust in air at 555℃. Its refractive index is 1.3663. It is miscible with water, ethanol and ether. It has strong alkaline and can react with mineral acid to form water-soluble salt. It can also react with acyl group to form acyl amide and react with nitrous acid to generate nitrosamines. It can be oxidized to form hydroxylamine or oxime. When burning in the air, the flame is light blue. It can react with phosgene to form carbonyl chloride and react with acrylonitrile to generate aminopropionitrile. It can strongly stimulate the skin and mucous membranes. Rat-oral LD50 is 400mg/kg. Storage should use stainless steel containers and stainless steel valves.
Ethylamine can be prepared by the reaction of ethyl iodide (ethyl chloride) with ammonia in liquid ammonia (ethanol solution) or by the high-pressure hydrogenation of acetonitrile in the catalyst of nickel. Ethylamine is mainly used as the raw materials of triazine herbicides to produce Atrazine (selective herbicides) and Simazine (pre-emergence herbicides of dry field). It can also be used as the raw materials of dyes, surfactants, detergents, lubricants and ion exchange resins, the stabilizer of resin and rubber slurry, antioxidants, the additives of oil refining, metallurgical mineral processing agents, pharmaceutical raw materials, solvents and extractants. The oxalates of the ethylamine can be used medicinally. | | Chemical properties | colorless volatile liquid; ammonia smell; alkaline; miscible with water, ethanol and ether. | | Uses | 1. Used for the production of dyes, pharmaceuticals, surfactants, herbicides, rubber vulcanization accelerator and ion exchange resins.
2. Ethylamine is the intermediates of antiseptics of cymoxanil and ethirimol, pesticide of amphetamines, and herbicides of atrazine, west grass net, simazine, benthiocarb and napropamide.
3. Ethylamine can be used for the production of triazine herbicides, including atrazine and simazine. Both herbicides use cyanuric chloride as raw materials, and also have similar production processes. (also known as Terrazine) has wider range of applications than Simazine, but also can kill the anti-Simazin weeds. Atrazine is developed and produced by the Swiss Geigy company in 1985, and later developed into the world's largest production herbicide. Ethylamine is also used in the production of dyes, rubber accelerators, surfactants, antioxidants, ion exchange resins, aircraft fuels, solvents, detergents, lubricants, metallurgical mineral processing agent, as well as the production of cosmetics and pharmaceuticals.
4. Used for organic synthesis, and also used as dye intermediates, stabilizers and emulsifiers
5. Used for the synthesis of organic resins and dyes. | | Production methods | 1. ethanol (gas phase) amination method: feed ethanol and ammonia by the ratio of 4: 1, and make them react with the dehydration catalysis of alumina at the temperature of 350-400℃ and under the pressure of 2.45-2.94MPa. In addition to the formation of ethylamine, the side reaction also produce diethylamine, triethylamine, ether, acetonitrile and ethylene. The crude ethylamine obtained by the condensation of the reaction gas is then taken for distillation to gather ammonia, with the content of more than 95%. Generally 50% aqueous solution is used as the commodity, per ton of which consumes ethano (95%) of about 1400kg.
2. Acetaldehyde hydrogen aminiation method: the reaction of acetaldehyde, hydrogen and ammonia with the catalysis of nickel can produce ethylamine. Firstly, the structure catalyst with nickel as the main catalyst, reduced copper and reduced chromium as the cocatalyst and kaolin as the carrier is charged into the reactor. Then pass into acetaldehyde at the space velocity of 0.03-0.15L•h-1 and control the ratio of hydrogen and acetaldehyde being 5: 1 and the ratio of ammonia and acetaldehyde being 0.4-3:1. The feedstock is vaporized and fed to the reactor at 80℃. The reaction temperature is controlled between 105 and 200 °C. The resulting product is cooled at-5°C and separated into ethylamine, diethylamine and triethylamine. Ethylamine is more readily available because of the faster formation of ethylamine than diethylamine or triethylamine. When the primary product is diethylamine or triethylamine, the resulting ethylamine should be recycled to the system for reaction.
3. The preparation method is ethanol gas phase amination. The reaction of ethanol and ammonia with the catalysis at the temperature of 390-400 °C and under the pressure of 2.53~3.04 MPa can produce crude ethylamine, and then the finished products can be derived by further fractionation.
CH3CH2OH + NH3 [Al2O3]→CH3CH2NH2 + H2O | | Hazards & Safety Information | Category: Flammable liquids
Toxicity classification: high toxicity
Acute Toxicity: Inhalation-Rat LC50: 3000 PPM/4 hours; Oral-Rat LD50: 400 mg/kg
Stimulation Data: Eye-Rabbit 5mg Severe; Skin-Rabbit 500 mg/24 h Mild
Explosive hazardous characteristics :
Mixed with air to form explosive mixtures;
Flammability Hazardous characteristics :
Easily combust when meeting fire, high temperature or oxidants;
Release toxic nitrogen oxide smoke when combusting.
Storage and transportation characteristics :
Storehouse should be low-temperature, well-ventilated and dry;
Stored separately with oxidants and acids
Fire extinguishing agent: mist water; dry powder, carbon dioxide
Occupational Standard: TWA 18 mg/m3; STEL 37mg/m3 | | Chemical Properties | Colorless to yellow gas; ammonia fishy aroma. | | Chemical Properties | Ethylamine is a colorless gas or water-white
liquid (below 17℃). Strong, ammonia-like odor. Shipped
as a liquefied compressed gas. | | Chemical Properties | Ethylamine is a very strong base and its complete solubility in water makes it ideal
as an intermediate in many chemical syntheses. As with other primary amines, its
chemical reactivity is dictated by the unshared pair of electrons on the nitrogen and
its most characteristic reaction is with acids to form salts. | | Physical properties | Colorless liquid or gas with a strong ammonia-like odor. An experimentally determined odor
threshold concentration of 21 ppbv was reported by Leonardos et al. (1969). Experimentally
determined detection and recognition odor threshold concentrations were 500 μg/m3 (270 ppbv)
and 1.5 mg/m3 (810 ppbv), respectively (Hellman and Small, 1974). | | Uses | In resin chemistry; stabilizer for
rubber latex; intermediate for dyestuffs, pharmaceuticals;
in oil refining | | Uses | Ethylamine is used in the manufacture ofdyes and resins, as a stabilizer for rubberlatex, and in organic synthesis. | | Uses | Dye intermediate, solvent extraction, petroleum
refining, stabilizer for rubber latex, detergents,
organic synthesis. | | Definition | ChEBI: A two-carbon primary aliphatic amine. | | Definition | ethylamine: A colourless flammablevolatile liquid, C2H5NH2; r.d. 0.69;m.p. –81°C; b.p. 16.6°C. It is a primaryamine made by reactingchloroethane with ammonia andused in making dyes. | | Production Methods | The methods employed for the production of ethylamine are similar to those used
for the methylamines. Differences involve the alcohol used and its ratio to other
reactants. The most common method involves continuously passing ammonia and
ethanol over a catalyst in a gas-solid heterogenous reaction. The temperature is
maintained at 300-500°C at 790-3550 kPa and the catalyst can be alumina, silica,
titania, or tungstic oxides. As this procedure produces a mixture of water, alcohol,
ammonia, and various amines, the amines of interest are continuously separated by
distillations and extractions. The amine can be produced from ethyl chloride and
alcoholic ammonia under heat and pressure or by hydrogenation of nitroethane
(HSDB 1989). Alternatively ammonia, ethanol and hydrogen over a dehydrogenation
catalyst are passed continuously over a catalyst (supported metallic silver,
nickel, or copper) in a gas-solid heterogenous reaction. The reaction is run at
130-250°C at 790-3550 kPa and also produces a mixture of amines. Ethylamine
can also be produced using a similar procedure which employs ammonia and an
aldehyde or ketone and hydrogen over a hydrogenation catalyst under the same
conditions. However, this method is more expensive and is therefore not commonly
used, except in special cases (Schweizer et al 1978).
Ethylamine also is a normal constituent of biological systems and is present in
the urine of animals and man (Beard and Noe 1981). The amine occurs widely in
the environment as a decomposition product of amino acids. It is formed, therefore,
in sewage during the decomposition of plant and animal wastes and is also
found in a variety of foods such as cheese, herring, spinach and freeze-dried coffee
(HSDB 1989; Lin et al 1983,1984). It is also a constituent of tobacco smoke and
has been detected in various surface waters at concentrations ranging between
1 and 37 p.p.m. Ethylamine also has been found in finished drinking water
(Neurath et al 1977; Scheiman et al 1974). As with other alkylamines, ethylamine
can be nitrosated to form the toxic product, 7V-nitrosoethylamine (Hussain et al
1974). | | Aroma threshold values | Very high strength odor; ammoniacal type; recommend smelling in a 0.01% solution or less | | General Description | A colorless liquid or a gas (boiling point 62°F) with an odor of ammonia. Flash point less than 0°F. Density of liquid 5.7 lb / gal. Corrosive to the skin and eyes. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion. Exposure of the closed container to intense heat may cause Ethylamine to rupture violently and rocket. | | Air & Water Reactions | Highly flammable. Water soluble. | | Reactivity Profile | Sensitive to heat. Reacts vigorously with oxidizing agents. Incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Incompatible with cellulose nitrate. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Also incompatible with oxidizing agents. A chemical base. Neutralizes acids to form salts plus water in an exothermic reaction Dissolves most paints, plastics and rubber . | | Hazard | Strong irritant. Flammable, dangerous fire
risk, flammable limits in air 3.5–14%. | | Health Hazard | Ethylamine is a severe irritant to the eyes,skin, and respiratory system. The pure liquidor its highly concentrated solution can causecorneal damage upon contact with eyes. Skincontact can result in necrotic skin burns.
Rabbits exposed to 100 ppm ethylaminefor 7 h/day, 5 days/week for 6 weeks mani fested irritation of cornea and lung, and liverand kidney damage (ACGIH 1986). A 4-hourexposure to 3000 ppm was lethal to rats. Theacute oral and dermal toxicity of this com pound was moderate in test animals.
LD50 value, oral (rats): 400 mg/kg
LD50 value, skin (rabbits): 390 mg/kg. | | Chemical Reactivity | Reactivity with Water No reaction; Reactivity with Common Materials: Will strip and dissolve paint; dissolves most plastic materials; can cause swelling of rubber by absorption. The reactions are not hazardous; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | | Industrial uses | Ethylamine has achieved widespread use as an intermediate in the manufacture of
a variety of products. It is used as a solvent for dyes, resins, and oils and as a
vulcanization accelerator for sulfur-cured rubbers as well as a stabilizer for rubber
latex (NIOSH 1981; HSDB 1989). The amine is used in the production of alkyl
isocyanates for intermediates in the manufacture of products such as pharmaceuticals
and resins. It also serves as an intermediate in the manufacture of triazine
herbicides, a corrosion inhibitor (1,3-diethyl thiourea), and an agent used in wash
and wear fabrics (dimethylolethyltriazone). Copious salts of ethylamine can also
be used in the refining of petroleum and vegetable oil (Sittig 1981). The amine also
has uses as an industrial solvent and as a chemical initiator in the preparation of
various solvents (HSDB 1989). | | Safety Profile | A poison by ingestion,
skin contact, and intravenous routes.
Moderately toxic by inhalation. A severe eye
irritant. A very dangerous fire hazard when exposed to heat or flame. Moderate
explosion hazard when exposed to spark or
flame. Keep away from heat and open
flame, can react vigorously with oxidizing
materials. To fight fire, stop flow of gas, use
alcohol foam, dry chemical. Incompatible
with cellulose nitrate or oxidzers. When
heated to decomposition it emits toxic
fumes of NOx. See also MINES. | | Potential Exposure | Monoethylamine (MEA) is used as an
intermediate in the manufacture of the following chemicals:
triazine herbicides, 1,3-diethylthiourea (a corrosion inhibitor);
ethylamino-ethanol; 4-ethylmorpholine (urethane foam catalyst); ethyl isocyanate; and dimethylolethyltriazone (agent
used in wash-and-wear fabrics). The cuprous chloride salts of
MEA are used in the refining of petroleum and vegetable oil. | | Environmental fate | Photolytic. The rate constant for the reaction of ethylamine and ozone in the atmosphere is 2.76
x 10-20 cm3/molecule?sec at 296 K (Atkinson and Carter, 1984). Atkinson (1985) reported a rate
constant of 6.54 x 10-11 cm3/molecule?sec for the vapor-phase reaction of ethylamine and OH
radicals at 25.5 °C. The half-life for this reaction is 8.6 h.
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. Reacts with OH radicals possibly forming acetaldehyde or acetamide
(Atkinson et al., 1978). When ethylamine over kaolin is heated to 600 °C, hydrogen and
acetonitrile formed as the major products. Trace amounts of ethylene, ammonia, hydrogen
cyanide, and methane were also produced. At 900 °C, however, acetonitrile was not produced
(Hurd and Carnahan, 1930).
Reacts with mineral acids forming water-soluble salts (Morrison and Boyd, 1971). | | Metabolism | Ethylamine is readily absorbed from the respiratory and gastrointestinal tracts.
When administered to humans as the HC1 form, about 32% of the ethylamine
could be recovered in the urine (Rechenberger 1984). It appears that ethylamine is
slowly oxidized by monoamine oxidase to form hydrogen peroxide and the
corresponding aldehyde. Subsequently, the peroxide is removed by catalase and
the aldehyde is likely converted to its carboxylic acid by aldehyde oxidase (Beard
andNoe 1981).
As with other alkylamines, a potential exists for in vivo nitrosation of ethylamine
from foods by the preservative sodium nitrite under the acidic conditions
found in the stomach (Lin et al 1983,1984). | | storage | Ethylamine should be stored in a flammable-liquids storage room or cabinet. It shouldbe stored away from oxidizing materials andsources of ignition. It is shipped in steelcylinders or drums. | | Shipping | UN1036, Ethylamine, Hazard Class: 2.1; Labels:
2.1-Flammable gas. Ethylamine, aqueous solution with not ,50% but not .70% ethylamine, Hazard Class: 3; Labels:
3-Flammable liquid, 8-Corrosive material. Cylinders must
be transported in a secure upright position, in a wellventilated 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 | Condense it in an all-glass apparatus cooled by circulating ice-water, and store it with KOH pellets below 0o. [Beilstein 4 IV 307.] | | Toxicity evaluation | The effects of ethylamine appear due primarily to its corrosive
action at all points of contact with the body. | | Incompatibilities | The aqueous solution is a strong base.
May form explosive mixture with air. Reacts violently
with strong acids; strong oxidizers; cellulose nitrate; and
organic compounds; causing fire and explosion hazard.
Also incompatible with organic anhydrides; isocyanates,
vinyl acetate; acrylates, substituted allyls; alkylene
oxides; epichlorohydrin, ketones, aldehydes, alcohols,
glycols, phenols, cresols, caprolactum solution. Attacksnonferrous metals: aluminum, copper, lead, tin, zinc, and
alloys; some plastics, rubber, and coatings. | | Waste Disposal | Return refillable compressed
gas cylinders to supplier. Controlled incineration; incinerator equipped with a scrubber or thermal unit to reduce
nitrogen oxides emissions |
| | Ethylamine Preparation Products And Raw materials |
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