| Identification | More | [Name]
Ethylenediamine | [CAS]
107-15-3 | [Synonyms]
1,2-DIAMINOETHANE
1,2-ETHANEDIAMINE
1,2-Ethylenediamine
EDA
ETHANE-1,2-DIAMINE
ETHYLENEDIAMINE
1,2-Diaminoaethan
1,2-Diamino-ethaan
1,2-Diaminoethan
1,2-diaminoethane(ethylenediamine)
1,2-Diamino-ethano
1,2-Ethandiamin
Aethaldiamin
Aethylenediamin
ai3-24231
algicode106l
amerstat274
beta-Aminoethylamine
caswellno437
Diaminoethane | [EINECS(EC#)]
203-468-6 | [Molecular Formula]
C2H8N2 | [MDL Number]
MFCD00008204 | [Molecular Weight]
60.1 | [MOL File]
107-15-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Ethylenediamine, a polyamine, is a strongly
alkaline, colorless, clear, thick liquid. Ammonia odor. A
solid below 8.5℃. The Odor Threshold is 1.0 ppm | [Melting point ]
8.5 °C(lit.)
| [Boiling point ]
118 °C(lit.)
| [density ]
0.899 g/mL at 25 °C(lit.)
| [vapor density ]
2.07 (vs air)
| [vapor pressure ]
10 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.4565(lit.)
| [Fp ]
93 °F
| [storage temp. ]
Flammables area | [solubility ]
ethanol: soluble(lit.) | [form ]
Liquid, Fuming In Air | [pka]
10.712(at 0℃) | [color ]
colorless to pale yellow | [Specific Gravity]
0.899 | [Odor]
Strong ammoniacal odor; ammonia-like mild and ammoniacal odor. | [PH]
12.2 (100g/l, H2O, 20℃) | [explosive limit]
2-17%(V) | [Water Solubility ]
miscible | [Sensitive ]
Air Sensitive | [Merck ]
14,3795 | [BRN ]
605263 | [Henry's Law Constant]
1.69(x 10-9 atm?m3/mol) at 25 °C (Westheimer and Ingraham, 1956) | [Dielectric constant]
16.0（18℃） | [Exposure limits]
TLV-TWA 10 ppm (～25 mg/m3) (ACGIH,
MSHA, and OSHA); IDLH 2000 ppm
(NIOSH). | [Contact allergens]
Ethylenediamine is used in numerous industrial processes
as a solvent for casein or albumin, as a stabilizer
in rubber latex, and as a textile lubricant. It can be
found in epoxy resin hardeners, cooling oils, fungicides,
and waxes. Contact dermatitis from ethylenediamine
is almost exclusively due to topical medicaments.
Occupational contact dermatitis in epoxy resin systems
is rather infrequent. Ethylenediamine can crossreact
with triethylenetetramine and diethylenetriamine.
Ethylenediamine was found to be responsible for sensitization
in pharmacists handling aminophylline suppositories,
in nurses preparing and administering
injectable theophylline, and in a laboratory technician
in the manufacture of aminophylline tablets | [InChIKey]
PIICEJLVQHRZGT-UHFFFAOYSA-N | [LogP]
-1.6 at 20℃ | [CAS DataBase Reference]
107-15-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethylenediamine(107-15-3) | [EPA Substance Registry System]
107-15-3(EPA Substance) |
| Hazard Information | Back Directory | [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.] |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R10:Flammable.
R21/22:Harmful in contact with skin and if swallowed .
R34:Causes burns.
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1604 8/PG 2
| [WGK Germany ]
2
| [RTECS ]
KH8575000
| [F ]
10-34 | [Autoignition Temperature]
716 °F | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29212100 | [Safety Profile]
A human poison by
inhalation. Experimental poison by
inhalation, intraperitoneal, subcutaneous,
and intravenous routes. Moderately toxic by
ingestion and skin contact, Experimental
reproductive effects. Corrosive. A severe
skin and eye irritant. An allergen and
sensitizer. Mutation data reported.
Flammable liquid when exposed to heat,
flame, or oxidizers. Can react violently with
acetic acid, acetic anhydride, acrolein, acrylic
acid, acrylonitrile, allyl chloride, CS2,
chlorosulfonic acid, epichlorohydrin,
ethylene chlorohydrin, HCl, mesityl oxide,
HNO3, oleum, AgClO4, H2SO4, Ppropiolactone, or vinyl acetate. To fight fwe,
use CO2, dry chemical, alcohol foam. When
heated to decomposition it emits toxic
fumes of NOx and NH3. See also MINES. | [Hazardous Substances Data]
107-15-3(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 1.16 g/kg (Smyth) | [IDLA]
1,000 ppm |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ammonium hydroxide-->Ammonia-->Piperazine-->Monoethanolamine-->1,2-Dichloroethane-->Dichloroethane-->Titanium-->PIPERAZINE HEXAHYDRATE-->N-Aminoethylpiperazine-->Polyamine N7 | [Preparation Products]
2-(2-Aminoethylamino)ethanol-->C-(1H-INDOL-5-YL)-METHYLAMINE-->Reactive Blue 198-->Imidocarb-->dimethyl p-octadecyl phenylsulfonyl amino propyl ammoium propylsulfonate-->N,N'-BIS(ETHYLENE)-P-TOLUENESULFONAMIDE-->Lofexidine-->acid washing corrosion inhibitor Sx-1-->2-Nitroaminoimidazoline-->2-Methylpyrazine-->2,3-Dimethylpyrazine-->2-Phenyl-2-imidazoline-->laurylamide propionate JHZ-101-->N,N'-Ethylenebis(stearamide)-->NABAM-->ETHYLEN-BIS-(4,6-DIMETHYL-TETRAHYDRO-1,3,5-THIADIAZIN-2-THION)-->Moxonidine-->CURING AGENT (POLYAMIDE BASE LIQUID) FOR EPOXY RES-->amidoamino acid-->noncyanide zinc plating additive XD-1-->2-Imidazolidone-->ETHYLENEDIAMINE DIACETATE-->additive EQD-3-->N-Acetylethylenediamine-->1-Boc-3-oxopiperazine-->Reactive Blue 231-->leveler DA-->2-Ethyl-3-methylpyrazine-->N-(1-Naphthyl)ethylenediamine dihydrochloride-->Cibenzoline-->Ethylenediamine dihydrochloride-->N,N'-Dibenzyl ethylenediamine diacetate-->noncyanide zinc plating bright additive-->5,6,7,8-Tetrahydroquinoxaline-->2,3-Diethylpyrazine-->hydrodewaxing catalysts for diesel fuel(series)-->Glycylglycine-->N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine-->3-(2-Aminoethylamino)propyl-dimethoxymethylsilane |
| Questions And Answer | Back Directory | [Description]
Ethylenediamine (EDA) is a clear and colorless product at normal temperature and pressure which has a characteristic smell of an amine. It is strongly alkaline and is miscible with water and alcohol. It is air sensitive and hygroscopic and absorbs carbon dioxide from the air. It is incompatible with aldehydes, phosphorus halides, organic halides, oxidising agents, strong acids, copper, its alloys, and its salts.
| [synthesis]
Ethylenediamine can be synthesized from ethanolamine (EA) with ammonia over acidic types of zeolite catalyst.2 It is produced industrially by the reaction of 1,2-dichloroethane with ammonia in a liquid base under high temperature and high presseure.3 The synthesis of ethylenediamine from 1,2-dichloroethane is ClCH2CH2Cl + 2NH3 → NH2CH2CH2NH2*2HCl
ClCH2CH2Cl + NH2CH2CH2NH2*2HCl + 2NH3 → NH2CH2C H2NHCH2CH2NH3*3HCl + NH4HCl
Nevertheless, there are too many byproducts during the reaction. The key of this synthesis is to improve the selectivity of reaction product and the application of advanced separation methods to obtain high product purity.
| [Application]
Ligands in coordination chemistry
With the two nitrogen atoms, which can donate their lone pairs of electrons, ethylenediamine is widely used as a chelating ligand for coordination chemistry to form bonds to a transition-metal ion such as nickel (II).3 The bonds form between the metal ion and the nitrogen atoms of ethylenediamine. Ethylenediaminetetraacetic acid (EDTA) is a derivate of ethylenediamine and it is a versatile chelating agent, which could form chelates with both transition-metal ions and main-group ions. Ethylenediamine is mainly used to synthesize ethylenediaminetetraacetic acid. EDTA is frequently used in soaps and detergents to form complexes with calcium and magnesium ions in hard water to improve the cleaning efficiency. Furthermore, EDTA is used extensively as a stabilizing agent in the food industry to promote color retention, to improve flavor retention, and to inhibit rancidity.
Pharmaceutical ingredient
Ethylenediamine is used to facilitate the dissolution of theophylline. This combination is known as aminophylline and used to treat and prevent wheezing and trouble breathing caused by ongoing lung disease (e.g. asthma, emphysema, chronic bronchitis).4 It is evidenced that there is no molecular association between theophylline and ethylenediamine in biological media. The bioavailability of ethylenediamine is approximately 34% and of theophylline is about 88%.5
Tetraacetylethylenediamine
Ethylenediamine is used as an intermediate in the manufacture of tetraacetyl ethylenediamine (TAED), a bleaching activator, which is used in detergents and additives for laundry washing and dishwashing.6 The amount of TAED used in household cleaning products in Europe was estimated to be 61,000 t in 2001.
Other applications
Ethylenediamine is in the manufacture of organic flocculants, urea resins, and fatty bisamides. It is used in the production of formulations for use in the printed circuit board and metal finishing industries. It is used as intermediate in the production of crop protection agents, hardeners for epoxy resins, leather industry, paint industry, fungicides in crop protection area, and textile industry.7 Ethylenediamine is also used as solvent and for the analytical chemistry. It is used to produce photographic fixer additive
| [References]
[1] Formation of metal complexes with ethylenediamine: a critical survey of equilibrium constants, enthalpy and entropy values, Pure & Applied Chemistry, vol. 56, 1984, pp.491-522
https://pdfs.semanticscholar.org/0a2c/9b67e3f39b4b4fc81a143b8aba7d9b82e35d.pdf
[2] K. Segawa, S. Mizuno, M. Sugiura, S. Nakata, Selective synthesis of ethylenediamine from ethanolamine over modified H-mordenite catalyst, Studies in Surface Science and Catalysis, vol. 101, 1996, pp. 267-276
https://www.sciencedirect.com/science/article/pii/S0167299196802370
[3] https://en.wikipedia.org/wiki/Ethylenediamine
[4] Norbert Rietbrock, B. G. Woodcock, A. H. Staib, Theophylline and other Methylxanthines, 1981, ISBN 978-3-663-05269-2
[5] Ian A. Cotgreave, John Caldwell, Comparative plasma pharmacokinetics of theophylline and ethylenediamine after the administration of aminophylline to man, Journal of Pharmacy and Pharmacology, vol. 35, 1983, pp. 378-382
https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.1983.tb02960.x
[6] http://www.heraproject.com/files/2-f-04-hera%20taed%20full%20web%20wd.pdf
[7] http://product-finder.basf.com/group/corporate/product-finder/en/brand/ETHYLENEDIAMINE
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