Chemical Properties
Tetraethylenepentamine is a colourless to greenish-yellow viscous liquid. It is readily soluble in water, ethanol, and most organic solvents, but insoluble in benzene and diethyl ether. The compound is hygroscopic and absorbs carbon dioxide from the air, exhibiting alkaline properties.
Uses
Solvent for sulfur, acid gases, and various
resins and dyes; saponifying agent for acidic materials;
manufacture of synthetic rubber; dispersant in
motor oils; intermediate for oil additives.
Definition
ChEBI: Tetraethylenepentamine is a polyazaalkane. It has a role as a copper chelator.
Preparation
Tetramethylenepentaamine is primarily produced by the amination of dichloroethane using ammonia water under high temperature and pressure. It is a key component in the co-production of polyethylenediamines, including ethylenediamine, diethylenetriamine, and triethylenetetramine.
Reactions
Tetramethylenepentaamine is an aliphatic polyamine whose molecular structure contains two primary amine groups (-NH₂) and three secondary amine groups (-NH-), a configuration that confers high reactivity. It exhibits strong basicity and can react with inorganic or organic acids to form the corresponding salts. The lone pair of electrons on the amino groups imparts strong nucleophilicity, enabling reactions such as alkylation with halogenated hydrocarbons, condensation with aldehydes and ketones, and hydrolysis of esters to form amides. Moreover, amino and imino groups within the same molecule or between different molecules can react to form cross-linked or linear polymers. Additionally, the nitrogen atoms in the molecule can act as coordinating centers, forming stable chelates with metal ions such as copper, zinc, and nickel.
General Description
A viscous liquid. Slightly less dense than water. Vapors heavier than air. Corrosive to the eyes, skin, mouth, throat and stomach. Vapors irritate the eyes and corrosive to the upper respiratory tract. Vapors may irritate the eyes. Flash point 325°F.
Air & Water Reactions
Soluble in water. Hygroscopic.
Reactivity Profile
1,4,7,10,13-Pentaazatridecane is hygroscopic. 1,4,7,10,13-Pentaazatridecane can react with oxidizing materials and strong acids. 1,4,7,10,13-Pentaazatridecane may attack some forms of plastics.
Hazard
Strong irritant to eyes and skin.
Health Hazard
Inhalation may cause nausea and slight irritation; compound is a sensitizer, and prolonged contact may cause asthma. Ingestion can cause burns of mouth, esophagus, and possibly stomach. Contact with eyes or skin may cause burns. Repeated skin contact may cause dermatitis.
Fire Hazard
Special Hazards of Combustion Products: Ammonia and toxic oxides of nitrogen may form in fires.
Safety Profile
Poison by ingestion and intravenous routes. Moderately toxic by skin contact. Mutation data reported. A corrosive irritant to skin, eyes, and mucous membranes. Combustible when exposed to heat or flame. Can react with oxidizing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.
Potential Exposure
Tetraethylenepentamine is used as a solvent for resins and dyes, in manufacture of synthetic rubber; and intermediate for oil additives; in papermaking.
Shipping
UN2320 Tetraethylenepentamine, Hazard class: 8; Labels: 8-Corrosive material.
Purification Methods
Distil the amine under vacuum. Also purify via its penta hydrochloride, nitrate or sulfate. Jonassen, Frey and Schaafsma [J Phys Chem 61 504 1957] cooled a solution of 150g of the base in 300mL of 95% EtOH, and added dropwise 180mL of conc HCl, keeping the temperature below 20o. The white precipitate was filtered off, crystallised three times from EtOH/water, then washed with diethyl ether and dried by suction. Reilley and Holloway [J Am Chem Soc 80 2917 1958], starting with a similar solution cooled to 0o, added slowly (keeping the temperature below 10o) a solution of 4.5g-moles of HNO3 in 600mL of aqueous 50% EtOH (also cooled to 0o). The precipitate was filtered by suction, recrystallised five times from aqueous 5% HNO3, then washed with acetone and absolute EtOH and dried at 50o. [For purification via the sulfate see Reilley and Vavoulis (Anal Chem 31 243 1959), and for an additional purification step using the Schiff base with benzaldehyde see Jonassen et al. J Am Chem Soc 79 4279 1957]. [Beilstein 4 IV 1244.]
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. This chemical is strongly alkaline; reacts with acids.
