Tetraethylenepentamine

Tetraethylenepentamine Property

Melting point:

-40 °C (lit.)

Boiling point:

340 °C

Density 

0.998 g/mL at 25 °C (lit.)

vapor density 

6.53 (vs air)

vapor pressure 

<0.01 mm Hg ( 20 °C)

refractive index 

n20/D 1.505(lit.)

Flash point:

365 °F

storage temp. 

Store below +30°C.

solubility 

6540g/l

form 

Liquid

pka

pK1:2.98(+5);pK2:4.72(+4);pK3:8.08(+3);pK4:9.10(+2);pK5:9.67(+1) (25°C,)

color 

Clear

PH

11.8 (20g/l, H2O, 20℃)

Odor

ammonia odor

explosive limit

0.1-15%(V)

Water Solubility 

SOLUBLE

Sensitive 

air sensitive

BRN 

506966

Henry's Law Constant

3.3×10¹⁴ mol/(m³Pa) at 25℃, HSDB (2015)

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, mineral acids, halogenated hydrocarbons, hydrogen peroxide.

InChI

1S/C8H23N5/c9-1-3-11-5-7-13-8-6-12-4-2-10/h11-13H,1-10H2

InChIKey

FAGUFWYHJQFNRV-UHFFFAOYSA-N

SMILES

NCCNCCNCCNCCN

CAS DataBase Reference

112-57-2(CAS DataBase Reference)

NIST Chemistry Reference

Tetraethylenepentamine(112-57-2)

EPA Substance Registry System

Tetraethylenepentamine (112-57-2)

Safety

Hazard Codes 

C,N

Risk Statements 

21/22-34-43-51/53

Safety Statements 

26-36/37/39-45-61

RIDADR 

UN 2320

WGK Germany 

2

RTECS 

KH8585000

F 

21

Autoignition Temperature

610 °F

TSCA 

TSCA listed

HazardClass 

8

PackingGroup 

III

HS Code 

29212900

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Acute Tox. 4 Dermal
Acute Tox. 4 Oral
Aquatic Chronic 2
Eye Dam. 1
Skin Corr. 1B
Skin Sens. 1

Hazardous Substances Data

112-57-2(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 3990 mg/kg LD50 dermal Rabbit 660 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H303May be harmfulif swallowed

H311Toxic in contact with skin

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

P405Store locked up.

P501Dispose of contents/container to..…

Tetraethylenepentamine Chemical Properties,Usage,Production

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.