ETHYLENEDIAMINE

PRODUCT IDENTIFICATION

CAS NO. 107-15-3

ETHYLENEDIAMINE

EINECS NO. 203-468-6
FORMULA H2NCH2CH2NH2
MOL WT. 60.10
H.S. CODE  

TOXICITY

Oral rat LD50: 500 mg/Kg
SYNONYMS 1,2-Ethylenediamine; 1,2-Diaminoethane; EDA;
Ethane-1,2-diamine; Aethaldiamin (German); Aethylenediamin (German); 1,2-diaminoaethan (German) ; 1,2-Diamino-ethaan (Dutch); 1, 2-Diamino-Ethano (Italian); Dimethylenediamine; Ethyleendiamine (Dutch); Ethylene-diamine (French); β-Aminoethylamine; 乙二胺 (Chinese)

SMILES

 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE Colorless liquid with amine like odor
MELTING POINT 8.5 C
BOILING POINT

118 C

SPECIFIC GRAVITY 0.899
SOLUBILITY IN WATER Soluble
pH

11.9 (25% sol.)

VAPOR DENSITY 2.07
AUTOIGNITION

385 C

NFPA RATINGS Health: 3; Flammability: 2; Reactivity: 0

REFRACTIVE INDEX

1.4565
FLASH POINT

 

STABILITY Stable under ordinary conditions

GENERAL DESCRIPTION & APPLICATIONS

Ethylenediamine is a colourless to yellowish, strongly alkaline liquid, melting at 8.5 C, boiling at 116 C; completely soluble in water and soluble alcohol. It is a manufactured chemical that does not occur naturally. It has two primary amine groups. There are homologous odd number amine (on even number linear carbon chain) series of ethylenediamines; diethylenetriamine (linear C-4 diamine), triethylenetetramine (linear C-6 triamine), tetraethylenepentamine (linear C-8 pentamine), and  pentaethylenehexamine (linear C-10 hexamine).

Diethylenediamine is the simplest cyclic ethyleneamine (C-4), called piperazine. It has two secondary amine groups in cyclic system. It is a deliquescent crystalline compound melting at 105 C; soluble in water, alcohol, glycerol, and glycols. It is used as a main ingredient of anthelmintics and psychoactive drugs. Aminoethylpiperazine is also a member of C- 6 cyclic ethyleneamine which has aminoethyl attached to a nitrogen in piperazine. Accordingly, it has one primary, one secondary, and one tertiary nitrogen atom. It is used in the synthesis of catalysts, epoxy curing agent, and corrosion inhibitors. Aminoethylethanolamine (AEEA) is an analogue of diethylenetriamine. A hydroxyl group replace for an primary amine group. AEEA has one primary amine, one secondary amine, and one primary hydroxyl group. AEEA is a useful intermediate in the production of surfactants, chelating agents, and curing agents. Other branched or cyclic ethylenediamines include N,N'-Bis-(2-aminoethyl)piperazine) [CAS #: 6531-38-0], N-[(2-aminoethyl)2-aminoethyl]piperazine) [CAS #: 24028-46-4], tris(2-aminoethyl)amine) [CAS #: 4097-89-6]. 

Ethylenediamines are produced by the reaction of aqueous ammonia with 1,2-dichloroethane. This process yields the mixture of polyamines in the form of hydrochloride salts. The next step is neutralisation of the salts with aqueous caustic soda to separate free amines. The individual free amines are isolated by fractional distillation. Ethylenediamines are capable of entering into a variety of reactions because of their combination of reactivity, basicity, and surface activity and of the basic functionality of the nitrogen atom. They are therefore important intermediates for a wide variety of chemical syntheses. Examples of products obtained by reacting amines are as follows:

  • with carboxylic acid dericatives (acids, esters, anhydrides, or acyl halides): amides and amidoamines
  • with fatty acid: imidazoline
  • with cyanides or nitriles: amidoamines, polyamides, imidazolines
  • with urea: substituted urea and ammonia
  • with ethyleneimines: hydroxyalkyl amine derivatives
  • with aliphatic alcohols and glycols: alkylated ethyleneamines or cyclic ethyleneamines
  • with alkyl or aryl halides: substituted amines
  • with aliphatic aldehydes: substituted imidazolidines
  • with carbon disulfide: thiocarbamates
  • with carbon dioxide: carbamate
  • with inorganic acids: water soluble salts

Ethylenediamine is used as a very important bidentate ligand forming chelate agents.  The main application is to produce chelating agents such as ethylenediaminetetraacetic acid (EDTA). It is used in the manufacture of carbamate fungicides,  surfactant and dyes. It is useful also in manufacturing accelerator or curing agent in epoxy industry. Additional applications include manufacturing photography development chemicals and cutting oils, bleaching activators for washing powders especially at low temperature, lubricant for plastics and polyamide process, and fuel additives.

Diethylenetriamine is a yellow, hygroscopic liquid; boiling point of 206 C; soluble in water and hydrocarbons. It is used as a solvent for sulfur, acidic gas, resin and as a fuel and oil field component. It is used as an Intermediate for organic synthesis (modified polyamides, corrosion inhibitors, fuel additives, epoxy curing agents, fabric softeners and adhesion promoters) and saponification agent for acidic materials.

Triethylenetetramine is a clear to yellowish oily liquid; melting point 12 C, boiling point 280 C. It is miscible with water and the solution is alkaline ( (pH 10 at 10% solution). It reacts with ketones, halogenated hydrocarbons, nitriles, epoxides, and with strong oxidants. Commercial triethylenetetramine is a mixture of linear TETA (typically 60%) and branched or cyclic TETA such as N,N'-Bis(2-aminoethyl)piperazine, N-[1-(2-piperazin-1-yl-ethyl)]ethane -1,2-diamine, tris-(2-aminoethyl)-amine. TETA and its derivatives are used as an epoxy curing agent. Their applications are similar to those of ethylenediamine and diethylenetriamine.

End uses of ethylenediamine family products include:

  • Dispersant-detergent
  • Modified Polyamides
  • Fabric Softeners
  • Ore Flotation Agents
  • Emulsifiers
  • Corrosion Inhibitors
  • Adhesives
  • Binding Agents
  • Chelating Agents
  • Bleach Activators
  • Epoxy Curing Agent
SALES SPECIFICATION

APPEARANCE

Colorless liquid with amine like odor
ASSAY

99.0% min

COLOR, APHA

20 max

SPECIFIC GRAVITY

0.897-0.910

DISTILLATION RANGE

115 C min (I.B.P), 119C max (D.P.)

WATER

0.55% max

TRANSPORTATION
PACKING 180kgs in drum, Iso-Tank
HAZARD CLASS 8,3 (Packing group: II)
UN NO. 1604
GENERAL DESCRIPTION OF CHELATING AGENT
Chelation is a chemical combination with a metal in complexes in which the metal is part of a ring. Organic ligand is called  chelator or chelating agent, the chelate is a metal complex. The larger number of ring closures to a metal atom is the more stable the compound. This phenomenon is called the chelate effect; it is generally attributed to an increase in the thermodynamic quantity called entropy that accompanies chelation. The stability of a chelate is also related to the number of atoms in the chelate ring. Monodentate ligands which have one coordinating atom like H2O or NH3 are easily broken apart by other chemical processes, whereas polydentate chelators, donating multiple binds to metal ion, provide more stable complexes. Chlorophyll, green plant pigment, is a chelate that consists of a central magnesium atom joined with four complex chelating agent (pyrrole ring). The molecular structure of the chlorophyll is similar to that of the heme bound to proteins to form hemoglobin, except that the latter contains iron(II) ion in the center of the porphyrin. Heme is an iron chelate. Chelation is applied in metal complex chemistry, organic and inorganic chemistry, biochemistry, and environment protection. It is used in chemotherapeutic treatments for metal poisoning. Chelating agents offers a wide range of sequestrants to control metal ions in aqueous systems. By forming stable water soluble complexes with multivalent metal ions,  chelating agents prevent undesired interaction by blocking normal reactivity of metal ions. EDTA, ethylenediaminetetraacetate (hexadentating), is a good example of common chelating agent which have nitrogen atoms and short chain carboxylic groups. The sodium salt of EDTA is used as an antidote for metal poisoning, an anticoagulant, and an ingredient in a variety of detergents.  Chelating agents are important in the field of soap, detergents, textile dyeing, water softening, metal finishing and plating, pulp and paper, enzyme deactivation, photo chemistry, and bacteriocides.

 

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