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Home > Encyclopedia > Tetraethylenepentamine

Tetraethylenepentamine

Tetraethylenepentamine structure

Tetraethylenepentamine 

structure
  • CAS No:

    112-57-2

  • Formula:

    C8H23N5

  • Chemical Name:

    Tetraethylenepentamine

  • Synonyms:

    1,2-Ethanediamine,N1-(2-aminoethyl)-N2-[2-[(2-aminoethyl)amino]ethyl]-;Tetraethylenepentamine;1,2-Ethanediamine,N-(2-aminoethyl)-N′-[2-[(2-aminoethyl)amino]ethyl]-;N1-(2-Aminoethyl)-N2-[2-[(2-aminoethyl)amino]ethyl]-1,2-ethanediamine;3,6,9-Triazaundecane-1,11-diamine;1,11-Diamino-3,6,9-triazaundecane;Tetren;TEP;1,4,7,10,13-Pentaazatridecane;Tetraethylpentylamine;DEH 26;3,6,9-Triaza-1,11-diaminoundecane;Ancamine TEPA;TEPA;NSC 88603;N-(2-Aminoethyl)-N′-(2-((2-aminoethyl)amino)ethyl)-1,2-ethanediamine;T 11509;Bis[2-(2-aminoethylamino)ethyl]amine;AFR-AN 6;TH 160;Insulcure 9;Epikure 927;Epikure Curing Agent 927;Tetraethylene pentaamine;115254-44-9;675120-38-4;778611-86-2;916431-34-0;107324-82-3;951317-92-3;1061621-16-6;1151794-16-9

  • Categories:

    Organic Chemistry  >  Amides

Description

colourless to green-yellow viscous liquid Tetraethylenepentamine is a yellow, viscous liquid.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.


Tetraethylenepentamine appears as 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.|Liquid|COLOURLESS-TO-YELLOW HYGROSCOPIC VISCOUS LIQUID.


Tetraethylenepentamine appears as 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.|Tetraethylenepentamine is a polyazaalkane. It has a role as a copper chelator.

Tetraethylenepentamine Basic Attributes

189.3

189.30

203-986-2

YZD1C9KQ28

1718

88603

2320

DTXSID7026108

VISCOUS, HYGROSCOPIC LIQUID|Yellow liquid

29212900

Characteristics

88.1

-3.16 (calculated)

Clear Liquid

0.9980 g/cm3 @ Temp: 20 °C

-30 °C

340.30 °C @ Press: 760 Torr

365 °F

n 20/D 1.505(lit.)

H2O: soluble

Store below +30°C.

<0.01 mm Hg ( 20 °C)

6.53 (vs air)

Intraperitoneal injection-Rat LD50: 205 mg/kg

Flammable; decomposes toxic nitrogen oxide gas upon heating

0.1-15%(V)

AMMONIACAL; DIAGREEABLE, PENETRATING

ALKALINE

Henry's Law constant= 3X10-20 atm-cu m/mole at 25 °C

pKa1 = 9.68; pKa2 = 9.10; pKa3 = 8.08; pKa4 = 4.72; pKa5 = 2.98 (conjugate acid)

Soluble in water. Hygroscopic.

Amines, Phosphines, and Pyridines

TETRAETHYLENEPENTAMINE is hygroscopic. This compound can react with oxidizing materials and strong acids. It may attack some forms of plastics. (NTP, 1992)

610 °F (USCG, 1999)|610 °F (321 °C)|321 °C

63.3 kJ/mol @ 1 atm

Safety Information

III

8

UN 2320 8/PG 3

2

21/22-34-43-51/53

26-36/37/39-45-61

KH8585000

C,N

The warehouse is ventilated, low-temperature and dry; stored separately from acids and oxidants.

Corrosive to skin and cornea

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

P273-P280-P305 + P351 + P338-P310

H302-H312-H314-H317-H411

Tetraethylenepentamine is an indirect food additive for use only as a component of adhesives.

Special Hazards of Combustion Products: Ammonia and toxic oxides of nitrogen may form in fires. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P363, P391, P405, and P501|H302 (99.94%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P285, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P342+P311, P361, P363, P391, P405, and P501|Aggregated GHS information provided by 1785 companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P333+P313, P363, P391, P403+P233, P405, and P501|H311: Toxic in contact with skin [Danger Acute toxicity, dermal]|P260, P261, P264, P272, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P333+P313, P361, P363, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Air-supplied respirator; rubber gloves; complete eye protection; impervious apron (USCG, 1999)

Slight, when exposed to heat or flame.

Explosive limits , vol% in air: 0.1 - 15

WATER OR FOAM MAY CAUSE FROTHING. "ALCOHOL" FOAM.|If material /is/ involved in /a/ fire use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

If material /is/ not involved in /a/ fire keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.|Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Avoid bodily contact with material.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for TETRAETHYLENEPENTAMINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

... STRONG IRRITANT TO EYES & SKIN.

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from strong acids, strong oxidants, chlorinated hydrocarbons and food and feedstuffs. Dry. Store in an area without drain or sewer access.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of mist may cause severe swelling of the throat.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

highly toxic

LD50 Rabbit single dose dermal 0.66 g/kg|LD50 White rat single-dose oral 2.1 g/kg|LD50 Rat oral 3.99 g/kg

Tetraethylenepentamine's use as a solvent for sulfur, acid gases, various resins and dyes, as a saponifying agent for acidic materials, in the manufacture of synthetic rubber, as a dispersant in motor oils, and as an intermediate for oil additives(1) indicates that it may be released to the environment in waste streams from its production and use(SRC).

TERRESTRIAL FATE: An estimated Koc value of 3.6(1,SRC) for tetraethylenepentamine indicates high mobility in soil(2) and leaching may occur(SRC). However, tetraethylenepentamine will exist primarily as a cation under environmental conditions (pH 5-9) and no experimental data are available which suggest whether it will adsorb to soil more strongly than its estimated Koc value indicates. Volatilization from moist soils is not expected to be rapid based upon a low Henry's Law constant. Amines are potentially susceptible to hydrolysis(1). Therefore, tetraethylenepentamine is expected to hydrolyze in moist soils; however, no rates were located(SRC). Furthermore, no data were located which suggest biodegradation is an important terrestrial fate process of tetraethylenepentamine(SRC).|AQUATIC FATE: Based on an estimated Henry's Law constant of 3.0X10-20 atm-cu m/mole at 25 °C(2), tetraethylenepentamine is expected to be essentially nonvolatile from water(1). An estimated Koc of 3.6 and BCF of 4.2 suggest that adsorption to sediment and bioconcentration in aquatic organisms may not be important fate processes for tetraethylenepentamine in water systems(1). Based on pKa1, pKa2, pKa3, pKa4, and pKa5 values of 9.68, 9.10, 8.08, 4.72, and 2.98(3), respectively, tetraethylenepentamine will exist primarily as a cation under environmental conditions (pH 5-9). However, no experimental data are available which suggest whether it will adsorb to sediment more strongly than its estimated Koc value indicates. Amines are potentially susceptible to hydrolysis(4). Therefore, tetraethylenepentamine may hydrolyze in aquatic environments, but no rates were located(SRC). Furthermore, no data were located which suggest biodegradation is an important environmental fate process of tetraethylenepentamine in aquatic systems(SRC).|ATMOSPHERIC FATE: Based on a measured vapor pressure of 8.0X10-7 mm Hg at 25 °C(1), tetraethylenepentamine may exist in both the particulate and vapor phases in the ambient atmosphere(3). Vapor phase tetraethylenepentamine is degraded in the ambient atmosphere by reaction with photochemically formed hydroxyl radicals; the half-life for this reaction in air can be estimated to be about 1.2 hrs(2,SRC). Particulate phase tetraethylenepentamine may be susceptible to dry deposition. Also, based on its complete water solubility at 20 °C(4), removal from air via wet deposition is likely to occur(SRC).

Based on a measured vapor pressure of 8.0X10-7 mm Hg at 25 °C(1), tetraethylenepentamine may exist in both the particulate and vapor phases in the ambient atmosphere(3). The rate constant for the vapor-phase reaction of tetraethylenepentamine with photochemically produced hydroxyl radicals can be estimated to be 3.06X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 1.2 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(2). Amines are potentially susceptible to hydrolysis(4). Therefore, tetraethylenepentamine is expected to hydrolyze; however, no rates were located(SRC).

Based on an estimated log Kow of -1.503(2), the BCF for tetraethylenepentamine can be estimated to be 4.2(SRC) using a recommended regression derived equation(1). This BCF value suggests that tetraethylenepentamine would not bioconcentrate in aquatic organisms(SRC).

Based on an estimated log Kow of -1.503(2) and a recommended regression derived equation(1), the Koc for tetraethylenepentamine can be estimated to be about 3.6(SRC). This Koc value suggests that tetraethylenepentamine will be highly mobile in soil and sediment(4). Based on pKa1, pKa2, pKa3, pKa4, and pKa5 values of 9.68, 9.10, 8.08, 4.72, and 2.98(3), respectively, tetraethylenepentamine will exist primarily as a cation under environmental conditions (pH 5-9); no experimental data are available which suggest whether the cation will adsorb more strongly than its estimated Koc value indicates(SRC).

The Henry's Law constant for tetraethylenepentamine can be estimated to be approximately 3X10-20 atm-cu m/mole at 25 °C using a chemical structure estimation method(1,SRC). This value of Henry's Law constant suggests that tetraethylenepentamine is essentially nonvolatile from water(2).

In occupational settings, workers may be exposed to tetraethylenepentamine through eye and skin contact. (SRC)|NIOSH (NOHS Survey 1972-1974) has statistically estimated that 18,020 workers are potentially exposed to tetraethylenepentamine in the USA(1). NIOSH (NOES Survey 1981-1983) has statistically estimated that 35,585 workers are potentially exposed to tetraethylenepentamine in the USA(2).

Drug Information

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. (USCG, 1999)|Corrosives

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)


Fresh air, rest. Half-upright position. Refer immediately for medical attention.


Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Put clothes in sealable container. Refer immediately for medical attention.


Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

EARLY TREATMENT FOR CORROSIVE BURNS OF ESOPHAGUS CONSISTS OF IV FLUID THERAPY, BROAD SPECTRUM ANTIBIOTICS, SEDATION, PARENTERAL HYDROCORTISONE & MORE IMPORTANTLY MAINTAINING PATENCY OF ESOPHAGUS FOLLOWED BY DILATATION. /ALKALIES/

... LIQUID CAN CAUSE SLIGHT SKIN BURNS.

TETRAEN

Serious local effects by all routes of exposure.

Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing.


Redness. Pain. Skin burns.


Redness. Pain. Burns.

Tetraethylenepentamine Use and Manufacturing

Methods of Manufacturing

REACTION OF AQUEOUS AMMONIA WITH 1,2-DICHLOROETHANE FOLLOWED BY NEUTRALIZATION (EG, WITH AQUEOUS CAUSTIC SODA) AND FRACTIONAL DISTILLATION

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.


Corrosion inhibitors and anti-scaling agents


Fuels and related products

Production

10,000,000 - 50,000,000 lb|(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

All other basic organic chemical manufacturing|1,2-Ethanediamine, N1-(2-aminoethyl)-N2-[2-[(2-aminoethyl)amino]ethyl]-: ACTIVE

The title method for the detn of ... tetraethylenepentamine was developed for the monitoring of occupational health hazard from inhalation after absorption in diluted mineral mixtures. The ion-pair HPLC or Spherisorb 5 ODS reversed-phase column was used in 70-90% MeCN with H2O soln of 5 mM Na 1-pentanesulfonate pH 3.5. The eluted dansylamines were monitored by UV or by fluorescence spectrometry (excitation and emission wavelengths 341 and 520 nm, resp). The range of fluorescence linearity with concn is 1-30 ug/ml.

Health Hazards -> Corrosives

Computed Properties

Molecular Weight:189.30
XLogP3:-2.9
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:189.19534575
Monoisotopic Mass:189.19534575
Topological Polar Surface Area:88.1
Heavy Atom Count:13
Complexity:78.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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