Chemical Properties
CLEAR liquid
Definition
ChEBI: An alkane-alpha,omega-diamine in which the alkane is ethane.
General Description
A clear colorless liquid with an ammonia-like odor. Flash point of 91°F and a melting point of 47°F. Corrosive to tissue. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion. Density 7.5 lb/gal. Used to make other chemicals and as a fungicide.
Reactivity Profile
A base. Highly reactive with many compounds. Can react violently with acetic acid, acetic anhydride, acrolein, acrylic acid, acrylonitrile, allyl chloride, carbon disulfide, chlorosulfonic acid, epichlorohydrin, ethylene chlorohydrin, hydrogen chloride, mesityl oxide, nitric acid, oleum, AgClO4, sulfuric acid, beta-propiolactone and vinyl acetate. Incompatible with strong acids, strong oxidizers (perchlorate salts), and chlorinated organic compounds. ETHYLENEDIAMINE(107-15-3) is also incompatible with halogenated organic compounds and metal halides. May react with nitromethane and diisopropyl peroxydicarbonate. May ignite on contact with cellulose nitrate. Readily absorbs carbon dioxide from the air to give crusty solid deposits. . ETHYLENEDIAMINE(107-15-3) reacts violently with ethylene chlorohydrin. (Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 1554.).
Air & Water Reactions
Highly flammable. Hygroscopic. Fumes in the air. Water soluble. Biodegrades readily.
Hazard
Toxic by inhalation and skin absorption,
strong irritant to skin and eyes. Flammable, moderate fire risk. Questionable carcinogen.
Health Hazard
Vapor inhalations at a concentration of 200 ppm for 5 to 10 minutes will lead to nasal irritation and produce a tingling sensation. Inhalation at concentrations of 400 ppm or greater leads to severe nasal irritation. Respiratory irritation may result. Many individuals are hypersensitive to ethylenediamine exposure; therefore, safe threshold limits are difficult to set.
Potential Exposure
Ethylenediamine is used as an intermediate; as a urine acidifier; as a solvent; an emulsifier for casein
and shellac solutions; a stabilizer in rubber late. A chemical
intermediate in the manufacture of dyes; corrosion inhibitors;
synthetic waxes; fungicides, resins, insecticides, asphalt wetting agents; and pharmaceuticals. Ethylenediamine is a degradation product of the agricultural fungicide Maneb.
Fire Hazard
Burning rate: 2.2 mm/minute. When exposed to heat or flame, the material has a moderate fire potential. The material can react readily with oxidizing materials. Containers may explode in heat of fire. Material emits nitrogen oxides when burned. Avoid carbon disulfide, silver perchlorate, imines, oxidizing materials. Stable. Hazardous polymerization may not occur.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. 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. If victim is conscious, administer water or
milk. Do not induce vomiting
Shipping
UN1604 Ethylenediamine, Hazard class: 8;
Labels: 8-Corrosive material, 3-Flammable liquid
Incompatibilities
Vapor may form explosive mixture with
air. Ethylenediamine is a medium strong base. Violent reaction with strong acids; strong oxidizers; chlorinated organic
compounds; acetic acid; acetic anhydride; acrolein, acrylic
acid; acrylonitrile, allyl chloride; carbon disulfide; chlorosulfonic acid; epichlorohydrin, ethylene chlorohydrin,
oleum, methyl oxide; vinyl acetate. Also incompatible with
silver perchlorate, 3-propiolactone, mesityl oxide; ethylene
dichloride; organic anhydrides; isocyanates, acrylates,
substituted allyls; alkylene oxides; ketones, aldehydes,
alcohols, glycols, phenols, cresols, caprolactum solution.
Attacks aluminum, copper, lead, tin, zinc, and alloys; some
plastics, rubber, and coatings.
Waste Disposal
Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).
Physical properties
Clear, colorless, volatile, slight viscous, hygroscopic liquid with a sweet, ammonia-like odor. The
average least detectable odor threshold concentrations in water at 60 °C and in air at 40 °C were
12 and 52 mg/L, respectively (Alexander et al., 1982).
Uses
[Note—Edamine is the recommended contraction for the ethylenediamine radical.].
Uses
Ethylenediamine is used as a stabilizerfor rubber latex, as an emulsifier, as aninhibitor in antifreeze solutions, and intextile lubricants. It is also used as a solvent for albumin, shellac, sulfur, and othersubstances.
Uses
Intermediate in the manufacture of
EDTA; catalytic agent in epoxy resins; dyes,
solvent stabilizer; neutralizer in rubber
products
Production Methods
The production of ethylene-1,2-diamine (EDA) is by the catalytic amination of
monoethanolamine or the reaction of aqueous ammonia with 1,2-dichloroethane
(Spitz 1979). U.S. Production is estimated at greater than 33,000 tons in 1975.
Chemical Reactivity
Reactivity with Water Gives off heat, but reaction is not hazardous; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Industrial uses
EDA functions as a reactive intermediate in the synthesis of carbamate fungicides
and in the preparation of dyes, synthetic waxes, resins, insecticides and asphalt
wetting agents (Parmeggiani 1983). EDA is a solvent for casein, albumin, shellac,
and sulfur; an emulsifier; a stabilizer for rubber latex; an inhibitor in antifreeze
solutions; and a pharmaceutic aid (aminophylline injection stabilizer) (Windholz
1983). It is also an important ingredient in hair-settings, cold wave lotions, and
nail polish (Arena 1979).
Environmental Fate
Chemical/Physical. Absorbs carbon dioxide forming carbonates (Patnaik, 1992; Windholz et al.,
1983).
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent
concentration of 893 mg/L. The adsorbability of the carbon used was 21 mg/g carbon (Guisti et
al., 1974).
Metabolism
EDA is absorbed through the skin (Beard and Noe 1981). The penetration rates,
distribution and excretion of topically applied [14C]-ethylenediamine have been
studied in the rat (Yang et al 1987). Male Wistar rats were percutaneously exposed
to solutions of 10, 25 or 50% EDA over about 10% of the body surface.
Absorption of EDA was concentration dependent, with about 12, 55 and 61%
being absorbed at the 70, 25 and 50% concentration respectively. The terminal
plasma half-life of EDA was approximately 4.5 h and the major route of excretion
was via the urine. The authors concluded that skin absorption is relatively low and
the reduced absorption at higher EDA concentrations may be due to epidermal
damage.
When male rats were given 5, 50 or 500 mg/kg doses of [14C]-EDA by oral,
endotracheal and i.v. routes, urinary excretion accounted for 42-65% of the
administered radioactivity (Yang and Tallant 1982). Fecal excretion amounted to
5-32% of the dose, depending on the route and 6-9% was eliminated in expired
air as 14CO2. As the dosage increased from 5 to 50 to 500 mg/kg, there was a
pattern of accumulated tissue EDA with a corresponding decrease in metabolite
formation. The route of administration did not appear to change the metabolic
profile. The major urinary metabolite in the rat was N-acetylethylenediamine
(Yang and Tallant 1982). Cotgreave and Caldwell (1983) found that EDA was not
detectable in the plasma 2 h after oral and i.v. administration of aminophylline in
three healthy human subjects. Davies et al (1983) observed that ethylenediamine
uptake in rat brain slices was temperature-dependent and appeared to take place by
both sodium dependent and sodium independent mechanisms. Yang et al (1984a)
demonstrated age- and, to a lesser extent, sex-related differences in the pharmacokinetics
of EDA in Fischer 344 rats.
storage
(1) Color Code—White: Corrosive or ContactHazard; Store separately in a corrosion-resistant location.(2) Color Code—Blue: Health Hazard/Poison: Store in asecure poison location. Prior to working with this chemicalyou should be trained on its proper handling and storage.Before entering confined space where this chemical may bepresent, check to make sure that an explosive concentrationdoes not exist. Ethylenediamine must be stored to avoidcontact with acetic acid, acetic anhydride, acrolein, acrylicacid, acrylonitrile, allyl chloride, carbon disulfide, chlorosulfonic acid, epichlorhydrin, ethylene chlorohydrin, oleum,methyl oxide, vinyl acetate, hydrogen chloride, and sulfuricacid since violent reactions occur. Store in tightly closedcontainers in a cool, well-ventilated area away from oxidizers (such as perchlorates, peroxides, permanganates, chlorates, and nitrates). Detached outdoor storage is preferred.Sources of ignition, such as smoking and open flames, areprohibited where ethylenediamine is handled, used, orstored. Metal containers involving the transfer of 5 gallonsor more of ethylenediamine should be grounded andbonded. Drums must be equipped with self-closing valves,pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening andclosing containers of ethylenediamine.
Purification Methods
It forms a constant-boiling (b 118.5o, monohydrate, m 10o) mixture with water (23w/w%). [It is hygroscopic and miscible with water.] Recommended purification procedure [Asthana & Mukherjee in J.F.Coetzee (ed), Purification of Solvents, Pergamon Press, Oxford, 1982 cf p 53]: to 1L of ethylenediamine is added 70g of type 5A Linde molecular sieves and shaken for 12hours. The liquid is decanted and shaken for a further 12hours with a mixture of CaO (50g) and KOH (15g). The supernatant is fractionally distilled (at 20:1 reflux ratio) in contact with freshly activated molecular sieves. The fraction distilling at 117.2o /760mm is collected. Finally it is fractionally distilled from sodium metal. All distillations and storage of ethylenediamine should be carried out under nitrogen to prevent reaction with CO2 and water. The material containing 30% water is dried with solid NaOH (600g/L) and heated on a water bath for 10hours. Above 60o, separation into two phases takes place. The hot ethylenediamine layer is decanted off, refluxed with 40g of sodium for 2hours and distilled [Putnam & Kobe Trans Electrochem Soc 74 609 1938]. Ethylenediamine is usually distilled under nitrogen. Alternatively, it is dried over type 5A Linde molecular sieves (70g/L), then a mixture of 50g of CaO and 15g of KOH/L, with further dehydration of the supernatant with molecular sieves followed by distillation from molecular sieves and, finally, from sodium metal. A spectroscopically improved material is obtained by shaking with freshly baked alumina (20g/L) before distillation. [Beilstein 4 IV 1166.]
