| Identification | More | [Name]
Ethyleneimine | [CAS]
151-56-4 | [Synonyms]
AZIRIDINE
Dimethyleneimine
ETHYLENEIMINE
ETHYLENIMINE
1H-Azirine, dihydro-
Aethylenimin
Aminoethylene
Azacyclopropane
Aziran
Azirane
Aziridin
aziridine(ethyleneimine)
dihydro-1h-azirin
Dihydro-1H-azirine
Dihydroazirene
dihydroazirine
Dimethylenimine
EI
ENT-50324
Ethirydine | [EINECS(EC#)]
205-793-9 | [Molecular Formula]
C2H5N | [MDL Number]
MFCD00039669 | [Molecular Weight]
43.07 | [MOL File]
151-56-4.mol |
| Chemical Properties | Back Directory | [Description]
Ethyleneimine is a colourless liquid with an ammonia-like smell or pungent odour. It is
highly flammable and reacts with a wide variety of materials. Ethyleneimine is used
in polymerisation products, as a monomer for polyethyleneimine and as a comonomer
for polymers, for example, with ethylenediamine. Polymerised ethyleneimine is used in
paper, textile chemicals, adhesive binders, petroleum, refining chemicals, fuels, lubricants,
coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange
resins, photographic chemicals, colloid flocculants, and surfactants. Ethyleneimine readily
polymerises, and it behaves like a secondary amine. Ethyleneimine is highly caustic,
attacking materials such as cork, rubber, many plastics, metals, and glass except those
without carbonate or borax. It polymerises explosively on contact with silver, aluminium,
or acid. The activity of ethyleneimine is similar to that of nitrogen and sulphur mustards.
Ethyleneimine is used as an intermediate in the production of triethylenemelamine. | [Appearance]
Ethyleneimine is a colorless volatile liquid with
an ammoniacal odor. | [Melting point ]
-78°C | [Boiling point ]
56°C | [density ]
0,83 g/cm3 | [vapor pressure ]
160 at 20 °C, 250 at 30 °C (quoted, Verschueren, 1983) | [refractive index ]
nD25 1.412 | [Fp ]
-11°C | [solubility ]
miscible with water and virtually all organic solvents | [form ]
Colorless liquid | [pka]
8.01(at 25℃) | [Odor]
Fishy; ammoniacal. | [Stability:]
Highly flammable. Reacts with a wide variety of materials. | [Water Solubility ]
miscible | [Henry's Law Constant]
1.33(x 10-7 atm?m3/mol) at 25 °C (quoted, Mercer et al., 1990) | [Dielectric constant]
18.3（25℃） | [Exposure limits]
TLV-TWA (skin) 0.5 ppm (～1 mg/m3)
(ACGIH, OSHA, and MSHA); Poten tial Human Carcinogen in the workplace
(OSHA), Potential Carcinogen (NIOSH). | [LogP]
-2.68--0.28 at 25℃ | [CAS DataBase Reference]
151-56-4(CAS DataBase Reference) | [IARC]
2B (Vol. 9, Sup 7, 71) 1999 | [NIST Chemistry Reference]
Ethylenimine(151-56-4) | [EPA Substance Registry System]
151-56-4(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
Ethyleneimine is a colorless liquid with an ammonia-like smell or pungent odor. It is
highly flammable and reacts with a wide variety of materials. Ethyleneimine is used in
polymerization products, as a monomer for polyethyleneimin, and as a comonomer for
polymers, e.g., with ethylenediamine. Polymerized ethylenimine is used in paper, textile
chemicals, adhesive binders, petroleum, refi ning chemicals, fuels, lubricants, coating resins,
varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic
chemicals, colloid fl occulants, and surfactants.
Ethyleneimine readily polymerizes, and it behaves like a secondary amine. Ethyleneimine
is highly caustic, attacking materials such as cork, rubber, many plastics, metals, and glas except those without carbonate or borax. It polymerizes explosively on contact with silver,
aluminum, or acid. The activity of ethyleneimine is similar to that of nitrogen and sulfur mustards.
Ethyleneimine is used as an intermediate in the production of triethylenemelamine.
Polymerized ethyleneimine is used in paper, textile chemicals, adhesive binders, petroleum,
refi ning chemicals, fuels, lubricants, coating resins, varnishes, lacquers, agricultural chemicals,
cosmetics, ion-exchange resins, photographic chemicals, colloid fl occulants, and surfactants | [General Description]
A clear colorless liquid with an ammonia-like odor. Flash point 12°F. Less dense than water. Flammable over a wide range of vapor-air concentrations. Vapors irritate the skin, eyes, nose, and throat. May be toxic by prolonged inhalation, skin absorption, or ingestion. Carcinogenic. Vapors heavier than air. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently. | [Reactivity Profile]
ETHYLENEIMINE vapors are not inhibited and may form polymers in vents or flame arresters, resulting in stopping of the vents. Produces toxic oxides of nitrogen during combustion. Reacts with sodium hypochlorite and other chlorinating agents to give the explosive compound 1-chloroazidine. Decomposes if heated under pressure. or else hazardous polymerization may occur. Incompatible with silver or aluminum, which induce polymerization May polymerize explosively upon contact with acids. Polymerization is catalyzed by carbon dioxide [EPA, 1998]. | [Air & Water Reactions]
Highly flammable. Soluble in water. | [Hazard]
Corrosive, absorbed by skin, causes tumors;
exposure should be minimized; a carcinogen. Dangerous fire and explosion hazard, flammable limits
in air 3.6–46%. Toxic by skin absorption; possible
carcinogen. | [Health Hazard]
Ethyleneimine is classified as extremely toxic with a probable oral lethal dose of 5-50 mg/kg which is approximately 7 drops to 1 teaspoonful for a 70 kg (150 lb.) person. Ethyleneimine gives inadequate warning when over-exposure is by inhalation or skin absorption. It is a severe blistering agent, causing third degree chemical burns of the skin. Also, it has a corrosive effect on mucous membranes and may cause scarring of the esophagus. It is corrosive to eye tissue and may cause permanent corneal opacity and conjunctival scarring. Severe exposure may result in overwhelming pulmonary edema. Renal damage has been described. Hemorrhagic congestion of all internal organs has been observed. | [Health Hazard]
Exposures to ethyleneimine cause adverse health effects and poisoning. Ingestion/swallowing,
inhalation, or absorption through exposures to skin cause severe irritation, blisters,
severe deep burns, and effects of sensitization. Ethyleninime is corrosive to the eye tissue
and may cause permanent corneal opacity and conjunctival scarring, severe respiratory
tract irritation, and effects of infl ammation in workers. Ethyleneimine is a severe blistering
agent, causing third degree chemical burns of the skin. The symptoms of toxicity include,
but are not limited to, cough, dizziness, headache, labored breathing, nausea, vomiting,
tearing and burning of the eyes, sore throat, nasal secretion, bronchitis, shortness of breath,
laryngeal edema, pronounced changes of the trachea and bronchi of lungs. Ethyleneimine
with its corrosive effects cause injury to the mucous membranes and acute oral exposure
may cause scarring of the esophagus in humans. The onset of symptoms and health effects
caused by ethyleneimine depends on exposure concentration. | [Potential Exposure]
Ethyleneimine is used in production
of binding agents; formation of plastics; and improving
paper strength; in many organic syntheses; as an intermediate and monomer for fuel oil and lubricating refining. The
polymerization products, polyethyleneimines, are used as
auxiliaries in the paper industry and as flocculation aids in
the clarification of effluents. It is also used in the textile
industry for increasing wet strength, flame-, water-, shrinkproofing, and stiffening | [Fire Hazard]
Irritating vapors are generated when heated. Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. May polymerize in fires with evolution of heat and container rupture. Runoff to sewer may create fire or explosion hazard. Ethyleneimine vapors are not inhibited and may form polymers in vents or flame arresters, resulting in stopping of the vents. Toxic oxides of nitrogen are produced during combustion. Upon treatment with sodium hypochlorite, ETHYLENEIMINE, INHIBITED(151-56-4) gives off the explosive compound 1-chloroazidine. Avoid acids, sodium hypochlorite. If heated under pressure, instability may result. Hazardous polymerization may occur. Avoid contact with silver or aluminum. Explosive polymerization may occur upon contact with acids. Polymerization is catalyzed by carbon dioxide. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
45 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately since eye splashes can cause
severe illness or death. If this chemical contacts the skin,
remove contaminated clothing and wash immediately with
soap and water. Seek medical attention immediately. If this
chemical has been inhaled, remove from exposure, begin
rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy | [Shipping]
UN1185 Ethyleneimine, stabilized, Hazard class:
6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable
liquid, Inhalation Hazard Zone A. PGI | [Incompatibilities]
May form explosive mixture with air.
Ethyleneimine is a medium strong base. Contact with
acids, aqueous acid conditions, oxidizers, aluminum, or
carbon dioxide may cause explosive polymerization.
Explosive silver derivatives may be formed with silver
alloys e.g., silver solder). Self-reactive with heat or atmospheric carbon dioxide. May accumulate static electrical
charges, and may cause ignition of its vapors. Attacks
rubber, coatings, plastics, and chemically active metals.
Ethyleneimine vapors are not inhibited and may form
polymers in vents or flame arresters, resulting in stopping
of the vents. | [Waste Disposal]
Controlled incineration; incinerator equipped with a scrubber or thermal unit to reduce
nitrogen oxides emissions | [Physical properties]
Clear, colorless, very flammable liquid with a very strong ammonia odor. Odor threshold
concentration is 1.5 ppm (quoted, Amoore and Hautala, 1983). | [Uses]
Ethyleneimine is used to manufacture triethylenemelamine
and is used in its polymeric form in paper and textile
chemicals, adhesive binders, petroleum-refining chemicals,
fuels and lubricants, coating resins, varnishes, lacquers,
agricultural chemicals, cosmetics, ion-exchange resins, photographic
chemicals, colloid flocculants, and surfactants. | [Uses]
Ethylenimine is used in the manufacture oftriethylenemelamine and other amines. | [Uses]
In the manufacture of triethylenemelamine. | [Definition]
ChEBI: Aziridine is a saturated organic heteromonocyclic parent, a member of aziridines and an azacycloalkane. It has a role as an alkylating agent. It is a conjugate base of an aziridinium. | [Production Methods]
Industrial quantities are made with monoethanolamine via a two-step chemical dehydration process using sulphuric acid and sodium hydroxide, or by reacting 1,2-dichloroethane with ammonia. The U.S. production in 1978 was over 1500 metric tons (Ham 1978). | [Origin]
Ethylenimine was first prepared in 1888 by GABRIEL, who mistakenly called it vinylamine. He prepared the ethylenimine by reacting 2-bromoethylamine hydrobromide with silver oxide or potassium hydroxide.
| [Flammability and Explosibility]
Highlyflammable | [Chemical Reactivity]
Reactivity with Water: Mild reaction, non-hazardous; Reactivity with Common Materials: Contact with silver or aluminum may cause polymerization; Stability During Transport: Stable unless heated under pressure; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Explosive polymerization can occur when in contact with acids; Inhibitor of Polymerization: None used. | [Industrial uses]
Approximately 50% of ethylenimine produced in the U.S. is polymerized to polyethyleneimine, used as a flocculant in water treatment, and as a wet-strength additive in the textile and paper industries. Polyethylenimine is also used in various adhesives and coatings and to laminate plastic films to paper, other cellulose materials, and metal foils for making cartons in the food industry. The adhesion properties of acrylic latex paints are improved by reaction of acid groups with ethylenimine. Ethylenimines are utilized in the textile industry to improve durability, crease resistance, flame resistance, and dyeing properties. Other uses are found in ion-exchange resin synthesis, in electroplating, as a rocket propellant binder, as a lubricating oil dispersant, and as a hardening agent in the preparation of photographic films. Ethylenimine is used in the manufacture of triethylene melamine, a cancer chemotherapy drug; various ethylenimines are used as insect chemosterilant agents for pest control (Ham 1978). | [Carcinogenicity]
The carcinogenicity of ethyleneimine
was evaluated in two strains of mice, and both gave
positive results. Groups of 18 male and 18 female
mice of B6C3F1 or B6AKR strains were treated orally
(initially by gavage, then in the diet) from age 7 days through
77–78 weeks. The time-weighted average (TWA) dose was
about 1.8 mg/kg/day. The incidence of hepatomas and lung
adenomas was significantly elevated in both strains and
sexes. In B6C3F1 mice, the incidence of hepatomas
and pulmonary adenomas was 15/17 and 15/17 in males
and 11/15 and 15/15 females, respectively. In the B6AKR strain, hepatomas and adenomas occurred in 9/16 and 12/16
males and in 2/11 and 10/11 females, respectively. In the
control groups, hepatomas were 8/79 and 0/87 in male and
female B6C3F1 mice and 5/90 and 1/82 in male and female
B6AKR mice. The respective incidence of pulmonary adenomas
was 5/79, 3/87, 10/90, and 3/82. The incidence of
hepatomas and pulmonary adenomas (reported as combined
tumors) was significantly (p＜0.01) elevated. | [Environmental Fate]
Photolytic. The vacuum UV photolysis (λ = 147 nm) and γ radiolysis of ethylenimine resulted
in the formation of acetylene, methane, ethane, ethylene, hydrogen cyanide, methyl radicals, and
hydrogen (Scala and Salomon, 1976). Photolysis of ethylenimine vapor at krypton and xenon lines
yielded ethylene, ethane, methane, acetylene, propane, butane, hydrogen, ammonia, and ethyleneimino
radicals (Iwasaki et al., 1973).
Chemical/Physical. Polymerizes easily (Windholz et al., 1983). Hydrolyzes in water forming
ethanolamine (HSDB, 1989). The estimated hydrolysis half-life in water at 25 °C and pH 7 is 154
d (Mabey and Mill, 1978). | [Metabolism]
When male Dow-Wistar rats were injected intraperitoneally with [14C]-ethylenimine (80mug), approximately half of the dose was excreted in the urine (Wright and Rowe 1967). The major portion of the radioactivity in the urine consisted of unidentified products, although a small amount was excreted unchanged. A small portion, 3-5%, was expired as 14C02, and 1-3% was expired as a volatile, basic material, probably ethylenimine, during 24 h. Significant amounts of radioactivity were accumulated in liver, intestines, cecum, spleen, and kidneys. After 24 h, tissue radioactivity became constant and essentially unavailable for further metabolism. The aziridine ring of drugs is readily cleaved by microsomal enzymes, possibly with intermediate formation of an N-oxide (Oelschlager and Al Shaik 1985). | [storage]
(1) Color Code—Red: Flammability Hazard: Storein a flammable liquid storage area or approved cabinetaway from ignition sources and corrosive and reactivematerials. (2) Color Code—Blue: Health Hazard/Poison:Store in a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Before entering confined space where this chemicalmay be present, check to make sure that an explosive concentration does not exist. Ethyleneimine must be inhibitedand stored to avoid contact with strong acids (such ashydrochloric, sulfuric, and nitric) and oxidizers (such asperchlorates, peroxides, permanganates, chlorates, andnitrates) since violent reactions occur. Store in tightlyclosed containers in a cool, well-ventilated area. Sources ofignition, such as smoking and open flames, are prohibitedwhere ethyleneimine is handled, used, or stored. Metal containers involving the transfer of 5 gallons or more of ethyleneimine should be grounded and bonded. Drums mustbe equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof ethyleneimine. Wherever ethyleneimine is used, handled,manufactured, or stored, use explosion-proof electricalequipment and fittings. A regulated, marked area should beestablished where this chemical is handled, used, or storedin compliance with OSHA Standard 1910.1045 | [Purification Methods]
Redistil it in an Ar or N2 atmosphere in a fume hood, and store it over KOH in sealed bottles in a refrigerator. Commercial aziridine has been dried over sodium and distilled from the metal through an efficient column before use [Jackson & Edwards J Am Chem Soc 83 355 1961, Wenker J Am Chem Soc 57 2328 1935]. It is a weaker base than Me2NH (pK2 5 10.87) but is caustic to the skin. It should not be inhaled, causes inflammation of the eyes, nose and throat, and one may become sensitized to it. It is soluble in H2O, has an ammoniacal smell and reacts with CO2. Pure aziridine is comparatively stable but polymerises in the presence of traces of H2O and is occasionally explosive in the presence of acids. CO2 is sufficiently acidic to cause polymerisation (forms linear polymers) which is not free radical promoted. It is stable in the presence of bases. The violet 2:1 Cu complex crystallises from EtOH containing a few drops of aziridine and adding Et2O, and has m 142o(dec). The picrate has m 142o. [O'Rourke et al. J Am Chem Soc 78 2159 1956.] It has also been dried over BaO and has been distilled from sodium under nitrogen. [Allen et al. Org Synth Coll Vol IV 433 1963, Beilstein 20 III/IV 1.] TOXIC. | [Toxicity evaluation]
Ethyleneimine is an extremely reactive alkylating agent that
undergoes ring-opening reactions with cellular nucleophiles. |
| Safety Data | Back Directory | [Hazard Codes ]
F;T,T,F,N,T+ | [Risk Statements ]
R11:Highly Flammable.
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .
R34:Causes burns.
R45:May cause cancer.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S53:Avoid exposure-obtain special instruction before use .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
1185 | [HazardClass ]
6.1(a) | [PackingGroup ]
I | [Precautions]
During use of ethyleninime, students and occupational workers should wear protective
equipment, such as gloves, safety glasses, and should have good ventilation. Ethyleninime
should be handled as a carcinogen. Ethyleninime vapor/air mixtures are explosive and
pose a risk of fi re and explosion on contact with acid(s), oxidants. | [Safety Profile]
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, tumorigenic, and teratogenic
data. Other experimental reproductive
effects. Poison by ingestion, skin contact,
inhalation, and intraperitoneal routes. Human mutation data reported. A skin, mucous
membrane, and severe eye irritant. An
allergc sensitizer of skin. Causes opaque cornea, keratoconus, and necrosis of cornea
(experimentally). Has been known to cause
severe human eye injury. Drinking of
carbonated beverages is recommended as an
antidote to ths material in stomach.
A very dangerous fire and explosion
hazard when exposed to heat, flame, or
oxidzers. Reacts violently with acids,
aluminum chloride + substituted anilines,
acetic acid, acetic anhydride, acrolein, acrylic
acid, allyl chloride, CS2, Cl2, chlorosulfonic
acid, epichlorohydrin, glyoxal, HCl, HF,
HNO3, oleum, P-propiolactone, Ag, NaOCl,
H2SO4, vinyl acetate. Reacts with chlorinating agents (e.g., sodum hypochlorite
solution) to form the explosive 1
chloroaziridine. Reacts with silver or its
alloys to form explosive silver derivatives.
Dangerous; heat and/or the presence of
catalytically active metals or chloride ions
can cause a violent exothermic reaction. To
fight fire, use alcohol foam, CO2, dry
chemical. When heated to decomposition it
emits acrid smoke and irritating fumes. | [Hazardous Substances Data]
151-56-4(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 15 mg/kg (Smyth) | [IDLA]
100 ppm |
|